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Table of Contents
MANAGEMENT'S DISCUSSION
INDEX TO CONSOLIDATED FINANCIAL STATEMENTS SIRIUS INTERNATIONAL INSURANCE GROUP, LTD.
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UNITED STATES
SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

SCHEDULE 14A

Proxy Statement Pursuant to Section 14(a) of
the Securities Exchange Act of 1934 (Amendment No.          )

Filed by the Registrant ý

Filed by a Party other than the Registrant o

Check the appropriate box:

o

 

Preliminary Proxy Statement

o

 

Confidential, for Use of the Commission Only (as permitted by Rule 14a-6(e)(2))

ý

 

Definitive Proxy Statement

o

 

Definitive Additional Materials

o

 

Soliciting Material under §240.14a-12

 

EASTERLY ACQUISITION CORP.

(Name of Registrant as Specified In Its Charter)

 

(Name of Person(s) Filing Proxy Statement, if other than the Registrant)

Payment of Filing Fee (Check the appropriate box):

ý

 

No fee required.

o

 

Fee computed on table below per Exchange Act Rules 14a-6(i)(1) and 0-11.
    (1)   Title of each class of securities to which transaction applies:
        
 
    (2)   Aggregate number of securities to which transaction applies:
        
 
    (3)   Per unit price or other underlying value of transaction computed pursuant to Exchange Act Rule 0-11 (set forth the amount on which the filing fee is calculated and state how it was determined):
        
 
    (4)   Proposed maximum aggregate value of transaction:
        
 
    (5)   Total fee paid:
        
 

o

 

Fee paid previously with preliminary materials.

o

 

Check box if any part of the fee is offset as provided by Exchange Act Rule 0-11(a)(2) and identify the filing for which the offsetting fee was paid previously. Identify the previous filing by registration statement number, or the Form or Schedule and the date of its filing.

 

 

(1)

 

Amount Previously Paid:
        
 
    (2)   Form, Schedule or Registration Statement No.:
        
 
    (3)   Filing Party:
        
 
    (4)   Date Filed:
        
 

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LOGO   LOGO

PROXY STATEMENT/PROSPECTUS
MERGER PROPOSED—YOUR VOTE IS VERY IMPORTANT



           The board of directors of Sirius International Insurance Group, Ltd. ("Sirius Group") and Easterly Acquisition Corp. ("Easterly") have each approved an Agreement and Plan of Merger, dated as of June 23, 2018 (as amended by the First Amendment to Agreement and Plan of Merger and Sponsor Letter, dated as of August 29, 2018, and as it may be further amended from time to time, the "Merger Agreement"), by and among Easterly, Sirius Group and Sirius Acquisitions Holding Company III, a wholly owned subsidiary of Sirius Group ("Merger Sub"), and the transactions contemplated by the Merger Agreement, including the merger of Merger Sub with and into Easterly with Easterly surviving the merger as a wholly owned subsidiary of Sirius Group (the "Merger").

           On the terms and subject to the conditions set forth in the Merger Agreement, at the closing of the Merger, all outstanding shares of Easterly common stock (other than shares subject to a valid redemption election, shares owned by Easterly, Sirius Group or Merger Sub and certain shares held by Easterly Acquisition Sponsor, LLC (the "Sponsor")) will be exchanged for newly issued common shares of Sirius Group at an exchange ratio (the "Exchange Ratio") that will be determined prior to the closing of the Merger and will be equal to a fraction determined by dividing (i) the estimated amount of cash per public share of Easterly common stock in Easterly's trust account (the "Trust Account") immediately prior to the closing of the Merger by (ii) (x) 1.05 multiplied by (y) Sirius Group's adjusted diluted book value per common share as of September 30, 2018 ("Sirius Group September 30 Adjusted DBVPS"). The Sirius Group September 30 Adjusted DBVPS will be calculated by dividing (i) the book value of Sirius Group, based on the unaudited GAAP consolidated financial statements of Sirius Group for the nine months ended September 30, 2018, decreased by the $7 million deferred underwriting fee payable by Easterly, and as adjusted by the GAAP accounting effect of the redemption of the Sirius Group Series A redeemable preference shares by (ii) the sum of (x) the fully diluted number of Sirius Group common shares issued and outstanding as of September 30, 2018 and (y) 593,000 Sirius Group common shares. In accordance with the Merger Agreement, Sirius Group delivered to Easterly its good faith estimate of 1.05 multiplied by the Sirius Group September 30 Adjusted DBVPS, equal to $17.22. If such estimate is used to determine the Exchange Ratio at the closing of the Merger, then the Merger Agreement provides for a post-closing adjustment if such estimate is different than the actual Sirius Group September 30 Adjusted DBVPS as finally determined after the closing of the Merger, as more fully described in the accompanying proxy statement/prospectus. Based on such estimate of the Sirius Group September 30 Adjusted DBVPS as of October 8, 2018 and funds in the Trust Account on September 30, 2018, the Exchange Ratio would be equal to 0.607. Investors are cautioned that 0.607 is only an estimate of the Exchange Ratio, has not been agreed as the final Exchange Ratio for purposes of the Merger Agreement, and is subject to change prior to the closing of the Merger.

           Additionally, each issued and outstanding public warrant to acquire shares of Easterly common stock will cease to represent a right to acquire shares of Easterly common stock and will be converted into a right to acquire Sirius Group common shares (a "converted warrant"), based upon the Exchange Ratio, as more fully described in the accompanying proxy statement/prospectus.

           Based on a per share value equal to (i) 1.05 multiplied by (ii) the Sirius Group September 30 Adjusted DBVPS, which is estimated as of October 8, 2018 to be $17.22, the aggregate value of the Merger consideration to be received by the Easterly stockholders (including the Sponsor) in respect of their shares of Easterly common stock pursuant to the Merger Agreement is estimated to be $165.5 million. Easterly has not obtained an opinion from an independent financial advisor in connection with the Merger and, consequently, there is no assurance from an independent source that the price Sirius Group is paying for Easterly is fair to Easterly's stockholders from a financial point of view.

           Based on the number of shares of Easterly common stock and Easterly warrants outstanding on September 30, 2018, Sirius Group expects to issue or reserve for issuance to Easterly public stockholders approximately 8.6 million common shares pursuant to the Merger Agreement (excluding the estimated 6.1 million Sirius Group common shares issuable upon exercise of the converted warrants). Sirius Group also expects to issue approximately 1.0 million common shares to the Sponsor, resulting in a total of approximately 9.6 million Sirius Group common shares issued in exchange for outstanding shares of Easterly common stock pursuant to the Merger Agreement. Upon the closing of the Merger, Easterly's public stockholders are expected to own approximately 6.8% of Sirius Group and CM Bermuda is expected to own approximately 83.2% of Sirius Group, and therefore CM Bermuda will continue to control Sirius Group following the Merger. The foregoing amounts assume, among other factors described in the accompanying proxy statement/prospectus, that the Exchange Ratio is equal to 0.607. If the facts differ from the assumptions, Easterly's stockholders may experience dilution of their ownership interest unless they elect to have their shares of Easterly common stock redeemed in connection with the Merger Proposal.

           Completion of the transactions contemplated by the Merger Agreement requires, among other things, the approval of Easterly's stockholders. To obtain this approval, Easterly will hold a special meeting of Easterly stockholders on November 2, 2018, as more fully described in the accompanying notice of special meeting. The Sponsor and Easterly's original independent directors have agreed to vote in favor of the proposals presented at the special meeting. After such meeting, and prior to the consummation of the Merger, Easterly stockholders may exercise their redemption rights as provided for by Easterly's charter. There is no specified maximum redemption threshold under Easterly's charter. In no event, however, will Easterly redeem public shares in an amount that would cause its net tangible assets to be less than $5,000,001. For illustrative purposes, if Easterly stockholders exercise their redemption rights such that Easterly's net tangible assets are reduced to $5,000,001, Easterly's public stockholders would be expected to own approximately 0.7% of Sirius Group, and the funds held in the Trust Account available to Sirius Group following the Merger would be approximately $15.8 million.

           Easterly's common stock, units and warrants are currently listed on the Nasdaq Capital Market under the symbols "EACQ," "EACQU" and "EACQW," respectively. At the closing of the Merger, Easterly units will separate into their components of one share of Easterly common stock and one-half of a warrant to purchase one share of Easterly common stock. Sirius Group has applied to list the Sirius Group common shares and converted warrants on the Nasdaq Stock Market under the symbols "SG" and "SGRP-W," respectively, effective as of the closing of the Merger. Completion of the transactions contemplated by the Merger Agreement requires that the Sirius Group common shares shall have been approved for listing on the Nasdaq Stock Market, subject to official notice of issuance. This listing condition may be waived by Sirius Group and Easterly.

           The accompanying proxy statement/prospectus contains detailed information about Sirius Group, Easterly, the Easterly special meeting, the Merger Agreement and the Merger. You are encouraged to read carefully the entire proxy statement/prospectus, including the section entitled "Risk Factors" beginning on page 44 of the enclosed proxy statement/prospectus, and all of its Annexes.

           We look forward to the successful combination of Sirius Group and Easterly.


GRAPHIC

Allan L. Waters
Chairman and Chief Executive Officer
Sirius International Insurance Group, Ltd.

 

GRAPHIC

Darrell W. Crate
Chairman
Easterly Acquisition Corp.

           The enclosed proxy statement/prospectus is dated October 12, 2018, and is first being mailed to stockholders of Easterly on or about October 13, 2018.

           NEITHER THE SECURITIES AND EXCHANGE COMMISSION NOR ANY STATE SECURITIES REGULATORY AGENCY HAS APPROVED OR DISAPPROVED THE SECURITIES TO BE ISSUED IN CONNECTION WITH THE TRANSACTIONS DESCRIBED IN THE ACCOMPANYING PROXY STATEMENT/PROSPECTUS, PASSED UPON THE MERITS OR FAIRNESS OF THE MERGER OR RELATED TRANSACTIONS OR PASSED UPON THE ADEQUACY OR ACCURACY OF THE DISCLOSURE IN THE ACCOMPANYING PROXY STATEMENT/PROSPECTUS. ANY REPRESENTATION TO THE CONTRARY CONSTITUTES A CRIMINAL OFFENSE.


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LOGO

EASTERLY ACQUISITION CORP.
205 Hudson Street, 7th Floor
New York, New York 10013

NOTICE OF SPECIAL MEETING OF STOCKHOLDERS
To Be Held at 10:00 a.m. Eastern time on Friday, November 2, 2018

TO THE STOCKHOLDERS OF EASTERLY ACQUISITION CORP.:

        NOTICE IS HEREBY GIVEN that a special meeting of stockholders (the "special meeting") of Easterly Acquisition Corp., a Delaware corporation ("Easterly"), will be held at 10:00 a.m. Eastern time on Friday, November 2, 2018, at the offices of Sidley Austin LLP locates at 787 Seventh Avenue, New York, New York 10019, or at such other time, on such other date and at such other place to which the meeting may be adjourned or postponed.

        You are cordially invited to attend the Easterly special meeting to vote on the following proposals:

            (a)   Proposal No. 1—The Merger Proposal—to consider and vote upon a proposal to approve and adopt the Agreement and Plan of Merger, dated as of June 23, 2018 (as amended pursuant to the First Amendment to Agreement and Plan of Merger and Sponsor Letter, dated as of August 29, 2018 (the "Amendment"), and as it may be further amended from time to time, the "Merger Agreement"), by and among Easterly, Sirius International Insurance Group, Ltd. ("Sirius Group") and Sirius Acquisitions Holding Company III, a wholly owned subsidiary of Sirius Group ("Merger Sub"), and the transactions contemplated by the Merger Agreement, including the merger of Merger Sub with and into Easterly with Easterly surviving the merger as a wholly owned subsidiary of Sirius Group (the "Merger").

            (b)   Proposal No. 2—The Adjournment Proposal—to consider and vote upon a proposal to adjourn the Easterly special meeting to a later date or dates, if necessary, to permit further solicitation of proxies if, based upon the tabulated vote at the time of the Easterly special meeting, there are not sufficient votes to approve one or more proposals presented to Easterly's stockholders for vote at such special meeting.

        These proposals are described further in the accompanying proxy statement/prospectus. Only holders of record of Easterly common stock at the close of business on October 2, 2018, the record date for the special meeting, are entitled to notice of the special meeting and to vote at the special meeting and any adjournments or postponements thereof. A complete list of Easterly stockholders of record entitled to vote at the special meeting will be available for ten days before the special meeting at Easterly's principal executive offices for inspection by stockholders during ordinary business hours for any purpose germane to the special meeting.

        Easterly stockholders are being provided the accompanying proxy statement/prospectus and proxy card in connection with the solicitation of proxies to be voted at the special meeting and at any adjournments or postponements thereof. Whether or not you plan to attend the special meeting, you are urged to read the accompanying proxy statement/prospectus carefully and submit your proxy as directed herein. Please pay particular attention to the section entitled "Risk Factors" beginning on page 44.

        After careful consideration, Easterly's board of directors has approved and adopted the Merger Agreement and recommends that Easterly's stockholders vote "FOR" the Merger Proposal and the Adjournment Proposal. When you consider the board recommendation of these proposals, you should keep in mind that Easterly's directors and officers have interests in the Merger that may conflict with


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your interests as a stockholder. See the section entitled "Proposal No. 1—The Merger Proposal—Certain Interests of Easterly's Directors and Officers and Others in the Merger."

        If you have any questions or need assistance voting your shares, please call Easterly's proxy solicitor, Morrow Sodali LLC, at (800) 662-5200 (banks and brokers call collect at (203) 658-9400).

        Your vote is very important. If you are a registered stockholder, please submit your proxy to have your shares voted as soon as possible by completing, signing, dating and returning the enclosed proxy card in the postage-paid envelope provided. If you hold your shares in "street name" through a bank, broker or other nominee, you will need to follow the instructions provided to you by your bank, broker or other nominee to ensure that your shares are represented and voted at the Easterly special meeting. The transactions contemplated by the Merger Agreement will be consummated only if the Merger Proposal is approved at the Easterly special meeting. The Merger Proposal is not conditioned on the approval of the Adjournment Proposal and the Adjournment Proposal is not conditioned on the approval of the Merger Proposal.

        If you fail to return your proxy card, and do not attend the special meeting in person, if you abstain from voting or if you hold your shares in "street name" and fail to instruct your bank, broker or other nominee how to vote, the effect will be that your shares will not be counted for purposes of determining whether a quorum is present at the Easterly special meeting and, if a quorum is present, will have same effect as a vote "AGAINST" the Merger Proposal but no effect on the vote for the Adjournment Proposal. If you are a stockholder of record and you attend the Easterly special meeting and wish to vote in person, you may vote in person, which will have the effect of revoking your proxy.

        Pursuant to Easterly's amended and restated certificate of incorporation, as amended ("Easterly's charter"), Easterly public stockholders may redeem shares of Easterly common stock for cash upon the closing of the Merger. The redemption amount would equal the pro rata share of the aggregate amount on deposit (as of two business days prior to the closing of the Merger) in the trust account (the "Trust Account") that holds the proceeds (less taxes payable and any interest that Easterly may withdraw to pay taxes) of Easterly's initial public offering (the "IPO") that closed on August 4, 2015. For illustrative purposes, based on funds in the Trust Account of approximately $148.5 million on September 30, 2018, the estimated per share redemption price would have been $10.45 per share. There is no specified maximum redemption threshold under Easterly's charter. In no event, however, will Easterly redeem public shares in an amount that would cause its net tangible assets to be less than $5,000,001.

        EASTERLY PUBLIC STOCKHOLDERS MAY ELECT TO REDEEM THEIR SHARES EVEN IF THEY VOTE FOR THE MERGER PROPOSAL. YOU MAY HAVE YOUR EASTERLY PUBLIC SHARES REDEEMED WHETHER OR NOT YOU ARE A HOLDER OF EASTERLY COMMON STOCK AS OF THE RECORD DATE FOR THE EASTERLY SPECIAL MEETING.

        TO EXERCISE YOUR REDEMPTION RIGHTS, YOU MUST (I) IF YOU HOLD EASTERLY UNITS, ELECT TO SEPARATE YOUR EASTERLY UNITS INTO THE UNDERLYING PUBLIC SHARES AND PUBLIC WARRANTS PRIOR TO EXERCISING YOUR REDEMPTION RIGHTS WITH RESPECT TO THE PUBLIC SHARES, (II) SUBMIT A WRITTEN REQUEST TO EASTERLY'S TRANSFER AGENT TO REDEEM YOUR EASTERLY PUBLIC SHARES FOR CASH, AND (III) DELIVER YOUR PUBLIC SHARES TO EASTERLY'S TRANSFER AGENT, PHYSICALLY OR ELECTRONICALLY USING DEPOSITORY TRUST COMPANY'S DWAC (DEPOSIT WITHDRAWAL AT CUSTODIAN) SYSTEM, IN EACH CASE IN ACCORDANCE WITH THE PROCEDURES AND DEADLINES DESCRIBED IN THE ACCOMPANYING PROXY STATEMENT/PROSPECTUS. IF THE MERGER IS NOT CONSUMMATED, THEN THE EASTERLY PUBLIC SHARES WILL NOT BE REDEEMED FOR CASH. IF YOU HOLD THE SHARES IN STREET NAME, YOU WILL NEED TO INSTRUCT THE ACCOUNT EXECUTIVE AT YOUR BANK, BROKER OR OTHER NOMINEE TO WITHDRAW THE SHARES FROM YOUR ACCOUNT IN ORDER TO EXERCISE YOUR REDEMPTION RIGHTS. SEE "PROPOSAL NO. 1—THE MERGER PROPOSAL—REDEMPTION RIGHTS" IN THE ACCOMPANYING PROXY STATEMENT/PROSPECTUS FOR MORE SPECIFIC INSTRUCTIONS.


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        An Easterly public stockholder, together with any of his, her or its affiliates or any other person with whom he, she or it is acting in concert or as a "group" (as defined under Section 13(d)(3) of the Securities Exchange Act of 1934, as amended), will be restricted from redeeming in the aggregate his, her or its shares or, if part of such a group, the group's shares, in excess of 15% of public shares of Easterly common stock. Holders of Easterly outstanding public warrants and units do not have redemption rights in connection with the Merger. Holders of outstanding units must separate the underlying public shares and public warrants prior to exercising redemption rights with respect to the public shares. The holders of shares of Easterly common stock issued prior to the IPO, which are referred to as "Founder Shares," have agreed to waive their redemption rights with respect to any shares of Easterly capital stock they may hold in connection with the consummation of the Merger, and the Founder Shares will be excluded from the pro rata calculation used to determine the per-share redemption price. Currently, Easterly's stockholders, which includes Easterly Acquisition Sponsor, LLC (the "Sponsor"), and Easterly's original independent directors and their permitted transferees, collectively own 25.8% of Easterly's issued and outstanding shares of common stock, including all of the Founder Shares. The Sponsor and Easterly's original independent directors have agreed to vote in favor of the proposals presented at the special meeting.

        On behalf of the Easterly board of directors, we thank you for your support and look forward to the successful completion of the Merger.

    Sincerely,

 

 

GRAPHIC

Darrell W. Crate
Chairman of the Board
Easterly Acquisition Corp.

 

 

October 12, 2018

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TABLE OF CONTENTS

ABOUT THIS PROXY STATEMENT/PROSPECTUS

  1

CAUTIONARY STATEMENT REGARDING FORWARD-LOOKING STATEMENTS

 
1

FREQUENTLY USED TERMS

 
4

QUESTIONS AND ANSWERS ABOUT THE MERGER, THE SPECIAL MEETING AND RELATED MATTERS

 
7

About the Merger

 
7

About the Redemption Rights of Easterly Public Stockholders

  16

About the Easterly Special Meeting

  19

SUMMARY

 
24

Parties to the Merger

 
24

The Merger Agreement

  25

Recent Developments Impacting the Exchange Ratio

  26

Agreements Related to the Merger Agreement

  26

Transactions Related to the Merger

  28

Beneficial Ownership of the Combined Company

  30

Corporate Structure of the Combined Company

  32

Directors and Executive Officers of the Combined Company

  32

Redemption Rights

  33

Accounting Treatment

  33

Appraisal Rights

  33

Easterly's Reasons for the Merger

  33

Sirius Group's Reasons for the Merger

  35

Risk Factors

  36

Quorum and Required Vote for Proposals for the Easterly Special Meeting of Stockholders

  36

Recommendation to Easterly Stockholders

  37

Regulatory Approval

  38

SUMMARY CONSOLIDATED HISTORICAL FINANCIAL DATA OF SIRIUS GROUP

 
39

SUMMARY CONSOLIDATED HISTORICAL FINANCIAL DATA OF EASTERLY

 
41

SUMMARY CONDENSED COMBINED UNAUDITED PRO FORMA FINANCIAL INFORMATION

 
42

RISK FACTORS

 
44

Risks Related to Sirius Group's Business and Industry

 
44

Risks Related to Tax Matters

  59

Risks Related to Sirius Group Common Shares

  66

Risks Related to Easterly and the Merger

  73

THE SPECIAL MEETING OF EASTERLY STOCKHOLDERS

 
85

General

 
85

Date, Time and Place of Special Meeting

  85

Voting Power; Record Date

  85

Vote of Easterly Founders and the Sponsor

  85

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Quorum and Required Vote for Proposals for the Easterly Special Meeting of Stockholders

  85

Recommendation to Easterly Stockholders

  86

Broker Non-Votes and Abstentions

  87

Voting Your Shares

  87

Revoking Your Proxy

  88

No Additional Matters May Be Presented at the Easterly Special Meeting

  88

Who Can Answer Your Questions About Voting

  88

Redemption Rights

  88

Appraisal Rights

  89

Accounting Treatment

  89

Proxy Solicitation Costs

  90

PROPOSAL NO. 1—THE MERGER PROPOSAL

 
91

The Merger Agreement

 
91

Conditions to Closing of the Merger

  95

Covenants of the Parties

  97

Tax Treatment

  103

Agreements Related to the Merger Agreement

  104

Transactions Related to the Merger

  107

Background of the Merger

  108

Easterly's Board of Directors' Reasons for Approval of the Merger

  112

Sirius Group's Board of Directors' Reasons for Approval of the Merger

  115

Certain Interests of Easterly's Directors and Officers and Others in the Merger

  117

Certain Interests of Sirius Group's Directors and Officers and Others in the Merger

  117

Potential Purchases of Public Shares

  118

Total Sirius Group Common Shares to be Issued in the Merger

  119

Recent Developments Impacting the Exchange Ratio

  120

Redemption Rights

  120

Appraisal Rights

  120

U.S. Federal Income Tax Considerations

  120

Approval of the Merger

  127

Vote Required for Approval

  128

Recommendation of the Board

  128

PROPOSAL NO. 2—THE ADJOURNMENT PROPOSAL

 
129

Consequences if the Adjournment Proposal is Not Approved

 
129

Vote Required for Approval

  129

Recommendation of the Board

  129

USE OF PROCEEDS

 
130

ACCOUNTING TREATMENT

 
130

SELECTED CONSOLIDATED HISTORICAL FINANCIAL DATA OF SIRIUS GROUP

 
131

SELECTED CONSOLIDATED HISTORICAL FINANCIAL DATA OF EASTERLY

 
134

UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL INFORMATION

 
136

COMPARATIVE PER SHARE DATA

 
144

MATERIAL TAX CONSEQUENCES

 
145

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INFORMATION ABOUT SIRIUS GROUP

  158

Overview

 
158

Competitive Strengths

  160

Strategies

  161

Corporate Structure

  162

Insurance and Reinsurance Overview

  163

Sirius Group's Products and Services

  163

Marketing and Distribution

  167

Underwriting and Pricing

  168

Claims Management

  168

Competition and Peers

  169

Catastrophe Risk Management

  169

Reinsurance Protection

  171

Reinsurance Recoverables by Rating

  173

Loss and LAE Reserves

  174

Investments

  175

Ratings

  180

Employees

  181

Properties

  181

Legal Proceedings

  181

REGULATION OF SIRIUS GROUP

 
182

Bermuda Insurance Regulation

 
182

U.S. Insurance Regulation

  191

European Insurance Regulation

  196

MANAGEMENT'S DISCUSSION AND ANALYSIS OF FINANCIAL CONDITION AND RESULTS OF OPERATIONS OF SIRIUS GROUP

 
202

MANAGEMENT OF SIRIUS GROUP

 
280

COMPENSATION DISCUSSION AND ANALYSIS OF SIRIUS GROUP

 
286

Executive Compensation Tables and Narratives

 
301

DIRECTOR COMPENSATION OF SIRIUS GROUP

 
308

INFORMATION ABOUT EASTERLY

 
309

General

 
309

Significant Activities since Inception

  309

Potential Purchases of Public Shares

  311

Redemption of Public Shares and Liquidation if No Initial Acquisition

  312

Employees

  316

Properties

  316

Legal Proceedings

  316

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ABOUT THIS PROXY STATEMENT/PROSPECTUS

        This document, which forms part of a registration statement on Form S-4 filed with the U.S. Securities and Exchange Commission by Sirius Group, constitutes a prospectus of Sirius Group under Section 5 of the U.S. Securities Act of 1933, as amended, with respect to the Sirius Group securities to be issued to Easterly security holders if the Merger is consummated. This document also constitutes a notice of meeting and a proxy statement under Section 14(a) of the U.S. Securities Exchange Act of 1934, as amended, with respect to the special meeting of Easterly stockholders, at which Easterly stockholders will be asked to consider and vote upon a proposal to approve and adopt the Merger Agreement and the transactions contemplated by the Merger Agreement, including the Merger, among other matters.


CAUTIONARY STATEMENT REGARDING FORWARD-LOOKING STATEMENTS

        This proxy statement/prospectus contains a number of forward-looking statements, including statements about the financial conditions, results of operations, earnings outlook and prospects of Sirius Group, Easterly and the combined company following the consummation of the Merger. Forward-looking statements are typically identified by words such as "plan," "believe," "expect," "anticipate," "intend," "outlook," "estimate," "forecast," "project," "continue," "could," "may," "might," "possible," "potential," "predict," "should," "would" and other similar words and expressions, but the absence of these words does not mean that a statement is not forward-looking. The forward-looking statements are based on the current expectations of the management of Sirius Group and Easterly, as applicable, and are inherently subject to uncertainties and changes in circumstance and their potential effects and speak only as of the date of such statement. There can be no assurance that future developments will be those that have been anticipated. These forward-looking statements involve a number of risks, uncertainties or other assumptions that may cause actual results or performance to be materially different from those expressed or implied by these forward-looking statements. These risks and uncertainties include, but are not limited to, those factors described in "Risk Factors," those discussed and identified in public filings made with the SEC by Easterly and the following:

    the occurrence of any event, change or other circumstances that could give rise to the termination of the Merger Agreement;

    the outcome of any legal proceedings that may be instituted against Sirius Group, Easterly and others following announcement of the Merger Agreement and transactions contemplated therein;

    the inability to complete the Merger, including due to the failure to obtain Easterly stockholder approval or the failure to receive approval to list the Sirius Group common shares on Nasdaq, or any substantial delay in the Merger;

    the risk that the proposed Merger disrupts current plans and operations of Sirius Group or Easterly as a result of the announcement and consummation of the transactions contemplated by the Merger Agreement;

    the ability to recognize the anticipated benefits of the combination of Sirius Group and Easterly;

    costs related to the proposed Merger and Sirius Group's status as a publicly traded company;

    Sirius Group's exposure to unpredictable catastrophic and casualty events and unexpected accumulations of attritional losses;

    increased competition from existing insurers and reinsurers and from alternative capital providers, such as insurance-linked funds and collateralized special purpose insurers;

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    decreased demand for Sirius Group's insurance or reinsurance products, consolidation and cyclical changes in the insurance and reinsurance industry;

    the inherent uncertainty of estimating loss and loss adjustment expenses reserves, including asbestos and environmental reserves, and the possibility that such reserves may be inadequate to cover Sirius Group's ultimate liability for losses;

    a decline in Sirius Group's operating subsidiaries' ratings with rating agencies;

    the risk that Sirius Group's reinsurance underwriting is dependent upon the underlying ceding companies' evaluation of risk;

    the risk that managing general underwriters and other agents acting on Sirius Group's behalf may act based on inaccurate or incomplete information regarding the accounts Sirius Group underwrites, or such agents may exceed their authority or commit fraud when binding policies on Sirius Group's behalf;

    the inherent uncertainty of modeling, pricing for, and managing insurance and reinsurance risk, including with respect to catastrophe and attritional losses that may be different than actual losses;

    the risk that Sirius Group may not adequately assess and price for the increased frequency and severity of catastrophes resulting from global climate change;

    the exposure of Sirius Group's investments to interest rate, credit, equity risks and market volatility, which may limit Sirius Group's net income and may affect the adequacy of its capital;

    the effects of volatility in the global economy and capital markets, which may impair Sirius Group's investment portfolio and affect the primary insurance market;

    the impact of various risks associated with transacting business in foreign countries, including foreign currency exchange-rate risk and political risks on investments in, and revenues from, Sirius Group's operations outside the U.S.;

    unexpected volatility or illiquidity associated with Sirius Group's investments;

    Sirius Group's ability to obtain reinsurance and retrocessional protection at reasonable prices or on terms that adequately protect it;

    Sirius Group's lack of profitability in recent periods and the potential volatility in its quarterly results;

    the potential effects on Sirius Group's business of emerging claim and coverage issues;

    Sirius Group's dependence on a small number of brokers and managing general underwriters for a large portion of its revenues;

    Sirius Group's exposure to the credit risk of reinsurance counterparties and intermediaries;

    risks relating to the inability of Sirius Group's operating subsidiaries to declare and pay dividends;

    the possibility that Sirius Group may become subject to additional onerous governmental or regulatory requirements or fail to comply with applicable regulatory requirements;

    uncertainties relating to the Eurozone, including the effects of the United Kingdom's referendum to leave the European Union, and U.S. health care legislation;

    operational risks, including system or human failures or cyber-attacks, which could result in Sirius Group incurring material losses;

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    risks associated with potential for loss of services of any one of Sirius Group's key personnel, and the risk that Sirius Group fails to attract or retain the executives and employees necessary to manage its business;

    unforeseen liabilities or asset impairments arising from possible acquisitions and dispositions of businesses or difficulties integrating acquired businesses;

    risks that Sirius Group may require additional capital in the future, which may not be available or may be available only on unfavorable terms;

    risks that Sirius Group's significant deferred tax assets may become materially impaired as a result of insufficient taxable income or a reduction in applicable corporate tax rates or other change in applicable tax law;

    risks relating to changes in regulatory regimes and/or accounting rules, which could result in significant changes to Sirius Group's financial results;

    the seasonality of Sirius Group's insurance and reinsurance business;

    risks relating to Sirius Group's indebtedness;

    the risk that Sirius Group will fail to comply with Nasdaq's continued listing standards;

    the limited liquidity and trading of Sirius Group's securities following the Merger; and

    risks related to Sirius Group's status as a foreign private issuer and controlled company.

        Should one or more of these risks or uncertainties materialize, or should any of the assumptions made by the management of Sirius Group and Easterly prove incorrect, actual results may vary in material respects from those projected in these forward-looking statements.

        All subsequent written and oral forward-looking statements concerning the Merger or other matters addressed in this proxy statement/prospectus and attributable to Sirius Group or Easterly or any person acting on their behalf are expressly qualified in their entirety by the cautionary statements included or referred to above. Except to the extent required by applicable law or regulation, Sirius Group and Easterly undertake no obligation to update these forward-looking statements to reflect events or circumstances after the date of this proxy statement/prospectus or to reflect the occurrence of unanticipated events.

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FREQUENTLY USED TERMS

        Unless otherwise stated or unless the context otherwise requires, the term "Sirius Group" refers to Sirius International Insurance Group, Ltd., a Bermuda exempted company, and, where the context requires, its consolidated subsidiaries, "Easterly" refers to Easterly Acquisition Corp., a Delaware corporation, and the term "combined company" refer to Sirius Group and Easterly together following the consummation of the Merger.

        In this document:

        "$," "USD" and "U.S. dollar" each refer to the United States dollar.

        "Adjournment Proposal" means a proposal to adjourn the special meeting of Easterly stockholders to a later date or dates, if necessary, to permit further solicitation of proxies if, based upon the tabulated vote at the time of the special meeting, there are not sufficient votes to approve one or more proposals presented to Easterly's stockholders for vote at such special meeting.

        "Amendment" means the First Amendment to Agreement and Plan of Merger and Sponsor Letter, dated as of August 29, 2018, by and among Sirius Group, Easterly, Merger Sub, CM Bermuda and Sponsor, a copy of which is attached to this proxy statement/prospectus as Annex C.

        "Closing" means the closing of the Merger.

        "CM Bermuda" means CM Bermuda Ltd., a Bermuda holding company, a wholly owned subsidiary of CMIG International and the sole holder of Sirius Group common shares prior to the Merger.

        "CMIG International" means CMIG International Holding Pte. Ltd., a Singapore holding company.

        "Code" means the Internal Revenue Code of 1986, as amended.

        "Common Shares Redemption Agreement" means the agreement to be entered into between Sirius Group and CM Bermuda pursuant to which, effective as of and subject to the closing of the Merger, Sirius Group will redeem Sirius Group common shares from CM Bermuda.

        "Companies Act" means the Companies Act 1981 (Bermuda), as amended.

        "Convertible Promissory Note" means the convertible promissory note, dated as of March 17, 2016, made by Easterly in favor of the Sponsor.

        "converted warrants" means the public warrants issued by Easterly to acquire shares of Easterly common stock that are outstanding immediately prior to the closing of the Merger, as converted in the Merger into warrants issued by Sirius Group to acquire Sirius Group common shares. The number of Sirius Group common shares subject to each converted warrant will be equal to the number of shares of Easterly common stock subject to each Easterly warrant immediately prior to the closing of the Merger multiplied by the Exchange Ratio, and such converted warrant will have an exercise price per Sirius Group common share equal to the exercise price per share of Easterly common stock subject to such Easterly warrant immediately prior to the closing of the Merger divided by the Exchange Ratio.

        "DGCL" means the Delaware General Corporation Law, as amended.

        "Easterly's charter" means Easterly's amended and restated certificate of incorporation, as amended.

        "Easterly common stock" means the common stock, par value $0.0001 per share, of Easterly.

        "Easterly special meeting" means the special meeting of stockholders of Easterly that is the subject of this proxy statement/prospectus.

        "Effective Time" means the time at which the Merger is consummated.

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        "Exchange Act" means the U.S. Securities Exchange Act of 1934, as amended.

        "Exchange Ratio" is the ratio determined pursuant to the Merger Agreement at which Easterly common stock will be converted into Sirius Group common shares and the public warrants will be converted into warrants to purchase Sirius Group common shares.

        "Extension Amendments" mean the amendments to Easterly's charter and the agreement governing the Trust Account to extend the deadline by which Easterly has to complete its initial business combination from June 30, 2018 to November 30, 2018, which were approved at Easterly's special meeting of stockholders held on June 28, 2018.

        "Founder Shares" means the 5,000,000 shares of Easterly common stock (after giving effect to (i) a stock dividend of 0.2 shares for each outstanding share of Easterly common stock on July 29, 2015 and (ii) the forfeiture of 175,000 shares in August 2015) that were issued to the Sponsor prior to the IPO (of which 72,000 Founder Shares were subsequently transferred to Easterly's original independent directors).

        "GAAP" means generally accepted accounting principles in the United States.

        "initial stockholders" means the Sponsor, Easterly's original independent directors and their permitted transferees that hold Founder Shares and Private Placement Warrants.

        "IMGAH" means IMG Acquisition Holdings, LLC, a Delaware limited liability company and the sole holder of Sirius Group Series A redeemable preference shares prior to the Merger.

        "IPO" means Easterly's initial public offering, consummated on August 4, 2015 through the sale of 20,000,000 public units, comprised of one share of Easterly common stock and one-half of one public warrant, at a price of $10.00 per unit.

        "IRS" means the U.S. Internal Revenue Service.

        "Lock-Up Agreements" means the Lock-Up Agreements that the Sponsor and CM Bermuda will each deliver to Sirius Group at the closing of the Merger, the form of which is attached to this proxy statement/prospectus as Annex F.

        "Merger" means the transactions contemplated by the Merger Agreement whereby, among other things, on the terms and subject to the conditions set forth in the Merger Agreement, (i) Merger Sub, a wholly owned subsidiary of Sirius Group, will merge with and into Easterly, (ii) Easterly will become a wholly owned subsidiary of Sirius Group, (iii) Sirius Group will issue its common shares to Easterly's stockholders in exchange for their Easterly common stock, resulting in former Easterly stockholders becoming shareholders of Sirius Group, and (iv) Easterly's public warrants to acquire Easterly common stock will be converted into warrants to acquire Sirius Group common shares.

        "Merger Agreement" means that certain Agreement and Plan of Merger, dated as of June 23, 2018, by and among Sirius Group, Easterly and Merger Sub, a copy of which is attached to this proxy statement/prospectus as Annex A, as amended from time to time, including by the Amendment.

        "Merger Proposal" means the proposal to approve and adopt the Merger Agreement and the transactions contemplated by the Merger Agreement, including the Merger.

        "Merger Sub" means Sirius Acquisitions Holding Company III, a Delaware corporation and a wholly owned subsidiary of Sirius Group.

        "Preference Shares Redemption Agreement" means that certain Redemption Agreement, dated as of July 14, 2018, among Sirius Group, IMGAH and Sirius Acquisitions Holding Company II.

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        "Private Placement Warrants" means the 6,750,000 private placement warrants issued to the Sponsor, at a price of $1.00 per warrant, in a private placement that occurred simultaneously with the completion of the IPO.

        "Promissory Note" means the promissory note, dated June 23, 2018, made by Easterly in favor of Sirius Group pursuant to which Sirius Group has agreed to loan Easterly $0.03 per month for every public share of Easterly common stock outstanding as of June 30, 2018, until the earlier of the consummation of the Merger and November 30, 2018, the form of which is attached to this proxy statement/prospectus as Annex D.

        "public shares" means shares of Easterly common stock issued in the IPO.

        "public warrants" means the warrants issued in the IPO, each of which is exercisable for one share of Easterly common stock, in accordance with its terms.

        "Registration Rights Agreement" means the Registration Rights Agreement that Sirius Group will enter into with the Sponsor and CM Bermuda at the closing of the Merger, the form of which is attached to this proxy statement/prospectus as Annex E.

        "SAP" means the statutory accounting principles prescribed or permitted by an applicable insurance regulator, including, if applicable, International Financial Reporting Standards.

        "SEC" means the U.S. Securities and Exchange Commission.

        "Securities Act" means the U.S. Securities Act of 1933, as amended.

        "Sirius Group common shares" means the common shares, par value $0.01 per share, of Sirius Group.

        "Sirius Group Private Placement" means the private placement of Sirius Group common shares, Sirius Group Series B preference shares and warrants to purchase Sirius Group common shares that Sirius Group expects to complete in connection with the closing of the Merger.

        "Sirius Group Private Placement Investors" means the investors purchasing Sirius Group securities in the Sirius Group Private Placement.

        "Sirius Group Series A redeemable preference shares" means the Series A redeemable preference shares, par value $0.01 per share, of Sirius Group.

        "Sirius Group Series B preference shares" means the Series B preference shares, par value $0.01 per share, of Sirius Group.

        "Sponsor" means Easterly Acquisition Sponsor, LLC, a Delaware limited liability company.

        "Sponsor Letter" means the letter agreement, dated as of June 23, 2018, among Easterly, the Sponsor and Sirius Group, a copy of which is attached to this proxy statement/prospectus as Annex B, as amended by the Amendment.

        "Transaction" means the transactions contemplated by the Merger Agreement.

        "Trust Account" means the segregated trust account located in the United States with Continental Stock Transfer & Trust Company acting as trustee into which the proceeds of the IPO and the sale of the Private Placement Warrants were placed at the closing of the IPO.

        "Warrant Amendment" means the Assignment, Assumption and Amendment Agreement that Sirius Group will enter into with Easterly and Continental Stock Transfer & Trust Company at the closing of the Merger, the form of which is attached to this proxy statement/prospectus as Annex G.

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QUESTIONS AND ANSWERS ABOUT THE MERGER, THE SPECIAL MEETING AND RELATED MATTERS

        The following questions and answers briefly address some commonly asked questions about the proposals to be presented at the Easterly special meeting, including with respect to the proposed Merger. The following questions and answers do not include all the information that is important to Easterly stockholders. Stockholders are urged to read carefully this entire proxy statement/prospectus, including the Annexes and the other documents referred to herein. See the section entitled "Where You Can Find More Information" beginning on page 357. The following questions and answers do not include all the information that may be important to you as an Easterly stockholder.

About the Merger

Q:
Why am I receiving this proxy statement/prospectus?

A:
Sirius Group, Easterly and Merger Sub entered into a Merger Agreement on June 23, 2018, providing for a Merger of Easterly and Sirius Group, whereby Merger Sub will be merged with and into Easterly, with Easterly surviving the merger as a wholly owned subsidiary of Sirius Group. Easterly common stock will be exchanged for Sirius Group common shares and the public warrants will become warrants to acquire Sirius Group common shares. A copy of the Merger Agreement is attached to this proxy statement/prospectus as Annex A. Easterly's stockholders are being asked to consider and vote upon a proposal to approve and adopt the Merger Agreement and the transactions contemplated by the Merger Agreement, including the Merger.

    This proxy statement/prospectus and its Annexes contain important information about the proposed Merger and the other matters to be acted upon at the Easterly special meeting. You should read this proxy statement/prospectus and its Annexes carefully and in their entirety.

Q:
What will happen in the Merger?

A:
Pursuant to the Merger, among other things:

Merger Sub will merge with and into Easterly, with Easterly surviving the Merger as a wholly owned subsidiary of Sirius Group.

Upon the effectiveness of the Merger, all shares of Easterly common stock (other than (i) shares of Easterly common stock with respect to which an Easterly stockholder has validly exercised its redemption rights, and that will be redeemed as provided for by Easterly's charter, (ii) shares of Easterly common stock held by Easterly as treasury stock or owned by Easterly, Sirius Group, Merger Sub, or any wholly owned subsidiary of Easterly or Sirius Group, which will be cancelled for no consideration and (iii) shares of Easterly common stock held by the Sponsor that will be cancelled pursuant to the Sponsor Letter) will be converted into Sirius Group common shares at the Exchange Ratio.

Each issued and outstanding public warrant to acquire shares of Easterly common stock will cease to represent a right to acquire shares of Easterly common stock and will be converted into a converted warrant. The number of Sirius Group common shares subject to each converted warrant will be equal to the number of shares of Easterly common stock subject to each Easterly warrant immediately prior to the closing of the Merger multiplied by the Exchange Ratio, and such converted warrant will have an exercise price per Sirius Group common share equal to the exercise price per share of Easterly common stock subject to such Easterly warrant immediately prior to the closing of the Merger divided by the Exchange Ratio.

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Q:
Following the Merger, will Easterly's securities continue to trade on a stock exchange?

A:
No, Easterly's units, common stock and warrants will no longer be listed on the Nasdaq Capital Market. Prior to the closing, Easterly's units, which currently are traded under the symbol "EACQU," will separate into their components of one share of Easterly common stock and one half of a warrant to purchase one share of Easterly common stock, which will be exchanged for Sirius Group common shares and become the converted warrants, respectively.

Q:
Following the Merger, will Sirius Group's securities trade on a stock exchange?

A:
Sirius Group has applied to list the Sirius Group common shares and converted warrants on the Nasdaq Stock Market under the symbols "SG" and "SGRP-W," respectively, effective as of the closing of the Merger. The listing of the Sirius Group common shares on the Nasdaq Stock Market, subject to official notice of issuance, is a condition to the completion of the transactions contemplated by the Merger Agreement. This listing condition may be waived by Sirius Group and Easterly.

Q:
What happens to the capital stock of Easterly in the Merger?

A:
There currently are 19,208,407 shares of Easterly common stock issued and outstanding, consisting of:

14,208,407 shares held by public stockholders; and

5,000,000 Founder Shares held by the Sponsor and Easterly's original independent directors.

    Upon the closing of the Merger, all shares of Easterly common stock (other than (i) shares of Easterly common stock with respect to which an Easterly stockholder has validly exercised its redemption rights, and that will be redeemed as provided for by Easterly's charter, (ii) shares of Easterly common stock held by Easterly as treasury stock or owned by Easterly, Sirius Group or Merger Sub or any wholly owned subsidiary of Easterly or Sirius Group, which will be cancelled for no consideration, and (iii) shares of Easterly common stock held by the Sponsor that will be cancelled pursuant to the Sponsor Letter) will be converted into Sirius Group common shares at the Exchange Ratio.

    The Exchange Ratio will be determined prior to the closing of the Merger and will be equal to a fraction determined by dividing (i) the estimated amount of cash per public share of Easterly common stock in the Trust Account immediately prior to the closing of the Merger by (ii) (x) 1.05 multiplied by (y) the Sirius Group September 30 Adjusted DBVPS. The Sirius Group September 30 Adjusted DBVPS is calculated by dividing (i) the book value of Sirius Group determined based on GAAP on a consolidated basis, based on the final, Sirius Group board of directors approved, unaudited GAAP consolidated financial statements of Sirius Group for the nine months ended September 30, 2018, decreased by the $7 million deferred underwriting fee payable by Easterly to Citigroup Global Markets Inc. as underwriter of the IPO, and as adjusted by the GAAP accounting effect of the redemption of the Sirius Group Series A redeemable preference shares by (ii) the sum of (x) the fully diluted number of Sirius Group common shares issued and outstanding as of September 30, 2018 and (y) 593,000 Sirius Group common shares. If an estimate of the Sirius Group September 30 Adjusted DBVPS is used to determine the Exchange Ratio at the closing of the Merger, then the Merger Agreement provides for a post-closing adjustment if such estimate is different than the actual Sirius Group September 30 Adjusted DBVPS as finally determined after the closing of the Merger. Such adjustment will result in either (x) the issuance of new Sirius Group common shares or a payment of cash by Sirius Group to CM Bermuda, if the Exchange Ratio is greater than it would have been using the actual Sirius Group September 30 Adjusted DBVPS or (y) the surrender to Sirius Group of Sirius Group

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    common shares owned by CM Bermuda or a payment of cash to Sirius Group from CM Bermuda if the Exchange Ratio is less than it would have been using the actual Sirius Group September 30 Adjusted DBVPS.

    Pursuant to the Sponsor Letter, the Sponsor will surrender and Easterly will cancel for no consideration between 3,328,000 and 4,528,000 (or such higher number of shares based on the adjustment described below) shares of Easterly common stock owned by the Sponsor, which amount will be determined at the Effective Time as follows: The base number of 3,928,000 canceled shares will be (i) decreased by 0.50 of a share of Easterly common stock for every $100 that the sum of (x) cash in the Trust Account at the closing of the Merger plus (y) the proceeds of any private placement of Sirius Group common shares (or securities convertible into Sirius Group common shares) in connection with the Merger (the sum of (x) and (y), the "Amount Raised") is greater than $120 million (provided, that if the Amount Raised is greater than or equal to $150 million, then, solely with respect to any portion of the Amount Raised that is funded from certain designated investors in such private placement, the number of canceled shares will be decreased by 0.25 (in lieu of 0.50) of a share of Easterly common stock for every $100 of the Reduced Rate Amount (as defined below)) or (ii) increased by 0.50 of a share of Easterly common stock for every $100 that the Amount Raised is less than $120 million. Notwithstanding the foregoing, the minimum number of canceled shares will be 3,328,000 and the maximum number of canceled shares will be 4,528,000, except that the Sponsor also agreed to surrender additional shares (which could result in more than 4,528,000 shares surrendered) in certain circumstances if the amount per share equal to (x) 1.05 multiplied by (y) the Sirius Group September 30 Adjusted DBVPS used in the calculation of the Exchange Ratio, as adjusted for the value of the warrants issued in the Sirius Group Private Placement, is less than $17.39. If the proceeds raised from the Sirius Group Private Placement Investors is less than $213 million (other than as a result of an investor failing to fund its obligations in breach of its subscription agreement at a time when Sirius Group is not then in material breach of any of its representations, warranties, covenants or agreements set forth in such subscription agreement at the time of such investor's breach of such subscription agreement), the proceeds of the Sirius Group Private Placement will be deemed to be $213 million for purposes of calculating the Amount Raised. The "Reduced Rate Amount" means the lesser of (a) the Amount Raised minus $150 million and (b) the Amount Raised that is funded from certain designated investors in such private placement.

    In addition, there currently are 16,750,000 warrants for Easterly common stock outstanding, consisting of:

    10,000,000 public warrants; and

    6,750,000 Private Placement Warrants held by the Sponsor.

    Pursuant to the Sponsor Letter, the Sponsor has agreed to cancel the 6,750,000 Private Placement Warrants at the closing of the Merger. Pursuant to the Merger Agreement, each issued and outstanding public warrant stock will cease to represent a right to acquire shares of Easterly common stock and will be converted into a converted warrant. The number of Sirius Group common shares subject to converted warrants will be equal to the number of shares of Easterly common stock subject to each Easterly warrant immediately prior to the closing of the Merger multiplied by the Exchange Ratio, and such converted warrant will have an exercise price per Sirius Group common share equal to the exercise price per share of Easterly common stock subject to such Easterly warrant immediately prior to the closing of the Merger divided by the Exchange Ratio.

    The converted warrants become exercisable 30 days after the completion of Merger and expire at 5:00 p.m. New York City time, five years after the completion of the Merger or earlier upon redemption or liquidation. Once the warrants become exercisable, Sirius Group may redeem the

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    issued and outstanding warrants in whole and not in part at a price of $0.01 per warrant, if the last sale price of Sirius Group common shares for any 20 trading days within a 30-trading day period equals or exceeds the price determined by dividing $18.00 by the Exchange Ratio. There will be a substantial number of converted warrants to purchase Sirius Group common shares issued and outstanding after the closing of the Merger. To the extent such converted warrants are exercised, additional Sirius Group common will be issued, which will result in dilution to the holders of Sirius Group common shares and increase the number of shares eligible for resale in the public market. Easterly public stockholders will be diluted by these issuances unless they elect to redeem their shares in connection with the Merger. Sales of substantial numbers of such shares in the public market or the fact that such converted warrants may be exercised could adversely impact the market price of Sirius Group common shares and the converted warrants.

Q:
What is the value of the Merger consideration to be received by Easterly stockholders?

A:
Based on a per share value equal to (i) 1.05 multiplied by (ii) the Sirius Group September 30 Adjusted DBVPS, which is estimated as of October 8, 2018 to be $17.22, the aggregate value of the Merger consideration to be received by the Easterly stockholders (including the Sponsor) in respect of their shares of Easterly common stock pursuant to the Merger Agreement is estimated to be $165.5 million. Easterly has not obtained an opinion from an independent financial advisor in connection with the Merger and, consequently, there is no assurance from an independent source that the price Sirius Group is paying for Easterly is fair to Easterly's stockholders from a financial point of view.

Q:
How was the estimate of Sirius Group September 30 Adjusted DBVPS determined?

A:
Late in the third quarter of 2018, there were numerous natural disasters around the world, including Typhoon Jebi in Japan, the Kerala Flood in India, Typhoons Mangkhut and Trami in Southeastern Asia, a tsunami in Indonesia, and Hurricane Florence in the eastern United States. Sirius Group has exposure to losses resulting from these and other natural disasters. Potential losses from these events take time to assess. Preliminary loss estimates are initially established based upon client information, catastrophe models, market loss data and underwriter judgement. Updated loss advices from clients are received over time as the losses develop.

    Sirius Group is in the process of evaluating available preliminary information in order to record an estimate of losses, including from these events, at September 30, 2018. It is currently estimated that the third quarter losses will likely be higher than previously estimated. Based upon this loss and other information available as of October 8, 2018, in accordance with the Merger Agreement, Sirius Group delivered to Easterly its good faith estimate of 1.05 multiplied by the Sirius Group September 30 Adjusted DBVPS, equal to $17.22, which is subject to adjustment post-closing, as more fully described herein.

    Based on an estimate, as of October 8, 2018, of the Sirius Group September 30 Adjusted DBVPS and funds in the Trust Account as of September 30, 2018, the Exchange Ratio would be equal to 0.607. Investors are cautioned that 0.607 is only an estimate of the Exchange Ratio, has not been agreed as the final Exchange Ratio for purposes of the Merger Agreement, and is subject to change prior to the closing of the Merger.

Q:
How will the Merger impact the Sirius Group shares issued and outstanding after the Merger?

A:
Based on the number of shares of Easterly common stock and Easterly warrants outstanding on September 30, 2018, Sirius Group expects to issue or reserve for issuance to Easterly public stockholders approximately 8.6 million common shares pursuant to the Merger Agreement (excluding 6.1 million Sirius Group common shares issuable upon exercise of the converted

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    warrants). Sirius Group also expects to issue approximately 1.0 million common shares to the Sponsor, resulting in a total of approximately 9.6 million Sirius Group common shares issued in exchange for outstanding shares of Easterly common stock pursuant to the Merger Agreement. Upon the closing of the Merger, Sirius Group's existing controlling shareholder, CM Bermuda, is expected to own approximately 83.2% of Sirius Group, the Sirius Group Private Placement Investors are expected to own approximately 9.2% of Sirius Group, Easterly's public stockholders (excluding Warrant holders) are expected to own approximately 6.8% of Sirius Group and the Sponsor and Easterly's directors and executive officers are expected to own approximately 0.8% of Sirius Group. The foregoing amounts assume that (i) the Exchange Ratio is equal to 0.607, (ii) no Easterly stockholders exercise their redemption rights in connection with the Merger Proposal, (iii) the Sponsor and Easterly's original independent directors retain 1.0 million shares of Easterly common stock after giving effect to the transactions contemplated by the Sponsor Letter, (iv) Sirius Group issues 11.7 million common shares and Series B preference shares convertible into common shares in connection with the Sirius Group Private Placement (based on subscriptions received as of October 8, 2018 and inclusive of participants in the Employee Share Purchase Plan) (v) Sirius Group redeems 14.5 million common shares from CM Bermuda for approximately $250 million pursuant to the redemption transaction described herein and (vi) all of the issued and outstanding Sirius Group Series A redeemable preference shares are redeemed for $95 million in cash prior to the closing of the Merger. Further, such percentages do not take into account (x) the issuance of any Sirius Group common shares upon the exercise of the converted warrants that may remain issued and outstanding following the Merger or that are issued pursuant to the Sirius Group Private Placement or (y) the issuance of up to 14.1 million Sirius Group common shares reserved for issuance pursuant to Sirius Group's Long Term Incentive Plan and 2018 Omnibus Incentive Plan. If the facts differ from these assumptions, Easterly's stockholders may experience dilution of their ownership interest unless they elect to have their shares of Easterly common stock redeemed in connection with the Merger Proposal. See the section entitled "Proposal No. 1—The Merger Proposal—The Merger Agreement—Merger Consideration" beginning on page 91 and "Security Ownership of Certain Beneficial Owners and Management" beginning on page 348 for further information.

Q:
How has the announcement of the Merger affected the trading price of the Easterly common stock and the public warrants?

A:
On June 22, 2018, the last trading date immediately prior to the announcement of the Merger, the closing trading prices of a share of Easterly common stock and a public warrant on the Nasdaq Capital Market were $10.30 and $0.32, respectively. On October 11, 2018, the date immediately prior to the date of this proxy statement/prospectus, the closing trading prices of a share of Easterly common stock and a public warrant on the Nasdaq Capital Market were $10.40 and $1.06, respectively.

Q:
What is the nature of Sirius Group's business and operations?

A:
Sirius Group is a Bermuda exempted company whose principal businesses are conducted through its insurance and reinsurance subsidiaries and other affiliates. Sirius Group's subsidiaries, including Sirius Bermuda Insurance Company Ltd. ("Sirius Bermuda"), Sirius International Insurance Corporation ("Sirius International"), Sirius America Insurance Company ("Sirius America") and Lloyd's Syndicate 1945 ("Syndicate 1945"), provide insurance, reinsurance and insurance services on a worldwide basis. Sirius Group writes treaty and facultative reinsurance, as well as primary insurance business. The majority of Sirius Group's treaty reinsurance premiums are derived from proportional and excess of loss reinsurance contracts, which in 2017 amounted to 44% and 30%, respectively, of its total net written premiums, while primary business represented 26% of total net written premiums. For more information about Sirius Group, see the sections entitled "Information

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    About Sirius Group," "Management's Discussion and Analysis of Financial Condition and Results of Operations of Sirius Group" and "Management of Sirius Group" beginning on pages 158, 202 and 280, respectively.

Q:
What revenue and net income has Sirius Group generated in 2017, 2016 and 2015?

A:
For the years ended December 31, 2017, 2016 and 2015, Sirius Group had total revenues approximately $1,134 million, $995 million and $1,107 million, respectively, with net (loss) income of $(156) million, $33 million and $291 million, respectively. Basic (loss) earnings per share for the years ended December 31, 2017, 2016 and 2015 was $(1.30), $0.27 and $2.43, respectively. See "Selected Consolidated Historical Financial Data of Sirius Group" beginning on page 131 and "Management's Discussion and Analysis of Financial Condition and Results of Operations of Sirius Group" beginning on page 202 for additional information.

Q:
Who will manage the combined company following the Merger?

A:
It is anticipated that the current executive officers of Sirius Group will manage the combined company upon the completion of the Merger. Additionally, it is anticipated that the board of directors of the combined company will be comprised of the current members of the board of directors of Sirius Group, and additional independent directors to be identified by Sirius Group. See the section entitled "Management of Sirius Group" beginning on page 280 for further information.

Q:
Is the Merger the first step in a "going-private" transaction?

A:
Easterly does not intend for the Merger to be the first step in a "going-private" transaction. One of the primary purposes of the Merger is to provide a platform for Sirius Group to access the U.S. public markets.

Q:
What conditions must be satisfied to complete the Merger?

A:
There are a number of closing conditions in the Merger Agreement, including, but not limited to, the following:

holders of at least a majority of the outstanding shares of Easterly common stock must approve and adopt the Merger Agreement;

the Sirius Group common shares issuable pursuant to the Merger Agreement and upon exercise of the converted warrants must be approved for listing on the Nasdaq Stock Market, subject to official notice of issuance;

there must not be in effect any order by a governmental entity of competent jurisdiction which prohibits, restrains or makes illegal the consummation of the transactions contemplated by the Merger Agreement;

Sirius Group's Registration Statement on Form S-4, of which this proxy statement/prospectus forms a part, must have become effective under the Securities Act and not be the subject of any stop order, and no proceedings for that purpose shall have been initiated or threatened by the SEC and not withdrawn; and

there must not have been any event or circumstance which resulted or that would reasonably be expected to result in a material adverse effect of Sirius Group or Easterly that is continuing.

    In addition, under Easterly's charter, Easterly may not redeem or repurchase Easterly common stock to the extent that such redemption would result in Easterly's failure to have net tangible

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    assets (as determined in accordance with Rule 3a51-1(g)(1) of the Exchange Act) in excess of approximately $5 million.

    For a summary of all of the conditions that must be satisfied or waived prior to completion of the Merger, see the section entitled "Proposal No. 1—The Merger Proposal—The Merger Agreement" beginning on page 91.

Q:
What interests do Easterly's directors and executive officers have in the Merger that could conflict with a public stockholder?

A:
Easterly's directors and executive officers may have interests in the Merger that are different from, in addition to or in conflict with, yours. These interests include:

the 400,000 to 1.6 million total Founder Shares that the Sponsor (or its members) will hold immediately prior to the Merger, which will be exchanged for Sirius Group common shares at the Exchange Ratio in connection with the Merger;

the 24,000 Founder Shares that one of Easterly's independent directors holds as of September 30, 2018, which will be exchanged for Sirius Group common shares at the Exchange Ratio in connection with the Merger;

if Easterly is unable to complete a business combination within the required time period, the Convertible Promissory Note issued to the Sponsor, in the amount of $895,000 at September 30, 2018 plus accrued interest, will not be repaid and all amounts owed thereunder will be forgiven except to the extent that Easterly has funds available to it outside of the Trust Account to repay such amounts;

if Easterly is unable to complete a business combination within the required time period, Easterly's Chairman, its Chief Executive Officer and David Cody will be personally liable to ensure that the proceeds in the Trust Account are not reduced by the claims of target businesses or claims of vendors or other entities that are owed money by Easterly for services rendered or contracted for or products sold to Easterly, but only if such a vendor or target business has not executed a waiver of claims against the Trust Account and except as to any claims under Easterly's indemnity of the underwriters; and

the continued indemnification of current directors and officers of Easterly and the continuation of directors' and officers' liability insurance after the Merger.

    Further, each of Easterly's directors, directly or indirectly, holds Founder Shares that are not subject to redemption and certain of Easterly's directors indirectly hold Private Placement Warrants that would retire worthless if a business combination is not consummated. As a result, Easterly's directors have a financial incentive to see a business combination consummated rather than lose whatever value is attributable to the Founder Shares and Private Placement Warrants. These interests may influence Easterly's directors in making their recommendation that you vote in favor of the Merger Proposal, and the transactions contemplated thereby.

Q:
What interests do Sirius Group's directors and executive officers have in the Merger?

A:
Sirius Group's directors and executive officers may have interests in the Merger that are different from, in addition to or in conflict with, yours. These interests include:

the directors and executive officers of Sirius Group will continue to be the directors and executive officers of the combined company;

in connection with the Merger, each executive officer of Sirius Group will receive a performance share unit award granted under the 2018 Omnibus Incentive Plan, with the target number of

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      performance share units equal to a specified dollar value divided by the per share value of Sirius Group common shares at the closing of the Merger. The performance share unit awards have been allocated to the executive officers as follows, based on the grant date value of the award at target levels of performance: Mr. Waters—$2,600,000; each of Mr. Boxer, Ms. Cramér Manhem and Mr. Oberting—$1,800,000; and Mr. Davis—$700,000. The performance share unit awards will be subject to vesting conditions and a commitment by the executive officer to purchase Sirius Group common shares having a value equal to the target award granted to the executive officer;

    in connection with the Merger, Sirius Group has implemented an Employee Share Purchase Plan, which provides all employees of Sirius Group with a one-time opportunity to purchase between 100 and 1,000 Sirius Group common shares at a price equal to 85% of market value for the first 100 shares and 100% of market value for the next 900 shares. For this purpose, the market value of the Sirius Group common shares will be equal to 1.05 times the Sirius Group September 30 Adjusted DBVPS. Employees have the option of paying for the shares upfront or, in the case of employees who are not executive officers, through a loan that is repaid over a two-year period through payroll deductions. As of October 8, 2018, over 400 employees have committed to purchase an aggregate of approximately 146,000 Sirius Group common shares under the Employee Share Purchase Plan prior to the consummation of the Merger;

    in connection with the Merger, the Compensation Committee amended the Sirius Group 2016 Long Term Incentive Plan (the "2016 LTIP") to provide for continued vesting of outstanding awards in the event of a termination of employment by Sirius Group without cause or by the executive officer due to good reason outside of the 24-month change in control period already provided for under the 2016 LTIP. In these qualifying terminations of employment events, each of our other named executive officers will continue to vest in outstanding awards for 12 months following a termination of employment. The ability to receive payments during these vesting continuation periods will be subject to actual performance; and

    in connection with the Merger, Sirius Group adopted the Sirius Group Severance and Change in Control Plan (the "Executive Severance Plan"), which provides executive officers with severance and post-employment benefits in the event of (i) an involuntary termination without cause or (ii) a resignation by the executive officer for good reason. For these qualifying terminations of employment prior to a change in control, our named executive officers will receive severance benefits equal to one times base salary, any earned but unpaid bonus for the year prior to termination, a pro-rata bonus for the year of termination, based on actual performance, and medical continuation benefits for 12 months. In the event of a qualifying termination of employment following a change in control, the severance benefits are the same, except the severance pay is increased to two times base salary for the named executive officers, the medical continuation period is increased to two years for the named executive officers, and the prorated bonus for the year of the termination will be paid at the target level of performance. Additionally, the Executive Severance Plan provides that in the event of a qualifying termination within 24 months following a change in control, all outstanding equity compensation awards will become fully vested, with the attainment or deemed attainment of any applicable performance conditions determined under the terms of the applicable equity compensation plan or award agreements. In order to be eligible to receive severance payments, pursuant to the Executive Severance Plan, the executive officer must execute a release in Sirius Group's favor. The Executive Severance Plan provides that, to the extent that Mr. Waters' or Ms. Cramér Manhem's employment agreements provide additional severance protections, they will continue to receive the employment agreement severance protections, to the extent they do not result in duplicative benefits under the Executive Severance Plan.

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Q:
What happens to Easterly if the Merger is not consummated?

A:
There are certain circumstances under which the Merger Agreement may be terminated. See the section entitled "Proposal No. 1—The Merger Proposal—The Merger Agreement" beginning on page 91 for information regarding the parties' specific termination rights.

    If, as a result of the termination of the Merger Agreement or otherwise, Easterly is unable to complete the Merger or another business combination transaction by November 30, 2018, Easterly's charter provides that Easterly will (i) cease all operations except for the purpose of winding up, (ii) as promptly as reasonably possible but not more than ten business days thereafter, redeem 100% of the public shares, at a per-share price, payable in cash, equal to the aggregate amount then on deposit in the Trust Account, including interest earned on the funds held in the Trust Account and not previously released to Easterly to pay its franchise and income taxes (which interest will be net of taxes payable and reduced by up to $100,000 to pay dissolution expenses), divided by the number of then outstanding public shares, which redemption will completely extinguish public stockholders' rights as stockholders (including the right to receive further liquidation distributions, if any), subject to applicable law, and (iii) as promptly as reasonably possible following such redemption, subject to the approval of Easterly's remaining stockholders and Easterly's board of directors, dissolve and liquidate, subject in each case to its obligations under Delaware law to provide for claims of creditors and the requirements of other applicable law. See the section entitled "Risk Factors—If Easterly is unable to effect a business combination by November 30, 2018, Easterly will be forced to liquidate and the public warrants will expire worthless" on page 75 and "—If Easterly is forced to liquidate, its stockholders may be held liable for claims by third parties against Easterly to the extent of distributions received by them" beginning on page 75. Holders of the Founder Shares have waived any right to any liquidation distribution with respect to those shares.

    In the event of liquidation, there will be no distribution with respect to Easterly's outstanding pubic warrants. Accordingly, the public warrants will expire worthless.

Q:
What happens to the funds held in the Trust Account upon consummation of the Merger?

A:
If the Merger is consummated, the funds held in the Trust Account will be released to (i) the surviving company for general corporate purposes, including making loans or contributing cash to other affiliates for working capital, organic growth and future potential acquisitions, (ii) pay unpaid franchise and income taxes of Easterly, (iii) Easterly stockholders who properly exercise their redemption rights, and (iv) pay up to $2 million of Easterly's liabilities, fees, costs and expenses and the $7 million deferred underwriting fee. The deferred underwriting fee will not change as a result of the amount of redemptions of Easterly common stock, and will not reduce the per-share amount that Easterly will distribute to stockholders who properly redeem their shares. The deferred underwriting fee will not be paid in the event that the Merger is not completed. See the section entitled "Use of Proceeds" on page 130.

    Following the consummation of the Merger, the combined company will be entitled to use the funds in the Trust Account. Other than the foregoing uses, the combined company does not have specific plans for any funds remaining from the Trust Account and will have broad discretion regarding how to use the funds that remain. These funds could be used in a manner with which you may not agree or applied in ways that do not improve the combined company's results of operations or increase the value of your investment.

Q:
When is the Merger expected to be completed?

A:
It is currently anticipated that the Merger will be consummated promptly following the Easterly special meeting of stockholders, provided that all other conditions to the consummation of the

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    Merger have been satisfied or waived. For a description of the conditions to the completion of the Merger, see the section entitled "The Merger Agreement—Conditions to Closing of the Merger" beginning on page 95.

Q:
Do Easterly stockholders have appraisal rights if they object to the proposed Merger?

A:
No. There are no appraisal rights available to holders of Easterly common stock in connection with the Merger.

About the Redemption Rights of Easterly Public Stockholders

Q:
Do I have redemption rights?

A:
If you are a holder of Easterly public shares, you may have your public shares redeemed for cash equal to your pro rata share of the aggregate amount on deposit in the Trust Account, which holds the proceeds of the IPO, as of two business days prior to the consummation of the Merger, including interest earned on the funds held in the Trust Account and not previously released to Easterly to pay its franchise and income taxes, upon the consummation of the Merger. You may have your Easterly public shares redeemed whether or not you are a holder of Easterly common stock as of the record date for the Easterly special meeting. For illustrative purposes, based on funds in the Trust Account of approximately $148.5 million on September 30, 2018, the estimated per share redemption price would have been approximately $10.45. This is slightly more than the $10.00 initial public offering price of Easterly's units. Additionally, shares properly tendered for redemption will only be redeemed if the Merger is consummated; otherwise, holders of such shares will only be entitled to a pro rata portion of the Trust Account including interest earned on the funds held in the Trust Account and not previously released to Easterly to pay franchise and income taxes (which interest will be net of taxes payable and reduced by up to $100,000 to pay dissolution expenses) in connection with the liquidation of the Trust Account.

Q:
Can the Sponsor or the Easterly independent directors redeem their Easterly common stock?

A:
All of the holders of Founder Shares, which includes the Sponsor and Easterly's original independent directors, have agreed to waive their redemption rights with respect to their Founder Shares and have agreed to waive their redemption rights with respect to any public shares that they may have acquired during or after the IPO in connection with the completion of the Merger. The Founder Shares will be excluded from the pro rata calculation used to determine the per-share redemption price.

Q:
Is there a limit on the number of shares I may redeem?

A:
A public stockholder, together with any of his, her or its affiliates or any other person with whom he, she or it is acting in concert or as a "group" (as defined in Section 13(d)(3) of the Exchange Act) will be restricted from seeking redemption rights with respect to 15% or more of the public shares of Easterly common stock. Accordingly, all shares in excess of 15% owned by a holder will not be redeemed for cash. On the other hand, a public stockholder who holds less than 15% of the public shares of common stock may redeem all of the public shares held by him, her or it for cash.

Q:
How will the level of redemptions affect the Merger?

A:
The fraction of a Sirius Group common share issuable for each share of Easterly common stock will not be impacted by the level of redemptions.

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Q:
How will the level of redemptions affect the combined company?

A:
The number of redemptions requested by Easterly stockholders would affect the amount of cash from the Trust Account available for general corporate purposes following the Merger. Each redemption of public shares by Easterly's public stockholders will decrease the amount in the Trust Account, which was approximately $148.5 million as of September 30, 2018. There is no specified maximum redemption threshold under Easterly's charter. In no event, however, will Easterly redeem public shares in an amount that would cause its net tangible assets to be less than $5,000,001. In addition, the number of redemptions requested by Easterly stockholders may result in a less liquid trading market for the combined company's common shares, fewer shareholders and the potential inability to meet Nasdaq's listing standards.

Q:
Will how I vote affect my ability to exercise redemption rights?

A:
No. You may exercise your redemption rights whether you vote your shares of Easterly common stock for or against the Merger Proposal. As a result, the Merger Proposal can be approved by stockholders who will redeem their shares and no longer remain stockholders. You may exercise your redemption rights whether or not you are a holder of Easterly common stock as of the record date for the Easterly special meeting.

Q:
How do I exercise my redemption rights?

A:
In order to exercise your redemption rights, you must, prior to 5:00 p.m. Eastern time on October 31, 2018 (two business days before the Easterly special meeting), (i) if you hold Easterly units, elect to separate your Easterly units into the underlying public shares and public warrants prior to exercising your redemption rights with respect to your public shares, (ii) submit a written request to Easterly's transfer agent that it redeem your public shares for cash, and (iii) deliver your stock to Easterly's transfer agent physically or electronically through The Depository Trust Company ("DTC"), in each case in accordance with the procedures described in this proxy statement/prospectus. The address of Continental Stock Transfer & Trust Company, Easterly's transfer agent, is listed under the question "Who can help answer my questions?" below. Any demand for redemption, once made, may be withdrawn at any time until the deadline for exercising redemption requests and thereafter, with Easterly's consent, until the vote is taken with respect to the Merger. If you delivered your shares for redemption to Easterly's transfer agent and decide within the required timeframe not to exercise your redemption rights, you may request that Easterly's transfer agent return the shares (physically or electronically). You may make such request by contacting Easterly's transfer agent at the phone number or address listed under "Who can help answer my questions?" below.

Q:
What are the U.S. federal income tax consequences as a result of the Merger?

    Sirius Group and Easterly intend to report the Merger as a tax-deferred "reorganization" for United States federal income tax purposes within the meaning of Section 368 of the Code. Assuming such treatment is respected, holders of Easterly common stock generally will not recognize gain or loss for U.S. federal income tax purposes as a result of the exchange of their Easterly common stock for Sirius Group common shares (except with respect to cash received in lieu of fractional shares). Neither Sirius Group nor Easterly intends to request any ruling or other guidance from the IRS on the United States federal income tax treatment of the Merger and no assurance can be given that the IRS would not challenge such treatment. The qualification of the Merger as a tax-deferred reorganization is not a condition to closing and the Merger Agreement does not include any covenant requiring Sirius Group to ensure that the Merger qualifies as a tax-deferred reorganization.

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    In connection with the registration statement of which this proxy statement/prospectus forms a part, Sirius Group has received an opinion of counsel that subject to certain representations, qualifications and assumptions it is more likely than not that the Merger will qualify as a "reorganization" within the meaning of section 368 of the Code. This opinion is subject to assumptions related to future events (described in more detail under "Proposal No. 1—The Merger Proposal—U.S. Federal Income Tax Considerations of the Merger to Holders of Easterly Common Stock or Easterly Warrants—Treatment of the Merger") because the qualification of the Merger as a reorganization depends on meeting certain technical requirements that cannot be determined at this time, and no assurance can be given that such assumptions will in fact be correct. More specifically, the treatment of the Merger as a reorganization would depend on whether sufficient stockholders of Easterly exchange their Easterly common stock for common shares of Sirius Group rather than redeem it for cash. If a significant number of stockholders decide to redeem their Easterly common stock, Easterly may not meet the "continuity of business enterprise" requirement necessary to qualify as a reorganization under Sections 368(a)(1)(B) and 368(a)(2)(E) of the Code and would not meet the requirement that it retain "substantially all" of its assets to qualify as a reorganization under Section 368(a)(2)(E) of the Code. Additionally, absent direct guidance, it is unclear whether certain transactions would result in the stockholders being treated as having received "boot" in the Merger, thereby denying the treatment of the Merger as a reorganization under Section 368(a)(1)(B) of the Code. These transactions include the post-closing adjustments reflecting the Exchange Ratio and the Promissory Note dated June 23, 2018, made by Easterly in favor of Sirius Group pursuant to which Sirius Group has agreed to lend Easterly $0.03 per month for every public share of Easterly common stock outstanding as of June 30, 2018, which loan is immediately payable back to Sirius Group if the Merger closes. While none of these transactions results in any former stockholder of Easterly receiving any cash or other property (other than common shares of Sirius Group) in the Merger in return for their Easterly common stock, no assurance can be given that the IRS would not challenge this treatment. Additionally, no assurance can be given that the IRS would not recharacterize the repurchase of Sirius Group stock held by CM Bermuda in an amount equal to the value of the Easterly Trust Account as a distribution by Easterly to Sirius Group notwithstanding that Sirius Group intends to use other sources of cash for such repurchase. If the transaction was so recharacterized, Easterly would neither meet the continuity of business enterprise requirement nor the "substantially all" requirement described above.

    If the IRS were to successfully challenge the tax-deferred reorganization treatment of the Merger, United States holders of Easterly common stock would recognize taxable gain or loss on the exchange of their Easterly common stock for common shares of Sirius Group in the Merger.

    You are strongly urged to consult with your own tax advisor to determine the particular U.S. federal, state or local or foreign income or other tax consequences of the Merger to you. See the section entitled "Proposal No. 1—The Merger Proposal—U.S. Federal Income Tax Considerations of the Merger to Holders of Easterly Common Stock or Easterly Warrants—Treatment of the Merger" on page 121.

Q:
What are the U.S. federal income tax considerations of exercising my redemption rights?

A:
Easterly stockholders who exercise their redemption rights to receive cash from the Trust Account in exchange for their shares of Easterly common stock generally will be required to treat the transaction as either a sale of such shares or a distribution with respect to such holder's shares of Easterly common stock. See the section entitled "Proposal No. 1—The Merger Proposal—U.S. Federal Income Tax Considerations of Redeeming Easterly Common Stock" beginning on page 124.

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Q:
If I am an Easterly warrant holder, can I exercise redemption rights with respect to my warrants?

A:
No. There are no redemption rights with respect to Easterly's warrants.

About the Easterly Special Meeting

Q:
What is being voted on at the Easterly special meeting?

A:
Below are the proposals on which Easterly's stockholders are being asked to consider and vote upon at the Easterly special meeting.

1.
Proposal No. 1—The Merger Proposal—To approve and adopt the Merger Agreement and the transactions contemplated by the Merger Agreement, including the Merger; and

2.
Proposal No. 2—The Adjournment Proposal—To approve the adjournment of the Easterly special meeting to a later date or dates, if necessary, to permit further solicitation of proxies in the event that, based upon the tabulated vote at the time of the Easterly special meeting, there are not sufficient votes to approve one or more proposals presented to Easterly's stockholders for vote at such special meeting. This proposal will only be presented at the Easterly special meeting if there are not sufficient votes to approve the one or more proposals presented to Easterly's stockholders for vote at such special meeting.

Your vote is important. You are encouraged to submit your proxy as soon as possible after carefully reviewing this proxy statement/prospectus and its Annexes.

Q:
Are the Merger Proposal and the Adjournment Proposal conditioned on each other?

A:
No. The Merger Proposal is not conditioned on the approval of the Adjournment Proposal and the Adjournment Proposal is not conditioned on the approval of the Merger Proposal.

Q:
What happens to Easterly if Easterly stockholders do not approve the Merger Proposal?

A:
If Easterly stockholders do not approve the Merger Proposal, then Easterly cannot consummate the Merger. If Easterly does not consummate the Merger and fails to complete an initial Merger by November 30, 2018, Easterly will be required to dissolve and liquidate the Trust Account.

Q:
Why is Easterly providing its stockholders with the opportunity to vote on the Merger Proposal?

A:
The Merger Proposal provides for the approval and adoption by Easterly stockholders of the Merger Agreement and the Merger. Easterly's charter requires that it provide all holders of its public shares with the opportunity to have their public shares redeemed upon the consummation of its initial business combination in conjunction with either a tender offer or a stockholder vote. For business and other reasons, Easterly has elected to provide Easterly stockholders with the opportunity to have their public shares redeemed in connection with a stockholder vote rather than pursuant to a tender offer. As a result, Easterly public stockholders will have the opportunity to redeem their public shares in connection with the closing of the Merger.

Q:
What happens if I sell my shares of Easterly common stock before the Easterly special meeting of stockholders?

A:
The record date for the Easterly special meeting of stockholders will be earlier than the date of the special meeting. If you transfer your shares of Easterly common stock after the record date, but before the Easterly special meeting of stockholders, unless the transferee obtains from you a proxy to vote those shares, you will retain your right to vote at the Easterly special meeting of stockholders.

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Q:
What vote is required to approve the proposals presented at the Easterly special meeting of stockholders?

A:
The approval of the Merger Proposal requires the affirmative vote of the holders of a majority of the outstanding shares of Easterly common stock. Accordingly, an Easterly stockholder's failure to vote by proxy or to vote in person at the Easterly special meeting of stockholders, an abstention from voting or a broker non-vote will have the same effect as a vote "AGAINST" the Merger Proposal. The approval of the Adjournment Proposal requires the affirmative vote of holders of a majority of the shares of Easterly common stock that are voted on such proposal at the Easterly special meeting of stockholders. Accordingly, an Easterly stockholder's failure to vote by proxy or to vote in person at the Easterly special meeting of stockholders or an abstention from voting will have no effect on the outcome of any vote on the Adjournment Proposals. A broker non-vote will have no effect on the Adjournment Proposal.

Q:
How many votes do I have at the Easterly special meeting of stockholders?

A:
For each proposal, Easterly's stockholders are entitled to one vote at the Easterly special meeting for each share of Easterly common stock held of record as of the record date. As of the close of business on the record date, there were 19,208,407 outstanding shares of Easterly common stock.

Q:
What constitutes a quorum at the Easterly special meeting of stockholders?

A:
Holders of a majority in voting power of Easterly's common stock issued and outstanding and entitled to vote at the Easterly special meeting, present in person or represented by proxy, constitute a quorum. In the absence of a quorum, a majority of Easterly stockholders, present in person or represented by proxy, will have power to adjourn the Easterly special meeting. As of the record date for the Easterly special meeting, the presence in person or by proxy of holders of at least 9,604,204 shares of Easterly common stock would be required to achieve a quorum.

Q:
How will the Sponsor and Easterly's directors and officers vote?

A:
In connection with the IPO, Easterly entered into agreements with the Sponsor and with Easterly's original independent directors, pursuant to which each agreed to vote their Founder Shares and any other shares acquired during and after the IPO in favor of the Merger Proposal. Additionally, the Sponsor Letter requires that Sponsor vote its shares of Easterly common stock in favor of the Merger. Neither the Sponsor nor Easterly's directors or officers have purchased any shares during or after the IPO and neither Easterly nor the Sponsor, its directors or its officers have entered into agreements, and are not currently in negotiations, to purchase shares. Currently, the Sponsor, Easterly's original independent directors and their permitted transferees own 25.8% of the issued and outstanding shares of Easterly common stock, consisting of 100% of the Founder Shares.

Q:
How do I vote?

A:
If you were a holder of record of Easterly common stock on October 2, 2018, the record date for the Easterly special meeting, you may vote or have your shares voted with respect to the applicable proposals:

in person at the Easterly special meeting of stockholders; or

by submitting a proxy to vote by completing, signing, dating and returning the enclosed proxy card in the postage-paid envelope provided.

    If you hold your shares in "street name," which means your shares are held of record by a broker, bank or other nominee, you should contact your broker, bank or nominee to ensure that votes related to the shares you beneficially own are properly counted. In this regard, you must provide

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    the record holder of your shares with instructions on how to vote your shares or, if you wish to attend the Easterly special meeting of stockholders and vote in person, obtain a proxy from your broker, bank or nominee.

Q:
What will happen if I sign and return my proxy card without indicating how I wish to vote?

A:
If you are a record holder, then signed and dated proxies received by Easterly without an indication of how the stockholder of record intends to vote on a proposal will be voted in favor of each proposal presented to the stockholders.

Q:
If my shares are held in "street name," will my broker, bank or nominee automatically vote my shares for me?

A:
No, except with respect to the Adjournment Proposal. Under the rules of various national and regional securities exchanges, your broker, bank or nominee cannot vote your shares with respect to non-discretionary matters unless you provide instructions on how to vote in accordance with the information and procedures provided to you by your broker, bank or nominee. Except for the Adjournment Proposal, we believe the proposals presented to the stockholders will be considered non-discretionary and therefore your broker, bank or nominee cannot vote your shares without your instruction. If you do not provide instructions with your proxy, your broker, bank or nominee may deliver a proxy card expressly indicating that it is NOT voting your shares; this indication that a broker, bank or nominee is not voting your shares is referred to as a "broker non-vote." Broker non-votes will not be counted for the purpose of determining the existence of a quorum or for purposes of determining the number of votes cast at the Easterly special meeting. Except with respect to the Adjournment Proposal, your broker, bank or nominee can vote your shares only if you provide instructions on how to vote. You should instruct your broker to vote your shares in accordance with directions you provide.

Q:
If I am not going to attend the Easterly special meeting of stockholders in person, should I return my proxy card instead?

A:
Yes. Whether you plan to attend the Easterly special meeting or not, please read this proxy statement/prospectus carefully, and submit your proxy to vote by completing, signing, dating and returning the enclosed proxy card in the postage-paid envelope provided.

Q:
May I change my vote after I have submitted my signed proxy card?

A:
Yes. You may change your vote by sending a later-dated, signed proxy card to Easterly's secretary at the address listed below so that it is received by its secretary prior to the Easterly special meeting of stockholders, or attending the Easterly special meeting in person and vote. You also may revoke your proxy by sending a notice of revocation to Easterly's secretary, which must be received by Easterly's secretary prior to the Easterly special meeting.

Q:
What should I do if I receive more than one set of voting materials?

A:
You may receive more than one set of voting materials, including multiple copies of this proxy statement/prospectus and multiple proxy cards or voting instruction cards. For example, if you hold your shares in more than one brokerage account, you will receive a separate voting instruction card for each brokerage account in which you hold shares. If you are a holder of record and your shares are registered in more than one name, you will receive more than one proxy card. Please complete, sign, date and return each proxy card and voting instruction card that you receive in order to cast your vote with respect to all of your shares.

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Q:
Who will solicit and pay the cost of soliciting proxies?

A:
Easterly will pay the cost of soliciting proxies for the Easterly special meeting. Easterly has engaged Morrow Sodali LLC ("Morrow Sodali") to assist in the solicitation of proxies for the Easterly special meeting. Easterly has agreed to pay Morrow Sodali a fee of $22,500, plus disbursements. Easterly will reimburse Morrow Sodali for reasonable out-of-pocket expenses and will indemnify Morrow Sodali and its affiliates against certain claims, liabilities, losses, damages and expenses. Easterly also will reimburse banks, brokers and other custodians, nominees and fiduciaries representing beneficial owners of shares of Easterly's common stock for their expenses in forwarding soliciting materials to beneficial owners of Easterly's common stock and in obtaining voting instructions from those owners. Easterly's directors, officers and employees, including David Cody, Darrell W. Crate, Avshalom Kalichstein, David W. Knowlton, Neil Medugno, Justin Tuck and Daniel Shea, may also solicit proxies by telephone, by facsimile, by mail, on the Internet or in person. They will not be paid any additional amounts for soliciting proxies.

Q:
What do I need to do now if I am an Easterly stockholder?

A:
You are urged to carefully read and consider the information contained in this proxy statement/prospectus, including the Annexes, and to consider how the Merger will affect you as an Easterly stockholder. You should then submit your proxy as soon as possible in accordance with the instructions provided in this proxy statement/prospectus and on the enclosed proxy card or, if you hold your shares through a brokerage firm, bank or other nominee, on the voting instruction form provided by the broker, bank or nominee.

Q:
Who can help answer my questions?

A:
If you have questions about the proposals or if you need additional copies of the proxy statement/prospectus or the enclosed proxy card, you should contact:

Easterly Acquisition Corp.
205 Hudson Street, 7th Floor
New York, NY 10013
Telephone: (646) 712-8300
Email: info@easterlyacquisition.com

        You may also contact Easterly's proxy solicitor at:

Morrow Sodali LLC
470 West Avenue, 3rd Floor
Stamford, CT 06902
Stockholders, please call toll free: (800) 662-5200
Banks and Brokerage Firms, please call collect: (203) 658-9400
Email: Easterly.info@morrowsodali.com

        To obtain timely delivery, Easterly's stockholders must request the materials no later than five business days prior to the Easterly special meeting.

        You may also obtain additional information about Easterly from documents filed with the SEC by following the instructions in the section entitled "Where You Can Find More Information" on page 357.

        If you intend to seek redemption of your public shares, you will need to send a letter demanding redemption and deliver your stock (either physically or electronically) to Easterly's transfer agent prior to 5:00 p.m. Eastern time on October 31, 2018 (two business days before the Easterly special meeting).

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If you have questions regarding the certification of your position or delivery of your stock, please contact:

Continental Stock Transfer & Trust Company
1 State Street Plaza, 30th Floor
New York, NY 10004
Attn: Mark Zimkind
Email: mzimkind@continentalstock.com

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SUMMARY

        This summary highlights selected information from this proxy statement/prospectus and does not contain all of the information that is important to you. To better understand the Merger and the proposals to be considered at the Easterly special meeting, you should read this entire proxy statement/prospectus carefully, including the Annexes and the other documents referred to herein. See also the section entitled "Where You Can Find More Information" on page 357. Most items in this summary include a page reference directing you to a more complete description of those items.

Parties to the Merger

    Easterly (page 309)

        Easterly Acquisition Corp. ("Easterly") is a special purpose acquisition company formed for the purpose of effecting a merger, capital stock exchange, asset acquisition, stock purchase, reorganization or similar business combination involving Easterly and one or more businesses.

        Easterly is a Delaware corporation formed in 2015. Its securities are traded on the Nasdaq Capital Market under the ticker symbols "EACQ," "EACQW" and "EACQU."

        The mailing address of Easterly's principal executive office is 205 Hudson Street, 7th Floor, New York, New York 10013.

    Sirius Group (page 158)

        Sirius International Insurance Group, Ltd. ("Sirius Group") is a Bermuda exempted company whose principal businesses are conducted through its insurance and reinsurance subsidiaries and other affiliates. Sirius Group's subsidiaries, including Sirius Bermuda Insurance Company Ltd. ("Sirius Bermuda"), Sirius International Insurance Corporation ("Sirius International"), Sirius America Insurance Company ("Sirius America") and Lloyd's Syndicate 1945 ("Syndicate 1945"), provide insurance, reinsurance and insurance services on a worldwide basis. Sirius Group writes treaty and facultative reinsurance, as well as primary insurance business. The majority of Sirius Group's treaty reinsurance premiums are derived from proportional and excess of loss reinsurance contracts, which in 2017 amounted to 44% and 30%, respectively, of its total net written premiums, while primary business represented 26% of total net written premiums. Sirius Group's primary business has historically been predominantly accident and health insurance.

        Sirius Group is, and will upon the consummation of the Merger be, considered a "foreign private issuer" under the rules and regulations of the SEC. In addition, Sirius Group will qualify as a "controlled company" within the meaning of Nasdaq rules. Sirius Group does not currently expect or intend to rely on the scaled disclosure practices permitted by the SEC or the alternate governance practices permitted by Nasdaq, and is voluntarily choosing to register and report using the SEC's domestic forms and comply with the Nasdaq governance practices applicable to domestic companies.

        Prior to the Merger, there is no public market for Sirius Group's securities. Sirius Group has applied to list the Sirius Group common shares and converted warrants on the Nasdaq Stock Market under the symbols "SG" and "SGRP-W," respectively, effective as of the closing of the Merger.

        The mailing address of Sirius Group's principal executive office is 14 Wesley Street Hamilton HM 11, Bermuda.

    Merger Sub

        Sirius Acquisitions Holding Company III ("Merger Sub") is a direct wholly owned subsidiary of Sirius Group and was incorporated in 2018 in the State of Delaware. Merger Sub has not engaged in any operations and exists solely to facilitate the Merger.

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The Merger Agreement (page 91)

        Pursuant to the Merger Agreement, Merger Sub will merge with and into Easterly, with Easterly surviving the Merger as a wholly owned subsidiary of Sirius Group.

        At the Effective Time, all shares of Easterly common stock (other than (i) shares of Easterly common stock with respect to which an Easterly stockholder has validly exercised its redemption rights, and that will be redeemed as provided for by Easterly's charter, (ii) shares of Easterly common stock held by Easterly as treasury stock or owned by Easterly, Sirius Group or Merger Sub or any wholly owned subsidiary of Easterly or Sirius Group, which will be canceled for no consideration, and (iii) shares of Easterly common stock held by the Sponsor that will be canceled pursuant to the Sponsor Letter) will be converted into Sirius Group common shares at the Exchange Ratio. The Exchange Ratio will be determined prior to the closing of the Merger and will be equal to a fraction determined by dividing (i) the estimated amount of cash per public share of Easterly common stock in the Trust Account immediately prior to the closing of the Merger by (ii) (x) 1.05 multiplied by (y) Sirius Group's adjusted diluted book value per common share as of September 30, 2018 ("Sirius Group September 30 Adjusted DBVPS"). The Sirius Group September 30 Adjusted DBVPS will be calculated by dividing (i) the book value of Sirius Group determined based on GAAP on a consolidated basis, based on the final, Sirius Group board of directors approved, unaudited GAAP consolidated financial statements of Sirius Group for the nine months ended September 30, 2018, decreased by the $7 million deferred underwriting fee payable by Easterly to Citigroup Global Markets Inc. as underwriter of Easterly's initial public offering, and as adjusted by the GAAP accounting effect of the redemption of the Sirius Group Series A redeemable preference shares by (ii) the sum of (x) the fully diluted number of Sirius Group common shares issued and outstanding as of September 30, 2018 and (y) 593,000 Sirius Group common shares. In accordance with the Merger Agreement, Sirius Group delivered to Easterly its good faith estimate of 1.05 multiplied by the Sirius Group September 30 Adjusted DBVPS, equal to $17.22. If such estimate is used to determine the Exchange Ratio at the closing of the Merger, then the Merger Agreement provides for a post-closing adjustment if such estimate is different than the actual Sirius Group September 30 Adjusted DBVPS as finally determined after the closing of the Merger. Such adjustment will result in either (x) the issuance of new Sirius Group common shares or a payment of cash by Sirius Group to CM Bermuda, if the Exchange Ratio is greater than it would have been using the actual Sirius Group September 30 Adjusted DBVPS or (y) the surrender to Sirius Group of Sirius Group common shares owned by CM Bermuda or a payment of cash to Sirius Group from CM Bermuda if the Exchange Ratio is less than it would have been using the actual Sirius Group September 30 Adjusted DBVPS.

        Based on such estimate of the Sirius Group September 30 Adjusted DBVPS as of October 8, 2018 and funds in the Trust Account on September 30, 2018, the Exchange Ratio would be equal to 0.607. Investors are cautioned that 0.607 is only an estimate of the Exchange Ratio, has not been agreed as the final Exchange Ratio for purposes of the Merger Agreement, and is subject to change prior to the closing of the Merger. The preliminary estimate of Sirius Group's adjusted diluted book value per common share as of September 30, 2018 included in this proxy statement/prospectus has been prepared by, and is the responsibility of, Sirius Group's management. PricewaterhouseCoopers LLP has not audited, reviewed, compiled, or applied agreed-upon procedures with respect to the preliminary financial data. Accordingly, PricewaterhouseCoopers LLP does not express an opinion or any other form of assurance with respect thereto.

        Additionally, each issued and outstanding public warrant to acquire shares of Easterly common stock will cease to represent a right to acquire shares of Easterly common stock and will be converted into a converted warrant. The number of Sirius Group common shares subject to each converted warrant will be equal to the number of shares of Easterly common stock subject to each Easterly warrant immediately prior to the closing of the Merger multiplied by the Exchange Ratio, and such converted warrant will have an exercise price per Sirius Group common share equal to the exercise

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price per share of Easterly common stock subject to such Easterly warrant immediately prior to the closing of the Merger divided by the Exchange Ratio.

        Based on an estimated Exchange Ratio of 0.607, each converted warrant would be exercisable for 0.607 Sirius Group common shares at an exercise price of $18.95 per Sirius Group common share. Investors are cautioned that 0.607 is only an estimate of the Exchange Ratio, has not been agreed as the final Exchange Ratio for purposes of the Merger Agreement, and is subject to change prior to the closing of the Merger. Easterly has not obtained an opinion from an independent financial advisor in connection with the Merger and, consequently, there is no assurance from an independent source that the price Sirius Group is paying for Easterly is fair to Easterly's stockholders from a financial point of view.

Recent Developments Impacting the Exchange Ratio (page 120)

        Late in the third quarter of 2018, there were numerous natural disasters around the world, including Typhoon Jebi in Japan, the Kerala Flood in India, Typhoons Mangkhut and Trami in Southeastern Asia, a tsunami in Indonesia, and Hurricane Florence in the eastern United States. Sirius Group has exposure to losses resulting from these and other natural disasters. Potential losses from these events take time to assess. Preliminary loss estimates are initially established based upon client information, catastrophe models, market loss data and underwriter judgement. Updated loss advices from clients are received over time as the losses develop.

        Sirius Group is in the process of evaluating available preliminary information in order to record an estimate of losses, including from these events, at September 30, 2018. It is currently estimated that the third quarter losses will likely be higher than previously estimated. Based upon this loss and other information available as of October 8, 2018, in accordance with the Merger Agreement, Sirius Group delivered to Easterly its good faith estimate of 1.05 multiplied by the Sirius Group September 30 Adjusted DBVPS, equal to $17.22, which is subject to adjustment post-closing, as more fully described herein.

Agreements Related to the Merger Agreement (page 104)

    Sponsor Letter

        Concurrently with the execution of the Merger Agreement, Easterly entered into the Sponsor Letter with the Sponsor and Sirius Group, pursuant to which, at the closing of the Merger, (i) the Sponsor will surrender and Easterly will cancel for no consideration between 3,328,000 and 4,528,000 (or such higher number of shares based on the adjustment described below) shares of Easterly common stock owned by the Sponsor, which amount will be determined at the Effective Time based on the amount of cash in the Trust Account at the closing of the Merger after giving effect to any redemptions of public shares of Easterly common stock and amounts raised in a private placement of Sirius Group common shares (or securities convertible into Sirius Group common shares) in connection with the Merger (as discussed in further detail below) and (ii) the Sponsor will surrender and Easterly will cancel for no consideration the 6,750,000 private placement warrants that were acquired by the Sponsor in a private placement concurrent with the closing of Easterly's initial public offering. The number of canceled shares will be determined as follows: The base number of 3,928,000 canceled shares will be (a) decreased by 0.50 of a share of Easterly common stock for every $100 that the sum of (I) cash in the Trust Account at the closing of the Merger plus (II) the proceeds of any private placement of Sirius Group common shares (or securities convertible into Sirius Group common shares) in connection with the Merger (the sum of (I) and (II), the "Amount Raised") is greater than $120 million (provided, that if the Amount Raised is greater than or equal to $150 million, then, solely with respect to any portion of the Amount Raised that is funded from certain designated investors in such private placement, the number of canceled shares will be decreased by 0.25 (in lieu of 0.50) of a share of Easterly common

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stock for every $100 of the Reduced Rate Amount (as defined below)) or (b) increased by 0.50 of a share of Easterly common stock for every $100 that the Amount Raised is less than $120 million. Notwithstanding the foregoing, the minimum number of canceled shares will be 3,328,000 and the maximum number of canceled shares will be 4,528,000, except that the Sponsor also agreed to surrender additional shares (which could result in more than 4,528,000 shares surrendered) in certain circumstances if the amount per share equal to (x) 1.05 multiplied by (y) the Sirius Group September 30 Adjusted DBVPS used in the calculation of the Exchange Ratio, as adjusted for the value of the warrants issued in the Sirius Group Private Placement, is less than $17.39. If the proceeds raised from the Sirius Group Private Placement Investors is less than $213 million (other than as a result of an investor failing to fund its obligations in breach of its subscription agreement at a time when Sirius Group is not then in material breach of any of its representations, warranties, covenants or agreements set forth in such subscription agreement at the time of such investor's breach of such subscription agreement), the proceeds of the Sirius Group Private Placement will be deemed to be $213 million for purposes of calculating the Amount Raised. The "Reduced Rate Amount" means the lesser of (x) the Amount Raised minus $150 million and (y) the Amount Raised that is funded from certain designated investors in such private placement.

        The Sponsor also agreed to (i) pay or reimburse all liabilities and obligations of Easterly due and owing or incurred at or prior to the closing of the Merger to the extent not repaid by Easterly using unrestricted cash and up to $2 million from the Trust Account, except for the $7 million deferred underwriting fee, which will be paid using cash released from the Trust Account, and (ii) contribute to Easterly for no consideration, as a contribution to the capital of Easterly, all amounts due and owing by Easterly to the Sponsor under the Convertible Promissory Note to the extent any such amount is not repaid at the closing of the Merger.

        For more information on the Sponsor Letter, please see the full text of the Sponsor Letter, which is attached as Annex B hereto.

    Promissory Note

        Concurrently with the execution of the Merger Agreement, Easterly issued Sirius Group the Promissory Note pursuant to which Sirius Group agreed to lend Easterly $0.03 per month for every public share of Easterly common stock outstanding as of June 30, 2018, until the earlier of the consummation of Easterly's initial business combination and November 30, 2018. The amounts will be lent to Easterly on the first business day of each month and will be deposited by Easterly into a special account within the Trust Account. The Promissory Note will bear interest in an amount equal to the income (if any) actually earned from investing the principal in the Trust Account and will be due upon the completion of Easterly's initial business combination, and will be canceled in case the Merger is not completed.

        For more information on the Promissory Note, please see the full text of the Promissory Note, which is attached as Annex D hereto.

    Registration Rights Agreement

        On the date of the closing of the Merger, Sirius Group will enter into the Registration Rights Agreement with the Sponsor and CM Bermuda substantially in the form attached as Annex E to this proxy statement/prospectus. Pursuant to the terms of the Registration Rights Agreement, CM Bermuda and the Sponsor will be entitled to certain registration rights described in the Registration Rights Agreement with respect to the Sirius Group common shares owned by CM Bermuda and the Sirius Group common shares receivable by the Sponsor upon the exchange of its Easterly common stock. Among other things, pursuant to the Registration Rights Agreement, CM Bermuda will be entitled to the right to initiate the filing of registrations statements, including for underwritten offerings, and

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unlimited piggyback registration rights. The Sponsor will be entitled to unlimited piggyback registration rights. The registration rights of CM Bermuda and the Sponsor are subject to customary black-out periods, cutback provisions and other limitations as set forth in the Registration Rights Agreement. Sirius Group will agree to pay certain fees and expenses relating to registrations under the Registration Rights Agreement.

        For more information on the Registration Rights Agreement, please see the full text of the form of Registration Rights Agreement which is attached as Annex E hereto.

    Lock-Up Agreements

        On the date of the closing of the Merger and as a condition precedent for the closing, the Sponsor and CM Bermuda will each deliver a Lock-Up Agreement to Sirius Group pursuant to which the Sponsor and CM Bermuda will agree not to sell any Sirius Group common shares for a period of 180 days from the Effective Time without the consent of Sirius Group, subject to specified exemptions.

        For more information on the Lock-Up Agreements, please see the full text of the form of the Lock-Up Agreement, which is attached as Annex F hereto.

    Warrant Amendment

        On the date of the closing of the Merger and as a condition precedent for the closing, Sirius Group, Easterly and Continental Stock Transfer & Trust Company will enter into the Warrant Amendment with respect to the Warrant Agreement, pursuant to which Easterly will assign to Sirius Group, and Sirius Group will assume, all of Easterly's right, title and interest in the Warrant Agreement. The Warrant Agreement, as amended by the Warrant Amendment, will govern the terms of the converted warrants.

        For more information on the Warrant Amendment, please see the full text of the form of the Warrant Amendment, which is attached as Annex G hereto.

Transactions Related to the Merger (page 107)

    Sirius Group Private Placement

        In connection with the closing of the Merger, Sirius Group expects to complete a private placement of Sirius Group Series B preference shares and Sirius Group common shares at a price per share equal to (i) 1.05 multiplied by (ii) the Sirius Group September 30 Adjusted DBVPS, estimated as of October 8, 2018 to be $17.22 (the "Sirius Group Private Placement"). On August 29, 2018, Sirius Group received subscriptions from affiliated funds of Gallatin Point Capital, The Carlyle Group, Centerbridge Partners, L.P. and Bain Capital Credit (the "Preference Share Investors") pursuant to which they have committed to purchase $205 million of Sirius Group Series B preference shares and $8 million of Sirius Group common shares in the private placement, which aggregate amount may be decreased to $111 million at Sirius Group's option. In addition, the Preference Share Investors will receive warrants that are exercisable for a period of five years after the issue date at a strike price equal to 125% of the per share purchase price, estimated as of October 8, 2018 to be $21.53. The form of subscription agreement, certificate of designation and warrant are filed as exhibits to the registration statement of which this proxy statement/prospectus forms a part.

        Members of Sirius Group's management team and board of directors have committed to purchase an aggregate of 569,000 common shares in the Sirius Group Private Placement.

        Gross proceeds of the Sirius Group Private Placement, together with cash in the Trust Account upon the closing of the Merger (which was $148.5 million as of September 30, 2018, before taking into account any redemptions of Easterly common stock or other transactions related to or in connection

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with the Merger Proposal), are intended to aggregate to up to $350 million. Assuming a private placement of $202 million at a price per share of $17.22, Sirius Group would issue 11.7 million common shares and Series B preference shares convertible into common shares in connection with the Sirius Group Private Placement (based on subscriptions received as of October 8, 2018 and inclusive of participants in the Employee Share Purchase Plan). Investors are cautioned that this is only an estimate based on the foregoing assumptions, and is subject to change prior to the closing of the Merger. The proceeds of the private placement will be used to redeem all outstanding Sirius Group Series A redeemable preference shares, and the remainder for general corporate purposes. The private placement is intended to be exempt from registration under U.S. securities laws pursuant to Section 4(a)(2) of the Securities Act and Regulation D and Regulation S thereunder.

        In connection with the closing of the Sirius Group Private Placement, Sirius Group, CM Bermuda and the Preference Share Investors will enter into a shareholders agreement (the "Shareholders Agreement"), which will govern certain matters with respect to the governance of Sirius Group, the voting of CM Bermuda's common shares, the repurchase of CM Bermuda's common shares and certain other matters. The form of Shareholders Agreement is filed as an exhibit to the registration statement of which this proxy statement/prospectus forms a part.

        Pursuant to the Shareholders Agreement, until the third anniversary of the date of the closing of the Sirius Group Private Placement: (i) CM Bermuda will vote in favor of the election of the number of Independent Directors (as such term is defined in the Shareholders Agreement) as is necessary to provide that at least a majority of the Board of Directors of Sirius Group is comprised of Independent Directors; and (ii) CM Bermuda will not vote in favor of the removal of any director (other than any director affiliated with CM Bermuda) other than for cause. After the third anniversary of the date of the closing of the Sirius Group Private Placement (or earlier in the event of an increase to the size of the Board of Directors), CM Bermuda will not vote in favor of the election of any director not then serving on the Board of Directors (including any election to fill a vacancy then existing on the Board of Directors as a result of death, resignation, removal, expansion of the Board of Directors or otherwise) who is not an Agreed Director. "Agreed Director" means an Independent Director mutually agreeable to CM Bermuda and Preference Share Investors representing a majority of the Sirius Group Series B preference shares; provided, that if CM Bermuda and the Preference Share Investors have not identified an Agreed Director after negotiating in good faith for a period of 60 days, then an Agreed Director means any Independent Director recommended for election by the Nominating & Governance Committee of the Sirius Group Board of Directors.

        Pursuant to the Shareholders Agreement, CM Bermuda will also agree to vote (i) in favor of a Qualified Sale Transaction (as such term is defined in the Shareholders Agreement) that is approved by a majority of Independent Directors and 80% of Sirius Group's voting shares after the first anniversary of the date of the closing of the Sirius Group Private Placement, and (ii) against any merger, amalgamation, consolidation or similar transaction or any sale or transfer of all or substantially all of Sirius Group's consolidated assets, in each case where the per share value of the consideration received by CM Bermuda in such transaction is greater than the per share value of the consideration received by any other holder of Sirius Group common shares.

        The Shareholders Agreement also grants the Preference Share Investors tag-along rights to the extent Sirius Group agrees to repurchase or redeem any common shares held by CM Bermuda.

        The Shareholders Agreement terminates on the date that fewer than 25% of the Sirius Group Series B preference shares issued in the Sirius Group Private Placement are outstanding, and earlier with respect to any Preference Share Investor at the time that it or its affiliates or permitted assigns ceases to own any Sirius Group Series B preference shares.

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    Common Shares Redemption Agreement

        Prior to the closing of the Merger, Sirius Group and CM Bermuda will enter into a redemption agreement (the "Common Shares Redemption Agreement"), pursuant to which, effective as of and subject to the closing of the Merger, Sirius Group will redeem Sirius Group common shares from CM Bermuda, at a price per share equal to (i) 1.05 multiplied by (ii) the Sirius Group September 30 Adjusted DBVPS, estimated as of October 8, 2018 to be $17.22, for an aggregate amount of between $120 million and $250 million, as elected by CM Bermuda at least two business days in advance of the closing of the Merger. Assuming a redemption amount of approximately $250 million at a price per share of $17.22, Sirius Group would redeem 14.5 million common shares from CM Bermuda in connection with the Common Shares Redemption Agreement. Investors are cautioned that this is only an estimate based on the foregoing assumptions, and is subject to change. In addition, in the event that the gross proceeds of the Sirius Group Private Placement are less than $202 million, the amount of Sirius Group common shares redeemed from CM Bermuda may be less than $250 million.

    Preference Shares Redemption Agreement

        On July 14, 2018, Sirius Group, IMGAH and Sirius Acquisitions Holding Company II entered into that certain Redemption Agreement (the "Preference Shares Redemption Agreement") pursuant to which, effective as of and subject to the closing of the Merger, Sirius Group has agreed to redeem all of the issued and outstanding Sirius Group Series A redeemable preference shares, which are held by IMGAH, for $95 million, payable in cash at the time of the redemption. Effective as of the completion of such redemption, the parties have agreed to terminate the registration rights agreement and the shareholder's agreement between Sirius Group and IMGAH. In addition, the parties agreed that any remaining contingent consideration in respect of the IMG acquisition, which may be in an amount of up to $50.0 million, will be paid in cash, not in Sirius Group Series A redeemable preference shares as previously contemplated in the agreement in respect of the IMG acquisition.

Beneficial Ownership of the Combined Company (page 348)

        It is anticipated that, upon completion of the Merger, and subject to the assumptions described below:

    Sirius Group's existing controlling shareholder, CM Bermuda, will own approximately 83.2% of Sirius Group;

    the Sirius Group Private Placement Investors (based on subscriptions received as of October 8, 2018 and inclusive of participants in the Employee Share Purchase Plan) will own approximately 9.2% of Sirius Group;

    Easterly's public stockholders will own approximately 6.8% of Sirius Group; and

    the Sponsor and Easterly's directors and executive officers will own approximately 0.8% of Sirius Group.

        These relative percentages assume that (i) the Exchange Ratio is equal to 0.607, (ii) no Easterly stockholders exercise their redemption rights in connection with the Merger Proposal, (iii) the Sponsor and Easterly's original independent directors retain 1.0 million shares of Easterly common stock after giving effect to the transactions contemplated by the Sponsor Letter, (iv) Sirius Group issues 11.7 million common shares and Series B preference shares convertible into common shares in connection with the Sirius Group Private Placement (based on subscriptions received as of October 8, 2018 and inclusive of participants in the Employee Share Purchase Plan), (v) Sirius Group redeems 14.5 million common shares from CM Bermuda for approximately $250 million pursuant to the Common Shares Redemption Agreement and (vi) all of the issued and outstanding Sirius Group Series A redeemable preference shares are redeemed for $95 million in cash pursuant to the

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Preference Shares Redemption Agreement prior to the closing of the Merger. Further, such percentages do not take into account (x) the issuance of any Sirius Group common shares upon the exercise of the converted warrants that may remain issued and outstanding following the Merger (which would be 6.1 million Sirius Group common shares using the assumed Exchange Ratio) or that are issued pursuant to the Sirius Group Private Placement (which are estimated to be approximately 5.4 million Sirius Group common shares) or (y) the issuance of up to 14.1 million Sirius Group common shares reserved for issuance pursuant to Sirius Group's Long Term Incentive Plan and 2018 Omnibus Incentive Plan. If the facts differ from these assumptions, Easterly's stockholders may experience dilution of their ownership interest unless they elect to have their shares of Easterly common stock redeemed in connection with the Merger Proposal.

        Assuming (a) the issuance of 6.1 million Sirius Group common shares pursuant to the converted warrants and 5.4 million Sirius Group common shares pursuant to the Sirius Group Private Placement warrants, but excluding the Sirius Group common shares reserved for issuance pursuant to Sirius Group's Long Term Incentive Plan and 2018 Omnibus Plan, and (b) the other assumptions set forth in clauses (i) through (vi) of the preceding paragraph, then ownership of the issued and outstanding Sirius Group common shares would be anticipated to be as follows:

    Sirius Group's existing controlling shareholder, CM Bermuda, will own approximately 76.3% of Sirius Group;

    the Sirius Group Private Placement Investors will own approximately 12.4% of Sirius Group (based on subscriptions received as of October 8, 2018 and inclusive of participants in the Employee Share Purchase Plan);

    Easterly's public stockholders will own approximately 10.6% of Sirius Group; and

    the Sponsor and Easterly's directors and executive officers will own approximately 0.7% of Sirius Group.

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Corporate Structure of the Combined Company (page 162)

        The following diagram illustrates the simplified corporate structure of the combined company immediately following the Merger.

GRAPHIC

Directors and Executive Officers of the Combined Company (page 280)

        The directors and executive officers of the combined company upon consummation of the Merger are expected to be as follows:

Name
  Position
Allan L. Waters   Chairman of the Board and Chief Executive Officer ("CEO"), Sirius Group
Kernan (Kip) V. Oberting   President and Chief Financial Officer ("CFO"), Sirius Group and President, Sirius Capital Markets, Inc.
Monica Cramér Manhem   Chief Operating Officer ("COO"), Sirius Group and President and CEO, Sirius International
Jeffrey W. Davis   Executive Vice President, Chief Risk Officer ("CRO") & Chief Actuary, Sirius Group
Gene Boxer   Executive Vice President, Chief Strategy Officer ("CSO") & Group General Counsel, Sirius Group
Laurence Liao   Director
Robert L. Friedman   Director
Meyer (Sandy) Frucher   Director

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        The board of directors of Sirius Group has designated a Management Committee comprised of Messrs. Waters, Oberting and Boxer and Ms. Cramér Manhem as the senior management and decision making body of Sirius Group responsible for the oversight of the day-to-day business operations of Sirius Group.

        Mr. Oberting and Ms. Cramér Manhem, who are currently directors of Sirius Group, are expected to resign as directors effective upon the consummation of the Merger. Sirius Group is in the process of identifying additional individuals who are expected to serve on the Sirius Group board of directors, in order to satisfy independence standards set forth in Nasdaq listing standards and Rule 10A-3 under the Exchange Act, subject to the transition rules available to newly public companies under the Nasdaq listing rules. It is anticipated that, upon consummation of the Merger, a majority of the members of the Sirius Group board of directors will qualify as independent directors in accordance with the applicable rules of Nasdaq.

Redemption Rights (page 88)

        Pursuant to Easterly's charter, holders of public shares may elect to have their shares redeemed for cash at the applicable redemption price per share calculated in accordance with Easterly's charter. As of September 30, 2018, this would have amounted to approximately $10.45 per share. If a holder exercises its redemption rights, then such holder will be exchanging its shares of Easterly common stock for cash and will no longer own shares of Easterly common stock. Such a holder will be entitled to receive cash for its public shares only if it properly demands redemption and delivers its shares (either physically or electronically) to Easterly's transfer agent in accordance with the procedures described herein. Easterly has no specified maximum redemption threshold under its charter. In no event, however, will Easterly redeem public shares in an amount that would cause its net tangible assets to be less than $5,000,001.

Accounting Treatment (page 89)

        The Merger is a capital transaction in substance whereby Easterly will be treated as the "acquired" company for financial reporting purposes. Accordingly, for accounting purposes, the Merger will be treated as the equivalent of Sirius Group issuing shares for the net assets of Easterly, which are comprised of cash and cash equivalents.

Appraisal Rights (page 89)

        Appraisal rights are not available to Easterly's stockholders in connection with the Merger.

Easterly's Reasons for the Merger (page 112)

        Easterly was organized for the purpose of effecting a merger, capital stock exchange, asset acquisition, stock purchase, reorganization or similar business combination with one or more businesses. Easterly sought to capitalize on the contacts and sources of its management team to identify, acquire and operate a business in the financial services industry, although Easterly was not limited to a particular industry or sector.

        In considering the Merger, Easterly's board of directors considered the following positive factors, although not weighted or in any order of significance:

    Easterly management's experience with insurance and reinsurance companies;

    Sirius Group's historical track record, including strong operating results;

    Sirius Group's unique European franchise, its global accident and health platform and a diversifying suite of insurance and reinsurance growth lines;

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    Sirius Group strong track record of shareholder returns, including the generation of over 13% annualized operating return to White Mountains Insurance Group during its ownership of Sirius Group from 2009 until the first quarter of 2016;

    Sirius Group's superior underwriting, with overall combined ratio averaging 5% outperformance over peers from 2009 through 2017;

    Sirius Group's strong customer relationships with 60% of its business from customer relationships of over 10 years and 30% of its business coming from customer relationships of over 20 years;

    Sirius Group's track record of successfully executing mergers and acquisitions, including the 2017 acquisitions of IMG and Armada; and

    Sirius Group's experienced and tenured management team. Sirius Group's management team has significant experience in the insurance and reinsurance industries. The executive management team averages over 30 years of insurance operations and mergers and acquisitions experience, with over 23 years at Sirius Group.

        In addition, Easterly's board of directors also considered the following risks and other potentially negative factors:

    the recent historical net losses and low net profit of Sirius Group. Easterly's board of directors noted that Sirius Group had a comprehensive (loss) income of approximately $(78) million, $(34) million and $196 million for 2017, 2016 and 2015 respectively;

    the potential for major catastrophes to have a negative impact on Sirius Group's results of operations and capital;

    the risk that some of the current public stockholders of Easterly would vote against the Merger Proposal, or exercise their redemption rights, thereby depleting the amount of cash available in the Trust Account and reducing the number of freely tradeable Sirius Group common shares after the closing;

    the risk that certain key employees and potential customers of Sirius Group might not choose to work at or with Sirius Group after the Merger;

    the risks related to the fact that CM Bermuda will continue to control Sirius Group after the consummation of the Merger and such control may negatively impact minority shareholders;

    the risks associated with the insurance and reinsurance industries in general;

    the risks associated with macroeconomic uncertainty and the effects it could have on Sirius Group's revenues;

    the risks of unknown future regulation, which could provide burdensome on the insurance and reinsurance industry;

    the risks associated with obtaining additional financing for Sirius Group's operations in the future;

    the risk of competition in the industry;

    the risk that the Merger might not be consummated in a timely manner or that the closing of the Merger might not occur despite the parties' efforts, including by reason of a failure to obtain the approval of Easterly's stockholders and fulfill the other closing conditions;

    the risk that the transactions contemplated by the Merger Agreement would not be completed in accordance with the terms of the Merger Agreement or at all;

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    the risk that Easterly's stockholders would not approve an extension request at the June 28, 2018 Easterly special meeting of stockholders, and that Easterly would not be unable to complete the Merger before its expiration without an extension;

    the risk of delisting of Easterly's securities prior to the Merger and being unable to list Sirius Group's securities on the Nasdaq Stock Market in connection with the Merger;

    the significant fees and expenses associated with completing the Merger and the substantial time and effort of management required to complete the Merger; and

    the fact that the Sponsor, and Easterly's officers and directors may have interests in the Merger that are different from, or are in addition to, the interests of Easterly's public stockholders, including the matters described under "Proposal No. 1—The Merger Proposal—Certain Interests of Easterly's Directors and Officers and Others in the Merger," below.

Sirius Group's Reasons for the Merger (page 115)

        In considering the Merger, Sirius Group's board considered the following positive factors, although not weighted or in any order of significance:

    Sirius Group's business, financial condition, competitive position, business strategy, strategic options and prospects, as well as risks involved in achieving these prospects, the nature of Sirius Group's business and the industry in which it competes, and current industry, economic and global market conditions, both on a historical and on a prospective basis, all of which led Sirius Group's board of directors to conclude that the Merger presented an opportunity to realize greater value than the value likely to be realized in the event Sirius Group did not pursue the Merger;

    the review by Sirius Group's board of directors of possible alternatives to the Merger, including (i) pursuing an initial public offering of Sirius Group common shares and (ii) a merger or other business combination with a strategic buyer, (iii) issuance of additional preference shares or common shares of Sirius Group to one or more third party investors to diversify Sirius Group's shareholder base; the timing and likelihood of actually achieving additional value from these alternatives, as well as the risks and uncertainties associated with such alternatives, and the assessment of Sirius Group's board of directors that the Merger was in the long-term best interest of Sirius Group and its shareholders, taking into account risks of execution as well as business, competitive, industry and market risk;

    the expected accelerated timeline and reduced cost for completion of the Merger as compared to possible alternatives to the Merger;

    the significant reduction in the dilution from the Merger since (i) the Sponsor will surrender and Easterly will cancel for no consideration between 3,328,000 and 4,528,000 shares of Easterly common stock owned by the Sponsor and (ii) the Sponsor will surrender and Easterly will cancel for no consideration the 6,750,000 private placement warrants that were acquired by the Sponsor in a private placement concurrent with the closing of Easterly's initial public offering;

    the totality of the terms of the Merger Agreement (including the representations, warranties, covenants and agreements of each party, the closing conditions, the lack of indemnification provisions, and the termination provisions) and the related agreements;

    the fact that the Merger Agreement and the transactions contemplated thereby were the product of extensive arms' length negotiations between representatives of Sirius Group and representatives of Easterly;

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    the potential positive impact of the public announcement of the Merger on Sirius Group's rating agencies, regulators, customers and employees and Sirius Group's ability to attract and retain key management, underwriting, administrative and other personnel;

    the fact that Sirius Group expects to become a publicly listed company with associated benefits of a public currency; and

    the fact that no federal or state regulatory approvals are necessary in connection with the Merger.

        In addition, Sirius Group's board also considered the following risks and other potentially negative factors:

    the risk that the potential benefits sought in the Merger might not be fully realized;

    the risk that the financial results of Sirius Group will not meet expectations given the current economic climate;

    the risk of delisting of Easterly's securities prior to the Merger and being unable to list Sirius Group's securities on the Nasdaq Stock Market in connection with the Merger;

    the risk that the Merger might not be completed in a timely manner or at all, including the risk that Easterly's public stockholders do not vote in favor of the Merger;

    the risk that compliance with rules and requirements applicable to public companies will be expensive and time consuming;

    the risk that Easterly shareholders will redeem their shares for their pro rata portion of the funds available in the Trust Account and thereby reduce the amount of funds held in the Trust Account;

    the limitations imposed on the conduct of Sirius Group's business prior to the completion of the Merger;

    the risk that the Merger will result in the diversion of management and employee attention, or have an adverse effect on customers and business relationships;

    the substantial costs to be incurred in connection with the Merger, including equity dilution on account of the issuance of shares to Easterly's stockholders, banker's expenses, costs of preparing and filing this proxy statement/prospectus and other transaction expenses arising from the Merger; and

    the other risks and uncertainties set forth in the section entitled "Risk Factors" beginning on page 44 of this proxy statement/prospectus.

Risk Factors (page 44)

        In evaluating the proposals set forth in this proxy statement/prospectus, you should carefully read this proxy statement/prospectus, including the Annexes, and especially consider the factors discussed in the section entitled "Risk Factors."

Quorum and Required Vote for Proposals for the Easterly Special Meeting of Stockholders (page 85)

        A quorum of Easterly stockholders is necessary to hold a valid meeting. A quorum will be present at the Easterly special meeting of stockholders if a majority in voting power of Easterly's common stock issued and outstanding and entitled to vote at the Easterly special meeting is present in person or represented by proxy. Abstentions will count as present for the purposes of establishing a quorum.

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        The approval of the Merger Proposal requires the affirmative vote of the holders of a majority of the outstanding shares of Easterly common stock. Accordingly, an Easterly stockholder's failure to vote by proxy or to vote in person at the Easterly special meeting of stockholders or an abstention from voting, or the failure of an Easterly stockholder who holds his or her shares in "street name" through a broker or other nominee to give voting instructions to such broker or other nominee (any failure to give instructions, a "broker non-vote") will have the same effect as a vote "AGAINST" the Merger Proposal. The approval of the Adjournment Proposal requires the affirmative vote of holders of a majority of the shares of Easterly common stock that are voted on such proposal at the Easterly special meeting of stockholders. Accordingly, an Easterly stockholder's failure to vote by proxy or to vote in person at the Easterly special meeting of stockholders or an abstention from voting will have no effect on the outcome of the vote on the Adjournment Proposal. A broker non-vote will have no effect on the Adjournment Proposal.

        The transactions contemplated by the Merger Agreement will be consummated only if the Merger Proposal is approved at the Easterly special meeting. The Merger Proposal is not conditioned on the approval of the Adjournment Proposal and the Adjournment Proposal is not conditioned on the approval of the Merger Proposal.

Recommendation to Easterly Stockholders (page 86)

        Easterly's board of directors believes that each of the Merger Proposal and the Adjournment Proposal to be presented at the Easterly special meeting of stockholders is advisable and in the best interests of Easterly and its stockholders and unanimously recommends that Easterly's stockholders vote "FOR" each of the proposals.

        When you consider the recommendation of Easterly's board of directors in favor of approval of these proposals, you should keep in mind that Easterly's directors and executive officers have interests in the Merger that are different from, or in addition to, your interests as an Easterly stockholder. These interests include, among other things:

    the 400,000 to 1.6 million total Founder Shares that the Sponsor (or its members) will hold immediately prior to the Merger, which will be exchanged for Sirius Group common shares at the Exchange Ratio in connection with the Merger;

    the 24,000 Founder Shares that one of Easterly's independent directors holds as of September 30, 2018, which will be exchanged for Sirius Group common shares at the Exchange Ratio in connection with the Merger;

    if Easterly is unable to complete a business combination within the required time period, the Convertible Promissory Note issued to the Sponsor (in the amount of $895,000 at September 30, 2018 plus accrued interest), will not be repaid and all amounts owed thereunder will be forgiven except to the extent that Easterly has funds available to it outside of the Trust Account to repay such amounts;

    if Easterly is unable to complete a business combination within the required time period, Easterly's Chairman, its Chief Executive Officer and David Cody will be personally liable to ensure that the proceeds in the Trust Account are not reduced by the claims of target businesses or claims of vendors or other entities that are owed money by Easterly for services rendered or contracted for or products sold to Easterly, but only if such a vendor or target business has not executed a waiver of claims against the Trust Account and except as to any claims under Easterly's indemnity of the underwriters; and

    the continued indemnification of current directors and officers of Easterly and the continuation of directors' and officers' liability insurance after the Merger.

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        Further, each of Easterly's directors, directly or indirectly, holds Founder Shares that are not subject to redemption and certain of Easterly's directors indirectly hold Private Placement Warrants that would retire worthless if a business combination is not consummated; as a result, Easterly's directors have a financial incentive to see a business combination consummated rather than lose whatever value is attributable to the Founder Shares and Private Placement Warrants. These interests may influence Easterly's directors in making their recommendation that you vote in favor of the Merger Proposal, and the transactions contemplated thereby.

Regulatory Approval

        The parties are not currently aware of any federal or state regulatory approvals that must be applied for or obtained in connection with the Merger.

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SUMMARY CONSOLIDATED HISTORICAL FINANCIAL DATA OF SIRIUS GROUP

        The following table sets forth summary consolidated historical financial information derived from Sirius Group's (i) audited financial statements included elsewhere in this proxy statement/prospectus as of December 31, 2017 and 2016 and for each of the three years ended December 31, 2017 and (ii) unaudited interim financial statements included elsewhere in this proxy statement/prospectus as of June 30, 2018 and for the six months ended June 30, 2018 and 2017. You should read the following summary financial information in conjunction with the section entitled "Management's Discussion and Analysis of Financial Condition and Results of Operations of Sirius Group" and Sirius Group's audited and unaudited interim financial statements appearing elsewhere in this proxy statement/prospectus.

 
  Six Months Ended June 30,   Years Ended December 31,  
 
  2018   2017   2017   2016   2015  
 
  (in millions, except for share and per share amounts)
 

Selected Statement of (Loss) Income Data

                               

Net earned insurance and reinsurance premiums

  $ 593.4   $ 467.8   $ 1,035.3   $ 890.1   $ 847.0  

Net investment income

    30.0     32.1     56.8     56.2     39.9  

Net realized investment (losses) gains

    4.1     (2.5 )   (27.2 )   288.3     138.5  

Net unrealized investment (losses) gains

    40.7     (22.5 )   (10.5 )   (238.2 )   102.5  

Other revenue

    79.0     2.3     21.7     9.1     (2.4 )

Loss and loss adjustment expenses

    292.4     255.4     811.2     519.3     422.7  

Insurance and reinsurance acquisition expenses

    129.8     94.0     197.2     210.3     189.8  

Other underwriting expenses

    81.4     57.9     106.1     107.3     107.9  

General and administrative expenses

    38.5     40.8     91.9     85.1     27.1  

Interest expense on debt

    15.5     9.6     22.4     34.6     26.6  

Net (loss) income attributable to common shareholder

    138.3     6.9     (156.1 )   32.5     291.2  

Comprehensive (loss) income attributable to common shareholder

    79.0     55.1     (78.3 )   (33.6 )   196.2  

Per Common Share Data:

   
 
   
 
   
 
   
 
   
 
 

Basic (loss) earnings per common share

  $ 1.11   $ 0.06   $ (1.30 ) $ 0.27   $ 2.43  

Diluted (loss) earnings per common share

  $ 1.11   $ 0.06   $ (1.30 ) $ 0.27   $ 2.43  

Cash dividends declared per common share

  $   $   $   $ 0.23   $  

Basic weighted average common shares outstanding(1)

    120,000,000     120,000,000     120,000,000     120,000,000     120,000,000  

Diluted weighted average common shares outstanding(2)

    120,000,000     120,000,000     120,000,000     120,000,000     120,000,000  

Operating Ratios:

   
 
   
 
   
 
   
 
   
 
 

Loss and loss adjustment expense ratio(3)

    49.3 %   54.6 %   78.4 %   58.3 %   49.9 %

Acquisition expense ratio(4)

    21.9 %   20.1 %   19.0 %   23.6 %   22.4 %

Other underwriting expense ratio(5)

    13.7 %   12.4 %   10.2 %   12.1 %   12.7 %

Combined ratio(6)

    84.9 %   87.1 %   107.6 %   94.0 %   85.0 %

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  As of June 30,
2018
  As of December 31,
2017
 
 
  (in millions, except for share and
per share amounts)

 

Selected Balance Sheet Data:

             

Total investments and cash

  $ 3,566.7   $ 3,604.3  

Reinsurance recoverable on unpaid losses

    358.3     319.7  

Total assets

    6,210.1     5,823.6  

Loss and loss adjustment expense reserves

    1,827.1     1,898.5  

Unearned insurance and reinsurance premiums

    800.5     506.8  

Debt

    695.9     723.2  

Total common shareholder's equity

    1,996.3     1,917.0  

Book value per common share

  $ 16.64   $ 15.98  

Diluted book value per common share

  $ 16.64   $ 15.98  

Common shares outstanding—basic(1)

    120,000,000     120,000,000  

Common shares outstanding—diluted(2)

    120,000,000     120,000,000  

(1)
As of June 30, 2018 and December 31, 2017, Sirius Group had 120,000,000 common shares outstanding. On April 27, 2016, Sirius Group split its 12,000 common shares by a multiple of 10,000 resulting in 120,000,000 common shares and changed the par value of the common shares from $1.00 per share to $0.01 per share. Sirius Group's basic and diluted earnings per share calculations have been retrospectively adjusted for all periods presented to reflect the change in capital structure.

(2)
As of June 30, 2018 and December 31, 2017, Sirius Group did not have any warrants outstanding, any employee stock plans issuing Sirius Group stock, or any other instruments that would give rise to additional Sirius Group shares outstanding. See Note 13 "Earnings per share" to Sirius Group's unaudited interim financial statements and Note 16 "Earnings per share" to Sirius Group's audited financial statements included elsewhere in this proxy statement/prospectus for additional information.

(3)
The loss and loss adjustment expense ratio is calculated by dividing loss and loss adjustment expenses by net earned insurance and reinsurance premiums.

(4)
The acquisition expense ratio is calculated by dividing insurance and reinsurance acquisition expenses by net earned insurance and reinsurance premiums.

(5)
The other underwriting expense ratio is calculated by dividing other underwriting expenses by net earned insurance and reinsurance premiums.

(6)
The combined ratio is calculated by combining the loss and loss adjustment ratio, the acquisition expense ratio, and the other underwriting expense ratio.

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SUMMARY CONSOLIDATED HISTORICAL FINANCIAL DATA OF EASTERLY

        The following table sets forth summary consolidated historical financial information derived from Easterly's (i) audited financial statements included elsewhere in this proxy statement/prospectus as of December 31, 2017 and for the years ended December 31, 2017 and 2016 and the period from April 29, 2015 (inception) to December 31, 2015 and (ii) unaudited financial statements included elsewhere in this proxy statement/prospectus as of June 30, 2018 and for the six months ended June 30, 2018 and 2017. You should read the following summary financial information in conjunction with the section entitled "Management's Discussion and Analysis of Financial Condition and Results of Operations of Easterly" and Easterly's financial statements and the related notes appearing elsewhere in this proxy statement/prospectus.

 
  Six Months
Ended
June 30, 2018
  Six Months
Ended
June 30, 2017
  Year Ended
December 31,
2017
  Year Ended
December 31,
2016
  April 29, 2015
(Inception) to
December 31,
2015
 

Statement of Operations Data:

                               

Operating expenses:

                               

Operating costs

  $ (976,215 ) $ (768,940 ) $ (1,293,499 ) $ (1,812,645 ) $ (979,434 )

State franchise taxes

    (120,488 )   (91,118 )   (181,118 )   (182,685 )   (121,858 )

Formation costs

                      (2,910 )

Loss from operations

    (1,096,703 )   (860,058 ) $ (1,474,617 ) $ (1,995,330 ) $ (1,104,202 )

Other income—interest income

    1,067,787     489,030     1,232,227     308,879     9,918  

Income (loss) before income tax expense

    2,899,755     (371,028 )   (242,390 )   (1,686,451 )   (1,094,284 )

Income tax expense

                     

Net income (loss)

  $ 2,899,755   $ (371,028 ) $ (242,390 ) $ (1,686,451 ) $ (1,094,284 )

Loss per common share:

                               

Basic and diluted

  $ 0.31   $ (0.12 ) $ (0.19 ) $ (0.29 ) $ (0.20 )

Weighted average shares outstanding (excluding shares subject to possible redemption):

                               

Basic and diluted

    6,553,463     6,383,279     6,412,873     6,221,263     5,469,153  

Cash Flow Data:

                               

Net cash used in operating activities

    (673,971 )   (626,482 ) $ (817,250 ) $ (479,543 ) $ (985,189 )

Net cash provided by (used in) investing activities

    5,610,230     154,554     50,126,164     216,448     (200,000,000 )

Net cash provided by financing activities

    (4,948,244 )   453,510     (49,319,611 )   15,000     201,257,855  

 

 
  As of
June 30,
2018
  As of
December 31,
2017
 

Balance Sheet Data:

             

Cash

  $ 1,889   $ 13,874  

Cash held in Trust Account—restricted

    146,665,970     151,208,413  

Total assets

    146,696,697     151,229,634  

Common stock, subject to possible redemption or tender, 12,674,622 and 13,544,944 shares at redemption value at June 30, 2018 and December 31, 2017, respectively

    130,833,516     136,335,119  

Total stockholders' equity

    5,000,001     5,000,001  

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SUMMARY CONDENSED COMBINED UNAUDITED PRO FORMA FINANCIAL INFORMATION

        The following tables set forth summary condensed combined pro forma financial information as of and for the six months ended June 30, 2018 and for the year ended December 31, 2017 to provide you with information about how the Merger and related transactions might have affected the historical financial statements of Sirius Group. The following summary condensed combined unaudited pro forma statements of (loss) income do not purport to represent, and are not necessarily indicative of, what the actual results of operations of the combined company would have been had these transactions taken place on the date indicated, nor are they indicative of the consolidated results of operations of the combined company for any future period. The following summary condensed combined unaudited pro forma balance sheet does not purport to represent, and is not necessarily indicative of, what the actual financial condition of the combined company would have been had these transactions taken place on the date indicated, nor is it indicative of the consolidated financial condition of the combined company as of any future date. The pro forma adjustments and assumptions are discussed in the section entitled "Unaudited Pro Forma Condensed Combined Financial Information".

 
  Pro forma
Six months ended
June 30, 2018
  Pro forma
Year ended
December 31, 2017
 
 
  (in millions, except for share and per share amounts)
 

Revenues

             

Net earned insurance and reinsurance premiums

  $ 593.4   $ 1,035.3  

Net investment income

    31.1     58.0  

Net realized and unrealized investment gains (losses)

    44.8     (37.7 )

Gain on forgiveness of debt

    2.9      

Other revenue

    101.1     79.7  

Total revenues

    773.3     1,135.3  

Expenses

             

Loss and loss adjustment expenses

    292.4     811.2  

Insurance and reinsurance acquisition expenses

    129.8     197.2  

Other underwriting expenses

    81.4     106.1  

General and administrative expenses

    40.9     98.4  

Intangible asset amortization expenses

    7.9     10.2  

Impairment of intangible assets

        5.0  

Accretion of fair value adjustment to loss and loss adjustment reserves

    0.1      

Interest expense on debt

    15.5     22.4  

Total expenses

    568.0     1,250.5  

Pre-tax income (loss)

    205.3     (115.2 )

Income tax expense

    (62.3 )   (26.4 )

Net income (loss)

    143.1     (141.6 )

Income attributable to non-controlling interests

    (0.6 )   (13.7 )

Accrued dividends on Series A redeemable preference shares

         

Net income (loss) attributable to common shareholders

  $ 142.5   $ (155.3 )

Per share data

             

Weighted average number of common shares outstanding—basic

    117,586,738     117,586,738  

Weighted average number of common shares outstanding—diluted

    118,451,870     117,586,738  

Basic earnings per share

  $ 1.07   $ (1.32 )

Diluted earnings per share

  $ 1.06   $ (1.32 )

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  As of June 30, 2018  
 
  (in millions)
 

Investments

  $ 3,436.7  

Cash

    110.7  

Total assets

  $ 6,206.7  

Loss and loss adjustment reserves

  $ 1,827.1  

Unearned insurance and reinsurance premiums

    800.5  

Debt

    695.9  

Total liabilities

    4,104.0  

Total equity

    1,901.4  

Total liabilities and shareholders' equity

  $ 6,206.7  

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RISK FACTORS

        You should carefully consider the following risk factors, in addition to the other information included in this proxy statement/prospectus, including matters addressed in the section entitled "Cautionary Statement Regarding Forward-Looking Statements" and the financial statements and notes to the financial statements included herein. Easterly and Sirius Group may face additional risks and uncertainties that are not presently known to them, or that Easterly and Sirius Group currently deem immaterial, which may also impair their businesses.

Risks Related to Sirius Group's Business and Industry

        The following risk factors apply to the business and operations of Sirius Group and will also apply to the business and operations of the combined company following the completion of the Merger.

Sirius Group is exposed to unpredictable catastrophic events that could adversely affect its results of operations and financial condition.

        Sirius Group writes reinsurance contracts and insurance policies that cover unpredictable catastrophic events. Covered unpredictable catastrophic events, predominantly in its property catastrophe excess line of business, include natural perils and other disasters, such as hurricanes, windstorms, earthquakes, floods, wildfires and severe winter weather. Catastrophes can also include terrorist attacks, explosions and infrastructure failures. Sirius Group has significant exposure to a potential major earthquake or series of earthquakes in California, the Midwestern United States, Canada, Japan and Latin America and to windstorm damage in Northern Europe, the Northeast United States, the United States Atlantic Coast (i.e., Massachusetts to Florida) and the United States Gulf Coast (i.e., Florida to Texas) regions and Japan.

        Similar exposures to losses caused by the same types of catastrophic events occur in other lines of business such as marine, aviation, contingency, casualty, trade credit and accident and health, including pandemic risk. Pandemic risk is the increase in mortality or morbidity over an annual period associated with a rapidly spreading virus (either within a highly populated geographic area or on a global basis) with a high mortality or morbidity rate. Sirius Group's catastrophe losses net of reinsurance and reinstatement premiums were $259 million, $109 million and $21 million for the years ended December 31, 2017, 2016 and 2015, respectively.

        The extent of catastrophe losses is a function of both the severity of the event and total amount of insured exposure affected by the event. Increases in the value and concentration of insured property or insured individuals, the effects of inflation, changes in weather patterns, such as climate change, and increased terrorism could increase the future frequency and/or severity of claims from catastrophic events. Claims from catastrophic events could materially adversely affect Sirius Group's results of operations and financial condition. Sirius Group's ability to write new reinsurance contracts and insurance policies could also be impacted as a result of corresponding reductions in Sirius Group's capital levels.

        Although Sirius Group attempts to manage its exposure to such events through a multitude of approaches, including geographic diversification, geographic limits, individual policy limits, exclusions or limitations from coverage, purchase of reinsurance and expansion of supportive collateralized capacity, the availability of these management tools may be dependent on market factors and, to the extent available, may not respond in the way that is expected. For instance, Sirius Group seeks to manage its exposure to catastrophe losses by limiting the aggregate insured value of policies in geographic areas with exposure to catastrophic events by estimating a probable maximum loss ("PML") for many different catastrophe scenarios and by buying reinsurance, including retrocession coverage. To manage and analyze aggregate insured values and PML, Sirius Group uses a variety of tools, including external and internal catastrophe modeling software packages. Estimates of PMLs are dependent on many

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variables, including assumptions about demand surge and storm surge, loss adjustment expenses, insurance-to-value for the underlying properties, the relationship of the actual event parameters to the modelled event and the quality of portfolio data provided to Sirius Group by ceding companies (in the case of Sirius Group's reinsurance operations). Accordingly, if these assumptions about the variables are incorrect, the losses Sirius Group might incur from an actual catastrophe could be materially higher than its expectation of losses generated from modelled catastrophe scenarios which could materially adversely affect Sirius Group's financial condition, liquidity or results of operations.

Given the inherent uncertainty of models, the usefulness of such models as a tool to evaluate risk is subject to a high degree of uncertainty that could result in actual losses that are materially different than Sirius Group's estimates including PMLs, and Sirius Group's financial results may be adversely impacted, perhaps significantly.

        Sirius Group uses third-party vendor analytic and modeling capabilities, including global property catastrophe models from AIR Worldwide Company ("AIR") and Risk Management Solutions Inc. ("RMS"), and Sirius Group's own proprietary models, including its property underwriting and pricing tool ("GPI"), which consolidates and reports on all its worldwide property exposures, to calculate expected PML from various property natural catastrophe scenarios. Sirius Group uses these models and software to help it control risk accumulation, inform management and other stakeholders of capital requirements and to improve the risk/return profile or minimize the amount of capital required to cover the risks in each reinsurance contract in Sirius Group's overall portfolio of reinsurance contracts. However, given the inherent uncertainty of modeling techniques and the application of such techniques, these models and databases may not accurately address a variety of matters impacting Sirius Group's coverages.

        For example, catastrophe modeling is dependent upon several broad economic and scientific assumptions, such as storm surge (the water that is pushed toward the shore by the force of a windstorm), demand surge (the localized increase in prices of goods and services that often follows a catastrophe) and zone density (the percentage of insured perils that would be affected in a region by a catastrophe). Third-party modeling software also does not provide information for all territories or perils (e.g., tsunami) for which Sirius Group writes business. Catastrophe modeling is inherently uncertain due to process risk (i.e., the probability and magnitude of the underlying event) and parameter risk (i.e., the probability of making inaccurate model assumptions).

        The inherent uncertainties underlying, or the incorrect usage or misunderstanding of these tools may lead to unanticipated exposure to risks relating to certain perils or geographic regions which could have a material adverse effect on Sirius Group's business, prospects, financial condition or results of operations.

Sirius Group's loss and LAE reserves may be inadequate to cover its ultimate liability for losses and as a result its financial results could be adversely affected.

        Sirius Group must maintain reserves adequate to cover its estimated ultimate liabilities for loss and loss adjustment expenses ("LAE"). Loss and LAE reserves are typically comprised of (i) case reserves for claims reported ("case reserves") and (ii) incurred but not reported ("IBNR") reserves for losses that have occurred but for which claims have not yet been reported and for expected future development on case reserves. These reserves are estimates of what the settlement and administration of claims will cost based on facts and circumstances then known to Sirius Group. These estimates involve actuarial and claims assessments, and requires Sirius Group to make a number of assumptions about future events that are subject to unexpected changes and are beyond its control, such as future trends in claim severity, frequency, inflation, legislative and judicial changes and other factors.

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        Because of uncertainties associated with estimating ultimate loss and LAE reserves, it is uncertain that Sirius Group's reserves are adequate. In the event that Sirius Group's reserves become insufficient to cover its actual losses and LAE, Sirius Group may need to add to its reserves, which could have a material adverse effect on Sirius Group's results of operations and financial condition.

        In addition, Sirius Group reserves for losses and LAE include an estimate of Sirius Group's ultimate liability for asbestos and environmental claims for which Sirius Group cannot estimate the ultimate value using traditional reserving techniques, and for which there are significant uncertainties in estimating the amount of Sirius Group's potential losses.

Sirius Group is reliant on financial strength and creditworthiness ratings, and any downgrade may have a material adverse effect on Sirius Group's business, prospects, financial condition, and results from operations.

        Third-party rating agencies assess and rate the financial strength, including claims-paying ability, of insurers and reinsurers. These ratings are based upon criteria established by the rating agencies and are subject to revision at any time at the sole discretion of the agencies. Some of the criteria relate to general economic conditions and other circumstances outside of the rated company's control. These financial strength ratings are used by policyholders, agents and brokers to assess the suitability of insurers and reinsurers as business counterparties and are an important factor in establishing the competitive position of insurance and reinsurance companies.

        The maintenance of an "A–" or better financial strength rating from A.M. Best Company Inc. ("A.M. Best") and/or S&P Global Ratings ("Standard & Poor's") is particularly important to the ability of Sirius Group's operating (re)insurance subsidiaries to bind property and casualty insurance and reinsurance business in most markets. General creditworthiness ratings are used by existing or potential investors to assess the likelihood of repayment on a particular debt issue. The maintenance of an investment grade creditworthiness rating (e.g., "BBB–" or better from Standard & Poor's or Fitch) is important to Sirius Group's ability to raise new debt with acceptable terms. Strong creditworthiness ratings are important factors that provide better financial flexibility when issuing new debt or restructuring existing debt.

        Rating agencies periodically evaluate Sirius Group to confirm that it continues to meet the criteria of the ratings previously assigned to Sirius Group.

        A downgrade, withdrawal or negative watch/outlook of the financial strength rating of Sirius Group's operating (re)insurance companies could severely limit or prevent Sirius Group from writing new policies or renewing existing policies, which could have a material adverse effect on Sirius Group's results of operations and financial condition. A downgrade, withdrawal or negative watch/outlook of Sirius Group's creditworthiness ratings could limit its ability to raise new debt or could make new debt more costly and/or have more restrictive conditions.

        Additionally, some of Sirius Group's assumed reinsurance contracts contain optional cancellation, commutation and/or funding provisions that would be triggered if A.M. Best and/or Standard & Poor's were to downgrade the financial strength ratings of Sirius Group's principal (re)insurance operating subsidiaries below "A-". A client may choose to exercise these rights depending on, among other things, the reasons for such a downgrade, the extent of the downgrade, the prevailing market conditions, the degree of unexpired coverage, and the pricing and availability of replacement reinsurance coverage. Sirius Group cannot predict in advance how many of its clients would actually exercise such rights in the event of such a downgrade, but widespread exercise of these options could be materially adverse.

        Following CMIG International's April 2016 acquisition of Sirius Group, A.M. Best issued a negative outlook in its rating of Sirius Group. The negative outlook reflected A.M. Best's concern over the credit profile of CMIG International, represented by CMIG International's high financial leverage. Fitch similarly lowered Sirius Group's rating by one notch due to its concern over CMIG International's short

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operating history, rapid business growth and high and increasing leverage. Sirius Group's credit ratings may continue to be impacted by actions taken by CMIG International.

Sirius Group's investment portfolio may suffer reduced returns or losses, which could adversely affect Sirius Group's results of operations and financial condition. Adverse changes in interest rates, foreign currency exchange rates, equity markets, debt markets or market volatility could result in significant losses to the fair value of Sirius Group's investment portfolio.

        Sirius Group's investment portfolio is overseen in accordance with the investment policy and guidelines approved by the Finance Committee of the Sirius Group board of directors. At June 30, 2018, Sirius Group's investment portfolio consisted of fixed-maturity investments (including U.S. and foreign government bonds, corporate debt, mortgage-backed, asset-backed and other fixed-maturity securities), short-term investments, equity securities, convertibles and other long-term investments, including hedge funds and private equity funds.

        Sirius Group invests to maximize long-term total returns (after-tax) while taking prudent levels of risk and maintaining a diversified portfolio subject to its investment guidelines, policy and various regulatory restrictions. However, investing entails substantial risks. Sirius Group may not achieve its investment objectives, and investment performance may vary substantially over time. Investment returns are an important part of Sirius Group's strategy to grow, and fluctuations in the fixed-income or equity markets could impair Sirius Group's results of operations and financial condition.

        Both Sirius Group's investment income and the fair market value of its investment portfolio are affected by general economic and market conditions, including fluctuations in interest rates, foreign currency exchange rates, debt market levels, equity market levels and market volatility.

        Interest rates are highly sensitive to many factors, including governmental monetary policies, domestic and international economic and political conditions and other factors beyond Sirius Group's control. In particular, a significant increase in interest rates could result in significant losses in the fair value of Sirius Group's investment portfolio. In addition, certain fixed-income securities, such as mortgage-backed and asset backed securities, carry prepayment risk or, in a rising interest rate environment, may not pre-pay as quickly as expected. Conversely, in a low interest rate environment, Sirius Group may be forced to reinvest proceeds from investments that have matured or have been prepaid or sold at lower yields, which will reduce Sirius Group's investment returns. Additionally, a change in interest rates could adversely affect Sirius Group's results of operations and financial condition.

        The table below summarizes the estimated effects of hypothetical increases and decreases in market interest rates on Sirius Group's fixed-maturity investments. The size of interest rate decreases presented may be limited in order to floor interest rates at a de minimis level.

($ in millions)
  Fair Value at
June 30, 2018
  Assumed Change
in Relevant
Interest Rate
  Estimated Fair
Value After
Change
in Interest Rate
  Pre-Tax Increase
(Decrease) in
Carrying Value
 

Fixed maturity investments

  $ 1,885.4     300 bp decrease   $ 2,021.1   $ 135.7  

          200 bp decrease     1,978.7     93.3  

          100 bp decrease     1,933.6     48.2  

          50 bp decrease     1,910.3     24.9  

          50 bp increase     1,857.8     (27.6 )

          100 bp increase     1,830.6     (54.8 )

          200 bp increase     1,776.0     (109.4 )

          300 bp increase   $ 1,721.5   $ (163.9 )

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        Sirius Group's investment portfolio is also exposed to investment credit risk, which is the risk that the value of certain investments may decrease due to a deterioration in the financial condition, operating performance or business prospects of, or the liquidity available to, one or more issuers of those securities or, in the case of mortgaged-back and other asset-backed securities, due to the deterioration of the loans or other assets that underlie the securities. Mortgage-backed securities are particularly sensitive to changes in U.S. economic conditions, including deterioration of the U.S. housing market and unemployment, among other factors.

        Sirius Group is also exposed to changes in equity markets. A significant decline in the equity markets, such as that experienced from September 2008 to March 2009, could have a material adverse effect on Sirius Group's results of operations and financial condition. Assuming a hypothetical 10% and 30% increase or decrease in the value of Sirius Group's equity securities and other long-term investments as of June 30, 2018, the carrying value of Sirius Group's equity securities and other long-term investments would have increased or decreased by approximately $73 million and $220 million pre-tax, respectively.

        Since a portion of Sirius Group's investment portfolio is invested in securities denominated in currencies other than the U.S. dollar, the value of Sirius Group's portfolio is sensitive to changes in foreign currency rates. Sirius Group is also exposed to changes in the volatility levels of various investment markets. The underlying conditions prompting such changes are outside of Sirius Group's control and could adversely affect the value of Sirius Group's investments and results of operations and financial condition.

An unexpected accumulation of attritional losses may adversely affect Sirius Group's operating results.

        In addition to Sirius Group's exposures to natural catastrophe and other large losses as discussed above, Sirius Group's operating results may be adversely affected by unexpectedly large accumulations of smaller losses. Sirius Group seeks to manage this risk by using appropriate underwriting processes to guide the pricing, terms and acceptance of risks. These processes, which may include pricing models, are intended to ensure that premiums received are sufficient to cover the expected levels of attritional losses and a contribution to the cost of natural catastrophes and large losses where necessary. However, it is possible that these underwriting approaches and/or pricing models may not work as intended and that actual losses from a class of risks may be greater than expected. Sirius Group's pricing models are also subject to the same limitations as the models used to assess exposures to natural catastrophe losses noted above. Accordingly, these factors could adversely impact Sirius Group's financial condition and/or operating results.

A decrease in the fair value of IMG, Armada and/or Sirius Group's intangible assets may result in future impairments.

        As of June 30, 2018, goodwill and intangible assets represented approximately 31% of Sirius Group's consolidated shareholders' equity. Goodwill and intangible assets are assessed for impairment on an annual basis or more frequently if events or changes in circumstances indicate that the carrying amount may not be recoverable. These assessments require Sirius Group to use significant judgment in making various estimates and assumptions, such as the determination of expected future cash flows and/or earnings, and actual results may ultimately be materially different from such estimates and assumptions. For example, expected future cash flows and/or earnings may be materially and negatively impacted as a result of, among other things, a decrease in renewals and new business, loss of key personnel, lower-than-expected yields and/or cash flows from Sirius Group's investment portfolio, as applicable, or higher-than-expected claims activity and incurred losses as well as other general economic factors. As a result of these potential changes, the estimated fair value of Sirius Group's goodwill and intangible assets may decrease, causing the carrying value to exceed the fair value and the goodwill and/or intangible assets to be impaired. If an impairment is determined to exist, the carrying value of

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the goodwill and/or intangible asset is adjusted to its implied fair value with the corresponding expense recorded in Sirius Group's income statement, as applicable, in the period in which the impairment is determined. If Sirius Group is required to record goodwill impairments in the future, its financial condition and results of operations would be negatively affected.

Sirius Group is exposed to unpredictable casualty insurance risks that could adversely affect its results of operations and financial condition.

        Sirius Group writes insurance and reinsurance policies covering casualty risks. Casualty insurance generally covers the financial consequences of the legal liability of an individual or organization resulting from negligent acts causing bodily injury and/or property damage to a third party. Claims from such business can take years to develop and settle and can be subject to unanticipated claims and economic inflation. Accordingly, if Sirius Group's pricing assumptions are incorrect, higher than expected losses could materially adversely affect Sirius Group's financial condition, liquidity or results of operations.

The property and casualty insurance and reinsurance industries are highly competitive and cyclical and Sirius Group may not be able to compete effectively in the future.

        The property and casualty insurance and reinsurance industries are highly competitive and have historically been cyclical, experiencing periods of severe price competition and less selective underwriting standards ("soft markets") followed by periods of relatively high prices and more selective underwriting standards ("hard markets"). Sirius Group competes with numerous reinsurance companies throughout the world and Lloyd's Syndicate 1945, the Lloyd's of London ("Lloyd's") syndicate that Sirius Group sponsors and that is managed through Sirius International's Managing Agent ("Syndicate 1945"), also competes with other Lloyd's syndicates and London market companies. Many of these competitors have greater financial, marketing and management resources available to them, including greater revenue and shareholders' equity, have established long-term and continuing business relationships throughout the insurance and reinsurance industries and may have higher financial strength ratings, which can be a significant competitive advantage for them.

        Soft primary insurance market conditions could lead to a significant reduction in reinsurance premium rates, less favorable contract terms and fewer submissions for Sirius Group's reinsurance underwriting capacity. The supply of reinsurance is also related to the level of reinsured losses and the level of industry capital which, in turn, may fluctuate in response to changes in rates of return earned in the reinsurance industry. As a result, the reinsurance business historically has been a cyclical industry characterized by periods of intense price competition due to excess underwriting capacity as well as periods when shortages of capacity permitted improvements in reinsurance rate levels and terms and conditions.

        In recent years, the persistent low interest rate environment and ease of entry into the reinsurance sector has led to increased competition from non-traditional sources of capital, such as insurance-linked funds or collateralized special purpose insurers, predominantly in the property catastrophe excess reinsurance market. This alternative capital provides collateralized property catastrophe protection in the form of catastrophe bonds, industry loss warranties and other risk-linked products that facilitate the ability of non-reinsurance entities, such as hedge funds and pension funds, to compete for property catastrophe excess reinsurance business outside of the traditional treaty market. This alternative capacity is also expanding into lines of business other than property catastrophe reinsurance.

        Consequently, the market is currently in a prolonged phase of the soft market cycle in many lines of business, particularly in certain property catastrophe excess reinsurance markets, and, as a result, many of Sirius Group's products are experiencing varying degrees of rate pressure. To the extent these

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trends continue or accelerate, Sirius Group's financial condition or operating results could be adversely affected.

Sirius Group may not successfully alleviate risk through reinsurance arrangements. Additionally, Sirius Group may not collect all amounts due from its reinsurers under its existing reinsurance arrangements.

        Sirius Group attempts to limit its risk of loss through the purchase of reinsurance, including retrocession coverage (i.e., the reinsurance of reinsurance). The availability and cost of reinsurance protection is subject to market conditions, which are outside of Sirius Group's control. In addition, the coverage provided by these reinsurance arrangements may be inadequate to cover Sirius Group's future liabilities. As a result, Sirius Group may not be able to successfully alleviate risk through these arrangements, which could have a material adverse effect on Sirius Group's results of operations and financial condition.

        Purchasing reinsurance does not relieve Sirius Group of the underlying obligations to policyholders or ceding companies, so any inability to collect amounts due from reinsurers could adversely affect Sirius Group's financial condition and results of operations. Inability to collect amounts due from reinsurers can result from a number of scenarios, including: (i) reinsurers choosing to withhold payment due to a dispute or other factors beyond Sirius Group's control; and (ii) reinsurers becoming unable to pay amounts owed to Sirius Group as a result of a deterioration in their financial condition. While Sirius Group regularly reviews the financial condition of its reinsurers and currently believes their financial condition is strong, it is possible that one or more of these reinsurers will be adversely affected by future significant losses or economic events, causing them to be unable or unwilling to pay amounts owed to Sirius Group.

        In addition, due to factors such as the price or availability of reinsurance coverage, Sirius Group sometimes decides to increase the amount of risk retained by purchasing less reinsurance. Such determinations have the effect of increasing Sirius Group's financial exposure to losses associated with such risks and, in the event of significant losses associated with a given risk, could have a material adverse effect on Sirius Group's financial condition and results of operations.

Sirius Group, or agents appointed by Sirius Group, may act based on inaccurate or incomplete information regarding the accounts Sirius Group underwrites, or such agents may exceed their authority or act fraudulently when binding policies on Sirius Group's behalf.

        Sirius Group, and its managing general underwriters ("MGUs") and other agents who have the ability to bind policies on Sirius Group's behalf, rely on information provided by insureds or their representatives when underwriting insurance policies. While Sirius Group may make inquiries to validate or supplement the information provided, Sirius Group may make underwriting decisions based on incorrect or incomplete information. It is possible that Sirius Group will misunderstand the nature or extent of the activities and the corresponding extent of the risks that Sirius Group insures because of its reliance on inadequate or inaccurate information. If any such agents exceed their authority or engage in fraudulent activities, Sirius Group's financial condition and results of operations could be materially adversely affected.

Unexpected volatility or illiquidity associated with some of Sirius Group's investments could significantly and negatively affect Sirius Group's financial results, liquidity and ability to conduct business.

        Sirius Group holds, or may in the future purchase, certain investments that include, but are not limited to, publicly traded equities, hedge funds, private equity funds, bonds, bank loans, emerging market debt, nonagency residential mortgage-backed securities, asset-backed securities, commercial mortgage-backed securities, derivatives and other investment products. During the height of the financial crisis, both fixed-income and equity markets were more illiquid and volatile than expected. If

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Sirius Group requires significant amounts of cash on short notice in excess of normal cash requirements, it may have difficulty selling these investments in a timely manner and/or be forced to sell them for less than it otherwise would have been able to realize. If Sirius Group is forced to sell its assets in unfavorable market conditions, there can be no assurance that it will be able to sell them for the prices at which it has recorded them and may be forced to sell them at significantly lower prices. As a result, Sirius Group's business, financial condition, liquidity or results of operations could be adversely affected.

        A portion of Sirius Group's investment portfolio consists of hedge fund and private equity fund investments. The underlying investments in these funds are typically publicly traded and private equity securities and investments, and, as such, are subject to market risks that are similar to Sirius Group's equity securities. However, these investments entail substantial risks and are generally illiquid. Redemption of investments in certain of these funds is subject to restrictions including lock-up periods where no redemptions or withdrawals are allowed, restrictions on redemption frequency and advance notice periods for redemptions. Amounts requested for redemptions remain subject to market fluctuations until the redemption effective date, which generally falls at the end of the defined redemption period.

Global climate change may have a material adverse effect on Sirius Group's operating results and financial condition.

        There are concerns that the higher level of weather-related catastrophes and other losses incurred by the industry in prior years is indicative of changing weather patterns, including as a result of global climate change, which could cause such events to persist. This would lead to higher overall losses that Sirius Group may not be able to recoup, particularly in the current economic and competitive environment, and higher reinsurance costs. In addition, rising sea levels are expected to add to the risks associated with coastal flooding in many geographical areas. Large scale climate change could increase both the frequency and severity of Sirius Group's loss costs associated with property damage and business interruption due to storms, floods and other weather-related events. Over the long-term, global climate change could impair Sirius Group's ability to predict the costs associated with future weather events and could also give rise to new environmental liability claims in the energy, manufacturing and other industries Sirius Group serves.

        Given the scientific uncertainty of predicting the effect of climate cycles and global climate change on the frequency and severity of natural catastrophes and the lack of adequate predictive tools, Sirius Group may be unable to adequately model the associated exposures and potential losses in connection with such catastrophes that could have a material adverse effect on Sirius Group's business, financial condition or results of operations.

Sirius Group has significant foreign operations that expose it to certain additional risks, including foreign currency risks and political risk.

        Through its multinational reinsurance operations, Sirius Group conducts business in a variety of foreign (non-U.S.) currencies, the principal exposures being the Swedish Krona, British Pound Sterling, Euro and Canadian dollar. As a result, a significant portion of Sirius Group's assets, liabilities, revenues and expenses are denominated in currencies other than the U.S. dollar and are therefore subject to foreign currency risk. Significant changes in foreign exchange rates may adversely affect Sirius Group's results of operations and financial condition.

        Sirius Group's foreign operations are also subject to legal, political and operational risks that may be greater than those present in the United States. As a result, Sirius Group's operations at these foreign locations could be temporarily or permanently disrupted.

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Sirius Group may suffer losses from unfavorable outcomes from litigation and other legal proceedings.

        In the ordinary course of business, Sirius Group is subject to litigation and other legal proceedings as part of the claims process, the outcomes of which are uncertain. Sirius Group maintains reserves for claims-related legal proceedings as part of its loss and LAE reserves. Adverse outcomes are possible and could negatively impact Sirius Group's financial condition.

        Furthermore, as industry practices and legal, judicial, social and other conditions change, unexpected issues related to claims and coverage may emerge. These issues may adversely affect Sirius Group's results of operations and financial condition by either extending coverage beyond Sirius Group's underwriting intent or by increasing the number and size of claims. In some instances, these changes may not become apparent until sometime after Sirius Group has issued the affected insurance contracts. Examples of emerging claims and coverage issues include, but are not limited to:

    new theories of liability and disputes regarding medical causation with respect to certain diseases;

    assignment-of-benefits agreements, where rights of insurance claims and benefits of the insurance policy are transferred to third parties, and which can result in inflated repair costs and legal expenses to insurers and reinsurers;

    claims related to data security breaches, information system failures or cyber-attacks; and

    claims related to blackouts caused by space weather.

        In addition, from time to time Sirius Group is subject to legal proceedings that are not related to the claims process. In the event of an unfavorable outcome in one or more non-claims legal matters, Sirius Group's ultimate liability may be in excess of amounts reserved and such additional amounts may be material to Sirius Group's results of operations and financial condition. Furthermore, it is possible that these non-claims legal proceedings could result in unexpected outcomes that may materially impact Sirius Group's business or operations.

The effects of, and uncertainty regarding, the U.K.'s withdrawal from the European Union could negatively impact Sirius Group's investment portfolio, business and results of operations.

        At a referendum in June 2016, the U.K. voted in favor of leaving the European Union, the process for which was commenced in March 2017 when the Prime Minister of the United Kingdom notified the European Council under Article 50 of the Treaty on the European Union of the United Kingdom's intention to leave. Since the referendum, there has been an increase in market volatility which has been further impacted by continuing uncertainty around the terms of the withdrawal. During withdrawal negotiations and beyond, the impact on the U.K. and European economies and the broader global economy could be significant, resulting in negative impacts, such as increased volatility and illiquidity, and potentially lower economic growth on markets in the U.K., Europe and globally, which may negatively impact the value of Sirius Group's investment portfolio, business and results of operations. The timing and terms of the U.K.'s withdrawal from the European Union could also have an adverse impact on the operation or prospects of Lloyd's. While Lloyd's has announced its intention to establish a European subsidiary company through which Lloyd's syndicates may be able to have access to the European Union single market, there can be no assurance that the Lloyd's European subsidiary will be authorized or that the arrangements envisaged will not result in increased costs for conducting business in the European Union's single market. In addition, Sirius International would lose its passporting rights to operate in the U.K. and its U.K. branch would be unable to operate should there be a withdrawal by the U.K. from the European Union without any agreement in place between the U.K. and the European Union, and without the U.K. government standing by its promise to allow financial institutions to operate under a temporary regime in the U.K.

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Sirius Group's reinsurance operations are largely dependent upon ceding companies' evaluation of risk.

        Sirius Group, like other reinsurance companies that write treaty reinsurance, generally does not evaluate separately each of the assumed individual insurance risks under Sirius Group's reinsurance contracts. As such, Sirius Group is largely dependent upon the cedents' original underwriting decisions. Sirius Group is subject to the risk that the cedents may not have adequately or accurately evaluated the risks that they have insured, and Sirius Group has reinsured, and that the premiums ceded may not adequately compensate Sirius Group for the risks it assumes. If Sirius Group's reserves are insufficient to cover the actual loss and LAE arising from Sirius Group's treaty reinsurance business, Sirius Group would have to strengthen its reserves and incur charges to its earnings. These charges could be significant and could have a material adverse effect on Sirius Group's results of operations and financial condition.

Consolidation in the insurance and reinsurance industries could adversely impact Sirius Group.

        The insurance and reinsurance industries have been consolidating over the past several years and the consolidation trend may continue and even accelerate in the near future. These consolidated client and competitor enterprises may try to use their enhanced market power to negotiate price reductions for Sirius Group's products and services and/or obtain a larger market share through increased line sizes. If competitive pressures reduce prices, Sirius Group would generally expect to reduce its future underwriting activities thus resulting in reduced premiums and a reduction in expected earnings. As the insurance industry consolidates, competition for customers will become more intense and the importance of sourcing and properly servicing each customer will become greater. Sirius Group could incur greater expenses relating to customer acquisition and retention, further reducing Sirius Group's operating margins. In addition, insurance companies that merge may be able to spread their risks across a consolidated, larger capital base so that they require less reinsurance. The number of companies offering retrocessional reinsurance may decline. Reinsurance intermediaries could also continue to consolidate, potentially adversely impacting Sirius Group's ability to access business and distribute its products. Sirius Group could also experience more robust competition from larger, better capitalized competitors. Any of the foregoing could adversely affect Sirius Group's business or its results of operations.

Since Sirius Group depends on a small number of brokers and MGUs for a large portion of its revenues, loss of business provided by any one of them could adversely affect Sirius Group.

        Sirius Group markets its reinsurance worldwide primarily through reinsurance brokers. The reinsurance brokerage industry generally, and Sirius Group's sources of business specifically, are concentrated. During 2017, 2016 and 2015, Sirius Group received 59%, 56% and 58%, respectively, of its reinsurance business from four major reinsurance brokers as follows: Aon Corporation and subsidiaries—22%, 22% and 24%, respectively; Guy Carpenter & Company and subsidiaries—18%, 18% and 18%, respectively; WT Butler and Co. Ltd.—10%, 8% and 7%, respectively; and Willis Group and subsidiaries—9%, 8% and 9%, respectively. A decision of one or more of these brokers to reduce substantially or eliminate its business with Sirius Group could adversely affect its business, results of operations or financial condition. In addition, numerous brokers and their affiliates have equity interests in reinsurance companies that compete with Sirius Group. These brokers may favor these reinsurers over other companies, including members of Sirius Group.

Sirius Group's reliance on intermediaries subjects it to the intermediaries' credit risk.

        In accordance with industry practice, Sirius Group frequently pays amounts owing in respect of claims under its contracts to reinsurance brokers and, to a lesser extent, MGUs that, in turn, make payments to the cedents. In the event that a broker or MGU fails to make such a payment, depending on the jurisdiction, Sirius Group may remain liable to the cedent for the deficiency. Conversely, when

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premiums for reinsurance contracts are paid to reinsurance brokers or MGUs for payment to Sirius Group, these premiums may be deemed to have been paid and the cedent may no longer be liable to Sirius Group for those amounts, whether or not actually received by Sirius Group. Intermediaries generally are less capitalized than the businesses Sirius Group reinsures and therefore may be unable to pay their debts when due. Consequently, Sirius Group faces credit risk associated with intermediaries during the payment process.

The regulatory framework under which Sirius Group operates and potential changes thereto could have a material adverse effect on its business.

        Sirius Group's activities are subject to extensive regulation under the laws and regulations of the U.S., the U.K., Bermuda, Sweden and the European Union and its member states and the other jurisdictions in which Sirius Group operates.

        Sirius Group's operations in each of these jurisdictions are subject to varying degrees of regulation and supervision. The laws and regulations of the jurisdictions in which Sirius Group's insurance and reinsurance subsidiaries are domiciled require, among other things, that these subsidiaries maintain minimum levels of statutory capital, surplus and liquidity, meet solvency standards, submit to periodic examinations of their financial condition and restrict payments of dividends, distributions and reductions of capital in certain circumstances. Statutes, regulations and policies to which Sirius Group's insurance and reinsurance subsidiaries are subject may also restrict the ability of these subsidiaries to write insurance and reinsurance policies, make certain investments and distribute funds.

        Sirius Group devotes a significant amount of time and resources to comply with various regulatory requirements imposed in Bermuda, Sweden, the U.S. and the U.K. There remains significant uncertainty as to the impact that these various regulations and legislation will have on Sirius Group. Such impacts could include constraints on Sirius Group's ability to move capital between subsidiaries or requirements that additional capital be provided to subsidiaries in certain jurisdictions, which may adversely impact Sirius Group's profitability. In addition, while Sirius Group currently has excess capital and surplus under applicable capital adequacy requirements, such requirements or similar regulations, in their current form or as they may be amended in the future, may have a material adverse effect on Sirius Group's business, financial condition or results of operations.

        Sirius Group's insurance and reinsurance operating subsidiaries may not be able to maintain necessary licenses, permits, authorizations or accreditations in territories where Sirius Group is currently engaged in business or obtain them in new territories, or may be able to do so only at significant cost. In addition, Sirius Group may not be able to comply fully with, or obtain appropriate exemptions from, the wide variety of laws and regulations applicable to insurance or reinsurance companies or holding companies. In addition to insurance and financial industry regulations, Sirius Group's activities are also subject to relevant economic and trade sanctions, money laundering regulations, and anti-corruption laws including the U.S. Foreign Corrupt Practices Act, U.K. Bribery Act 2010 and the Bermuda Bribery Act 2016, which may increase the costs of regulatory compliance, limit or restrict Sirius Group's ability to do business or engage in certain regulated activities, or subject Sirius Group to the possibility of regulatory actions or proceedings.

        There can be no assurance that Sirius Group, its employees, or its agents acting on Sirius Group's behalf are in full compliance with all applicable laws and regulations or their interpretation by the relevant authorities and, given the complex nature of the risks, it may not always be possible for Sirius Group to ascertain compliance with such laws and regulations. Failure to comply with or to obtain appropriate authorizations and/or exemptions under any applicable laws or regulations, including those referred to above, could subject Sirius Group to investigations, criminal sanctions or civil remedies, including fines, injunctions, loss of an operating license, reputational consequences, and other sanctions, all of which could have a material adverse effect on Sirius Group's business. Also, changes in the laws

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or regulations to which Sirius Group is subject could have a material adverse effect on its business. In addition, in most jurisdictions, government regulatory authorities have the power to interpret or amend applicable laws and regulations, and have discretion to grant, renew or revoke licenses and approvals Sirius Group needs to conduct its activities. Such governmental and regulatory authorities may require Sirius Group to incur substantial costs in order to comply with such laws and regulations.

Risks associated with changes in U.S. health care legislation could negatively affect Sirius Group's accident and health business.

        Sirius Group derives revenues from, among other things, the provision of accident and health premiums in the U.S., that is, providing insurance to institutions that participate in the U.S. healthcare delivery infrastructure. Changes in U.S. healthcare legislation, specifically the Patient Protection and Affordable Care Act of 2010 (the "Healthcare Act") (and legislative reforms related thereto), have made significant changes to the regulation of health insurance including, but not limited to, the healthcare delivery system, the healthcare cost reimbursement structure in the U.S. and the rate of growth of health care costs in the U.S. and may negatively affect Sirius Group's accident and health business. In addition, Sirius Group may be subject to regulations, guidance or determinations emanating from the various regulatory authorities authorized under the Healthcare Act. It is difficult to predict the effect that the Healthcare Act, or any regulatory pronouncement made thereunder, will have on Sirius Group's results of operations or financial condition.

Sirius Group may be unable to adequately maintain its systems and safeguard the security of its data, which may adversely impact Sirius Group's ability to operate its business and cause reputational harm and financial loss.

        Because Sirius Group's business and operations rely on secure and efficient information technology systems, Sirius Group depends on its ability and the ability of certain third parties, including vendors and business partners, to access Sirius Group's computer systems to perform necessary functions such as providing quotes and product pricing, billing and processing premiums, administering claims, and reporting its financial results. The functioning of these systems may be impacted by any number of events, including power outages, natural and man-made catastrophes, and cyber-attacks. In the event Sirius Group is unable to access its systems, or any third-party system that it relies upon, Sirius Group's ability to operate its business effectively may be significantly impaired.

        Sirius Group's business also depends upon its ability to securely process, store, transmit and safeguard confidential and proprietary information that is in Sirius Group's possession. This information includes confidential information relating to Sirius Group's business, and personally identifiable information ("PII") and protected health information ("PHI") belonging to employees, customers, claimants and business partners. As Sirius Group's systems may be vulnerable to a variety of forms of unauthorized access that could result in a data breach, including hackers, computer viruses, and other cyber-attacks, as well as breaches that result from dishonest employees, errors by employees or lost or stolen computer devices, Sirius Group may not be able to protect the confidentiality of such information.

        Third parties present an additional risk of cyber-related events. Sirius Group outsources certain technological and business process functions to third-party providers. Sirius Group relies on these third parties to maintain and store PII and PHI and other confidential information on their systems. As needed, Sirius Group also transmits such information by e-mail and other electronic means. Sirius Group attempts to establish sufficient controls and secure capabilities to transmit such information and to prevent unauthorized disclosure, but these controls may not be sufficient. Furthermore, third-party providers may not have appropriate controls in place to protect such information.

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        Sirius Group's computer systems have been and will continue to be the target of cyber-attacks, although Sirius Group is not aware that it has experienced a material cybersecurity breach. Sirius Group is also not aware of any third-party vendor having experienced a material cybersecurity breach that impacted Sirius Group's data. The risk of cyber-attack may increase, and Sirius Group may experience more significant attacks in the future. The risks identified above could expose Sirius Group to data breaches, disruptions of service, financial losses and significant increases in compliance costs and reputational harm to Sirius Group, any of which could affect its business and results of operations.

        In addition, a data breach that involves the compromise of PII or PHI could subject Sirius Group to legal liability or regulatory action under data protection and privacy laws and regulations enacted by federal, state and foreign governments, or other regulatory bodies. In particular, the European Union has passed the General Data Protection Regulation ("GDPR"), which came into force in May 2018. The GDPR includes more stringent operational requirements on entities that receive or process personal data (as compared to previous European Union law), along with significant penalties for non-compliance. As a result, Sirius Group's ability to conduct its business and Sirius Group's results of operations might be materially and adversely affected.

Operational risks, including human or systems failures, are inherent in Sirius Group's business.

        Operational risks and losses can result from many sources including fraud, errors by employees, failure to document transactions properly or to obtain proper internal authorization, failure to comply with regulatory requirements or information technology failures.

        Sirius Group's modeling, underwriting and information technology and application systems are critical to its business and reputation. Moreover, Sirius Group's technology and applications have been an important part of its underwriting process and ability to compete successfully. Such technology is and will continue to be a very important part of the underwriting process. Sirius Group has also licensed certain systems and data from third parties. Sirius Group cannot be certain that it will have access to these, or comparable service providers, or that Sirius Group's technology or applications will continue to operate as intended. In addition, Sirius Group cannot be certain that these service providers or consultants could be replaced without slowing Sirius Group's underwriting response time. A major defect or failure in Sirius Group's internal controls or information technology and application systems could result in management distraction, harm to Sirius Group's reputation, a loss or delay of revenues or increased expense.

Sirius Group depends on key personnel to manage the business effectively and they may be difficult to replace.

        Sirius Group's performance substantially depends on the efforts and abilities of its management team and other executive officers and key employees. Furthermore, much of Sirius Group's competitive advantage is based on the expertise, experience and know-how of its key management personnel. Sirius Group does not have fixed-term employment agreements with many of its key employees or key-man life insurance and the loss of one or more of these key employees could adversely affect Sirius Group's business, results of operations and financial condition. Sirius Group's success also depends on the ability to hire and retain additional personnel. Difficulty in hiring or retaining personnel could adversely affect Sirius Group's results of operations and financial condition.

Sirius Group faces unforeseen liabilities arising from possible acquisitions and dispositions of businesses or difficulties integrating acquired businesses.

        Sirius Group has engaged in acquisitions of businesses in the past, including the acquisitions of ArmadaCorp Capital, LLC ("Armada") and International Medical Group Acquisition, Inc. ("IMG") in

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2017, and may continue to do so in the future. Any future acquisitions may expose it to operational challenges and risks, including:

    integrating financial and operational reporting systems;

    establishing satisfactory budgetary and other financial controls;

    funding increased capital needs and overhead expenses;

    obtaining management personnel required for expanded operations;

    funding cash flow shortages that may occur if anticipated sales and revenues are not realized or are delayed, whether by general economic or market conditions or unforeseen internal difficulties;

    the value of assets acquired may be lower than expected or may diminish due to credit defaults or changes in interest rates and liabilities assumed may be greater than expected;

    the assets and liabilities acquired by Sirius Group may be subject to foreign currency exchange rate fluctuation; and

    financial exposures in the event that the sellers of the entities acquired are unable or unwilling to meet their indemnification, reinsurance and other obligations to Sirius Group.

        Sirius Group's ability to achieve the benefits anticipated from any business acquisition will depend in large part upon its ability to successfully integrate such businesses in an efficient and effective manner. Sirius Group may not be able to integrate such businesses successfully, or the process may take longer than expected. The integration of operations may require the dedication of significant management resources, which may distract management's attention from day-to-day business. If Sirius Group is unable to successfully integrate the operations of such acquired businesses, it may be unable to realize the full benefits it expects to achieve as a result of such acquisitions and Sirius Group's business and results of operations may be lower than expected.

Sirius Group may require additional capital in the future, which may not be available or may only be available on unfavorable terms.

        Sirius Group's future capital requirements depend on many factors, including regulatory requirements, the ability to write new business successfully, the frequency and severity of catastrophic events, and the ability to establish premium rates and reserves at levels sufficient to cover losses. Sirius Group may need to raise additional funds through financings or curtail its growth and reduce its assets. Any equity or debt financing, if available at all, may be on unfavorable terms. Disruption in the financial markets may limit Sirius Group's ability to access capital required to operate its business and Sirius Group may be forced to delay raising capital or bear a higher cost of capital, which could decrease Sirius Group's profitability and significantly reduce its financial flexibility. In addition, if Sirius Group experiences a credit rating downgrade, withdrawal or negative watch/outlook in the future, it could incur higher borrowing costs and may have more limited means to access capital. If Sirius Group cannot obtain adequate capital on favorable terms or at all, its business, results of operations and financial condition could be adversely affected.

Sirius Group has incurred losses in the past and may incur losses in the future.

        Sirius Group had a comprehensive (loss) income of approximately $(78) million, $(34) million and $196 million for 2017, 2016 and 2015, respectively. Sirius Group expects to incur increased operating expenses related to its growth initiatives, including the purchase of two MGUs, and primary insurance platform to support its business. If revenue fails to grow at anticipated rates, or if operating costs rise without a commensurate increase in revenue, then the imbalance between revenue and operating expenses will negatively impact Sirius Group's liquidity as well as its ability to achieve profitability in

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upcoming quarters. Sirius Group's lack of recent profitability may indicate that it needs to re-evaluate its plan of operations or change its strategies in order to generate a profit. A lack of profitability could adversely affect the price of its common shares and liquidity.

Sirius Group's results of operations may fluctuate significantly from period to period and may not be indicative of its long-term prospects.

        Sirius Group's results of operations may fluctuate significantly from period to period. These fluctuations result from a variety of factors, including the seasonality of the insurance and reinsurance business, the volume and mix of reinsurance and insurance products that Sirius Group writes, loss experience on Sirius Group's insurance and reinsurance liabilities, the performance of Sirius Group's investment portfolio and its ability to assess and integrate its risk management strategy effectively. In particular, Sirius Group seeks to underwrite products and make investments to achieve long-term results. As a result, at any given time, Sirius Group's short-term results of operations may not be indicative of its long-term prospects.

Sirius Group is a holding company with no direct operations, and its insurance and reinsurance subsidiaries' ability to pay dividends and other distributions to Sirius Group is restricted by law.

        Sirius Group is a holding company and carries out its business through its insurance and reinsurance subsidiaries. Accordingly, Sirius Group is dependent upon receipt of funds from other members of Sirius Group to fulfil its obligations. Sirius Group's subsidiaries may not be able to generate cash flow sufficient to pay a dividend or distribute funds to Sirius Group. In addition, under the insurance laws of certain jurisdictions in which Sirius Group's insurance and reinsurance subsidiaries are domiciled, an insurer or reinsurer is restricted with respect to the timing or the amount of dividends it may pay without prior approval by their relevant regulatory authorities.

        Sirius Group's top tier regulated insurance and reinsurance operating subsidiary, Sirius Bermuda Insurance Company Ltd. ("Sirius Bermuda"), has the ability to pay approximately $637 million of dividends to Sirius Group without prior approval of regulatory authorities during 2018, subject to meeting all appropriate liquidity and solvency requirements. Sirius Bermuda indirectly owns Sirius International Insurance Corporation, Sirius America Insurance Company and Sirius Group's other insurance and reinsurance operating companies, each of which are limited in their ability to pay dividends by the insurance laws of their relevant jurisdictions. See "Regulation of Sirius Group—Bermuda Insurance Regulation."

        As of June 30, 2018, Sirius Group and its intermediate holding companies had $47 million of net unrestricted cash, short-term investments and fixed-maturity investments outside of its regulated and unregulated insurance and reinsurance operating subsidiaries. Management believes that Sirius Group's cash balances, cash flows from operations and cash flows from investments are adequate to meet expected cash requirements for the foreseeable future on both a holding company and operating subsidiary level. However, if Sirius Group's insurance and reinsurance subsidiaries cannot pay dividends in future periods, it may have difficulty servicing its debt and meeting its holding company expenses. Dividend payments and other distributions from Sirius Group's subsidiaries also may be subject to withholding taxes, which would reduce the amount available to service Sirius Group's debt.

The current state of the global economy and capital markets increases the possibility of adverse effects on Sirius Group's financial position and results of operations. Economic downturns could impair Sirius Group's investment portfolio and affect the primary insurance market, which could, in turn, harm Sirius Group's results of operations and reduce the volume of new business.

        Global capital markets in the U.S. and Europe, as well as other leading markets, continue to experience volatility. Although conditions may be improving, the longer this economic situation persists,

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the greater the probability that these risks could have an adverse effect on Sirius Group's financial results. This may be evidenced in several ways including, but not limited to, a potential reduction in Sirius Group's premium income, financial losses in Sirius Group's investment portfolio and decreases in revenue and net income.

        Unfavorable economic conditions also could increase Sirius Group's funding costs, limit its access to the capital markets or result in a decision by lenders not to extend credit to Sirius Group. These events could prevent Sirius Group from increasing its underwriting activities and negatively impact Sirius Group's results of operations. In addition, Sirius Group's cedents and other counterparties may be affected by such developments in the financial markets, which could adversely affect their ability to meet their obligations to Sirius Group.

Risks Related to Tax Matters

        The following risk factors apply to the business and operations of Sirius Group and ownership of Sirius Group common shares and will also apply to the business and operations of the combined company and ownership of the combined company's common shares following the completion of the Merger.

Sirius Group has significant deferred tax assets, which may become devalued if either Sirius Group does not generate sufficient future taxable income or applicable corporate tax rates are reduced.

        Sirius Group's total net deferred tax liability as of December 31, 2017 was $38 million. Of that amount, $18 million relates to net deferred tax assets in the U.S. subsidiaries, $190 million relates to net deferred tax assets in Luxembourg subsidiaries, $11 million relates to net deferred tax assets in the United Kingdom subsidiaries, $257 million relates to net deferred tax liabilities in Sweden subsidiaries. Net deferred tax assets and liabilities reflect carryforward tax attributes and temporary differences between the book basis and tax basis of various assets and liabilities. Utilization of most deferred tax assets is dependent on generating sufficient future taxable income in the appropriate jurisdiction and/or entity. If it is determined that it is more likely than not that sufficient future taxable income will not be generated, Sirius Group would be required to increase applicable valuation allowance(s). Most of Sirius Group's deferred tax assets are determined by reference to applicable corporate income tax rates, in particular in the U.S., Luxembourg and Sweden. Accordingly, in the event of new legislation that reduces any such corporate income tax rates, the carrying value of certain of Sirius Group's deferred tax assets would decrease. A material devaluation in Sirius Group's deferred tax assets due to either insufficient taxable income or lower corporate income tax rates would have an adverse effect on Sirius Group's results of operations and financial condition.

Two of Sirius Group's Swedish non-insurance subsidiaries are involved in tax disputes.

        The Swedish Tax Authority ("STA") has denied deductions claimed by two of Sirius Group's Swedish subsidiaries in certain tax years for interest they paid on intra-group debt instruments. Sirius Group is currently challenging the STA's denial in court based on the technical merits. Sirius Group's reserve for uncertain tax positions has taken into account relevant developments in these tax disputes and in applicable Swedish tax law including recent case law. Sirius Group also has taken into account the Stock Purchase Agreement by which Sirius Group was sold to CMIG International in 2016. Pursuant to such agreement, the seller agreed to indemnify the buyer and Sirius Group for, among other things, (i) any additional tax liability in excess of Sirius Group's accounting for uncertain tax positions for tax periods prior to the sale of Sirius Group to CMIG International, and (ii) an impairment in Sirius Group's net deferred tax assets resulting from a final determination by a tax authority. While Sirius Group intends to continue challenging the STA's denial based on the technical merits, the ultimate resolution of these tax disputes is uncertain and no assurance can be given that there will be no material changes to Sirius Group's operating results or balance sheet in connection with these uncertain tax positions or the related indemnification.

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Sirius Group may be treated as a PFIC, in which case a U.S. holder of Sirius Group common shares would be subject to disadvantageous rules under U.S. federal income tax laws.

        If Sirius Group is considered a passive foreign investment company ("PFIC") for U.S. federal income tax purposes, a U.S. shareholder will be subject to adverse tax consequences, including subjecting the U.S. shareholder to a greater tax liability than might otherwise apply and subjecting the U.S. shareholder to tax on amounts in advance of when tax would otherwise be imposed, in which case its investment in Sirius Group could be materially adversely affected. In addition, if Sirius Group were considered a PFIC, upon the death of any U.S. individual owning shares, such individual's heirs or estate would not be entitled to a "step-up" in the basis of the shares that might otherwise be available under U.S. federal income tax laws. A U.S. shareholder may avoid some of the adverse tax consequences of owning an equity interest in a PFIC by making a qualified electing fund election. If Sirius Group is a PFIC, an electing U.S. shareholder is likely to recognize income in a taxable year in amounts significantly greater than the distributions received from Sirius Group, if any, in such taxable year.

        Sirius Group will be treated as a PFIC for U.S. federal income tax purposes in any taxable year for which either (i) at least 75% of Sirius Group's gross income consists of certain types of "passive income" or (ii) at least 50% of the average value of Sirius Group's assets produce, or are held for the production of, "passive income." Unless an exception applies, "passive income" includes dividends, interest, rents and royalties. For these purposes, if Sirius Group owns (directly or indirectly) at least 25% (by value) of the stock of another corporation, for purposes of determining whether Sirius Group is a PFIC, Sirius Group is treated as if it held the proportionate share of the assets of such other corporation, and as if it received directly the proportionate share of the income of such other corporation. Under a specific exception, as amended by the 2017 tax reform known as the Tax Cuts and Jobs Act (Pub. L. 115-97) ("2017 Tax Cuts and Jobs Act"), passive income does not include income derived in the active conduct of an insurance business by a qualifying insurance corporation. Whether an insurance company is a qualifying insurance corporation is determined based on an assets to liability test. The test requires the insurance company to have applicable insurance liabilities in excess of 25% of its total assets as reported on the company's financial statements.

        Based on Sirius Group's assets, income and activities, including those of its subsidiaries engaged in the active conduct of an insurance business, Sirius Group does not expect that it will be treated as a PFIC in 2018; however, this conclusion is not free from doubt and the IRS could take the position that Sirius Group is a PFIC. While Sirius Group expects its insurance subsidiaries will qualify for the active insurance income exception for qualified insurance corporations, absent regulations and other detailed guidance relating to the interpretations of the 2017 Tax Cuts and Jobs Act, there can be no assurance that Sirius Group's insurance subsidiaries will meet the requirements for this exception. Moreover, PFIC classification is a factual determination made annually, and even if Sirius Group is not a PFIC in 2018, it could become a PFIC in later years. Accordingly, Sirius Group cannot assure you that it will not be treated as a PFIC for 2018 or for any future year. Please see "Material Tax Consequences—Material U.S. Tax Consequences—Taxation of U.S. Holders—PFIC Provisions" for a more comprehensive discussion regarding Sirius Group's status as a PFIC and the tax consequences to U.S. holders of Sirius Group common shares if Sirius Group is treated as a PFIC.

Sirius Group may become subject to increased taxation in Bermuda and other countries as a result of the OECD's plan on "base erosion and profit shifting".

        The Organisation for Economic Cooperation and Development ("OECD"), with the support of the Group of Twenty ("G20"), initiated the "base erosion and profit shifting" ("BEPS") project in 2013 in response to concerns that international tax standards have not kept pace with changes in global business practices and that changes are needed to international tax laws to address situations where multinational enterprises may pay little or no tax in certain jurisdictions by shifting profits away from

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jurisdictions where the activities creating those profits may take place. In October 2015, the OECD issued "final reports" in connection with the BEPS project. The final reports were approved for adoption by the G20 finance ministers in November 2015 and provide the basis for international standards for corporate taxation, which are designed to prevent, among other things, treaty-shopping, the artificial shifting of income to tax havens and low-tax jurisdictions, the erosion of the tax base through interest deductions on intercompany debt and the artificial avoidance of permanent establishments (i.e., tax nexus with a jurisdiction). Action 6 (treaty abuse) led to the development of a global multilateral instrument to incorporate and facilitate changes to tax treaties, which was signed on June 7, 2017.

        Legislation to adopt these standards has been enacted or is currently under consideration in a number of jurisdictions, including country-by-country reporting. As a result, Sirius Group's earnings may be subject to income tax, or intercompany payments may be subject to withholding tax, in jurisdictions where they are not currently taxed or at higher rates of tax than currently taxed. The applicable tax authorities could also attempt to apply such taxes to past earnings and payments. Any such additional taxes could materially increase Sirius Group's effective tax rate. Also, the adoption of these standards may increase the complexity and costs associated with tax compliance and adversely affect Sirius Group's financial position and results of operations.

Sirius Group may become subject to income tax (or an increased amount of income tax) in one or more countries, including the United States, which could materially reduce Sirius Group's after-tax returns and the value of Sirius Group common shares.

        Due to their business operating models, a portion of the income of two of Sirius Group's foreign insurance companies is treated as effectively connected with a U.S. trade or business, and Sirius Group complies with the applicable U.S. income tax filing and payment requirements accordingly. Other than these deemed U.S. businesses, Sirius Group (including its foreign subsidiaries) currently intends to conduct substantially all of its businesses and operations in a manner such that it will not otherwise be engaged in a trade or business in the United States and will not be subject to more U.S. income tax than it currently incurs. However, the matter is not free from doubt in light of the applicable tax law and guidance regarding activities that constitute being engaged in a trade or business in the United States for U.S. federal income tax purposes. Accordingly, Sirius Group cannot assure you that the IRS will not contend, perhaps successfully, that a foreign entity in Sirius Group is engaged in a trade or business in the United States or is subject to more U.S. income tax than it currently incurs. A foreign corporation deemed to be so engaged would be subject to U.S. federal income tax, as well as branch profits tax, on its income that is treated as effectively connected with the conduct of that trade or business unless the corporation is entitled to relief under an applicable tax treaty.

        Sirius Group could become subject to income tax in one or more countries, including the United States, as a result of activities performed by it, adverse developments or changes in law, contrary conclusions by the relevant tax authorities or other causes. The imposition of any of these income taxes could materially reduce Sirius Group's post-tax returns available for distributions on, and consequently the value of, Sirius Group common shares.

The impact of Bermuda's letter of commitment to the OECD to eliminate harmful tax practices is uncertain and could adversely affect Sirius Group's tax status in Bermuda.

        The OECD has published reports and launched a global dialogue among member and non-member countries on measures to limit harmful tax competition. These measures are largely directed at counteracting the effects of tax havens and preferential tax regimes in countries around the world. According to the OECD, Bermuda is a jurisdiction that has substantially implemented the internationally agreed tax standard and as such is listed on the OECD 'white list'. However, Sirius

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Group is unable to predict whether any changes will be made to this classification or whether any such changes will subject Sirius Group or its Bermuda operations to additional taxes.

An "ownership change" could limit Sirius Group's ability to utilize tax loss and credit carryforwards in the United States to offset future taxable income.

        As of December 31, 2017, Sirius Group had a deferred tax asset (net of valuation allowance) in the United States of approximately $49 million representing tax attributes including net operating loss carryforwards and tax credit carryforwards. Sirius Group's ability to use the tax attributes underlying such deferred tax asset to offset future taxable income may be significantly limited if Sirius Group experiences an "ownership change" as defined in Section 382 of the Code. In general, an ownership change will occur when the percentage of ownership (by value) of one or more "5-percent shareholders" (as defined in the Code) in Sirius Group common shares has increased by more than 50% over the lowest percentage owned by such shareholders at any time during the prior three years (calculated on a rolling basis). An entity that experiences an ownership change generally will be subject to an annual limitation on its pre-ownership change tax loss and credit carryforwards equal to the equity value of the corporation immediately before the ownership change, multiplied by the long-term, tax-exempt rate posted monthly by the IRS (subject to certain adjustments). The limitation on Sirius Group's ability to utilize tax loss and credit carryforwards arising from an ownership change under Section 382 would depend on the value of Sirius Group's equity at the time of any ownership change. If Sirius Group were to experience an "ownership change", it is possible that a significant portion of Sirius Group's tax loss and credit carryforwards could expire before Sirius Group would be able to use them to offset future taxable income.

The ongoing effects of the 2017 Tax Cuts and Jobs Act and BEAT could make Sirius Group's results difficult to predict.

        Sirius Group's effective tax rate may fluctuate in the future as a result of the 2017 Tax Cuts and Jobs Act, which included significant enacted changes in U.S. income tax law that had a meaningful impact on Sirius Group's provision for income taxes and requires significant judgments and estimates in the interpretation and calculations. Sirius Group made reasonable estimates of the effects and recorded provisional amounts in its financial statements for the year ended December 31, 2017. However, Sirius Group cannot assure that the IRS will apply the new tax law in a way similar to Sirius Group's interpretation.

        The enacted tax legislation included, among other new provisions, a reduction in the corporate tax rate, new limitations on the deductibility of net interest, and the Base Erosion and Anti-Abuse Minimum Tax ("BEAT"). Subject to any regulations issued by the U.S. Department of the Treasury, the BEAT levies a significant tax on cross border payments to related group companies. This tax will subject intragroup reinsurance arrangements to a base erosion tax on premiums ceded. While Sirius Group intends to operate in a manner that limits its exposure to BEAT, at this time, absent regulations and other detailed guidance, uncertainty about the financial impact on Sirius Group of this new tax remains and Sirius Group cannot reassure you it will not be subject to material amounts of BEAT in the future. Accordingly, BEAT could materially impact Sirius Group's provision for taxes in the future.

Sirius Group may be subject to tax withholding under FATCA, which may reduce investment returns and distributions to shareholders.

        The Hiring Incentives to Restore Employment Act provides that a 30% withholding tax will be imposed on certain payments of U.S. source income and certain payments of proceeds from the sale of property that could give rise to U.S. source interest or dividends unless Sirius Group and the applicable foreign subsidiaries enter into an agreement with the IRS to disclose the name, address and taxpayer identification number of certain U.S. persons that own, directly or indirectly, an interest in Sirius

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Group as well as certain other information relating to any such interest (these rules are commonly known as the Foreign Account Tax Compliance Act, or "FATCA"). The IRS has released regulations and other guidance that provide for the phased implementation of the foregoing withholding and reporting requirements. On December 19, 2013, the United States Department of the Treasury signed a Model 2 non-reciprocal intergovernmental agreement (the "Model 2 IGA") with Bermuda. The Model 2 IGA modifies the foregoing requirements but generally requires similar information to be disclosed to the IRS. Although Sirius Group will attempt to satisfy any obligations imposed on it to avoid the imposition of this withholding tax, no assurance can be given that it will be able to satisfy these obligations. If Sirius Group or its subsidiaries become subject to a withholding tax as a result of FATCA, the return of all shareholders may be materially adversely affected.

U.S. tax-exempt organizations who own Sirius Group common shares may recognize unrelated business taxable income.

        A U.S. tax-exempt organization may recognize unrelated business taxable income if Sirius Group is a "controlled foreign corporation" (which we also refer to as a "CFC") as discussed below, and the organization is a 10% U.S. Shareholder, or if the related person insurance income ("RPII") inclusion rules above apply. U.S. tax-exempt organizations should consult their own tax advisors regarding the risk of recognizing unrelated business taxable income as a result of the ownership of Sirius Group common shares. A "10% U.S. Shareholder" is a U.S. person who owns (directly, indirectly through foreign entities or constructively) at least 10% of the total combined voting power of Sirius Group's voting shares, or at least 10% of the total value of shares of all classes of stock of such foreign corporation.

Changes in United States federal income tax law and other jurisdictions could materially adversely affect an investment in Sirius Group common shares.

        The U.S. federal income tax laws and interpretations regarding whether a company is engaged in a trade or business within the United States or whether a company is a CFC or PFIC or has RPII are subject to change, possibly on a retroactive basis. Treasury regulations were issued in proposed form regarding the application of the PFIC rules to an insurance company. Additionally, the 2017 Tax Cuts and Jobs Act changed in material ways the tests for whether a foreign insurance company is a PFIC, and no regulations have yet been issued with respect to these new rules. Additionally, the Treasury regulations regarding RPII are still in proposed form. New Treasury regulations or pronouncements interpreting or clarifying such rules may be forthcoming from the IRS. It is not possible to predict if, when or in what form such guidance will be provided and whether such guidance will be applied on a retroactive basis. Due to the absence of specific authority with respect to these issues, the amount, timing and character of income, gain or loss recognized with respect to a U.S. shareholder could be significantly different from that described herein. See "Material Tax Consequences—Material U.S. Tax Consequences." Additionally changes in tax law in non-U.S. jurisdictions may also adversely affect Sirius Group's tax treatment and that of its subsidiaries. You are urged to consult your own tax advisor regarding the tax consequences of owning Sirius Group shares in your particular circumstances.

Reduced U.S. federal income tax rates for qualified dividend income may not be available in the future.

        As long as Sirius Group common shares are readily tradable on an established securities market in the United States and it is not a PFIC, then under current U.S. law, dividends paid on Sirius Group common shares to U.S. individual shareholders should qualify as "qualified dividend income" and be eligible for reduced U.S. federal income tax rates. The U.S. Congress has, in the past, considered legislation that would exclude shareholders of foreign corporations from this preferential U.S. federal income tax treatment unless either (i) the corporation is organized or created under the laws of a country that has entered into a "comprehensive income tax treaty" with the United States or (ii) the stock of such corporation is readily tradable on an established securities market in the United States

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and the corporation is organized or created under the laws of a country that has a "comprehensive income tax system" that the U.S. Secretary of the Treasury determines is satisfactory for this purpose. Sirius Group would likely not satisfy either of these tests and, accordingly, if this or similar legislation were to become law, individual U.S. shareholders would no longer qualify for reduced U.S. federal income tax rates on dividends paid by it.

Sirius Group may be treated as a CFC and might be subject to the rules for related person insurance income, and in either case this may subject a U.S. holder of Sirius Group common shares to disadvantageous rules under U.S. federal income tax laws.

        A CFC for U.S. federal income tax purposes is any foreign corporation if, on any day of the taxable year, 10% U.S. Shareholders own (directly, indirectly through foreign entities or by attribution by application of certain constructive ownership rules) more than 50% (25% in the case of certain insurance companies) of the total combined voting power of all classes of that corporation's voting shares, or more than 50% (25% in the case of certain insurance companies) of the total value of all the corporation's shares. If Sirius Group is a CFC, each 10% U.S. Shareholder must annually include in its income its pro rata share of Sirius Group's "subpart F income," and its "global intangible low-taxed income" even if no distributions are made. Given Sirius Group's current share ownership, it believes it is unlikely that any U.S. person who acquires Sirius Group common shares in the Merger will become a 10% U.S. Shareholder. However, because of the complexity of the attribution rules contained in the Code, Sirius Group cannot be certain that this will be the case.

        If, with respect to any of Sirius Group's non-U.S. insurance subsidiaries, (i) 20% or more of the gross income in any taxable year is attributable to insurance or reinsurance policies of which the direct or indirect insureds are direct or indirect U.S. shareholders of Sirius Group (regardless of the number of shares owned by those shareholders) or persons related to such U.S. shareholders and (ii) direct or indirect insureds, whether or not U.S. persons, and persons related to such insureds own directly or indirectly 20% or more of the voting power or value of Sirius Group's shares, any U.S. person who owns any shares directly or indirectly on the last day of the taxable year would most likely be required to include its allocable share of the RPII of the applicable subsidiary for the taxable year in its income, even if no distributions are made. Sirius Group believes it is not likely that these conditions will be satisfied. However, Sirius Group cannot assure you that this will be the case. Consequently, Sirius Group cannot assure you that a person who is a direct or indirect U.S. shareholder will not be required to include amounts in its income in respect of RPII in any taxable year.

        See "Material Tax Consequences—Material U.S. Tax Consequences—Taxation of U.S. Holders—CFC Provisions" for a more comprehensive discussion regarding our status as a CFC and the tax consequences to U.S. holders of Sirius Group common shares if Sirius Group is treated as a CFC or if the RPII inclusion rules apply.

Sirius Group may become subject to taxes in Bermuda after March 31, 2035, which may have a material adverse effect on its results of operations and your investment.

        The Bermuda Minister of Finance, under the Exempted Undertakings Tax Protection Act 1966 of Bermuda, as amended, has given Sirius Group and each of its Bermuda incorporated subsidiaries an assurance that if any legislation is enacted in Bermuda that would impose tax computed on profits or income, or computed on any capital asset, gain or appreciation, or any tax in the nature of estate duty or inheritance tax, then the imposition of any such tax will not be applicable to any such entity or any of its operations, shares, debentures or other obligations until March 31, 2035, except insofar as such tax applies to persons ordinarily resident in Bermuda or to any taxes payable by it in respect of real property owned or leased by it in Bermuda. See "Material Tax Consequences—Material Bermuda Tax Consequences". Given the limited duration of the Bermuda Minister of Finance's assurance, there can be no assurance that Sirius Group will not be subject to any Bermuda tax after March 31, 2035.

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U.S. Treasury Regulations may limit Sirius Group's ability to make acquisitions of U.S.-domiciled companies using corporate stock.

        On April 4, 2016 and July 12, 2018, the IRS and the Treasury Department issued final and temporary regulations on corporate inversions. Among other provisions, the regulations provide for a "cash box rule" that in general reduces a foreign corporation's value by the percentage of passive assets it holds for the purpose of applying the inversion ownership test. Failure of such test could result in the acquiring corporation being taxed as a U.S. corporation. As a result of these regulations, the size of any U.S. company that Sirius Group could acquire for stock may need to be dramatically reduced to avoid severe adverse tax consequences. Sirius Group would need to monitor its passive assets to avoid such adverse tax consequences.

The tax treatment of the Merger is not entirely clear. Neither Easterly nor Sirius Group have sought a ruling from the IRS that the Merger will be treated as tax-deferred reorganization for United States federal income tax purposes and Sirius Group is not obligated by the terms of the Merger Agreement to ensure that the Merger will so qualify.

        Sirius Group and Easterly intend to report the Merger as a tax-deferred "reorganization" for United States federal income tax purposes within the meaning of Section 368 of the Code. Assuming such treatment is respected, holders of Easterly common stock generally will not recognize gain or loss for U.S. federal income tax purposes as a result of the exchange of their Easterly common stock for Sirius Group common shares (except with respect to cash received in lieu of fractional shares). Neither Sirius Group nor Easterly intends to request any ruling or other guidance from the IRS on the United States federal income tax treatment of the Merger and no assurance can be given that the IRS would not challenge such treatment. The qualification of the Merger as a tax-deferred reorganization is not a condition to closing and the Merger Agreement does not include any covenant requiring Sirius Group to ensure that the Merger qualifies as a tax-deferred reorganization.

        In connection with the registration statement of which this proxy statement/prospectus forms a part, Sirius Group has received an opinion of counsel that subject to certain representations, qualifications and assumptions it is more likely than not that the Merger will qualify as a "reorganization" within the meaning of section 368 of the Code. This opinion is subject to assumptions related to future events (described in more detail under "Proposal No. 1—The Merger Proposal—U.S. Federal Income Tax Considerations of the Merger to Holders of Easterly Common Stock or Easterly Warrants—Treatment of the Merger") because the qualification of the Merger as a reorganization depends on meeting certain technical requirements that cannot be determined at this time, and no assurance can be given that such assumptions will in fact be correct. More specifically, the treatment of the Merger as a reorganization would depend on whether sufficient stockholders of Easterly exchange their Easterly common stock for common shares of Sirius Group rather than redeem it for cash. If a significant number of stockholders decide to redeem their Easterly common stock, Easterly may not meet the "continuity of business enterprise" requirement necessary to qualify as a reorganization under Sections 368(a)(1)(B) and 368(a)(2)(E) of the Code and would not meet the requirement that it retain "substantially all" of its assets to qualify as a reorganization under Section 368(a)(2)(E) of the Code. Additionally, absent direct guidance, it is unclear whether certain transactions would result in the stockholders being treated as having received "boot" in the Merger, thereby denying the treatment of the Merger as a reorganization under Section 368(a)(1)(B) of the Code. These transactions include the post-closing adjustments reflecting the Exchange Ratio and the Promissory Note dated June 23, 2018, made by Easterly in favor of Sirius Group pursuant to which Sirius Group has agreed to lend Easterly $0.03 per month for every public share of Easterly common stock outstanding as of June 30, 2018, which loan is immediately payable back to Sirius Group if the Merger closes. While none of these transactions results in any former stockholder of Easterly receiving any cash or other property (other than common shares of Sirius Group) in the Merger in return for their Easterly common stock, no

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assurance can be given that the IRS would not challenge this treatment. Additionally, no assurance can be given that the IRS would not recharacterize the repurchase of Sirius Group stock held by CM Bermuda in an amount equal to the value of the Easterly Trust Account as a distribution by Easterly to Sirius Group notwithstanding that Sirius Group intends to use other sources of cash for such repurchase. If the transaction was so recharacterized, Easterly would neither meet the continuity of business enterprise requirement nor the "substantially all" requirement described above.

        If the IRS were to successfully challenge the tax-deferred reorganization treatment of the Merger, United States holders of Easterly common stock would recognize taxable gain or loss on the exchange of their Easterly common stock for common shares of Sirius Group in the Merger.

        You are strongly urged to consult with your own tax advisor to determine the particular U.S. federal, state or local or foreign income or other tax consequences of the Merger to you. For more information see the section entitled "Proposal No. 1—The Merger Proposal—U.S. Federal Income Tax Considerations of the Merger to Holders of Easterly Common Stock or Easterly Warrants—Treatment of the Merger."

Risks Related to Sirius Group Common Shares

        The following risk factors apply to the common shares of Sirius Group and will also apply to the common shares of the combined company following the completion of the Merger.

There can be no assurance that Sirius Group common shares and the converted warrants will be approved for listing on Nasdaq in connection with the Merger, or if approved, that Sirius Group will be able to comply with the continued listing standards of Nasdaq.

        Easterly's common stock, units and warrants are currently listed on the Nasdaq Capital Market. In connection with the Merger, Sirius Group will be required to demonstrate compliance with Nasdaq's initial listing requirements, which are more rigorous than Nasdaq's continued listing requirements, in order to list its securities on Nasdaq. Sirius Group's eligibility for listing may depend on, among other factors, the number of shares of Easterly common stock that are redeemed in connection with the Merger Proposal and the number of Sirius Group common shares purchased in the Employee Share Purchase Plan and Sirius Group Private Placement. There can be no assurance that Sirius Group will be able to meet Nasdaq's initial listing requirements at the time of the Merger.

        If Sirius Group common shares and the converted warrants are not approved for listing on Nasdaq in connection with the Merger or, after the Merger, Nasdaq delists Sirius Group common shares and the converted warrants from trading on its exchange for failure to meet the listing standards, Sirius Group and its shareholders could face significant material adverse consequences including:

    a limited availability of market quotations for Sirius Group securities;

    a determination that Sirius Group common shares are a "penny stock," which will require brokers trading in Sirius Group common shares to adhere to more stringent rules, possibly resulting in a reduced level of trading activity in the secondary trading market for Sirius Group common shares;

    a limited amount of analyst coverage; and

    a decreased ability to issue additional securities or obtain additional financing in the future.

        The National Securities Markets Improvement Act of 1996, which is a federal statute, prevents or preempts the states from regulating the sale of certain securities, which are referred to as "covered securities." If Sirius Group's securities are not approved for listing on Nasdaq, its securities would not be covered securities and Sirius Group would be subject to regulation in each state in which it offers its securities.

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Fulfilling Sirius Group's obligations incident to being a public company, including with respect to the requirements of the Sarbanes-Oxley Act of 2002, will be expensive and time consuming, and any delays or difficulties in satisfying these obligations could have a material adverse effect on Sirius Group's future results of operations and share price.

        Prior to the completion of the Merger, Sirius Group has operated as a private company, and prior to April 2016 as a subsidiary of a public company, and has not been subject to the same financial and other reporting and corporate governance requirements as a public company. As a public company, Sirius Group will be required, among other things, to:

    prepare and file periodic reports in compliance with the federal securities laws;

    define and expand the roles and the duties of its board of directors and its committees;

    institute more comprehensive compliance, investor relations and internal audit functions; and

    evaluate and maintain its system of internal control over financial reporting, and report on management's assessment thereof, in compliance with rules and regulations of the SEC and the Public Company Accounting Oversight Board.

        The changes necessitated by becoming a public company will require a significant commitment of additional resources and management oversight, which will increase Sirius Group's operating costs and could divert attention away from the day-to-day management of the business. These changes will also place significant additional demands on Sirius Group's finance and accounting staff, as they adjust to working for a newly public company, and on Sirius Group's financial accounting and information systems. Other expenses associated with being a public company include, but are not limited to, increases in auditing, accounting and legal fees and expenses, investor relations expenses, increased directors' fees and director and officer liability insurance costs, registrar and transfer agent fees and listing fees.

        In particular, upon completion of the Merger, the Sarbanes-Oxley Act of 2002 will require Sirius Group to document and test the effectiveness of its internal control over financial reporting in accordance with an established internal control framework, and to report on management's conclusions as to the effectiveness of its internal controls. Likewise, Sirius Group's independent registered public accounting firm will be required to provide an attestation report on the effectiveness of Sirius Group's internal control over financial reporting pursuant to Section 404(b) of the Sarbanes-Oxley Act of 2002, starting with the filing of Sirius Group's annual report on Form 10-K for the year ended December 31, 2019. In addition, upon completion of the Merger, Sirius Group will be required under the Exchange Act to maintain disclosure controls and procedures and internal control over financial reporting. Any failure to implement required new or improved controls, or difficulties encountered in their implementation, could harm Sirius Group's operating results or cause it to fail to meet its reporting obligations. If management is unable to conclude that Sirius Group has effective internal control over financial reporting, investors could lose confidence in the reliability of its financial statements. This could result in a decrease in the value of Sirius Group common shares. Failure to comply with the Sarbanes-Oxley Act of 2002 could potentially subject Sirius Group to sanctions or investigations by the SEC, Nasdaq or other regulatory authorities.

There may be sales of a substantial amount of Sirius Group common shares after the Merger, and the sale or availability for sale of substantial amounts of Sirius Group common shares could adversely affect their market price.

        Upon completion of the Merger and based on the assumptions described in the next paragraph, there are expected to be 126.8 million Sirius Group common shares issued and outstanding. It is anticipated that (i) Sirius Group's existing controlling shareholder, CM Bermuda, will own approximately 83.2% of Sirius Group, (ii) the Sirius Group Private Placement Investors will own

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approximately 9.2% of Sirius Group (based on subscriptions received as of October 8, 2018 and inclusive of participants in the Employee Share Purchase Plan), (iii) Easterly's public stockholders will own approximately 6.8% of Sirius Group and (iv) the Sponsor and Easterly's directors and executive officers will own approximately 0.8% of Sirius Group.

        These relative percentages assume that (i) the Exchange Ratio is equal to 0.607, (ii) no Easterly stockholders exercise their redemption rights in connection with the Merger Proposal, (iii) the Sponsor and Easterly's original independent directors retain 1.0 million shares of Easterly common stock after giving effect to the transactions contemplated by the Sponsor Letter, (iv) Sirius Group issues 11.7 million common shares and Series B preference shares convertible into common shares in connection with the Sirius Group Private Placement (based on subscriptions received as of October 8, 2018 and inclusive of participants in the Employee Share Purchase Plan), (v) Sirius Group redeems 14.5 million common shares from CM Bermuda for approximately $250 million pursuant to the Common Shares Redemption Agreement and (vi) all of the issued and outstanding Sirius Group Series A redeemable preference shares are redeemed for $95 million in cash pursuant to the Preference Shares Redemption Agreement prior to the closing of the Merger. Further, such percentages do not take into account (x) the issuance of any Sirius Group common shares upon the exercise of the converted warrants that may remain issued and outstanding following the Merger (which would be 6.1 million Sirius Group common shares using the assumed Exchange Ratio) or that are issued pursuant to the Sirius Group Private Placement (which are estimated to be approximately 5.4 million Sirius Group Common Shares) or (y) the issuance of up to 14.1 million Sirius Group common shares reserved for issuance pursuant to Sirius Group's Long Term Incentive Plan and 2018 Omnibus Incentive Plan. If the facts differ from these assumptions, Easterly's stockholders may experience dilution of their ownership interest unless they elect to have their shares of Easterly common stock redeemed in connection with the Merger Proposal.

        Subject to applicable restrictions and limitations under Rule 144 of the Securities Act and, with respect to the Sponsor, the Lock-Up Agreements, all of the Sirius Group common shares issued in the Merger are expected to be eligible for sale in the public market. In addition, following the Merger, Sirius Group will be required to file one or more registration statements relating to the offer and sale of the approximately 106.0 million Sirius Group common shares held by CM Bermuda (subject to the Lock-Up Agreement) and the approximately 11.7 million Sirius Group common shares beneficially owned by the Sirius Group Private Placement Investors. Upon effectiveness of such registration statements, these parties may sell large amounts of Sirius Group common shares in the open market or in privately negotiated transactions, which could have the effect of increasing the volatility in Sirius Group common share price or putting significant downward pressure on the price of Sirius Group common shares.

        Sales of substantial amounts of Sirius Group common shares in the public market after the Merger, or the perception that such sales will occur, could adversely affect the market price of Sirius Group common shares and make it difficult for it to raise funds through securities offerings in the future.

Sirius Group's shareholders will be subject to significant dilution upon the occurrence of certain events, which could result in a decrease in the Sirius Group common share price.

        If the Merger is completed, the issued and outstanding public warrants to purchase an aggregate of 10.0 million shares of Easterly common stock will be converted into warrants to acquire 6.1 million Sirius Group common shares using the estimated Exchange Ratio of 0.607. The converted warrants will become exercisable in accordance with the terms of the warrant agreement governing those securities as amended by the Warrant Amendment. These converted warrants will become exercisable 30 days after the completion of the Merger. Based on the estimated Exchange Ratio of 0.607, the exercise price of these converted warrants will be $18.95 per Sirius Group common share.

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        In addition, Sirius Group has 14.1 million common shares reserved or designated for future issuance pursuant to the Sirius Group Long Term Incentive Plan and 2018 Omnibus Incentive Plan. In connection with the Merger, the Compensation Committee has approved grants of performance share unit awards to members of management under the 2018 Omnibus Incentive Plan. The aggregate number of shares subject to these awards, determined at the target level of performance, is projected to have a grant date value of $15 million.

        Sales of substantial amounts of Sirius Group common shares into the public markets by the holders of these warrants, performance share unit awards and other grants following their exercise or vesting will be dilutive to Sirius Group's existing shareholders and could result in a decrease in the Sirius Group common share price.

Future issuances of any equity securities may dilute the interests of Sirius Group's shareholders and decrease the trading price of Sirius Group common shares.

        Any future issuance of equity securities could dilute the interests of Sirius Group's shareholders and could substantially decrease the trading price of Sirius Group common shares. Sirius Group may issue equity or equity-linked securities in the future for a number of reasons, including to finance Sirius Group's operations and business strategy (including in connection with acquisitions and other transactions), to adjust Sirius Group's ratio of debt to equity, to satisfy its obligations upon the exercise of then-outstanding options or other equity-linked securities, if any, or for other reasons.

The valuation ascribed to the Sirius Group common shares in the Merger may not be indicative of the price that will prevail in the trading market following the closing.

        Prior to the closing, there has not been a public market for Sirius Group's securities. Accordingly, the valuation ascribed to the Sirius Group common shares in the Merger may not be indicative of the price that will prevail in the trading market following the closing. If an active market for Sirius Group's securities develops and continues, the trading price of Sirius Group's securities following the closing could be volatile and subject to wide fluctuations in response to various factors, some of which are beyond Sirius Group's control. Any of the factors listed below could have a material adverse effect on your investment in Sirius Group's securities and Sirius Group's securities may trade at prices significantly below the value ascribed to them in the Merger. In such circumstances, the trading price of Sirius Group's securities may not recover and may experience a further decline.

        Factors affecting the trading price of Sirius Group's securities may include:

    actual or anticipated fluctuations in Sirius Group's periodic financial results or the financial results of companies perceived to be similar to Sirius Group;

    changes in the market's expectations about Sirius Group's operating results;

    Sirius Group's operating results failing to meet the expectation of securities analysts or investors in a particular period;

    changes in financial estimates and recommendations by securities analysts concerning Sirius Group or its industry in general;

    operating and stock price performance of other companies that investors deem comparable to Sirius Group;

    changes in laws and regulations affecting Sirius Group's business;

    Sirius Group's ability to meet compliance requirements;

    commencement of litigation involving Sirius Group;

    changes in Sirius Group's capital structure, such as future issuances of securities or the incurrence of additional debt;

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    the volume of Sirius Group common shares available for public sale;

    any major change in Sirius Group's board of directors or management;

    sales of substantial amounts of common shares by Sirius Group's directors, executive officers or significant shareholders or the perception that such sales could occur; and

    general economic and political conditions such as recessions, interest rates, international currency fluctuations and acts of war or terrorism or other catastrophes.

        Broad market and industry factors may materially harm the market price of Sirius Group's securities irrespective of its operating performance. The stock market in general, and Nasdaq in particular, has experienced price and volume fluctuations that have often been unrelated or disproportionate to the operating performance of the particular companies affected. The trading prices and valuations of these stocks, and of Sirius Group's securities, may not be predictable. A loss of investor confidence in the market for insurance securities or the stocks of other companies which investors perceive to be similar to Sirius Group could depress Sirius Group's share price regardless of Sirius Group's business, prospects, financial conditions or results of operations. A decline in the market price of Sirius Group's securities also could adversely affect Sirius Group's ability to issue additional securities and its ability to obtain additional financing in the future.

Sirius Group's controlling shareholder, CM Bermuda, will have significant influence over Sirius Group after the Merger, which could limit your ability to influence the outcome of key transactions, including a change of control. CM Bermuda's interests may not be aligned with your interests on any matter requiring shareholder approval, and actions taken by CMIG International, CM Bermuda's controlling shareholder, could be adverse to Sirius Group and its other stockholders.

        In April 2016, CMIG International, through its Bermuda holding company CM Bermuda, acquired 100% of Sirius Group from our former parent company. Immediately following the completion of the Merger, it is expected that CM Bermuda will beneficially own, and be entitled to vote, approximately 83.2% of Sirius Group's issued and outstanding common shares. As a result, subject to the terms of the Shareholders Agreement, CM Bermuda will have the ability to elect all the members of Sirius Group's board of directors and thereby control its business and affairs, including any determinations with respect to mergers or other business combinations, the acquisition or disposition of assets, the incurrence of indebtedness, the issuance of any additional common shares or other equity securities, the repurchase or redemption of common shares and the payment of dividends. In addition, CM Bermuda will be able to determine the outcome of all matters requiring shareholder approval and, subject to the terms of the Shareholders Agreement, will be able to cause or prevent a change of control of Sirius Group and could preclude any unsolicited acquisition of Sirius Group. CM Bermuda's interests may not be aligned with your interests on any matter requiring shareholder approval. In addition, the concentration of ownership could deprive you of an opportunity to receive a premium for your common shares as part of a sale of Sirius Group, and may ultimately affect the market price of Sirius Group common shares.

        Under Bermuda law, CM Bermuda may be able to acquire compulsorily the common shares of minority holders by a procedure under the Companies Act known as a "scheme of arrangement." A scheme of arrangement could be effected by obtaining the agreement of Sirius Group and of holders of common shares, representing in the aggregate a majority in number and at least 75% in value of the common shareholders present and voting at a court ordered meeting held to consider the scheme of arrangement. The scheme of arrangement must then be sanctioned by the Bermuda Supreme Court. If a scheme of arrangement receives all necessary agreements and sanctions, upon the filing of the court order with the Registrar of Companies in Bermuda, all holders of common shares could be compelled to sell their shares under the terms of the scheme of arrangement. Upon consummation of the Merger,

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CM Bermuda is expected to own in excess of 75% of Sirius Group's common shares and, therefore, CM Bermuda could choose to implement a scheme of arrangement.

        In addition, in connection with CMIG International's acquisition of Sirius Group, CMIG International initially recognized most of the acquired assets and liabilities at fair value for its own reporting but chose not to elect "push down" accounting for Sirius Group. The application of "push down accounting" by CMIG International would be material to the financial statements of Sirius Group.

As a "controlled company" within the meaning of Nasdaq rules, Sirius Group qualifies for exemptions from certain corporate governance requirements. Sirius Group has the opportunity to elect any of the exemptions afforded a controlled company, but does not expect to do so.

        Because CM Bermuda will control more than a majority of the total voting power of Sirius Group common shares following the completion of the Merger, Sirius Group will be a "controlled company" within the meaning of Nasdaq rules. Under these rules, a company of which more than 50% of the voting power is held by another person or group of persons acting together is a "controlled company" and may elect not to comply with certain stock exchange rules regarding corporate governance, including:

    the requirement that a majority of its board of directors consist of independent directors;

    the requirement that its director nominees be selected or recommended for the board's selection by a majority of the board's independent directors in a vote in which only independent directors participate or by a nominating committee comprised solely of independent directors, in either case, with a formal written charter or board resolutions, as applicable, addressing the nominations process and such related matters as may be required under the federal securities laws; and

    the requirement that its compensation committee be composed entirely of independent directors with a written charter addressing the committee's purpose and responsibilities.

        Sirius Group does not currently expect or intend to rely on any of these exemptions, but there is no assurance that it will not rely on these exemptions in the future. If Sirius Group were to utilize some or all of these exemptions, you may not have the same protections afforded to shareholders of companies that are subject to all of the Nasdaq rules regarding corporate governance, and the trading price of Sirius Group common shares may be materially adversely affected.

As a "foreign private issuer" under the rules and regulations of the SEC, Sirius Group is permitted to file less or different information with the SEC than a company incorporated in the United States or otherwise subject to these rules, and to follow certain home country corporate governance practices in lieu of certain Nasdaq requirements applicable to U.S. issuers. Sirius Group has the opportunity to elect any of these exemptions afforded a foreign private issuer, but does not expect to do so.

        Sirius Group is, and will upon the consummation of the Merger be, considered a "foreign private issuer" under the rules and regulations of the SEC. Accordingly, Sirius Group will not be required to file periodic reports and financial statements with the SEC as frequently or within the same time frames as U.S. companies with securities registered under the Exchange Act. In addition, Sirius Group is not required to comply with other regulations applicable to U.S. companies, including Regulation FD, which imposes restrictions on the selective disclosure of material information to shareholders. Furthermore, as a "foreign private issuer" whose common shares will be listed on Nasdaq, Sirius Group is permitted to follow certain home country corporate governance practices in lieu of certain Nasdaq requirements.

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        Sirius Group does not currently expect or intend to rely on the scaled disclosure practices permitted by the SEC or the alternate governance practices permitted by Nasdaq, but there is no assurance that it will not rely on these exemptions in the future. If Sirius Group were to utilize some or all of these exemptions, you may not be provided with the same disclosures or have the same protections afforded to shareholders of companies that are subject to all of the SEC's disclosure requirements and Nasdaq rules regarding corporate governance, and the trading price of Sirius Group common shares may be materially adversely affected.

Sirius Group will have to rely principally on dividends and other distributions on equity paid by Sirius Group's operating subsidiaries and limitations on their ability to pay dividends to Sirius Group could adversely impact shareholders' ability to receive dividends on Sirius Group common shares.

        Dividends and other distributions on equity paid by Sirius Group's operating subsidiaries will be Sirius Group's principal source for cash in order for Sirius Group to be able to pay any dividends and other cash distributions to its shareholders. If Sirius Group's operating subsidiaries incur debt on their own behalf in the future, the instruments governing the debt may restrict their ability to pay dividends or make other distributions to Sirius Group.

You will have limited ability to bring an action against Sirius Group or against Sirius Group's directors and officers, or to enforce a judgment against Sirius Group or them, because Sirius Group is incorporated in Bermuda and because certain of Sirius Group's directors and officers reside outside the United States.

        Sirius Group is incorporated in Bermuda and conducts much of its operations outside the United States. Certain of Sirius Group's officers and directors reside outside the United States and a substantial portion of the assets of those persons are located outside of the United States. As a result, it could be difficult or impossible for you to bring an action against Sirius Group or against these individuals in Bermuda in the event that you believe that your rights have been infringed under the applicable securities laws or otherwise. Even if you are successful in bringing an action of this kind, the laws of Bermuda could render you unable to enforce a judgment against Sirius Group's assets or the assets of Sirius Group's directors and officers.

        In addition, class actions and derivative actions are generally not available to shareholders under Bermuda law. The Bermuda courts, however, would ordinarily be expected to permit a shareholder to commence an action in the name of a company to remedy a wrong to the company where the act complained of is alleged to be beyond the corporate power of the company or illegal, or would result in the violation of the company's memorandum of association or bye-laws, including any breach of fiduciary duty claims in cases where the actions from which such claims arise have not been ratified by a majority of the shareholders.

        As a result of the above, Sirius Group shareholders may have more difficulty in protecting their interests in the face of actions taken by management, members of the board of directors or controlling shareholders than they would as public shareholders of a U.S. company.

Sirius Group common shares to be received by Easterly stockholders as a result of the Merger will have different rights from Easterly common stock.

        Following the completion of the Merger, Easterly stockholders will no longer be stockholders of Easterly, but will instead be shareholders of Sirius Group. There will be differences between the current rights of an Easterly stockholder and the rights to which an Easterly stockholder will be entitled as a Sirius Group shareholder following the completion of the Merger. See the section of this proxy statement/prospectus entitled "Comparison of Rights of Shareholders of Easterly and Sirius Group" for additional information about the different rights associated with Sirius Group common shares.

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If, following the Merger, securities or industry analysts do not publish or cease publishing research or reports about Sirius Group, its business or its industry, or if they change their recommendations regarding Sirius Group common shares adversely, the price and trading volume of the common shares could decline.

        The trading market for Sirius Group common shares will be influenced by the research and reports that industry or securities analysts may publish about Sirius Group, its business, its industry or its competitors. Securities and industry analysts do not currently, and may never, publish research on Sirius Group. If no securities or industry analysts commence coverage of Sirius Group, its share price and trading volume would likely be negatively impacted. If any of the analysts who may cover Sirius Group change their recommendation regarding Sirius Group common shares adversely, or provide more favorable relative recommendations about Sirius Group's competitors, the price of Sirius Group common shares would likely decline. If any analyst who may cover Sirius Group were to cease coverage of Sirius Group or fail to regularly publish reports on it, Sirius Group could lose visibility in the financial markets, which in turn could cause its share price or trading volume to decline.

Risks Related to Easterly and the Merger

        The following risk factors apply to the business and operations of Easterly and to the Merger.

Nasdaq may delist Easterly's securities from trading on its exchange prior to the Merger, which could limit investors' ability to make transactions in Easterly's securities and subject it to additional trading restrictions.

        Easterly cannot assure you that Easterly's securities will continue to be listed on Nasdaq in the future and prior to the Merger. In order to continue listing Easterly's securities on Nasdaq prior to the Merger, Easterly must maintain certain financial, distribution and stock price levels. Generally, Easterly must maintain a minimum amount in stockholders' equity (generally $2,500,000) and a minimum number of holders of its securities (generally 300 round-lot holders). Additionally, Nasdaq listing rules require that a special purpose acquisition company like Easterly complete its initial business combination within 36 months of the effectiveness of its IPO registration statement. Easterly's IPO registration statement was declared effective on July 29, 2015 and, therefore, Easterly is subject to delisting as a result of the failure to complete an initial business combination prior to July 29, 2018. On August 7, 2018, Easterly received formal notification from the Listing Qualifications Department of the Nasdaq Stock Market regarding the failure to meet such requirement and that Nasdaq has initiated procedures to delist Easterly's securities from the Nasdaq Stock Market.

        In addition, on April 2, 2018, Easterly received a notification letter from the staff of the Listing Qualifications Department of The Nasdaq Stock Market notifying it that it no longer complies with Nasdaq Listing Rule 5550(a)(3) for continued listing due to its failure to maintain a minimum of 300 public holders of Easterly common stock. On May 21, 2018, Easterly submitted to Nasdaq a plan to regain compliance. On May 31, 2018, Nasdaq granted Easterly an extension until July 29, 2018 to regain compliance. As of July 29, 2018, Easterly had not regained compliance with such requirement. On August 7, 2018, Easterly received formal notification from the Listing Qualifications Department regarding the failure to meet such requirement by the extended deadline and that Nasdaq has initiated procedures to delist Easterly's securities from the Nasdaq Stock Market.

        Easterly has appealed Nasdaq's decision to a Nasdaq Listing Qualifications Panel. While the appeal is pending, Easterly's securities will remain listed pending the decision of a Nasdaq Listing Qualifications Panel. However, there can be no assurance that such appeal will be successful.

        If Nasdaq delists Easterly's securities from trading on its exchange and Easterly is not able to list its securities on another national securities exchange, Easterly expects its securities could be quoted on

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an over-the-counter market. If this were to occur, Easterly could face significant material adverse consequences, including:

    a limited availability of market quotations for its securities;

    reduced liquidity for its securities;

    a determination that its common stock is a "penny stock," which will require brokers trading in Easterly common stock to adhere to more stringent rules and possibly result in a reduced level of trading activity in the secondary trading market for its securities;

    a limited amount of news and analyst coverage; and

    a decreased ability to issue additional securities or obtain additional financing in the future.

        The National Securities Markets Improvement Act of 1996, which is a federal statute, prevents or preempts the states from regulating the sale of certain securities, which are referred to as "covered securities." Because Easterly's units, common stock and warrants are currently listed on Nasdaq, its units, common stock and warrants are covered securities. Although the states are preempted from regulating the sale of Easterly's securities, the federal statute does allow the states to investigate companies if there is a suspicion of fraud, and, if there is a finding of fraudulent activity, then the states can regulate or bar the sale of covered securities in a particular case. While Easterly is not aware of a state having used these powers to prohibit or restrict the sale of securities issued by blank check companies, other than the state of Idaho, certain state securities regulators view blank check companies unfavorably and might use these powers, or threaten to use these powers, to hinder the sale of securities of blank check companies in their states. Further, if Easterly were no longer listed on Nasdaq, its securities would not be covered securities and Easterly would be subject to regulation in each state in which it offers its securities.

Sirius Group may apply the net proceeds released from the Trust Account in a manner that does not increase the value of your investment.

        If the Merger is consummated, the funds held in the Trust Account will be released to (i) the surviving company for general corporate purposes, including making loans or contributing cash to other affiliates for working capital, organic growth and future potential acquisitions, (ii) pay unpaid franchise and income taxes of Easterly, (iii) Easterly stockholders who properly exercise their redemption rights, and (iv) pay up to $2 million of Easterly's liabilities, fees, costs and expenses and the $7 million deferred underwriting fee. Following the consummation of the Merger, the combined company will be entitled to use the funds in the Trust Account. Other than the foregoing uses, the combined company does not have specific plans for any funds remaining from the Trust Account and will have broad discretion regarding how to use the funds that remain. These funds could be used in a manner with which you may not agree or applied in ways that do not improve the combined company's results of operations or increase the value of your investment.

The proceeds available to the combined company after the Merger will be reduced to the extent Easterly's stockholders exercise their redemption rights in connection with the Merger and will also be reduced to the extent of transaction expenses of each of Easterly and Sirius Group, which will be payable by the combined company. This may adversely affect the combined company's business and future operations.

        The amount of proceeds available to the combined company after the Merger will depend in part on the extent to which Easterly stockholders exercise their right to redeem their shares into cash in connection with the Merger. As of September 30, 2018, Easterly has approximately $148.5 million in the Trust Account that will be available for general corporate purposes after the Merger prior to the payment of $2 million of fees and expenses and the $7 million deferred underwriting fee. This amount could be reduced to as low as zero. Easterly has no specified maximum redemption threshold under its

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charter. In no event, however, will Easterly redeem public shares in an amount that would cause its net tangible assets to be less than $5,000,001. The proceeds available to the combined company will be reduced in proportion to such redemptions, and will also be reduced to the extent of all transaction expenses, which will be payable by the combined company. Reduced proceeds may adversely affect the combined company's business and future operations.

Upon the closing of the Merger, Sirius Group will be obligated to pay certain transaction expenses and fees as well as other expenses required to complete the Merger, and the combined company may not have sufficient funds at closing to repay these amounts.

        The combined company will also be obligated to pay closing fees and expenses related to the Merger at the closing of the Merger, some of which cannot be determined at this time. If sufficient funds are not in the Trust Account at closing to pay for such obligations, costs and expenses, the combined company will be required to raise additional funds on terms that may not be favorable or renegotiate such obligations, which may result in additional costs and expenses to the combined company. If the combined company cannot satisfy such obligations via additional financings or through renegotiation, it may be in default on such obligations and will not have sufficient capital to fund the operations of the business, and its business, financial condition and results of operations could be adversely affected.

If Easterly is unable to effect a business combination by November 30, 2018, Easterly will be forced to liquidate and the public warrants will expire worthless.

        If Easterly does not complete a business combination by November 30, 2018 or extend such deadline to a later date by obtaining the approval of Easterly's stockholders at a special meeting of Easterly's stockholders, Easterly's charter provides that it will (i) cease all operations except for the purpose of winding up, (ii) as promptly as reasonably possible, subject to lawfully available funds therefor, redeem 100% of the public shares in consideration of a per-share price, payable in cash, equal to the quotient obtained by dividing (a) the aggregate amount then on deposit in the Trust Account, including interest but net of franchise and income taxes payable (which interest will be net of taxes payable and reduced by up to $100,000 to pay dissolution expenses), by (b) the total number of then issued and outstanding public shares, which redemption will completely extinguish rights of the public stockholders (including the right to receive further liquidation distributions, if any), subject to applicable law, and (iii) as promptly as reasonably possible following such redemptions, subject to the approval of the remaining stockholders and the board of directors in accordance with applicable law, dissolve and liquidate, subject in each case to Easterly's obligations under the DGCL to provide for claims of creditors and other requirements of applicable law. In the event of liquidation, there will be no distribution with respect to Easterly's outstanding warrants. Accordingly, the public warrants will expire worthless.

        For illustrative purposes, based on funds in the Trust Account of approximately $148.5 million on September 30, 2018, the estimated per share redemption price would have been approximately $10.45. This is slightly more than the $10.00 IPO price of Easterly's units.

If Easterly is forced to liquidate, its stockholders may be held liable for claims by third parties against Easterly to the extent of distributions received by them.

        Under the DGCL, stockholders may be held liable for claims by third parties against a corporation to the extent of distributions received by them in a dissolution. The pro rata portion of the Trust Account distributed to the public stockholders upon the redemption of 100% of the public shares in the event Easterly does not consummate an initial business combination by November 30, 2018 may be considered a liquidation distribution under Delaware law. If a corporation complies with certain procedures set forth in Section 280 of the DGCL intended to ensure that it makes reasonable provision

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for all claims against it, including a 60-day notice period during which any third-party claims can be brought against the corporation, a 90-day period during which the corporation may reject any claims brought, and an additional 150-day waiting period before any liquidating distributions are made to stockholders, any liability of stockholders with respect to a liquidating distribution is limited to the lesser of such stockholder's pro rata share of the claim or the amount distributed to the stockholder, and any liability of the stockholder would be barred after the third anniversary of the dissolution. However, Easterly intends to redeem its public shares as soon as reasonably possible following November 30, 2018 in the event Easterly does not consummate an initial business combination and, therefore, Easterly does not intend to comply with those procedures.

        Because Easterly will not be complying with Section 280, Section 281(b) of the DGCL requires Easterly to adopt a plan, based on facts known to it at such time that will provide for the payment of all existing and pending claims or claims that may be potentially brought against Easterly within the 10 years following dissolution. If Easterly's plan of distribution complies with Section 281(b) of the DGCL, any liability of its stockholders with respect to a liquidating distribution is limited to the lesser of such stockholder's pro rata share of the claim or the amount distributed to the stockholder, and any liability of the stockholder would likely be barred after the third anniversary of the dissolution. There can be no assurance that Easterly will properly assess all claims that may be potentially brought against it. As such, Easterly's stockholders could potentially be liable for any claims to the extent of distributions received by them (but no more) and any liability of its stockholders may extend beyond the third anniversary of such date. Furthermore, if the pro rata portion of the Trust Account distributed to Easterly's public stockholders upon the redemption of 100% of the public shares in the event its does not consummate an initial business combination within the required timeframe is not considered a liquidation distribution under Delaware law and such redemption distribution is deemed to be unlawful, then pursuant to Section 174 of the DGCL, the statute of limitations for claims of creditors could then be six years after the unlawful redemption distribution, instead of three years, as in the case of a liquidation distribution.

        If Easterly is forced to file a bankruptcy case or an involuntary bankruptcy case is filed against it which is not dismissed, any distributions received by stockholders could be viewed under applicable debtor/creditor and/or bankruptcy laws as either a "preferential transfer" or a "fraudulent conveyance." As a result, a bankruptcy court could seek to recover all amounts received by Easterly's stockholders. Furthermore, because Easterly intends to distribute the proceeds held in the Trust Account to its public stockholders promptly after November 30, 2018 in the event it does not consummate an initial business combination, this may be viewed or interpreted as giving preference to Easterly's stockholders over any potential creditors with respect to access to or distributions from Easterly's assets. Furthermore, Easterly's board of directors may be viewed as having breached its fiduciary duties to Easterly's creditors and/or may have acted in bad faith, thereby exposing itself and Easterly to claims of punitive damages, by paying Easterly's stockholders from the Trust Account prior to addressing the claims of creditors. There can be no assurance that claims will not be brought against Easterly for these reasons.

If Easterly is unable to complete the Merger by November 30, 2018, Easterly's charter provides that it shall cease operations and promptly dissolve and wind up. In such event, third parties may bring claims against Easterly and, as a result, the proceeds held in the Trust Account could be reduced and the per share liquidation price received by stockholders could be less than $10.00 per share.

        Easterly must complete a business combination by November 30, 2018 or extend such deadline to a later date by obtaining the approval of Easterly's stockholders at a special meeting of Easterly's stockholders, when, pursuant to Easterly's charter, it will cease all operations except for the purpose of winding up and it will be required to dissolve and liquidate. In such event, third parties may bring claims against it. Although Easterly has obtained waiver agreements from many of the vendors and service providers it has engaged and prospective target businesses with which it has negotiated, whereby

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such parties have waived any right, title, interest or claim of any kind in or to any monies held in the Trust Account for the benefit of Easterly's public stockholders, there is no guarantee that such parties will not bring claims seeking recourse against the Trust Account including, but not limited to, fraudulent inducement, breach of fiduciary responsibility or other similar claims, as well as other claims challenging the enforceability of the waiver, in each case in order to gain advantage with respect to a claim against Easterly's assets, including the funds held in the Trust Account. Further, Easterly could be subject to claims from parties not in contract with it or who have not executed a waiver. Darrell Crate, Easterly's Chairman, Avshalom Kalichstein, its Chief Executive Officer and director, and David Cody have agreed that they will be jointly and severally liable to Easterly if and to the extent any claims by a vendor for services rendered or products sold to it, or a prospective target business with which it has discussed entering into a transaction agreement, reduce the amount of funds in the Trust Account. This liability will not apply with respect to any claims by a third party who executed a waiver of any and all rights to seek access to the Trust Account or to any claims under Easterly's indemnity of the underwriters of the IPO against certain liabilities, including liabilities under the Securities Act. Moreover, in the event that an executed waiver is deemed to be unenforceable against a third party, then they will not be responsible to the extent of any liability for such third-party claims. Easterly has not independently verified whether they have sufficient funds to satisfy their indemnity obligations, and Easterly has not asked Messrs. Crate, Kalichstein or Cody to reserve for such indemnification obligations. Therefore, Easterly cannot assure you that they would be able to satisfy those obligations. If they assert that they are unable to satisfy their obligations or that they have no indemnification obligations related to a particular claim, Easterly's independent directors would determine whether to take legal action against them to enforce their indemnification obligations. While Easterly currently expects that its independent directors would take legal action on Easterly's behalf against them to enforce their indemnification obligations to it, it is possible that Easterly's independent directors, in exercising their business judgment, may choose not to do so if, for example, the cost of such legal action is deemed by the independent directors to be too high relative to the amount recoverable, or if the independent directors determine that a favorable outcome is not likely. If Easterly's independent directors choose not to enforce these indemnification obligations, the amount of funds in the Trust Account available for distribution to Easterly's public stockholders may be reduced below $10.00 per share.

If the Adjournment Proposal is not approved, and an insufficient number of votes have been obtained to authorize the consummation of the Merger, Easterly's directors will not have the ability to adjourn the Easterly special meeting to a later date in order to solicit further votes, and, therefore, the Merger will not be approved.

        If approved by the stockholders, the Adjournment Proposal will provide Easterly's directors with additional time, if needed, to solicit proxies in favor of the proposals. If the Adjournment Proposal is not approved, and the remaining proposals fail to pass such that the Merger cannot be consummated, the Merger will not be completed. Because Easterly must consummate a business combination by the termination date of November 30, 2018 or extend such deadline to a later date by obtaining the approval of Easterly's stockholders at a special meeting of Easterly's stockholders, if the Merger is not approved, Easterly may not be able to consummate another transaction within the remaining time period, and as a result, it is likely that Easterly will have to redeem all of its public shares for their pro rata portions of the Trust Account and, promptly following such redemption, dissolve and liquidate.

The Sponsor and Easterly's original independent directors have agreed to vote in favor of the Merger, regardless of how Easterly's public stockholders vote.

        Unlike blank check companies in which the founders agree to vote their founder shares in accordance with the majority of the votes cast by the public stockholders in connection with an initial business combination, the Sponsor and Easterly's independent directors have agreed to vote any shares

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of Easterly common stock owned by them in favor of Easterly's initial business combination. As of the date hereof, the Sponsor and Easterly's original independent directors and their permitted transferees own 25.8% of Easterly's issued and outstanding shares of common stock. Accordingly, it is more likely that the necessary stockholder approval will be received for the Merger than would be the case if the Sponsor and Easterly's independent directors agreed to vote any shares of Easterly common stock owned by them in accordance with the majority of the votes cast by Easterly's public stockholders.

Because the market price of Sirius Group common shares and the converted warrants will fluctuate and because there is currently no trading market for the Sirius Group common shares or the converted warrants, Easterly securityholders cannot be sure of the value of the consideration they will receive when the Merger is completed, and the value may be less than what respective securityholders originally paid for their shares of Easterly common stock or public warrants.

        If the Merger is completed, Easterly stockholders will receive a fraction of a Sirius Group common share equal to the Exchange Ratio for each share of Easterly common stock for which the stockholder did not validly exercise redemption rights, and each issued and outstanding public warrant to purchase shares of Easterly common stock will be converted into a warrant to purchase the same fraction of a Sirius Group common share. The value of Sirius Group common shares and the converted warrants may vary significantly from the closing price of the Easterly common stock and the public warrants on the date the Merger was announced, on the date the parties entered into the Merger Agreement, on the date that this proxy statement/prospectus was mailed to Easterly's stockholders or on the date of the special meeting of Easterly's stockholders, or thereafter. No trading market for Sirius Group common shares or the converted warrants currently exists and, therefore, Easterly's securityholders cannot be sure of the price at which the Sirius Group common shares or converted warrants will trade if the Merger is completed. Therefore, the value of the Sirius Group common shares and/or the converted warrants that Easterly's securityholders receive in the Merger may be lower than what Easterly's securityholders originally paid for their corresponding securities of Easterly prior to the Merger.

Easterly has not obtained an opinion from an independent financial advisor, and consequently, there is no assurance from an independent source that the price Sirius Group is paying for Easterly is fair to Easterly's stockholders from a financial point of view.

        Easterly is not required to and has not obtained an opinion from an independent financial advisor that the price Sirius Group is paying for Easterly is fair to Easterly's stockholders from a financial point of view. The Easterly board of directors has determined that the Merger consideration is fair from a financial point of view. The determination has been made by Easterly's board of directors based upon standards generally accepted by the financial community, such as potential sales, earnings and cash flow, and the price for which comparable businesses or assets have been valued. Easterly's stockholders will be relying on the judgment of Easterly's board of directors with respect to such matters, and the conclusion of the board of directors may differ from the conclusion that an independent financial advisor would have reached when valuing Sirius Group's business. In addition, the absence of an opinion from an independent financial advisor may lead a larger number of stockholders to vote against the Merger Proposal or demand redemption of their shares in connection therewith, which could impact the parties' ability to complete the Merger and, if such redemptions decrease the public "float" and number of beneficial owners of Easterly's common stock, Sirius Group's ability to list its common shares on Nasdaq in connection therewith.

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Easterly will not have any right to make damage claims against Sirius Group for the breach of any representation or warranty made by Sirius Group in the Merger Agreement.

        The Merger Agreement provides that all representations and warranties of the parties contained therein shall not survive the closing of the Merger. Accordingly, there are no remedies available to the parties with respect to any breach of representations and warranties of the parties to the Merger Agreement after the closing. As a result, Easterly will have no remedy available to it if the Merger is consummated and it is later revealed that there was a breach of any of the representations and warranties made by Sirius Group at the time of the Merger.

If Easterly's stockholders fail to comply with the redemption requirements specified in this proxy statement/prospectus, they will not be entitled to redeem their shares of Easterly common stock for a pro rata portion of the Trust Account.

        Holders of public shares are not required to affirmatively vote against the Merger Proposal in order to exercise their rights to redeem their shares for a pro rata portion of the Trust Account. In order to exercise their redemption rights, they are required to submit a request in writing and deliver their stock (either physically or electronically) to Easterly's transfer agent at least two business days prior to the Easterly special meeting of the Stockholders. Stockholders electing to redeem their shares will receive their pro rata portion of the Trust Account less franchise and income taxes payable, calculated as of two business days prior to the anticipated consummation of the Merger. See the section entitled "The Special Meeting of Easterly Stockholders" for additional information on how to exercise your redemption rights.

Stockholders of Easterly who wish to have their shares redeemed for a pro rata portion of the Trust Account must comply with specific requirements for redemption that may make it more difficult for them to exercise their redemption rights prior to the deadline for exercising redemption rights.

        Public stockholders who wish to redeem their shares for a pro rata portion of the Trust Account must, among other things, tender their certificates to Easterly's transfer agent or deliver their shares to the transfer agent electronically through DTC prior to 5:00 p.m. New York time, on the second business day prior to the Easterly special meeting. In order to obtain a physical stock certificate, a stockholder's broker and/or clearing broker, DTC and Easterly's transfer agent will need to act to facilitate this request. It is Easterly's understanding that stockholders should generally allot at least two weeks to obtain physical certificates from the transfer agent. However, because Easterly does not have any control over this process or over the brokers or DTC, it may take significantly longer than two weeks to obtain a physical stock certificate. If it takes longer than anticipated to obtain a physical certificate, stockholders who wish to redeem their shares may be unable to obtain physical certificates by the deadline for exercising their redemption rights and thus will be unable to redeem their shares.

Public stockholders, together with any affiliates of theirs or any other person with whom they are acting in concert or as a "group," will be restricted from seeking redemption rights with respect to more than 15% of the public shares.

        A public stockholder, together with any of his, her or its affiliates or any other person with whom he, she or it is acting in concert or as a "group," will be restricted from seeking redemption rights with respect to more than 15% of the public shares. Accordingly, if you hold more than 15% of the public shares and the Merger Proposal is approved, you will not be able to seek redemption rights with respect to the full amount of your shares and may be forced to hold the shares in excess of 15% or sell them in the open market. Easterly cannot assure you that the value of such excess shares will appreciate over time following the Merger or that the market price of Easterly common stock will exceed the per-share redemption price.

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Since the Sponsor, Easterly's officers, directors and their affiliates will lose their entire investment in Easterly if the Merger is not completed, they may have had a conflict of interest in identifying and selecting Sirius Group for Easterly's initial business combination.

        After giving effect to the July 3, 2015 stock dividend, expiration of Easterly's overallotment that was partially exercised and the transfer of 24,000 shares to Easterly's original independent directors, the Sponsor currently owns an aggregate of 4,928,000 Founder Shares for an aggregate purchase price of $25,000. All of such Founder Shares will be worthless if an initial business combination is not consummated. The personal and financial interests of the Sponsor, Easterly's officers, directors and their affiliates may have influenced their motivation in identifying and selecting Sirius Group for its target business combination and consummating the Merger.

Directors of Easterly have potential conflicts of interest in recommending that stockholders vote in favor of approval of the Merger Proposal and the Adjournment Proposal.

        When considering Easterly's board of directors' recommendation that Easterly's stockholders vote in favor of the approval of the Merger Proposal and the Adjournment Proposal, Easterly's stockholders should be aware that directors and executive officers of Easterly have interests in the Merger that may be different from, or in addition to, the interests of its stockholders. These interests include:

    the 400,000 to 1.6 million total Founder Shares that the Sponsor (or its members) will hold immediately prior to the Merger, which will be exchanged for Sirius Group common shares at the Exchange Ratio in connection with the Merger;

    the 24,000 Founder Shares that one of Easterly's independent directors holds as of September 30, 2018, which will be exchanged for Sirius Group common shares at the Exchange Ratio in connection with the Merger;

    if Easterly is unable to complete a business combination within the required time period, the Convertible Promissory Note issued to the Sponsor, in the amount of $895,000 at September 30, 2018 plus accrued interest, will not be repaid and all amounts owed thereunder will be forgiven except to the extent that Easterly has funds available to it outside of the Trust Account to repay such amounts;

    if Easterly is unable to complete a business combination within the required time period, Easterly's Chairman, its Chief Executive Officer and David Cody will be personally liable to ensure that the proceeds in the Trust Account are not reduced by the claims of target businesses or claims of vendors or other entities that are owed money by Easterly for services rendered or contracted for or products sold to Easterly, but only if such a vendor or target business has not executed a waiver of claims against the Trust Account and except as to any claims under Easterly's indemnity of the underwriters; and

    the continued indemnification of current directors and officers of Easterly and the continuation of directors' and officers' liability insurance after the Merger.

        Further, each of Easterly's directors, directly or indirectly, holds Founder Shares that are not subject to redemption; as a result, Easterly's directors have a financial incentive to see a Merger consummated rather than lose whatever value is attributable to the Founder Shares and Private Placement Warrants. These interests may influence Easterly's directors in making their recommendation that you vote in favor of the Merger Proposal, and the transactions contemplated thereby.

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The exercise of discretion by Easterly's directors and officers and Sirius Group in agreeing to changes to the terms of or waivers of closing conditions in the Merger Agreement may result in a conflict of interest when determining whether such changes to the terms of the Merger Agreement or waivers of conditions are appropriate and in the best interests of Easterly's stockholders.

        In the period leading up to the closing of the Merger, other events may occur that, pursuant to the Merger Agreement, would require Easterly or Sirius Group to agree to amend the Merger Agreement, to consent to certain actions or to waive rights that it is entitled to under those agreements. Such events could arise because of changes in the course of Sirius Group's or Easterly's business, a request by such party to undertake actions that would otherwise be prohibited by the terms of the Merger Agreement or the occurrence of other events that would have a material adverse effect on Sirius Group's or Easterly's business and would entitle the other party to terminate the Merger Agreement. In any of such circumstances, it would be in the discretion of the other party, acting through its board of directors, to grant its consent or waive its rights. The existence of the financial and personal interests of the directors described elsewhere in this proxy statement/prospectus may result in a conflict of interest on the part of one or more of the directors between what he may believe is best for Easterly and its stockholders and what he may believe is best for himself or his affiliates in determining whether or not to take the requested action. As of the date of this proxy statement/prospectus, neither Easterly nor Sirius Group believe there will be any changes or waivers that its directors and officers would be likely to make after stockholder approval of the Merger has been obtained. While certain changes could be made without further stockholder approval, if there is a change to the terms of the transaction that would have a material impact on the Easterly stockholders, Easterly will be required to circulate a new or amended proxy statement/prospectus or supplement thereto and resolicit the vote of Easterly's stockholders with respect to the Merger Proposal.

Easterly or Sirius Group may waive one or more of the conditions to the Merger.

        Easterly or Sirius Group may agree to waive, in whole or in part, some of the conditions to its respective obligations to complete the Merger, to the extent permitted by Easterly's charter and applicable laws. For example, it is a condition to Easterly's obligations to close the Merger that the representations and warranties of Sirius Group are true and correct in all respects as of the date of the Merger Agreement and as of the date of the closing of the Merger (or an earlier date to the extent that an earlier date is referenced in the representation and warranty), except for certain of the representations and warranties, for such inaccuracies that, individually or in the aggregate, would not result in a Material Adverse Effect (as defined in the Merger Agreement) on Sirius Group and its subsidiaries taken as a whole. It is also a condition to the Merger that the Sirius Group common shares issuable pursuant to the Merger Agreement and upon exercise of the converted warrants shall have been approved for listing on the Nasdaq Stock Market, subject to official notice of issuance. This listing condition may be waived by Sirius Group and Easterly. Under applicable law and Easterly's charter, neither Sirius Group nor Easterly is able to waive the condition that Easterly's stockholders approve the Merger.

Easterly's financial statements included in this proxy statement/prospectus do not take into account the consequences to Easterly of a failure to complete a business combination by November 30, 2018.

        If the proceeds held outside the Trust Account and any loans under the Convertible Promissory Note are insufficient to identify and evaluate target businesses, perform business due diligence on prospective target businesses, travel to and from the offices, plants or similar locations of prospective target businesses or their representatives or owners, review corporate documents and material agreements of prospective target businesses, structure, negotiate and complete a business combination, Easterly may need to raise additional capital through additional loans or additional investments from the Sponsor, an affiliate of the Sponsor or certain of Easterly's officers and directors. None of the

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Sponsor, any affiliate of the Sponsor, or Easterly's officers and directors are under any obligation to loan Easterly funds. The uncertainty regarding the lack of resources to pay the above noted expenses raises substantial doubt about Easterly's ability to continue as a going concern. No adjustments have been made to the carrying amounts of assets or liabilities should Easterly be unable to continue operations.

Easterly and Sirius Group will be subject to business uncertainties and contractual restrictions while the Merger is pending.

        Uncertainty about the effect of the Merger on employees and third parties may have an adverse effect on Easterly and Sirius Group. These uncertainties may impair Easterly's or Sirius Group's ability to retain and motivate key personnel and could cause third parties that deal with any of them to defer entering into contracts or making other decisions or seek to change existing business relationships. If key employees depart because of uncertainty about their future roles and the potential complexities of the Merger, Easterly's or Sirius Group's business could be harmed.

Easterly will incur significant transaction and transition costs in connection with the Merger.

        Easterly expects to incur significant, non-recurring costs in connection with consummating the Merger. Easterly may incur additional costs to maintain employee morale and to retain key employees. Easterly will also incur significant fees and expenses relating to financing arrangements and legal, accounting and other transaction fees and costs associated with the Merger. Some of these costs are payable regardless of whether the Merger is completed. The Sponsor has agreed to pay or reimburse Easterly for a portion of such costs only if the Merger is consummated.

In connection with the stockholder vote to approve the Merger Proposal, the Sponsor, Easterly's directors, officers or advisors, or their respective affiliates may elect to purchase shares from public stockholders, which may influence the vote on the Merger Proposal and reduce the public "float" of Sirius Group common shares upon completion of the Merger.

        In connection with the stockholder vote to approve the proposed Merger, the Sponsor, Easterly's directors, officers or advisors, or their respective affiliates may privately negotiate transactions to purchase shares from stockholders who would have otherwise elected to have their shares redeemed for a per-share pro rata portion of the Trust Account in conjunction with their consideration of a proposal to approve the Merger, although they are under no obligation to do so. The purpose of any such purchases would be to increase the likelihood of obtaining stockholder approval of the Merger. This may result in the approval of the Merger Proposal, which may not otherwise have been possible. In addition, if such purchases are made, the public "float" of Easterly's common stock and the number of beneficial holders of Easterly's securities, and thus the public "float" of Sirius Group's common shares and the number of beneficial holders of Sirius Group's securities immediately after the Merger, may be reduced, possibly making it difficult for Sirius Group to obtain or maintain the listing of its common shares on Nasdaq.

The unaudited pro forma financial information included in this document may not be indicative of what the combined company's actual financial position or results of operations would have been.

        The unaudited pro forma financial information in this proxy statement/prospectus is presented for illustrative purposes only and is not necessarily indicative of what the combined company's actual financial position or results of operations would have been had the Merger been completed on the dates indicated. See the section entitled "Unaudited Pro Forma Condensed Combined Financial Information" for more information.

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Easterly's ability to consummate the Merger successfully and Sirius Group's ability to operate the business successfully thereafter will be largely dependent upon the efforts of certain key personnel of Sirius Group. The loss of such key personnel could negatively impact the operations and profitability of the post-combination business.

        Easterly's ability to successfully effect the Merger and Sirius Group's ability to successfully operate the business following the Merger is dependent upon the efforts of certain key personnel, including the key personnel of Sirius Group. It is possible that Sirius Group will lose some key personnel as a result of the Merger, which could negatively impact the operations and profitability of Sirius Group's post-combination business. These individuals may be unfamiliar with the requirements of operating a company regulated by the SEC, which could cause it to have to expend time and resources helping them become familiar with such requirements.

Unlike some other blank check companies, Easterly does not have a specified maximum redemption threshold. The absence of such a redemption threshold will make it easier for Easterly to consummate the Merger even if a substantial number of Easterly stockholders redeem.

        Since Easterly has no specified maximum redemption threshold, its structure is different in this respect from the structure that has been used by some blank check companies. Previously, some blank check companies would not be able to consummate a business combination if the holders of such companies' public shares elected to redeem or convert more than a specified percentage of the shares sold in such companies' initial public offerings, which percentage threshold was typically between 19.99% and 39.99%.

        As a result, Easterly may be able to consummate the Merger even though a substantial number of Easterly public stockholders have redeemed their shares. In no event, however, will Easterly redeem public shares in an amount that would cause its net tangible assets to be less than $5,000,001. Redemptions of Easterly public shares by Easterly public stockholders will decrease the amount of cash available to the combined company following the closing of the Merger.

Easterly public stockholders do not have any rights or interests in funds from the Trust Account, except under certain limited circumstances. Therefore, in order to liquidate your investment, holders may be forced to sell their public shares or warrants, potentially at a loss.

        Easterly's public stockholders are entitled to receive funds from the Trust Account only upon the earlier to occur of: (i) the consummation of its initial business combination; (ii) the expiration or termination of any tender offer conducted by it in connection with a proposed business combination not otherwise withdrawn; (iii) the redemption of its public shares if it is unable to consummate a business combination by November 30, 2018, subject to applicable law; or (iv) otherwise upon its liquidation or in the event its board of directors resolves to liquidate the Trust Account and ceases to pursue the consummation of a business combination prior to November 30, 2018 (Easterly's board of directors may determine to liquidate the Trust Account prior to such expiration if it determines, in its business judgment, that it is improbable within the remaining time to identify an attractive business combination or satisfy regulatory and other business and legal requirements to consummate a business combination). In addition, if Easterly is unable to consummate an initial business combination by November 30, 2018 or extend such deadline to a later date by obtaining the approval of Easterly's stockholders at a special meeting of Easterly's stockholders, for any reason, compliance with Delaware law may require that Easterly submit a plan of dissolution to its then-existing stockholders for approval prior to the distribution of the proceeds held in the Trust Account. In that case, public stockholders may be forced to wait beyond November 30, 2018 before they receive funds from the Trust Account. In no other circumstances will a public stockholder have any right or interest of any kind in the Trust Account. Accordingly, to liquidate your investment, holders may be forced to sell their public shares or warrants, potentially at a loss.

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The Exchange Ratio may be determined prior to the Merger using an estimate of Sirius Group's September 30 Adjusted DBVPS.

        If the closing of the Merger occurs prior to Sirius Group filing with the SEC its financial statements for the quarter ended September 30, 2018, then the Exchange Ratio may be calculated using an estimate of the Sirius Group September 30 Adjusted DBVPS, and such estimate may not be the same as the actual Sirius Group September 30 Adjusted DBVPS, as determined in accordance with the Merger Agreement. In such instance, the amount of the Exchange Ratio may not be the same as it would be if the actual Sirius Group September 30 Adjusted DBVPS was used in the calculation. If an estimated Sirius Group September 30 Adjusted DBVPS is used, and this estimate is different than the actual Sirius Group September 30 Adjusted DBVPS, Easterly stockholders will not receive any different or additional consideration.

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THE SPECIAL MEETING OF EASTERLY STOCKHOLDERS

General

        Easterly is furnishing this proxy statement/prospectus to its stockholders as part of the solicitation of proxies by its board of directors for use at the Easterly special meeting of stockholders to be held on Friday, November 2, 2018, and at any adjournment or postponement thereof. This proxy statement/prospectus is first being furnished to Easterly's stockholders on or about October 13, 2018. This proxy statement/prospectus provides you with information you need to know to be able to vote or instruct your vote to be cast at the Easterly special meeting of stockholders.

Date, Time and Place of Special Meeting

        The Easterly special meeting of stockholders will be held at 10:00 a.m. Eastern time, on Friday, November 2, 2018, at the offices of Sidley Austin LLP, 787 Seventh Avenue, New York, NY 10019, or such other date, time and place to which such meeting may be adjourned or postponed, to consider and vote upon the proposals.

Voting Power; Record Date

        You will be entitled to vote or direct votes to be cast at the Easterly special meeting of stockholders if you owned shares of Easterly common stock at the close of business on October 2, 2018, which is the record date for the Easterly special meeting of stockholders. You are entitled to one vote for each share of Easterly common stock that you owned as of the close of business on the record date. If your shares are held in "street name" or are in a margin or similar account, you should contact your broker, bank or other nominee to ensure that votes related to the shares you beneficially own are properly counted. On the record date, there were 19,208,407 shares of Easterly common stock outstanding, of which 14,208,407 are public shares and 5,000,000 are Founder Shares held by the Sponsor and Easterly's original independent directors.

Vote of Easterly Founders and the Sponsor

        In connection with the IPO, Easterly entered into an agreement with its initial stockholders pursuant to which the initial stockholders agreed to vote the Founder Shares and any other shares acquired during and after the IPO in favor of the Merger Proposal. This agreement also applies to the Sponsor and Easterly's original independent directors as it relates to the Founder Shares and the requirement to vote their Founder Shares in favor of the Merger Proposal. Additionally, the Sponsor Letter requires that Sponsor vote its shares of Easterly common stock in favor of the Merger.

        All of the holders of Founder Shares, including the Sponsor and Easterly's original independent directors, have agreed to waive their redemption rights with respect to their Founder Shares and Easterly's initial stockholders have agreed to waive their redemption rights with respect to any public shares that they may have acquired during or after the IPO in connection with the completion of Merger. The Founder Shares held by Easterly's initial stockholders have no redemption rights upon Easterly's liquidation and will be worthless if no business combination is effected by Easterly prior to November 30, 2018. However, the initial stockholders are entitled to redemption rights upon Easterly's liquidation with respect to any public shares they may own.

Quorum and Required Vote for Proposals for the Easterly Special Meeting of Stockholders

        A quorum of Easterly's stockholders is necessary to hold a valid meeting. A quorum will be present at the Easterly special meeting of stockholders if a majority of the Easterly common stock outstanding and entitled to vote at the Easterly special meeting of stockholders is represented in person

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or by proxy. Abstentions and broker non-votes will count as present for the purposes of establishing a quorum.

        The approval of the Merger Proposal requires the affirmative vote of the holders of a majority of the outstanding shares of Easterly common stock. Accordingly, an Easterly stockholder's failure to vote by proxy or to vote in person at the Easterly special meeting of stockholders or an abstention from voting, or he failure of an Easterly stockholder who holds his or her shares in "street name" through a broker or other nominee to give voting instructions to such broker or other nominee (any failure to give instructions, a "broker non-vote") will have the same effect as a vote "AGAINST" the Merger Proposal. The approval of the Adjournment Proposal requires the affirmative vote of holders of a majority of the shares of Easterly common stock that are voted on such proposal at the Easterly special meeting of stockholders. Accordingly, an Easterly stockholder's failure to vote by proxy or to vote in person at the Easterly special meeting of stockholders or an abstention from voting will have no effect on the outcome of any vote on the Adjournment Proposals. A broker non-vote will have no effect on the Adjournment Proposal.

        The transactions contemplated by the Merger Agreement will be consummated only if the Merger Proposal is approved at the Easterly special meeting. The Merger Proposal is not conditioned on the approval of the Adjournment Proposal and the Adjournment Proposal is not conditioned on the approval of the Merger Proposal.

Recommendation to Easterly Stockholders

        Easterly's board of directors believes that each of the Merger Proposal and the Adjournment Proposal to be presented at the Easterly special meeting of stockholders is in the best interests of Easterly and its stockholders and unanimously recommends that its stockholders vote "FOR" each of the proposals.

        When you consider the recommendation of Easterly's board of directors in favor of approval of the Merger Proposal, you should keep in mind that Easterly's directors and officers have interests in the Merger that are different from, or in addition to, your interests as a stockholder. These interests include, among other things:

    the 400,000 to 1.6 million total Founder Shares that the Sponsor (or its members) will hold immediately prior to the Merger, which will be exchanged for Sirius Group common shares at the Exchange Ratio in connection with the Merger;

    the 24,000 Founder Shares that one of Easterly's independent directors holds as of September 30, 2018, which will be exchanged for Sirius Group common shares at the Exchange Ratio in connection with the Merger;

    if Easterly is unable to complete a business combination within the required time period, the Convertible Promissory Note issued to the Sponsor, in the amount of $895,000 at September 30, 2018 plus accrued interest, will not be repaid and all amounts owed thereunder will be forgiven except to the extent that Easterly has funds available to it outside of the Trust Account to repay such amounts;

    if Easterly is unable to complete a business combination within the required time period, Easterly's Chairman, its Chief Executive Officer and David Cody will be personally liable to ensure that the proceeds in the Trust Account are not reduced by the claims of target businesses or claims of vendors or other entities that are owed money by Easterly for services rendered or contracted for or products sold to Easterly, but only if such a vendor or target business has not executed a waiver of claims against the Trust Account and except as to any claims under Easterly's indemnity of the underwriters; and

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    the continued indemnification of current directors and officers of Easterly and the continuation of directors' and officers' liability insurance after the Merger.

        Further, each of Easterly's directors, directly or indirectly, holds Founder Shares that are not subject to redemption; as a result, Easterly's directors have a financial incentive to see a Merger consummated rather than lose whatever value is attributable to the Founder Shares. These interests may influence Easterly's directors in making their recommendation that you vote in favor of the Merger Proposal, and the transactions contemplated thereby.

Broker Non-Votes and Abstentions

        Under the rules of various national and regional securities exchanges, your broker, bank or nominee cannot vote your shares with respect to non-discretionary matters unless you provide instructions on how to vote in accordance with the information and procedures provided to you by your broker, bank or nominee. Except with respect to the Adjournment Proposal, Easterly believes the proposals presented to Easterly's stockholders will be considered non-discretionary and therefore your broker, bank or nominee cannot vote your shares without your instruction. If you do not provide voting instructions to your bank, broker or other nominee Easterly will receive a proxy card from your bank, broker or other nominee indicating that it is NOT voting your shares; this indication that a bank, broker or nominee is not voting your shares is referred to as a "broker non-vote."

        With respect to the Easterly special meeting of stockholders, abstentions are considered present for the purposes of establishing a quorum but will have the same effect as a vote "AGAINST" the Merger Proposal but will have no effect on the outcome of any vote on the Adjournment Proposal. Broker non-votes will have the effect of a vote "AGAINST" the Merger Proposal and will have no effect on the Adjournment Proposal.

Voting Your Shares

        Each share of Easterly common stock that you own in your name entitles you to one vote on each of the proposals for the Easterly special meeting of stockholders. Your one or more proxy cards show the number of shares of Easterly common stock that you own.

        There are several ways to vote your shares or submit your proxy:

    You can submit your proxy to vote your shares by completing, signing, dating and returning the enclosed proxy card in the postage-paid envelope provided. If you hold your shares in "street name" through a bank, broker or other nominee, you will need to follow the instructions provided to you by your bank, broker or other nominee to ensure that your shares are represented and voted at the special meeting. If you vote by proxy card, your "proxy," whose name is listed on the proxy card, will vote your shares as you instruct on the proxy card. If you sign and return the proxy card but do not give instructions on how to vote your shares, your shares of Easterly common stock will be voted, as recommended by Easterly's board of directors. With respect to proposals for the Easterly special meeting of stockholders, that means: "FOR" the Merger Proposal and "FOR" the Adjournment Proposal.

    You can attend the Easterly special meeting and vote in person. You will be given a ballot when you arrive. However, if your shares of common stock are held in the name of your broker, bank or other nominee, you must get a proxy from the broker, bank or other nominee in order to be able to vote your shares at the special meeting.

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Revoking Your Proxy

        If you give a proxy, you may revoke it at any time before the Easterly special meeting, or at such meeting by doing any one of the following:

    you may send another proxy card with a later date;

    you may notify Daniel Shea, Easterly's Secretary, in writing before the Easterly special meeting that you have revoked your proxy; or

    you may attend the Easterly special meeting, revoke your proxy, and vote in person, as indicated above.

No Additional Matters May Be Presented at the Easterly Special Meeting

        The Easterly special meeting of stockholders has been called only to consider the approval of the Merger Proposal and the Adjournment Proposal. Under Easterly's bylaws, other than procedural matters incident to the conduct of the Easterly special meeting, no other matters may be considered at the Easterly special meeting if they are not included in the notice of the Easterly special meeting.

Who Can Answer Your Questions About Voting

        If you have any questions about how to vote or direct a vote in respect of your shares of Easterly common stock, you may call Morrow Sodali, Easterly's proxy solicitor, at (800) 662-5200 (toll free) or Banks and Brokerage Firms, please call collect: (203) 658-9400.

Redemption Rights

        Pursuant to Easterly's charter, any holders of its public shares may demand that such shares be redeemed in exchange for a pro rata share of the aggregate amount on deposit in the Trust Account, less franchise and income taxes payable, calculated as of two business days prior to the consummation of the Merger. If demand is properly made and the Merger is consummated, these shares, immediately prior to the Merger, will cease to be issued and outstanding and will represent only the right to receive a pro rata share of the aggregate amount on deposit in the Trust Account which holds the proceeds of the IPO as of two business days prior to the consummation of the Merger, less franchise and income taxes payable, upon the consummation of the Merger. For illustrative purposes, based on funds in the Trust Account of approximately $148.5 million on September 30, 2018, the estimated per share redemption price would have been approximately $10.45.

        Redemption rights are available to holders of public shares of Easterly common stock whether or not they are a holders of Easterly common stock as of the record date for the Easterly special meeting. Redemption rights are not available to holders of warrants in connection with the Merger.

        In order to exercise your redemption rights, you must, prior to 5:00 p.m. Eastern time on October 31, 2018 (two business days before the Easterly special meeting):

    If you hold Easterly units, elect to separate your Easterly units into the underlying public shares and public warrants prior to exercising your redemption rights with respect to the public shares;

    Submit a request in writing that Easterly redeem your public shares for cash to Continental Stock Transfer & Trust Company, Easterly's transfer agent, at the following address:

Continental Stock Transfer & Trust Company
1 State Street Plaza, 30th Floor
New York, New York 10004
Attn: Mark Zimkind
Email: mzimkind@continentalstock.com

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    Deliver your public shares either physically or electronically through DTC to Easterly's transfer agent. Stockholders seeking to exercise their redemption rights and opting to deliver physical certificates should allot sufficient time to obtain physical certificates from the transfer agent. It is Easterly's understanding that stockholders should generally allot at least two weeks to obtain physical certificates from the transfer agent. However, Easterly does not have any control over this process and it may take longer than two weeks. Stockholders who hold their shares in street name will have to coordinate with their bank, broker or other nominee to have the shares certificated or delivered electronically. If you do not submit a written request and deliver your public shares as described above, your shares will not be redeemed.

        Any demand for redemption, once made, may be withdrawn at any time until the deadline for exercising redemption requests and thereafter, with Easterly's consent, until the vote is taken with respect to the Merger. If you delivered your shares for redemption to Easterly's transfer agent and decide within the required timeframe not to exercise your redemption rights, you may request that its transfer agent return the shares (physically or electronically). You may make such request by contacting Easterly's transfer agent at the phone number or address listed above.

        Prior to exercising redemption rights, stockholders should verify the market price of Easterly common stock as they may receive higher proceeds from the sale of their common stock in the public market than from exercising their redemption rights if the market price per share is higher than the redemption price. Easterly cannot assure you that you will be able to sell your shares of Easterly common stock in the open market, even if the market price per share is higher than the redemption price stated above, as there may not be sufficient liquidity in Easterly common stock when you wish to sell your shares.

        If you exercise your redemption rights, your shares of Easterly common stock will cease to be outstanding immediately prior to the Merger and will only represent the right to receive a pro rata share of the aggregate amount on deposit in the Trust Account. You will no longer own those shares. You will be entitled to receive cash for these shares only if you properly demand redemption.

        If the Merger is not approved and Easterly does not consummate an initial business combination by November 30, 2018 or extend such deadline to a later date by obtaining the approval of Easterly's stockholders at a special meeting of Easterly's stockholders, Easterly will be required to dissolve and liquidate and its warrants will expire worthless.

Appraisal Rights

        Appraisal rights are not available to holders of shares of Easterly common stock or warrants in connection with the Merger.

Accounting Treatment

        The Merger is a capital transaction in substance whereby Easterly will be treated as the "acquired" company for financial reporting purposes. This determination was primarily based on the following: Sirius Group will own the majority of the outstanding common shares of the combined company, the current executive officers of Sirius Group will manage the combined company, the board of directors of the combined company will be comprised of the current members of the board of directors of Sirius Group, and Sirius Group's operations will be the operations of the combined company. Accordingly, for accounting purposes, the Merger will be treated as the equivalent of Sirius Group issuing shares for the net assets of Easterly, which are comprised of cash and cash equivalents. The net assets of Easterly will be stated at historical cost, with no goodwill or other intangible assets recorded. All the expenses incurred by Sirius Group related to the Merger will be charged to Additional paid-in surplus.

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Proxy Solicitation Costs

        Easterly will pay the cost of soliciting proxies for the Easterly special meeting. Easterly has engaged Morrow Sodali to assist in the solicitation of proxies for the Easterly special meeting. Easterly has agreed to pay Morrow Sodali a fee of $22,500, plus disbursements. Easterly will reimburse Morrow Sodali for reasonable out-of-pocket expenses and will indemnify Morrow Sodali and its affiliates against certain claims, liabilities, losses, damages and expenses. Easterly also will reimburse banks, brokers and other custodians, nominees and fiduciaries representing beneficial owners of shares of Easterly common stock for their expenses in forwarding soliciting materials to beneficial owners of Easterly common stock and in obtaining voting instructions from those owners. Easterly's directors, officers and employees may also solicit proxies by telephone, by facsimile, by mail, on the Internet or in person. They will not be paid any additional amounts for soliciting proxies.

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PROPOSALS TO BE CONSIDERED BY EASTERLY'S STOCKHOLDERS

PROPOSAL NO. 1—THE MERGER PROPOSAL

        Easterly is asking its stockholders to approve and adopt the Merger Agreement and the Merger. For a summary of and detailed information regarding this proposal, see the information about the Merger Agreement throughout this proxy statement/prospectus, including the information set forth in the section entitled "The Merger Agreement" below. You are urged to read this proxy statement/prospectus in its entirety for more detailed information concerning the Merger, including the Merger Agreement, which is attached as Annex A to this proxy statement/prospectus, as amended by the Amendment, which is attached as Annex C to this proxy statement/prospectus.

The Merger Agreement

        This section of the proxy statement/prospectus describes the material provisions of the Merger Agreement, but does not purport to describe all of the terms of the Merger Agreement. The following summary is qualified in its entirety by reference to the complete text of the Merger Agreement, which is attached as Annex A to this proxy statement/prospectus, and the Amendment, which is attached as Annex C to this proxy statement/prospectus. You are urged to read the Merger Agreement in its entirety because it is the primary legal document that governs the Merger.

        The Merger Agreement contains representations, warranties and covenants that the respective parties made to each other as of the date of the Merger Agreement or other specific dates. The assertions embodied in those representations, warranties and covenants were made for purposes of the contract among the respective parties and are subject to important qualifications and limitations agreed to by the parties in connection with negotiating the Merger Agreement. In particular, in reviewing the representations and warranties contained in the Merger Agreement and described in this summary, it is important to bear in mind that the representations and warranties were negotiated with the principal purposes of establishing the circumstances in which a party to the Merger Agreement may have the right not to close the Merger if the representations and warranties of the other party prove to be untrue due to a change in circumstance or otherwise, and allocating risk between the parties to the Merger Agreement. The representations and warranties may also be subject to a contractual standard of materiality different from those generally applicable to investors and reports and documents filed with the SEC, and in some cases were qualified by the disclosure letter delivered by the party making the representations and warranties, which such disclosures are not reflected in the text of the Merger Agreement. Moreover, information concerning the subject matter of the representations and warranties, which do not purport to be accurate as of the date of this proxy statement/prospectus, may have changed since the date of the Merger Agreement and subsequent developments or new information qualifying a representation or warranty may or may not have been included in this proxy statement/prospectus.

    Structure of the Merger

        Subject to the terms and conditions of the Merger Agreement, the Merger Agreement provides for the merger of Merger Sub with and into Easterly, with Easterly surviving the Merger as a wholly owned subsidiary of Sirius Group. In addition, the Merger Agreement provides that, if elected by Sirius Group, the Merger will be restructured as a direct merger of Easterly with and into Sirius Group, with Sirius Group surviving the Merger. Sirius Group does not plan on making such election at this time.

    Merger Consideration

        Pursuant to the Merger Agreement, upon the effectiveness of the Merger (the "Effective Time"), all shares of Easterly common stock (other than (i) shares of Easterly common stock with respect to which an Easterly stockholder has validly exercised its redemption rights, and that will be redeemed as provided for by Easterly's charter, or any wholly owned subsidiary of Easterly or Sirius Group, which

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will be canceled for no consideration, (ii) shares of Easterly common stock held by Easterly as treasury stock or owned by Easterly, Sirius Group or Merger Sub and (iii) shares of Easterly common stock held by the Sponsor that will be canceled pursuant to the Sponsor Letter) will be converted into Sirius Group common shares at the Exchange Ratio (together with cash in lieu of fractional shares of Sirius Group common shares, as described below, the "merger consideration"). The Exchange Ratio will be determined prior to the closing of the Merger and will be equal to a fraction determined by dividing (a) the estimated amount of cash per public share of Easterly common stock in the Trust Account at the Effective Time by (b) (I) 1.05 multiplied by (II) the Sirius Group September 30 Adjusted DBVPS. The Sirius Group September 30 Adjusted DBVPS is calculated by dividing (A) the book value of Sirius Group determined based on GAAP on a consolidated basis, as set forth in the final, Sirius Group board of directors approved, unaudited GAAP consolidated financial statements of Sirius Group for the nine months ended September 30, 2018 (the "September 30 Book Value"), decreased by the $7 million deferred underwriting fee payable by Easterly to Citigroup Global Markets Inc. as underwriter of the IPO, and as adjusted by the GAAP accounting effect of the redemption of the Sirius Group Series A redeemable preference shares by (B) the sum of (x) the fully diluted number of Sirius Group common shares issued and outstanding as of September 30, 2018 and (y) 593,000 Sirius Group common shares. Sirius Group is required to deliver to Easterly its proposed calculation of September 30 Book Value and the Sirius Group September 30 Adjusted DBVPS no later than five business days after the date that the Registration Statement of which this proxy statement/prospectus forms a part is declared effective (but if the Registration Statement is declared effective on or after September 30, 2018, then no earlier than October 5, 2018) (such estimates being the "Estimated September 30 Book Value" and the "Estimated Sirius Group September 30 Adjusted DBVPS"). Easterly has five business days to review and agree to or dispute the accuracy of such calculation. If a dispute notice is delivered by Easterly within such time period, Sirius Group and Easterly will jointly request that a mutually agreed upon nationally recognized independent accounting firm (the "Accounting Firm"), make a binding determination only as to the items set forth in the dispute notice. At least two business days prior to the date of the closing of the Merger (or such other time as may be mutually agreed between Sirius Group and Easterly), Easterly will notify Sirius Group in writing of its good faith calculation of the number of shares of Easterly common stock outstanding as of the closing of the Merger and the estimated amount of cash per public share of Easterly common stock in the Trust Account at the Effective Time. Using such amounts and the Estimated Sirius Group September 30 Adjusted DBVPS as finally determined pursuant to the Merger Agreement, Sirius Group will then calculate the final Exchange Ratio, unless such calculation is done after Sirius Group files with the SEC its financial statements for the quarter ended September 30, 2018, in which case Sirius Group shall prepare its good faith calculation of the September 30 Book Value and the Sirius Group September 30 Adjusted DBVPS, which shall be submitted for the review and approval by Sirius Group's Audit & Risk Management Committee (such calculations, the "Final September 30 Book Value" and "Final Sirius Group September 30 Adjusted DBVPS"), and Sirius Group shall calculate the Exchange Ratio using the Final Sirius Group September 30 Adjusted DBVPS and not the Estimated Sirius Group September 30 Adjusted DBVPS.

        If the Estimated Sirius Group September 30 Adjusted DBVPS is used to determine the Exchange Ratio at the closing of the Merger, then the Merger Agreement provides for a post-closing adjustment if such estimate is different than the Final Sirius Group September 30 Adjusted DBVPS as finally determined after the closing of the Merger. Such adjustment will result in either (x) the issuance of new Sirius Group common shares or a payment of cash by Sirius Group to CM Bermuda if the Exchange Ratio is greater than it would have been using the Final Sirius Group September 30 Adjusted DBVPS or (y) the surrender to Sirius Group of Sirius Group common shares owned by CM Bermuda or a payment of cash to Sirius Group from CM Bermuda if the Exchange Ratio is less than it would have been using the Final Sirius Group September 30 Adjusted DBVPS.

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        Additionally, each issued and outstanding public warrant to acquire shares of Easterly common stock will cease to represent a right to acquire shares of Easterly common stock and will be converted into a converted warrant. The number of Sirius Group common shares subject to each converted warrant will be equal to the number of shares of Easterly common stock subject to each Easterly warrant immediately prior to the closing of the Merger multiplied by the Exchange Ratio, and such converted warrant will have an exercise price per Sirius Group common share equal to the exercise price per share of Easterly common stock subject to such Easterly warrant immediately prior to the closing of the Merger divided by the Exchange Ratio.

    Fractional Shares

        Notwithstanding any other provision of the Merger Agreement, no fractional shares of Sirius Group common shares will be issued upon the conversion of Easterly common stock in the Merger, but in lieu thereof each holder of shares of Easterly common stock otherwise entitled to a fractional Sirius Group common share will be entitled to receive, from the exchange agent (as defined below), a cash payment, without interest, in lieu of such fractional Sirius Group common share representing such holder's proportionate interest, if any, in the net proceeds from the sale by the exchange agent in one or more transactions of Sirius Group common shares equal to the excess of (i) the aggregate number of Sirius Group common shares to be delivered to the exchange agent by Sirius Group pursuant to the Merger Agreement over (ii) the aggregate number of whole Sirius Group common shares to be distributed to the holders of Easterly common stock pursuant to the Merger Agreement (such excess, the "Excess Shares"). As soon as reasonably practicable after the Effective Time, the exchange agent, as agent for the former holders of Easterly common stock that would otherwise receive fractional Sirius Group common shares, will sell the Excess Shares at then-prevailing prices on the Nasdaq.

        The sale of the Excess Shares by the exchange agent, as agent for the former holders of Easterly common stock that would otherwise receive fractional Sirius Group common shares, will be executed on the Nasdaq through one or more member firms of the Nasdaq and will be executed in round lots to the extent practicable. The net proceeds of any such sale or sales of Excess Shares to be distributed to the former holders of Easterly common stock will be reduced by any and all commissions, transfer taxes and other out-of-pocket transaction costs, as well as any expenses, of the exchange agent incurred in connection with such sale or sales. Until the net proceeds of such sale or sales have been distributed to the former holders of Easterly common stock, the exchange agent will hold such net proceeds in trust for such holders that would otherwise receive fractional Sirius Group common shares (the "Common Shares Trust"). The exchange agent will determine the portion of the Common Shares Trust to which each former holder of Easterly common stock will be entitled, if any, by multiplying the amount of the aggregate proceeds comprising the Common Shares Trust by a fraction, the numerator of which is the amount of the fractional share interest to which such former holder of Easterly common stock would otherwise be entitled and the denominator of which is the aggregate amount of fractional share interests to which all former holders of Easterly common stock would otherwise be entitled.

        As soon as reasonably practicable after the determination of the amount of cash, if any, to be paid to former holders of Easterly common stock in lieu of any fractional Sirius Group common shares, the exchange agent will make available such amounts to such holders of Easterly Common Stock without interest, subject to and in accordance with the exchange procedures described below.

    Exchange Procedures

        Prior to the Effective Time, Sirius Group will designate a nationally recognized financial institution reasonably acceptable to Sirius Group to act as exchange agent (the "exchange agent"), and will deposit with the exchange agent the full number of Sirius Group common shares issuable in exchange for outstanding Easterly shares under the Merger Agreement.

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        As soon as reasonably practicable after the Effective Time, Sirius Group will cause the exchange agent to mail to each record holder of a certificate representing any shares of Easterly common stock whose shares were converted into a right to receive the merger consideration a customary letter of transmittal and instructions for surrendering the certificate in exchange for payment of the merger consideration. Upon surrender of a certificate (or an affidavit of loss in lieu thereof) and upon delivery of a duly executed letter of transmittal in proper form and such other documentation as may be reasonably required by exchange agent, the holder of such certificate will be entitled to receive the portion of the aggregate merger consideration payable to such holder pursuant to the Merger. The surrendered certificates representing shares of Easterly common stock will be canceled. Payment of the merger consideration with respect to shares of Easterly common stock represented by book-entry will be made as promptly as practicable following the Effective Time without any action on the part of the person in whose name such book-entry shares are registered. No interest will be paid or will accrue on the cash payable upon surrender of any certificate representing any shares of Easterly common stock.

        You should not return your stock certificates with the enclosed proxy card, and you should not send in your stock certificates to the exchange agent until you receive a letter of transmittal from the exchange agent with instructions for the surrender of your stock certificates.

    Lost, Stolen and Destroyed Certificates

        If an Easterly stock certificate is lost, stolen or destroyed, the holder of such certificate must deliver an affidavit of that fact prior to receiving any merger consideration and, if required by Sirius Group, may also be required to provide a bond (in a customary amount) prior to receiving any merger consideration.

    Conversion of Stock of Merger Sub

        At the Effective Time, all issued and outstanding common stock of Merger Sub will be converted into and become 1,000 fully paid and nonassessable shares of common stock, par value $0.01 per share, of the surviving company. These shares will constitute the only outstanding share of capital stock of the surviving company as of the Effective Time and will be owned by Sirius Group.

    Closing and Effective Time of the Merger

        The Merger may be consummated no later than three business days following the satisfaction or waiver of the conditions described below under the subsection entitled "Conditions to Closing of the Merger."

    Material Adverse Effect

        Under the Merger Agreement, a "Material Adverse Effect" with respect to any party is any event, change, effect, development, state of facts, condition, circumstance or occurrence that individually or in the aggregate (i) has or would be reasonably expected to have a material adverse effect on the business, results of operations, assets, liabilities or financial condition of such party and its subsidiaries, taken as a whole, except to the extent such material adverse effect results from (a) any changes in regional or global economic conditions, including changes affecting credit, financial or capital markets or changes in interest rates or exchange rates, (b) any changes in conditions generally affecting any of the industries in which such party and its subsidiaries operate, (c) any decline in market price or trading volume or the credit rating of such party or the securities of such party (it being understood that the facts or occurrences giving rise to or contributing to such decline may be taken into account in determining whether there has been or would be a Material Adverse Effect), (d) any regulatory, legislative or political conditions, in each case in the United States or any other jurisdiction, (e) any failure, in and of itself, by such party to meet any internal or external projections, forecasts, estimates

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or predictions in respect of revenues, earnings, or other financial or operating metrics for any period (it being understood that the facts or occurrences giving rise to or contributing to such failure may be taken into account in determining whether there has been or would be a Material Adverse Effect, (f) the execution and delivery of the Merger Agreement or the public announcement, performance, pendency or consummation of the Merger or any of the other transactions contemplated by the Merger Agreement, including the impact thereof on the relationships, contractual or otherwise, of such party or any of its subsidiaries with customers, employees, suppliers or other parties or any litigation arising from the Merger Agreement or the transactions contemplated by the Merger Agreement, (g) any change or prospective change in applicable laws, regulation or GAAP or SAP (or authoritative interpretations thereof), (h) any geopolitical conditions, the outbreak or escalation of hostilities, any acts of war, sabotage or terrorism, or any escalation or worsening of any such acts of war, sabotage or terrorism, (i) any action permitted or required to be taken pursuant to or in accordance with the Merger Agreement or taken at the request of the other party or with the other party's express written consent, or (j) volcanoes, tsunamis, pandemics, earthquakes, floods, storms, hurricanes, tornados or other natural disasters; provided, however, that clauses (a), (b), d), (h) and (j) may be taken into account to the extent that such changes in conditions have a greater adverse materially disproportionate effect on such party and its subsidiaries, taken as a whole, relative to the adverse effect such changes have on others operating in the industries in which such party and any of its subsidiaries operate or (ii) would prevent or materially delay the consummation by Easterly or Sirius Group, as applicable, of the Merger and the other transactions contemplated by the Merger Agreement on a timely basis.

Conditions to Closing of the Merger

    Conditions to Easterly's, Sirius Group's and Merger Sub's Obligations

        The obligations of Easterly, Sirius Group and Merger Sub to consummate the Merger are subject to the satisfaction, at or prior to the closing date, of each of the following conditions (which may be waived, in whole or in part, to the extent permitted by law, by Sirius Group and Easterly):

    The required vote of the stockholders of Easterly approving the Merger Proposal must have been obtained.

    The Sirius Group common shares issuable in the Merger or upon exercise of the converted warrants shall have been approved for listing on Nasdaq, subject to official notice of issuance.

    There must not be in effect any order by a governmental entity of competent jurisdiction which prohibits, restrains or makes illegal the consummation of the Merger or the other transactions contemplated by the Merger Agreement.

    Sirius Group's Registration Statement on Form S-4, of which this proxy statement/prospectus forms a part, must have become effective under the Securities Act and not be the subject of any stop order, and no proceedings for that purpose shall have been initiated or threatened by the SEC and not withdrawn.

    All consents, authorizations or approvals of any regulatory authorities required to consummate the Merger shall have been obtained and remain in full force and effect, and all statutory waiting periods relating to such approvals, authorizations and consents shall have expired or been terminated.

    The Warrant Amendment shall have been entered into by the parties thereto.

    The Sponsor Letter shall be in full force and effect.

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    Conditions to Sirius Group's and Merger Sub's Obligations

        The obligations of Sirius Group and Merger Sub to consummate the Merger are subject to the satisfaction, on or prior to the closing date, of each of the following conditions (which may be waived in whole or in part by Sirius Group):

    The representations and warranties of Easterly, disregarding all qualifications and exceptions contained therein relating to materiality or Material Adverse Effect, must be true and correct as of the date of the Merger Agreement and as of the closing date as if made on and as of such date (or, if given as of a specific date, at and as of such date), except where the failure of such representations and warranties to be true and correct would not reasonably be expected to have a Material Adverse Effect with respect to Easterly, subject to a more stringent standard in the case of certain fundamental representations.

    Easterly must have performed and complied in all material respects with all obligations, covenants and agreements required by the Merger Agreement to be performed or complied with by Easterly at or prior to the closing.

    Easterly must deliver a statement that it is not, and has not been, a "Unites States real property holding corporation."

    Easterly shall have delivered or caused to be delivered the Registration Rights Agreement and a Lock-Up Agreement executed by the Sponsor.

    Since the date of the Merger Agreement, there must not have been any event or circumstance which resulted in or that would reasonably be expected to result in a Material Adverse Effect of Easterly that is continuing.

    Conditions to Easterly's Obligations

        The obligations of Easterly to consummate the Merger are subject to the satisfaction, at or prior to the closing date, of each of the following conditions (which may be waived in whole or in part by Easterly):

    The representations and warranties of Sirius Group and Merger Sub, disregarding all qualifications and exceptions contained in such representations and warranties relating to materiality or Material Adverse Effect, must be true and correct as of the date of the Merger Agreement and as of the closing date as if made on and as of such date (or, if given as of a specific date, at and as of such date), except where the failure of such representations and warranties to be true and correct would not have (and would not reasonably be expected to have) a Material Adverse Effect with respect to Sirius Group, subject to a more stringent standard in the case of certain fundamental representations.

    Each of Sirius Group and Merger Sub must have performed and complied in all material respects with all obligations, covenants and agreements required by the Merger Agreement to be performed or complied with by Sirius Group and Merger Sub at or prior to the closing.

    Sirius Group shall have delivered or caused to be delivered the Registration Rights Agreement and a Lock-Up Agreement executed by it.

    Since the date of the Merger Agreement, there must not have been any event or circumstance which resulted in or that would reasonably be expected to result in a Material Adverse Effect of Sirius Group that is continuing.

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    Representations and Warranties

        Under the Merger Agreement, Easterly made customary representations and warranties, including those relating to: organization and good standing; capitalization; authorization of agreement; consents and approvals of third parties; conflicts; subsidiaries; filings with the SEC and financial statements; no undisclosed liabilities; absence of certain developments; information supplied for this proxy statement/prospectus; litigation; compliance with laws; employee matters; properties; taxes; material contracts; intellectual property; indebtedness; brokers' fees; status under the Investment Company Act; stockholder approvals; transactions with affiliates; and the Trust Account.

        Under the Merger Agreement, Sirius Group made customary representations and warranties, including those relating to: organization and good standing; capitalization; subsidiaries; authorization of agreement; consents and approvals of third parties; conflicts; financial statements; no undisclosed liabilities; absence of certain developments; information supplied for this proxy statement/prospectus; litigation; compliance with laws; regulatory reports; employee matters; environmental matters; properties; material contracts; taxes; risk-based capital; insurance regulatory matters and agreements with regulators; reinsurance contracts; actuarial reports; ratings; intellectual property; insurance; brokers' fees; transactions with affiliates; and agreements with regulatory agencies.

Covenants of the Parties

    Covenants of Easterly

        Easterly made certain covenants under the Merger Agreement, including, among others, the following:

    Easterly will carry on its business in the ordinary course consistent with past practice in all material respects, except as permitted by the Merger Agreement, as set forth in the disclosure letter delivered by Easterly to Sirius Group, as required by law, or as consented to by Sirius Group in writing (such consent not to be unreasonably withheld, conditioned or delayed) and use commercially reasonable efforts to preserve intact its present business organization and advantageous business relationships.

    Subject to certain exceptions, Easterly will not:

    incur any indebtedness;

    adjust, split, combine or reclassify any shares of its capital stock;

    make, declare or pay any dividend, or make any other distribution on, or directly or indirectly redeem, purchase or otherwise acquire, any shares of their capital stock, other than with respect to redemptions of Easterly common stock in connection with the Merger and the Extension Amendments;

    issue, sell or otherwise permit to become outstanding any additional shares of its capital stock or securities convertible or exchangeable into, or exercisable for, any shares of its capital stock or any options, warrants, or other rights of any kind to acquire any shares of capital stock;

    sell, transfer, mortgage, encumber or otherwise dispose of any of its material properties, business or assets to any individual, corporation or other entity;

    acquire any other entity or business;

    terminate, materially amend, renew or waive any material provision of, any material contract, other than normal renewals in the ordinary course of business, except for the Extension Amendments, enter into any contract that would constitute a material contract if it were in effect on the date of the Merger Agreement;

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      hire any employee or consultant or adopt any employee benefit plan;

      settle any material proceeding;

      amend its certificate of incorporation or bylaws, except for the Extension Amendments;

      merge or consolidate itself with any other Person, or restructure, reorganize or completely or partially liquidate or dissolve;

      implement or adopt any change in its accounting principles, practices or methods, other than as may be required by GAAP, SAP or by applicable laws;

      enter into any material new line of business;

      make, or commit to make, any capital expenditures;

      prepare or file any tax return inconsistent with prior practice, make, change or revoke any material tax election, change an annual tax accounting period, adopt or change any material tax accounting method, file any amended tax return, enter into any closing (or similar) agreement with respect to taxes, settle or compromise any tax claim, audit, assessment or dispute or surrender any right to claim a refund, offset or any other reduction in tax liability, request any ruling or similar guidance with respect to taxes, or agree to an extension or waiver of the statute of limitations with respect to a material amount of taxes;

      take, or fail to take, any action that is intended to or would reasonably be expected to result in the failure of any of the conditions to closing of the Merger to be satisfied; or

      agree to take, make any commitment to take, or adopt any resolutions of its board of directors or similar governing body in support of, any of the actions prohibited by the above covenants.

    Easterly will make all necessary filings with respect to the transactions contemplated by the Merger Agreement under the Securities Act and the Exchange Act and applicable "blue sky" laws and rules and regulations thereunder.

    Prior to closing of the Merger, Easterly will take all such steps as may be required to cause any dispositions of shares of common stock of Easterly resulting from the Merger by each individual who is subject to the reporting requirements of Section 16(a) of the Exchange Act with respect to Easterly to be exempt under Rule 16b-3 promulgated under the Exchange Act.

    Easterly will cease any existing discussions and negotiations with any third parties conducted prior to the date of the Merger Agreement with respect to any acquisition proposal (other than proposals in which Easterly would acquire less than 5% of the equity interests or assets of such other party, if such acquisition did not constitute a Business Combination (as defined in Easterly's charter) and will not enter into any contract with respect to any acquisition proposal until the earlier of the consummation of the Merger or the termination of the Merger Agreement. Until the earlier of the consummation of the transactions contemplated by the Merger Agreement or the valid termination of the Merger Agreement, Easterly will not, directly or indirectly, through any affiliate or any of its or their officers, directors, employees, attorneys, equity holders, financial advisors, accountants or other representatives or agents, directly or indirectly, (i) initiate, solicit, pursue, discuss, inquire or encourage any inquiries or the making of any proposal that constitutes an acquisition proposal, (ii) continue or engage in negotiations or discussions concerning, or provide any information to or request any information from any person or entity relating to, any acquisition proposal other than information to or from any other person or entity which is traditionally provided in the regular course of business to third parties where Easterly and its officers, directors and affiliates have no reason to believe that such information may be utilized to evaluate any such acquisition proposal, or (iii) agree to,

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      approve or recommend, or otherwise enter into any contract with respect to, any acquisition proposal.

    Following Easterly's receipt of the funds held in the Trust Account at the closing of the Merger, Easterly will pay all liabilities and obligations of Easterly using unrestricted cash and up to $2 million from the Trust Account (and not, for the avoidance of doubt, any funds held in or released from the Trust Account in excess of $2 million) and, to the extent such unrestricted cash is not sufficient to discharge all such liabilities and obligations, such liabilities and obligations will be paid by the Sponsor pursuant to the Sponsor Letter. However, the $7 million deferred underwriting fee payable by Easterly to Citigroup Global Markets Inc. as underwriter of the IPO will be paid out of the funds released from the Trust Account.

    Prior to the closing of the Merger, if requested in writing by Sirius Group, Easterly will commence a tender offer pursuant to which it will offer to purchase up to such number of the public warrants at a cash price for each public warrant as mutually agreed between Sirius Group and Easterly. However, Sirius Group has determined that it will not request Easterly to complete such a tender offer.

    Until the closing of the Merger, (i) Easterly will provide Sirius Group with a draft copy of any income and other material tax returns at least 30 days prior to their due date and will not file such tax return without the consent of Sirius Group (which consent shall not be unreasonably withheld, conditioned or delayed), (ii) Easterly will give Sirius Group and its advisors a reasonable opportunity to participate any in discussions with any tax authority, and provide Sirius Group with draft copies of any materials intended to be submitted to any tax authority reasonably in advance of such submission, and (iii) Sirius Group and Easterly will cooperate in good faith with each other with respect to matters related to the taxes of Easterly.

    For all tax purposes, Sirius Group and Easterly agree to treat the Promissory Note, (i) as a collateral arrangement to secure the payment of a termination fee to Easterly in the event the Merger does not close, which collateral will be returned to Sirius Group if the Merger closes, and (ii) Sirius Group as the owner of the cash proceeds of such loan at all times, and to file all tax returns consistently therewith.

    Easterly will provide Sirius Group with prompt notice of and copies of all proceedings and correspondence relating to any legal proceeding against Easterly, its subsidiary or any of their respective directors or officers by any stockholder of Easterly arising out of or relating to the Merger Agreement or the Merger. Easterly will not settle or offer to settle any such legal proceeding without the prior written consent of Sirius Group (which consent shall not be unreasonably withheld, conditioned or delayed).

Covenants of Sirius Group

        Sirius Group made certain covenants under the Merger Agreement, including, among others, the following:

    Sirius Group and its subsidiaries will carry on their businesses in the ordinary course consistent with past practice in all material respects and will not take, or fail to take, any action that is intended to or would reasonably be expected to result in the failure of any of the conditions to closing of the Merger to be satisfied, except, in each case, as permitted in the Merger Agreement, as set forth in the disclosure letter delivered by Sirius Group to Easterly or as required by law.

    Subject to certain exceptions, Sirius Group will not:

    adjust, split, combine or reclassify any of its equity interests;

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      make, declare or pay any dividend, or make any other distribution on, or directly or indirectly redeem, purchase or otherwise acquire, any of its equity interests (except (i) dividends paid by any of the wholly owned subsidiaries of Sirius Group to Sirius Group or any of its wholly owned subsidiaries, (ii) the acceptance of Sirius Group common shares as payment for the exercise price of options or for withholding taxes incurred in connection with the exercise of options or the vesting or settlement of Sirius Group equity awards and dividend equivalents thereon, if any, in each case in accordance with past practice and the terms of the applicable award agreements) or (iii) required dividends or distributions in respect of Sirius Group Series A redeemable preference shares; or

      issue, sell or otherwise permit to become outstanding any additional equity interests or shares of capital stock or securities convertible or exchangeable into, or exercisable for, any shares of capital stock or any options, warrants, or other rights of any kind to acquire any equity interests or shares of capital stock except (i) to the extent such issuance or sale would otherwise be permitted under the next bullet point, (ii) for the issuance of Sirius Group equity awards and (iii) pursuant to the exercise of Sirius Group equity awards or the settlement or vesting of Sirius Group equity awards in accordance with their terms.

    Subject to certain exceptions, Sirius Group will cease any existing discussions and negotiations with any third parties conducted prior to the date of the Merger Agreement with respect to any acquisition proposal (other than proposals with respect to less than 10% of Sirius Group's equity interests or less than 50% of Sirius Group's assets) and will not enter into any contract with respect to any acquisition proposal until the earlier of the consummation of the Merger or the termination of the Merger Agreement. Until such time, and subject to certain exceptions, none of Sirius Group or any of its subsidiaries will, directly or indirectly, through any affiliate or any of its or their officers, directors, employees, attorneys, equity holders, financial advisors, accountants or other representatives or agents or otherwise, (i) initiate, solicit, pursue, discuss or encourage any inquiries or the making of any proposal that constitutes an acquisition proposal, (ii) continue or engage in negotiations or discussions concerning, or provide any non-public information to any person or entity relating to, any acquisition proposal other than information to any other person or entity which is traditionally provided in the regular course of business to third parties where Sirius Group and its officers, directors, employees, attorneys, equity holders, financial advisors, accountants or other representatives or agents have no reason to believe that such information may be utilized to evaluate any such acquisition proposal, or (iii) agree to, approve or recommend, or otherwise enter into any contract with respect to, any acquisition proposal.

    For a period of six years after the closing, (i) Sirius Group will maintain in effect the current policies of directors' and officers' liability insurance maintained by Sirius Group (provided that Sirius Group may substitute policies with a substantially comparable insurer of at least the same coverage and amounts containing terms and conditions which are no less advantageous to the insured) with respect to claims against the directors and officers arising from facts or events which occurred at or before the closing of the Merger (including the transactions contemplated thereby); provided, however, that Sirius Group is not required to expend, on an annual basis, an amount in excess of 300% of the aggregate annual premium paid as of the date of the Merger Agreement by Easterly for such insurance, or (ii) Easterly will, prior to the closing of the Merger, obtain a six-year "run-off" or "tail" directors' and officers' liability insurance policy under Easterly's existing directors and officers insurance policy.

    Sirius Group will use its reasonable best efforts to cause the Sirius Group common shares to be issued in the Merger and upon exercise of the converted warrants to be listed on the Nasdaq Stock Market, subject to official notice of issuance.

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    Mutual Covenants

    Sirius Group, Merger Sub, and Easterly agreed to give prompt notice to the others if any of them (i) receives any notice or other communication from any governmental entity, Lloyd's or Nasdaq (or any other securities market) in connection with the transactions contemplated by the Merger Agreement or (ii) becomes aware of the occurrence of an event that would reasonably be expected to prevent or materially delay the consummation of the Merger or that would reasonably be expected to result in any of the conditions to the Merger not being satisfied.

    Upon reasonable notice and subject to certain conditions, Sirius Group and Easterly agreed to give the officers, employees, accountants, counsel and other representatives of Sirius Group, Merger Sub and Easterly, during normal business hours during the period prior to the closing of the Merger, reasonable access to all of its and its subsidiaries' properties, books, contracts, commitments and records, and to its and its subsidiaries' officers, employees, accountants, counsel and other representatives and, during such period, each party will, and will cause its subsidiaries to, promptly make available to the other party, subject, in the case of competitively sensitive information, to any customary "clean-room" arrangements agreed between the parties, (i) a copy of each report, schedule, registration statement and other document filed or received by it during such period pursuant to the requirements of federal securities laws and (ii) all other information concerning its business, properties and personnel as the other party may reasonably request.

    Sirius Group and Easterly agreed to cooperate with each other and use their reasonable best efforts to promptly prepare and file all necessary documentation, to effect all applications, notices, petitions and filings, to obtain as promptly as practicable all permits, consents, approvals and authorizations of all third parties, governmental entities and Lloyd's which are necessary or advisable to consummate the Merger, and to comply with the terms and conditions of all such permits, consents, approvals and authorizations of all such governmental entities and Lloyd's. The parties will cooperate with each other in connection therewith. Sirius Group and Easterly will consult with each other with respect to the obtaining of all permits, consents, approvals and authorizations of all third parties and governmental entities necessary or advisable to consummate the Merger and each party will keep the other reasonably apprised of the status of matters relating to completion of the Merger and will consult with the other in advance of any meeting or conference with any governmental entity or Lloyd's in connection with the Merger. Sirius Group and Easterly will each use its reasonable best efforts to (i) take all action reasonably necessary to ensure that no state takeover statute or similar law is or becomes applicable to the Merger and (ii) if any state takeover statute or similar law becomes applicable to the Merger, take all action to enable the Merger to be consummated as promptly as practicable on the terms contemplated by the Merger Agreement and otherwise minimize the effect of such law on the Merger.

    Sirius Group and Easterly will each use its reasonable best efforts to (i) avoid the entry of, or to have vacated, lifted, reversed or overturned any decree, judgment, injunction or other order, whether temporary, preliminary or permanent, that would restrain, prevent or delay the closing of the Merger, and (ii) avoid or eliminate each and every impediment so as to enable the closing of the Merger to occur as soon as possible, including proposing, negotiating, committing to and effecting, by consent decree, hold separate order, or otherwise, the sale, divestiture or disposition of businesses or assets of Easterly, Sirius Group and their subsidiaries. Sirius Group, Easterly and their subsidiaries will not be required to take, or agree to take, any actions that, individually or in the aggregate, would reasonably be expected to have a material and adverse effect on Sirius Group, any Sirius Group subsidiary or Easterly (in any case, measured on a scale relative to Easterly, Sirius Group and any Sirius Group subsidiary on a combined basis).

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    Survival of Representations and Warranties

        The representations and warranties of the parties contained in the Merger Agreement will not survive the closing of the Merger.

    Termination

        The Merger Agreement may be terminated and the transactions contemplated by the Merger Agreement may be abandoned any time prior to the closing as follows:

    by mutual written consent of Sirius Group and Easterly;

    by Sirius Group or Easterly if any governmental entity of competent jurisdiction has issued a final and non-appealable order permanently restraining, enjoining or otherwise prohibiting the transactions contemplated by the Merger Agreement or if any governmental entity that must grant a required consent has denied approval of the transactions contemplated by the Merger Agreement and such denial has become final and non-appealable;

    by Sirius Group or Easterly on or after November 30, 2018 (the "Outside Date"), if the closing has not occurred by the close of business on that date; provided that this right to terminate will not be available to Sirius Group or Easterly, as applicable, if such party's action or failure to act constitutes a material breach or violation of any of its covenants, agreements or other obligations under the Merger Agreement and such material breach or violation has been the principal cause of or directly resulted in (A) the failure to satisfy the conditions to the obligations of the terminating party to consummate the Merger prior to such date or (B) the failure of the closing to occur by such date;

    by Sirius Group or Easterly if the Easterly stockholder approval of the Merger Proposal has not been obtained at the Easterly special meeting of stockholders or at any adjournment or postponement of the meeting;

    by Easterly, if Sirius Group or Merger Sub has breached or failed to perform any of its representations, warranties, covenants or agreements, which breach or failure to perform, if occurring or continuing on the closing date, (i) would give rise to the failure of a condition to closing of the Merger and (ii) is not cured by the earlier of the Outside Date and 30 days following written notice of such breach, or by its nature or timing is incapable of being cured during such period; provided, that Easterly is not then in material breach of any of its representations, warranties, covenants or agreements;

    by Sirius Group, if prior to the Easterly stockholder approval of the Merger Agreement and the Merger, if the Easterly board of directors has made an adverse recommendation change or Easterly has breached any of its covenants to obtain the Easterly stockholder approval or not to solicit an acquisition proposal; or

    by Sirius Group, if (i) Easterly has breached or failed to perform any of its representations, warranties, covenants or agreements set forth in the Merger Agreement, which breach or failure to perform, if occurring or continuing on the date of the closing of the Merger, (a) would give rise to the failure of a condition closing of the Merger and (b) is not cured by the earlier of the Outside Date and 30 days following written notice of such breach, or by its nature or timing is incapable of being cured during such period; provided, that Sirius Group is not then in material breach of any of its representations, warranties, covenants or agreements or (ii) Easterly's board of directors shall have (a) withheld, withdrawn or modified or qualified, or proposed publicly to withhold, withdraw or modify or qualify, in a manner adverse to Sirius Group, the approval, determination of advisability, or recommendation by the Easterly board of directors or such committee of this Agreement, the Merger and the other transactions contemplated thereby, (b) made any other public statement in connection with the Easterly special meeting by or on

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      behalf of the Easterly board of directors that would reasonably be expected to have the same effect or (c) approved, determined to be advisable, or recommended, or proposed publicly to approve, determine to be advisable or recommend, any Easterly Acquisition Proposal (as defined in the Merger Agreement).

        In the event of termination of the Merger Agreement, the Merger Agreement will become void and there will be no liability or obligation on the part of any party thereto, provided that a party will still be liable for a willful breach of the Merger Agreement. Certain provisions of the Merger Agreement and the provisions of the confidentiality agreement between Sirius Group and Easterly will survive any termination of the Merger Agreement.

    Fees and Expenses

        Sirius Group is responsible for all expenses related to (i) the filing or similar fees in connection with obtaining any required approvals of governmental entities, (ii) the filing of Sirius Group's Registration Statement on Form S-4, of which this proxy statement/prospectus forms a part, and (iii) all SEC filing fees related to the Merger. All other fees and expenses incurred by Easterly or Sirius Group will be borne solely by the party that incurred such fees and expenses.

    Amendment

        The Merger Agreement can be amended, supplemented or changed, and any provision of the Merger Agreement can be waived, only by a written instrument signed by Easterly, Sirius Group and Merger Sub; provided, that no amendment of the Merger Agreement may be made following the adoption of the Merger Agreement by the Easterly stockholders unless, to the extent required, such amendment is approved by such stockholders.

    Specific Performance

        The parties are entitled under the Merger Agreement to an injunction or injunctions to prevent breaches of the Merger Agreement or to enforce specifically the performance of the terms and provisions of the Merger Agreement (including the parties' obligation to consummate the Merger) without proof of actual damages, in addition to any other remedy to which they are entitled at law or in equity. Each of the parties also waived (i) any defense in any action for specific performance that a remedy at law would be adequate and (ii) any requirement under any law to post security or a bond as a prerequisite to obtaining equitable relief.

    Governing Law

        The Merger Agreement is governed by the laws of the State of Delaware, without giving effect to principles of conflicts of law thereof.

Tax Treatment

        Sirius Group and Easterly intend to report the Merger as a tax-deferred "reorganization" for United States federal income tax purposes within the meaning of Section 368 of the Code. Assuming such treatment is respected, holders of Easterly common stock generally will not recognize gain or loss for U.S. federal income tax purposes as a result of the exchange of their Easterly common stock for Sirius Group common shares (except with respect to cash received in lieu of fractional shares). Neither Sirius Group nor Easterly intends to request any ruling or other guidance from the IRS on the United States federal income tax treatment of the Merger and no assurance can be given that the IRS would not challenge such treatment. The qualification of the Merger as a tax-deferred reorganization is not a condition to closing and the Merger Agreement does not include any covenant requiring Sirius Group to ensure that the Merger qualifies as a tax-deferred reorganization.

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        In connection with the registration statement of which this proxy statement/prospectus forms a part, Sirius Group has received an opinion of counsel that subject to certain representations, qualifications and assumptions it is more likely than not that the Merger will qualify as a "reorganization" within the meaning of section 368 of the Code. This opinion is subject to assumptions related to future events (described in more detail under "Proposal No. 1—The Merger Proposal—U.S. Federal Income Tax Considerations of the Merger to Holders of Easterly Common Stock or Easterly Warrants—Treatment of the Merger") because the qualification of the Merger as a reorganization depends on meeting certain technical requirements that cannot be determined at this time, and no assurance can be given that such assumptions will in fact be correct. More specifically, the treatment of the Merger as a reorganization would depend on whether sufficient stockholders of Easterly exchange their Easterly common stock for common shares of Sirius Group rather than redeem it for cash. If a significant number of stockholders decide to redeem their Easterly common stock, Easterly may not meet the "continuity of business enterprise" requirement necessary to qualify as a reorganization under Sections 368(a)(1)(B) and 368(a)(2)(E) of the Code and would not meet the requirement that it retain "substantially all" of its assets to qualify as a reorganization under Section 368(a)(2)(E) of the Code. Additionally, absent direct guidance, it is unclear whether certain transactions would result in the stockholders being treated as having received "boot" in the Merger, thereby denying the treatment of the Merger as a reorganization under Section 368(a)(1)(B) of the Code. These transactions include the post-closing adjustments reflecting the Exchange Ratio and the Promissory Note dated June 23, 2018, made by Easterly in favor of Sirius Group pursuant to which Sirius Group has agreed to lend Easterly $0.03 per month for every public share of Easterly common stock outstanding as of June 30, 2018, which loan is immediately payable back to Sirius Group if the Merger closes. While none of these transactions results in any former stockholder of Easterly receiving any cash or other property (other than common shares of Sirius Group) in the Merger in return for their Easterly common stock, no assurance can be given that the IRS would not challenge this treatment. Additionally, no assurance can be given that the IRS would not recharacterize the repurchase of Sirius Group stock held by CM Bermuda in an amount equal to the value of the Easterly Trust Account as a distribution by Easterly to Sirius Group notwithstanding that Sirius Group intends to use other sources of cash for such repurchase. If the transaction was so recharacterized, Easterly would neither meet the continuity of business enterprise requirement nor the "substantially all" requirement described above.

        If the IRS were to successfully challenge the tax-deferred reorganization treatment of the Merger, United States holders of Easterly common stock would recognize taxable gain or loss on the exchange of their Easterly common stock for common shares of Sirius Group in the Merger.

        You are strongly urged to consult with your own tax advisor to determine the particular U.S. federal, state or local or foreign income or other tax consequences of the Merger to you. For more information see the section entitled "Proposal No. 1—The Merger Proposal—U.S. Federal Income Tax Considerations of the Merger to Holders of Easterly Common Stock or Easterly Warrants—Treatment of the Merger."

Agreements Related to the Merger Agreement

        This section describes the material provisions of certain additional agreements entered into or to be entered into in connection with the Merger, but does not purport to describe all of the terms thereof. A copy of the Sponsor Letter, which was entered into concurrently with the Merger Agreement, is attached as Annex B. A copy of the Promissory Note, which was entered into concurrently with the Merger Agreement, is attached as Annex D. The form of the Registration Rights Agreement is attached as Annex E. The form of the Lock-Up Agreement is attached as Annex F. The form of the Warrant Amendment is attached as Annex G. Stockholders and other interested parties are urged to read such agreements in their entirety.

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    Sponsor Letter

        Concurrently with the execution of the Merger Agreement, Easterly entered into the Sponsor Letter with the Sponsor and Sirius Group, pursuant to which, at the closing of the Merger, the Sponsor will surrender and Easterly will cancel for no consideration between 3,328,000 and 4,528,000 (or such higher number of shares based on the adjustment described below) shares of Easterly common stock owned by the Sponsor, which amount will be determined at the Effective Time as follows: The base number of 3,928,000 canceled shares will be (i) decreased by 0.50 of a share of Easterly common stock for every $100 that the sum of (x) cash in the Trust Account at the closing of the Merger plus (y) the proceeds of any private placement of Sirius Group common shares (or securities convertible into Sirius Group common shares) in connection with the Merger (the sum of (x) and (y), the "Amount Raised") is greater than $120 million (provided, that if the Amount Raised is greater than or equal to $150 million, then, solely with respect to any portion of the Amount Raised that is funded from certain designated investors in such private placement, the number of canceled shares will be decreased by 0.25 (in lieu of 0.50) of a share of Easterly common stock for every $100 of the Reduced Rate Amount (as defined below)) or (ii) increased by 0.50 of a share of Easterly common stock for every $100 that the Amount Raised is less than $120 million. Notwithstanding the foregoing, the minimum number of canceled shares will be 3,328,000 and the maximum number of canceled shares will be 4,528,000, except that the Sponsor also agreed to surrender additional shares (which could result in more than 4,528,000 shares surrendered) in certain circumstances if the amount per share equal to (x) 1.05 multiplied by (y) the Sirius Group September 30 Adjusted DBVPS used in the calculation of the Exchange Ratio, as adjusted for the value of the warrants issued in the Sirius Group Private Placement, is less than $17.39. If the proceeds raised from the Sirius Group Private Placement Investors is less than $213 million (other than as a result of an investor failing to fund its obligations in breach of its subscription agreement at a time when Sirius Group is not then in material breach of any of its representations, warranties, covenants or agreements set forth in such subscription agreement at the time of such investor's breach of such subscription agreement), the proceeds of the Sirius Group Private Placement will be deemed to be $213 million for purposes of calculating the Amount Raised. The "Reduced Rate Amount" means the lesser of (a) the Amount Raised minus $150 million and (b) the Amount Raised that is funded from certain designated investors in such private placement.

        The Sponsor also agreed to (i) pay or reimburse all liabilities and obligations of Easterly due and owing or incurred at or prior to the Effective Time to the extent not repaid by Easterly using unrestricted cash and up to $2 million from the Trust Account, except for the $7 million deferred underwriting fee, which will be paid using cash released from the Trust Account, and (ii) contribute to Easterly for no consideration, as a contribution to the capital of Easterly, all amounts due and owing by Easterly to the Sponsor under the Convertible Promissory Note to the extent any such amount is not repaid at the closing of the Merger.

        For more information on the Sponsor Letter, please see the full text of the Sponsor Letter, which is attached as Annex B hereto.

    Promissory Note

        Concurrent with the execution of the Merger Agreement, Easterly issued Sirius Group the Promissory Note pursuant to which Sirius Group agreed to lend Easterly $0.03 per month for every public share of Easterly common stock outstanding as of June 30, 2018, until the earlier of the consummation of Easterly's initial business combination and November 30, 2018. The amounts will be lent to Easterly on the first business day of each month and will be deposited by Easterly into a special account within the Trust Account. The Promissory Note will bear interest in an amount equal to the income (if any) actually earned from investing the principal in the Trust Account and will be due upon the completion of Easterly's initial business combination, and will be cancelled in case the Merger is not completed.

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        For more information on the Promissory Note, please see the full text of the Promissory Note, which is attached as Annex D hereto.

    Registration Rights Agreement

        On the date of the closing of the Merger and as a condition precedent for the closing, Sirius Group, the Sponsor and CM Bermuda will enter into the Registration Rights Agreement, which will govern certain rights and obligations of Sirius Group, the Sponsor and CM Bermuda with respect to the registration of the Sirius Group common shares issuable to the Sponsor upon the exchange of Easterly common stock in pursuant to the Merger and the Sirius Group common shares owned by CM Bermuda.

        CM Bermuda will be entitled to demand that Sirius Group register all or part of its Sirius Group common shares, including for underwritten offerings, twice in any consecutive 12-month period.

        Additionally, the Sponsor and CM Bermuda are entitled to "piggy-back" registration rights with respect to any underwritten offering proposed by Sirius Group on its own behalf or on behalf of others, other than such offerings (i) under any employee stock plan or other employee benefit plan arrangement, (ii) of debt convertible into equity securities, (iii) for a dividend reinvestment plan or (iv) for an exchange offer or offering of securities solely to Sirius Group's existing shareholders.

        The registration rights of the Sponsor and CM Bermuda are subject to customary black-out periods, cutback provisions and other limitations as set forth in the Registration Rights Agreement. Sirius Group will agree to pay certain fees and expenses relating to registrations under the Registration Rights Agreement.

        For more information on the Registration Rights Agreement, please see the full text of the form of Registration Rights Agreement, which is attached as Annex E hereto.

    Lock-Up Agreements

        On the date of the closing of the Merger and as a condition precedent for the closing, the Sponsor and CM Bermuda will each deliver a Lock-Up Agreement to Sirius Group pursuant to which the Sponsor and CM Bermuda will agree not to sell any Sirius Group common shares for a period of 180 days from the Effective Time without the consent of Sirius Group, subject to specified exemptions. Sirius Group may consent to such a sale at any time without prior notice.

        For more information on the Lock-Up Agreements, please see the full text of the form of the Lock-Up Agreement, which is attached as Annex F hereto.

    Warrant Amendment

        On the date of the closing of the Merger and as a condition precedent for the closing, Sirius Group, Easterly and Continental Stock Transfer & Trust Company, will enter into the Warrant Amendment with respect to the Warrant Agreement, dated as of July 29, 2015 (the "Warrant Agreement"), between Easterly and Continental Stock Transfer & Trust Company, pursuant to which Easterly will assign to Sirius Group, and Sirius Group will assume, all of Easterly's right, title and interest in the Warrant Agreement. The Warrant Agreement, as amended by the Warrant Amendment, will govern the terms of the converted warrants.

        For more information on the Warrant Amendment, please see the full text of the form of the Warrant Amendment, which is attached as Annex G hereto.

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Transactions Related to the Merger

    Sirius Group Private Placement

        In connection with the closing of the Merger, Sirius Group expects to complete the Sirius Group Private Placement. On August 29, 2018, Sirius Group received subscriptions from affiliated funds of Gallatin Point Capital, The Carlyle Group, Centerbridge Partners, L.P. and Bain Capital Credit (the "Preference Share Investors") pursuant to which they have committed to purchase $205 million of Sirius Group Series B preference shares and $8 million of Sirius Group common shares in the private placement, which aggregate amount may be decreased to $111 million at Sirius Group's option. In addition, the Preference Share Investors will receive warrants that are exercisable for a period of five years after the issue date at a strike price equal to 125% of the per share purchase price, estimated as of October 8, 2018 to be $21.53. The form of subscription agreement, certificate of designation and warrant are filed as exhibits to the registration statement of which this proxy statement/prospectus forms a part.

        Members of Sirius Group's management team and board of directors have committed to purchase an aggregate of 569,000 common shares in the Sirius Group Private Placement.

        Gross proceeds of the Sirius Group Private Placement, together with cash in the Trust Account upon the closing of the Merger (which was $148.5 million as of September 30, 2018, before taking into account any redemptions of Easterly common stock or other transactions related to or in connection with the Merger Proposal), are intended to aggregate to up to $350 million. Assuming a private placement of $202 million at a price per share of $17.22, Sirius Group would issue 11.7 million common shares and Series B preference shares convertible into common shares in connection with the Sirius Group Private Placement (based on subscriptions received as of October 8, 2018 and inclusive of participants in the Employee Share Purchase Plan). Investors are cautioned that this is only an estimate based on the foregoing assumptions, and is subject to change prior to the closing of the Merger. The proceeds of the private placement will be used to redeem all outstanding Sirius Group Series A redeemable preference shares, and the remainder for general corporate purposes. The private placement will be exempt from registration under U.S. securities laws pursuant to Section 4(a)(2) of the Securities Act and Regulation D and Regulation S thereunder.

        In connection with the closing of the Sirius Group Private Placement, Sirius Group, CM Bermuda and the Preference Share Investors will enter into a shareholders agreement (the "Shareholders Agreement"), which will govern certain matters with respect to the governance of Sirius Group, the voting of CM Bermuda's common shares, the repurchase of CM Bermuda's common shares and certain other matters. The form of Shareholders Agreement is filed as an exhibit to the registration statement of which this proxy statement/prospectus forms a part.

        Pursuant to the Shareholders Agreement, until the third anniversary of the date of the closing of the Sirius Group Private Placement: (i) CM Bermuda will vote in favor of the election of the number of Independent Directors (as such term is defined in the Shareholders Agreement) as is necessary to provide that at least a majority of the Board of Directors of Sirius Group is comprised of Independent Directors; and (ii) CM Bermuda will not vote in favor of the removal of any director (other than any director affiliated with CM Bermuda) other than for cause. After the third anniversary of the date of the closing of the Sirius Group Private Placement (or earlier in the event of an increase to the size of the Board of Directors), CM Bermuda will not vote in favor of the election of any director not then serving on the Board of Directors (including any election to fill a vacancy then existing on the Board of Directors as a result of death, resignation, removal, expansion of the Board of Directors or otherwise) who is not an Agreed Director. "Agreed Director" means an Independent Director mutually agreeable to CM Bermuda and Preference Share Investors representing a majority of the Sirius Group Series B preference shares; provided, that if CM Bermuda and the Preference Share Investors have not identified an Agreed Director after negotiating in good faith for a period of 60 days, then an Agreed

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Director means any Independent Director recommended for election by the Nominating & Governance Committee of the Sirius Group Board of Directors.

        Pursuant to the Shareholders Agreement, CM Bermuda will also agree to vote (i) in favor of a Qualified Sale Transaction (as such term is defined in the Shareholders Agreement) that is approved by a majority of Independent Directors and 80% of Sirius Group's voting shares after the first anniversary of the date of the closing of the Sirius Group Private Placement, and (ii) against any merger, amalgamation, consolidation or similar transaction or any sale or transfer of all or substantially all of Sirius Group's consolidated assets, in each case where the per share value of the consideration received by CM Bermuda in such transaction is greater than the per share value of the consideration received by any other holder of Sirius Group common shares.

        The Shareholders Agreement also grants the Preference Share Investors tag-along rights to the extent Sirius Group agrees to repurchase or redeem any common shares held by CM Bermuda.

        The Shareholders Agreement terminates on the date that fewer than 25% of the Sirius Group Series B preference shares issued in the Sirius Group Private Placement are outstanding, and earlier with respect to any Preference Share Investor at the time that it or its affiliates or permitted assigns ceases to own any Sirius Group Series B preference shares.

    Common Shares Redemption Agreement

        Prior to the closing of the Merger, Sirius Group and CM Bermuda will enter into the Common Shares Redemption Agreement, pursuant to which, effective as of and subject to the closing of the Merger, Sirius Group will redeem Sirius Group common shares from CM Bermuda, at a price per share equal to (i) 1.05 multiplied by (ii) the Sirius Group September 30 Adjusted DBVPS, estimated as of October 8, 2018 to be $17.22, for an aggregate amount of between $120 million and $250 million, as elected by CM Bermuda at least two business days in advance of the closing of the Merger. Assuming a redemption amount of approximately $250 million at a price per share of $17.22, Sirius Group would redeem 14.5 million common shares from CM Bermuda in connection with the Common Shares Redemption Agreement. Investors are cautioned that this is only an estimate based on the foregoing assumptions, and is subject to change. In addition, in the event that the gross proceeds of the Sirius Group Private Placement are less than $202 million, the amount of Sirius Group common shares redeemed from CM Bermuda may be less than $250 million.

    Preference Shares Redemption Agreement

        On July 14, 2018, Sirius Group, IMGAH and Sirius Acquisitions Holding Company II entered into the Preference Shares Redemption Agreement, pursuant to which, effective as of and subject to the closing of the Merger, Sirius Group has agreed to redeem all of the issued and outstanding Sirius Group Series A redeemable preference shares, which are held by IMGAH, for $95 million payable in cash at the time of the redemption. Effective as of the completion of such redemption, the parties have agreed to terminate the registration rights agreement and the shareholder's agreement between Sirius Group and IMGAH. In addition, the parties agreed that any remaining contingent consideration in respect of the IMG acquisition, which may be in an amount of up to $50.0 million, will be paid in cash, not in Sirius Group Series A redeemable preference shares, as previously contemplated in the agreement in respect of the IMG acquisition.

Background of the Merger

        On August 4, 2015, Easterly consummated the IPO of 20,000,000 units, with each unit consisting of one share of Easterly common stock and one half of one public warrant. Each whole public warrant entitles the holder thereof to purchase one share of Easterly common stock at an exercise price of $11.50 per share. The units in the IPO were sold at an offering price of $10.00 per unit, generating

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total gross proceeds of $200,000,000. Prior to the consummation of the IPO, on May 4, 2015, the Sponsor purchased 4,312,500 Founder Shares, for an aggregate purchase price of $25,000 or approximately $0.006 per share. Prior to the IPO, the Sponsor transferred 60,000 Founder Shares (not including the forfeited overallotment Founder Shares) to each of the three original independent directors, who agreed to serve on Easterly's board of directors upon the closing of the IPO. On July 29, 2015, Easterly effected a stock dividend of 0.2 shares for each outstanding share of Easterly common stock, resulting in the Sponsor and officers and directors holding an aggregate of 5,175,000 Founder Shares. As a result of the underwriters partially utilizing their over-allotment option, the Sponsor forfeited 175,000 shares, which Easterly canceled.

        Simultaneously with the IPO, Easterly consummated the private sale of 6,750,000 Private Placement Warrants to the Sponsor at a price of $1.00 per warrant, generating gross proceeds of $6,750,000. After deducting underwriting discounts and commissions and offering expenses, approximately $200,000,000 (or approximately $10.00 per unit sold in the IPO), including approximately $195,000,000 of the net proceeds of the IPO and $5,000,000 from the sale of the Private Placement Warrants, was placed in the Trust Account with Continental Stock Transfer & Trust Company as trustee. The trust proceeds are invested in U.S. government treasury bills with a maturity of 180 days or less or money market funds meeting certain conditions under Rule 2a-7 under the Investment Company Act of 1940, as amended, which invest only in direct U.S. government treasury obligations.

        Except for a portion of the interest income that may be released to Easterly to pay any income or franchise taxes, none of the funds held in the Trust Account will be released until the earlier of (i) the completion of its initial business combination and (ii) the redemption of 100% of its public shares if Easterly is unable to consummate a business combination by November 30, 2018, subject to the requirements of law. After the payment of approximately $750,000 in expenses relating to the IPO, approximately $1,000,000 of the net proceeds of the IPO and private placement of the Private Placement Warrants was not deposited into the Trust Account and was retained by Easterly for working capital purposes. The net proceeds deposited into the Trust Account remain on deposit in the Trust Account earning interest. As of September 30, 2018, there was approximately $148.5 million held in the Trust Account and $102,338 held outside the Trust Account available for working capital purposes. For the six-month period ended June 30, 2018 and the twelve-month periods ended December 31, 2017 and December 31, 2016, Easterly withdrew $137,543, $226,553 and $216,448, respectively of interest earned to pay for franchise taxes.

        Prior to the consummation of the IPO, neither Easterly, nor anyone on its behalf, contacted any prospective target business or had any substantive discussions, formal or otherwise, with respect to a transaction with Easterly.

        After Easterly's IPO, Easterly's officers and directors commenced an active search for prospective businesses and assets to acquire in Easterly's initial business combination. During this search process, Easterly contacted more than 200 companies, including JH Capital Group Holdings, LLC ("JH Capital") and Sungevity, Inc. ("Sungevity"), had conversations with 73 companies or their representatives, and entered into detailed discussions with at least 11 possible target businesses (or their representatives). The majority of the possible target businesses with which Easterly had detailed discussions were financial services companies.

        Following a series of meeting and due diligence on JH Capital between February 10, 2016 and April 18, 2016, Easterly determined that JH Capital's business was not suitable to be a public company at the time primary due to the nascence of certain business lines and therefore did not make a proposal of terms for a business combination at that time. Specifically, JH Capital's advocacy and lending segments were newly acquired or newly formed and had not achieved scale to be meaningful to the overall earnings of JH Capital.

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        On June 28, 2016, Easterly entered into a definitive agreement with respect to a business combination with Sungevity. Following the execution of such definitive agreement, Easterly ceased formal discussions with potential business combination partners, including JH Capital. Easterly was unable to consummate the business combination with Sungevity because there was not sufficient support from Easterly's stockholders and Easterly and Sungevity would not have had access to sufficient cash in the trust account to adequately provide for Sungevity's cash needs. On December 31, 2016, Easterly terminated the definitive agreement with Sungevity.

        Following the termination of the definitive agreement with Sungevity, Easterly commenced again an active search process for prospective businesses and assets to acquire in Easterly's initial business combination. During this new search process, Easterly had conversations with 90 companies or their representatives, and entered into detailed discussions with at least 32 possible target businesses (or their representatives). The majority of the possible target businesses with which Easterly had detailed discussions were financial services companies. Easterly engaged in negotiations with two of these possible target businesses and began drafting and negotiating transaction documents. One target company was a servicer of a sub-prime credit card lender and the other was a real estate services company. However, Easterly came to the conclusion that, based on the sizes of these two businesses and non-recurring nature of their business models, they were not suitable business combination candidates.

        On April 25, 2017, Easterly reinitiated conversations with JH Capital. Between April 25, 2017 and June 27, 2017, Easterly and JH Capital performed due diligence on each other and negotiated a definitive agreement for a business combination between Easterly and JH Capital. On June 28, 2017, Easterly, JH Capital and the other parties thereto executed a definitive agreement for a business combination between Easterly and JH Capital. On May 31, 2018, Easterly and JH Capital terminated the definitive agreement by mutual agreement because they mutually agreed that it was not in the best interests of Easterly's stockholders and JH Capital's equityholders to proceed with the business combination and for JH Capital to become a public company at that time.

        Following termination of the definitive agreement for the business combination between Easterly and JH Capital, on May 31, 2018, Citigroup Global Markets Inc. contacted Easterly and presented Easterly with the opportunity to explore a business combination with Sirius Group.

        On May 31, 2018, Sirius Group sent Easterly a non-disclosure letter agreement for the purposes of exchanging confidential information with Easterly, which was executed that day.

        On June 1, 2018, Easterly's management team and its advisers were given access to Sirius Group's online data room and Easterly began its due diligence of Sirius Group and its operations.

        On June 2, 2018, Messrs. Waters, Oberting, Salamone, Papamichael and Boxer, members of Sirius Group's management, and Mr. Kalichstein, Easterly's Chief Exective Officer, participated in a conference call in which Easterly was given an introduction to Sirius Group's business and an overview of Sirius Group's business lines, its history under the ownership of White Mountains Insurance Group and subsequent ownership by CM Bermuda, the Sirius Group ownership structure, its business structure, its investment portfolio and its insurance ratings.

        On June 6, 2018, Messrs. Oberting, Davis, Salamone, Papamichael and Boxer met Mr. Kalichstein to continue diligence and discussions of transaction terms at Sirius Group's offices in New York, New York. Sirius Group and Easterly reviewed topics including, but not limited to, (i) Sirius Group's actuarial and risk management policies and procedures, including a review of Sirius Group's risk policy guidelines, its largest risk exposures and stress testing, its capital management and its loss reserving process, (ii) accounting and finance, including group structure and organization, a line by line review of the historical income statement, balance sheet, and cash flow statement, accounting policies, processes to prepare for public company accounting, tax planning, and internal controls, and (iii) strategic

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planning, including Sirius Group's 2018 budget and three year financial plan. During this meeting, the terms for the exchange of Sirius Group common shares for shares of Easterly common stock were discussed in principle.

        On June 8, 2018, the parties proposed, and agreed to, the exchange of a fraction of a Sirius Group common share for each share of Easterly common stock based on 1.05x Sirius Group's June 30, 2018 diluted book value per common share, which exchange ratio when determined at the closing of the Merger will determine the relative ownership of the combined company. On June 8, 2018, Sirius Group sent Easterly a non-binding draft term sheet that contemplated the terms of Merger, including the exchange of a fraction of a Sirius Group common share for each share of Easterly common stock based on 1.05x Sirius Group's June 30, 2018 diluted book value per common share. On June 8, 2018 and June 10, 2018, Easterly sent Sirius Group a revised draft of the non-binding term sheet reflecting discussions between the parties on terms related to the conditions to closing, the cancellation of the Sponsor's Easterly common stock and Private Placement Warrants, and payment of expenses.

        On June 10, 2018, Easterly sent Sirius Group a draft merger agreement with respect to the proposed business combination that included terms providing for the exchange of a fraction of a Sirius Group common share for each share of Easterly common stock based on 1.05x Sirius Group's June 30, 2018 diluted book value per common share.

        On June 12 and June 13, 2018, Sirius Group sent Easterly a revised draft of the non-binding term sheet reflecting discussions between the parties on terms related to the number of shares of the Sponsor's Easterly common stock that would be canceled. On June 13, 2018, Sirius Group and Easterly agreed on the final terms of the non-binding term sheet.

        On June 13, 2018, members of Easterly's and Sirius Group's management teams participated in follow-up due diligence conference call in which Easterly and Sirius Group further discussed Sirius Group's underwriting and outward reinsurance strategy.

        On June 14, 2018, Easterly sent Sirius Group drafts of the Sponsor Letter and the Promissory Note.

        On June 16, 2018, Sirius Group sent Easterly revised drafts of the Merger Agreement, the Sponsor Letter and the Promissory Note.

        On June 18, 2018, Easterly sent Sirius Group revised drafts of the Merger Agreement, the Sponsor Letter and the Promissory Note and initial drafts of the Warrant Amendment and Easterly's disclosure letter.

        On June 19, 2018, Sirius Group sent Easterly revised drafts of the Merger Agreement, the Sponsor Letter and the Promissory Note, and initial drafts of the Registration Rights Agreement and the Lock-Up Agreements.

        On June 20, 2018, Sirius Group sent Easterly a draft of Sirius Group's disclosure letter and comments on Easterly's disclosure letter and the Warrant Amendment. On June 20, 2018, Easterly provided comments on Sirius Group's disclosure letter.

        On June 21 and 22, 2018, Sirius Group and Easterly finalized the Merger Agreement, the Sponsor Letter, the Promissory Note, the disclosure letters, the Registration Rights Agreement and Lock-Up Agreements.

        On June 22, 2018, the Easterly board of directors conducted a meeting to consider the draft Merger Agreement, the related agreements, the proposed Merger and the related transactions. Mr. Kalichstein gave the Easterly board of directors an overview of the Merger Agreement and related documents and informed them that the Merger Agreement was complete. Following a review of the Merger Agreement and discussion among the members of the board and Easterly's management about

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Sirius Group and its business and operations, the Easterly board of directors unanimously approved and adopted the Merger Agreement, the Merger, the Sponsor Letter, the Promissory Note and the related transactions, and authorized management to execute the Merger Agreement, the Sponsor Letter and the Promissory Note.

        On June 22, 2018, the Sirius Group board of directors conducted a meeting, at which a quorum was present in Bermuda or participating telephonically from outside of the United States, to consider the draft Merger Agreement, the related agreements, the proposed Merger and the related transactions. Mr. Boxer gave the Sirius Group board of directors an overview of the Merger Agreement and related documents and discussed certain implications as a result of the Merger on Sirius Group's existing shareholders. Following a review of the Merger Agreement and discussion among the members of the board and Sirius Group's management, the Sirius Group board of directors participating in the meeting unanimously approved and adopted the Merger Agreement, the Merger, the Sponsor Letter, the Promissory Note and the related transactions, and authorized management to execute the Merger Agreement, the Sponsor Letter and the Promissory Note.

        On June 23, 2018, representatives of Easterly and Sirius Group and members of their respective legal teams exchanged and released their signatures to the Merger Agreement, the Sponsor Letter and the Promissory Note.

        On June 25, 2018, a press release was issued announcing the Merger and shortly thereafter Easterly filed a Current Report on Form 8-K attaching the press release and the investor presentation to be used in meetings later in the day as well as the Merger Agreement and its exhibits. That day, Easterly's and Sirius Group's management teams held a pre-recorded conference call to describe Sirius Group and the transaction for Easterly's stockholders and the investment community.

        On June 28, 2018, Easterly held a special meeting of stockholders and 18,704,279 of the 20,015,577 outstanding shares of Easterly common stock were voted in favor of the proposal to amend Easterly's charter to extend the date by which Easterly had to consummate a business combination until November 30, 2018, and the proposal to amend the agreement with respect to the Trust Account to provide for the extension until November 30, 2018. The holders of 807,170 public shares of Easterly common stock properly exercised their right to convert their shares into cash at a conversion price of approximately $10.32 per share. In connection with the approval of this extension, pursuant to the Promissory Note, Sirius Group agreed to lend Easterly $0.03 per month for every public share of Easterly common stock outstanding as of June 30, 2018, until the earlier of the consummation of Easterly's initial business combination and November 30, 2018. The amounts will be lent to Easterly on the first business day of each month and will be deposited by Easterly into a special account within the Trust Account.

        On August 29, 2018, Sirius Group, Merger Sub, Easterly, the Sponsor and CM Bermuda entered into the Amendment, wherein, among other things, the parties amended the date as of which the Exchange Ratio would be calculated to be September 30, 2018 rather than June 30, 2018 (as the later calculation date was closer to the expected closing date of the transaction), provided for a post-closing adjustment if an estimated Sirius Group September 30 Adjusted DBVPS is used to calculate the Exchange Ratio and amended the calculation of the number of shares of Easterly common stock surrendered by the Sponsor upon closing of the Merger in connection with the Sirius Group Private Placement.

Easterly's Board of Directors' Reasons for Approval of the Merger

        Before reaching its decision to approve the Merger Agreement and the Merger, Easterly's board of directors reviewed the results of Easterly management's due diligence and spoke with the entire

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management team of Easterly and discussed the diligence findings of third party advisors and consultants. Such discussions included:

    An overview of the public markets in general and the insurance and reinsurance sector, in particular.

    A summary and review of the transaction structure presented by Easterly management and counsel.

    A review of Sirius Group's existing and historical litigation and major contracts by Easterly management and counsel.

    A summary of the financial and accounting, actuarial, insurance, tax and employee diligence by Easterly management and counsel.

        Easterly's board considered a wide variety of factors in connection with its evaluation of the Merger. In light of the complexity of those factors, its board of directors, as a whole, did not consider it practicable to, nor did it attempt to, quantify or otherwise assign relative weights to the specific factors it took into account in reaching its decision. Individual directors may have given different weight to different factors. In Easterly's prospectus for its IPO, Easterly identified the following general criteria and guidelines that it believed would be important in evaluating prospective target businesses:

    Financial services sector targets. Easterly would seek to acquire businesses in the financial services sectors.

    Long-term global demographic and macroeconomic trends, which will influence the direction of the retirement, asset management and insurance sectors. Easterly would seek to acquire businesses that have the opportunity to take advantage of demographic and macroeconomic trends that are effecting the financial services sectors.

    Convergence of technological solutions with financial products, distribution and user access. Easterly would seek to acquire one or more businesses that it believed will utilize technology to enhance its business, utilize customer data and provide services more efficiently.

    Ongoing global regulatory regime changes and reforms create a changing landscape for current market participants. Easterly would seek to acquire a business that can take advantage of changing regulations and reforms.

        In considering the Merger, Easterly's board of directors concluded that Sirius Group substantially met the above criteria. In particular, the board of directors considered the following positive factors:

    Easterly management's experience with insurance and reinsurance companies;

    Sirius Group's historical track record, including strong operating results;

    Sirius Group's unique European franchise, its global accident and health platform and a diversifying suite of insurance and reinsurance growth lines;

    Sirius Group strong track record of shareholder returns, including the generation of over 13% annualized operating return to White Mountains Insurance Group during its ownership of Sirius Group from 2009 until the first quarter of 2016;

    Sirius Group's superior underwriting, with overall combined ratio averaging 5% outperformance over peers from 2009 through 2017;

    Sirius Group's strong customer relationships with 60% of its business from customer relationships of over 10 years and 30% of its business coming from customer relationships of over 20 years;

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    Sirius Group's track record of successfully executing mergers and acquisitions, including the 2017 acquisitions of IMG and Armada; and

    Sirius Group's experienced and tenured management team. Sirius Group's management team has significant experience in the insurance and reinsurance industries. The executive management team averages over 30 years' of insurance operations and mergers and acquisitions experience, with over 23 years at Sirius Group.

        In addition, Easterly's board of directors also considered the following risks and other potentially negative factors:

    the recent historical net losses and low net profit of Sirius Group. Easterly's board of directors noted that Sirius Group had a comprehensive (loss) income of approximately $(78) million, $(34) million and $196 million for 2017, 2016 and 2015 respectively;

    the potential for major catastrophes to have a negative impact on Sirius Group's results of operations and capital;

    the risk that some of the current public stockholders of Easterly would vote against the Merger Proposal, or exercise their redemption rights, thereby depleting the amount of cash available in the Trust Account and reducing the number of freely tradeable Sirius Group common shares after the closing;

    the risk that certain key employees and potential customers of Sirius Group might not choose to work at or with Sirius Group after the Merger;

    the risks related to the fact that CM Bermuda will continue to control Sirius Group after the consummation of the Merger and such control may negatively impact minority shareholders;

    the risks associated with the insurance and reinsurance industries in general;

    the risks associated with macroeconomic uncertainty and the effects it could have on Sirius Group's revenues;

    the risks of unknown future regulation, which could provide burdensome on the insurance and reinsurance industry;

    the risks associated with obtaining additional financing for Sirius Group's operations in the future;

    the risk of competition in the industry;

    the risk that the Merger might not be consummated in a timely manner or that the closing of the Merger might not occur despite the parties' efforts, including by reason of a failure to obtain the approval of Easterly's stockholders and fulfill the other closing conditions;

    the risk that the transactions contemplated by the Merger Agreement would not be completed in accordance with the terms of the Merger Agreement or at all;

    the risk that Easterly's stockholders would not approve an extension request at the June 28, 2018 Easterly special meeting of stockholders, and that Easterly would not be unable to complete the Merger before its expiration without an extension;

    the risk of delisting of Easterly's securities prior to the Merger and being unable to list Sirius Group's securities on the Nasdaq Stock Market in connection with the Merger;

    the significant fees and expenses associated with completing the Merger and the substantial time and effort of management required to complete the Merger; and

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    the fact that the Sponsor, and Easterly's officers and directors may have interests in the Merger that are different from, or are in addition to, the interests of Easterly's public stockholders, including the matters described under "Proposal No. 1—The Merger Proposal—Certain Interests of Easterly's Directors and Officers and Others in the Merger," below.

        After consideration of these factors, the Easterly board of directors determined that these risks could be mitigated or managed by the combined company following the Merger, were reasonably acceptable under the circumstances, and that, overall, these risks were significantly outweighed by the potential benefits of the Merger.

Sirius Group's Board of Directors' Reasons for Approval of the Merger

        In reaching its decision to approve the Merger Agreement and the Merger, the Sirius Group board of directors consulted with Sirius Group's management and reviewed various financial data and evaluation materials. The summary set forth below briefly describes the primary reasons, factors and information taken into account by the Sirius Group board of directors in reaching its conclusion. The Sirius Group board of directors did not assign any relative or specific weights to the factors considered in reaching such determination, and individual directors may have given differing weights to different factors. The explanation of Sirius Group's reasons for approving the Merger and all other information presented in this section is forward-looking in nature and, therefore, should be read in light of the factors discussed under "Cautionary Statement Regarding Forward-Looking Statements."

        The Sirius Group board of directors considered the following potentially positive factors, among others, in connection with its review and analysis of the Merger, including:

    Sirius Group's business, financial condition, competitive position, business strategy, strategic options and prospects, as well as risks involved in achieving these prospects, the nature of Sirius Group's business and the industry in which it competes, and current industry, economic and global market conditions, both on a historical and on a prospective basis, all of which led Sirius Group's board of directors to conclude that the Merger presented an opportunity to realize greater value than the value likely to be realized in the event Sirius Group did not pursue the Merger;

    the review by Sirius Group's board of directors of possible alternatives to the Merger, including (i) pursuing an initial public offering of Sirius Group common shares, (ii) a merger or other business combination with a strategic buyer, and (iii) issuance of additional preference shares or common shares of Sirius Group to one or more third party investors to diversify Sirius Group's shareholder base; the timing and likelihood of actually achieving additional value from these alternatives, as well as the risks and uncertainties associated with such alternatives, and the assessment of Sirius Group's board of directors that the Merger was in the long-term best interest of Sirius Group and its shareholders, taking into account risks of execution as well as business, competitive, industry and market risk;

    the expected accelerated timeline and reduced cost for completion of the Merger as compared to possible alternatives to the Merger;

    the significant reduction in the dilution from the Merger since (i) the Sponsor will surrender and Easterly will cancel for no consideration between 3,328,000 and 4,528,000 shares of Easterly common stock owned by the Sponsor and (ii) the Sponsor will surrender and Easterly will cancel for no consideration the 6,750,000 private placement warrants that were acquired by the Sponsor in a private placement concurrent with the closing of Easterly's initial public offering;

    the totality of the terms of the Merger Agreement (including the representations, warranties, covenants and agreements of each party, the closing conditions, the lack of indemnification provisions, and the termination provisions) and the related agreements;

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    the fact that the Merger Agreement and the transactions contemplated thereby were the product of extensive arms' length negotiations between representatives of Sirius Group and representatives of Easterly;

    the potential positive impact of the public announcement of the Merger on Sirius Group's rating agencies, regulators, customers and employees and Sirius Group's ability to attract and retain key management, underwriting, administrative and other personnel;

    the fact that Sirius Group expects to become a publicly listed company with associated benefits of a public currency; and

    the fact that no federal or state regulatory approvals are necessary in connection with the Merger.

        The Sirius Group board of directors also considered a number of potentially negative factors in its deliberations concerning the Transaction, including:

    the risk that the potential benefits sought in the Merger might not be fully realized;

    the risk that the financial results of Sirius Group will not meet expectations given the current economic climate;

    the risk of delisting of Easterly's securities prior to the Merger and being unable to list Sirius Group's securities on the Nasdaq Stock Market in connection with the Merger;

    the risk that the Merger might not be completed in a timely manner or at all, including the risk that Easterly's public stockholders do not vote in favor of the Merger;

    the risk that compliance with rules and requirements applicable to public companies will be expensive and time consuming;

    the risk that Easterly shareholders will redeem their shares for their pro rata portion of the funds available in the Trust Account and thereby reduce the amount of funds held in the Trust Account;

    the limitations imposed on the conduct of Sirius Group's business prior to the completion of the Merger;

    the risk that the Merger will result in the diversion of management and employee attention, or have an adverse effect on customers and business relationships;

    the substantial costs to be incurred in connection with the Merger, including equity dilution on account of the issuance of shares to Easterly's stockholders, banker's expenses, costs of preparing and filing this proxy statement/prospectus and other transaction expenses arising from the Merger; and

    the other risks and uncertainties set forth in the section entitled "Risk Factors" beginning on page 44 of this proxy statement/prospectus.

        The foregoing information and factors considered by the Sirius Group board of directors are not intended to be exhaustive but are believed to include all of the material factors considered by the Sirius Group board of directors.

        In view of the wide variety of factors considered in connection with its evaluation of the merger and the complexity of these matters, Sirius Group's board of directors did not find it useful, and did not attempt, to quantify or rank these factors. In considering the factors described above, individual members of Sirius Group's board of directors may have given different weight to different factors. Sirius Group's board of directors considered all of the factors as a whole and considered the factors in their totality to be favorable and to support the decision to approve the Merger Agreement and the Merger.

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        Achieving Sirius Group's objectives from the Merger is subject to risks, some of which are discussed in the section entitled "Risk Factors" beginning on page 44 of this proxy statement/prospectus.

Certain Interests of Easterly's Directors and Officers and Others in the Merger

        When you consider the recommendation of Easterly's board of directors in favor of approval of the Merger, you should keep in mind that its board of directors and officers have interests in the Merger that are different from, or in addition to, your interests as a stockholder. These interests include, among other things:

    the 400,000 to 1.6 million total Founder Shares that the Sponsor (or its members) will hold immediately prior to the Merger, which will be exchanged for Sirius Group common shares at the Exchange Ratio in connection with the Merger;

    the 24,000 Founder Shares that one of Easterly's independent directors holds as of September 30, 2018, which will be exchanged for Sirius Group common shares at the Exchange Ratio in connection with the Merger;

    if Easterly is unable to complete a business combination within the required time period, the Convertible Promissory Note issued to the Sponsor, in the amount of $895,000 at September 30, 2018 plus accrued interest, will not be repaid and all amounts owed thereunder will be forgiven except to the extent that Easterly has funds available to it outside of the Trust Account to repay such amounts;

    if Easterly is unable to complete a business combination within the required time period, Easterly's Chairman, its Chief Executive Officer and David Cody will be personally liable to ensure that the proceeds in the Trust Account are not reduced by the claims of target businesses or claims of vendors or other entities that are owed money by Easterly for services rendered or contracted for or products sold to Easterly, but only if such a vendor or target business has not executed a waiver of claims against the Trust Account and except as to any claims under Easterly's indemnity of the underwriters; and

    the continued indemnification of current directors and officers of Easterly and the continuation of directors' and officers' liability insurance after the Merger.

        Further, each of Easterly's directors, directly or indirectly, holds Founder Shares that are not subject to redemption and certain of Easterly's directors indirectly hold Private Placement Warrants that would retire worthless if a business combination is not consummated; as a result, Easterly's directors have a financial incentive to see a business combination consummated rather than lose whatever value is attributable to the Founder Shares and Private Placement Warrants. These interests may influence Easterly's directors in making their recommendation that you vote in favor of the Merger Proposal, and the transactions contemplated thereby.

Certain Interests of Sirius Group's Directors and Officers and Others in the Merger

        Sirius Group's board of directors and officers have interests in the Merger that are different from, or in addition to, your interests as a stockholder. These interests include, among other things:

    The directors and executive officers of Sirius Group will continue to be the directors and executive officers of the combined company;

    In connection with the Merger, each executive officer of Sirius Group will receive a performance share unit award granted under the 2018 Omnibus Incentive Plan, with the target number of performance share units equal to a specified dollar value divided by the per share value of Sirius Group common shares at the closing of the Merger. The performance share unit awards have been allocated to the executive officers as follows, based on the grant date value of the award at

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      target levels of performance: Mr. Waters—$2,600,000; each of Mr. Boxer, Ms. Cramér Manhem and Mr. Oberting—$1,800,000; and Mr. Davis—$700,000. The performance share unit awards will be subject to vesting conditions and a commitment by the executive officer to purchase Sirius Group common shares having a value equal to the target award granted to the executive officer;

    in connection with the Merger, Sirius Group has implemented an Employee Share Purchase Plan, which provides all employees of Sirius Group with a one-time opportunity to purchase between 100 and 1,000 Sirius Group common shares at a price equal to 85% of market value for the first 100 shares and 100% of market value for the next 900 shares. For this purpose, the market value of the Sirius Group common shares will be equal to 1.05 times the Sirius Group September 30 Adjusted DBVPS. Employees have the option of paying for the shares upfront or, in the case of employees who are not executive officers, through a loan that is repaid over a two-year period through payroll deductions. As of October 8, 2018, over 400 employees have committed to purchase an aggregate of approximately 146,000 Sirius Group common shares under the Employee Share Purchase Plan prior to the consummation of the Merger;

    in connection with the Merger, the Compensation Committee amended the Sirius Group 2016 Long Term Incentive Plan (the "2016 LTIP") to provide for continued vesting of outstanding awards in the event of a termination of employment by Sirius Group without cause or by the executive officer due to good reason outside of the 24-month change in control period already provided for under the 2016 LTIP. In these qualifying terminations of employment events, each of our other named executive officers will continue to vest in outstanding awards for 12 months following a termination of employment. The ability to receive payments during these vesting continuation periods will be subject to actual performance; and

    in connection with the Merger, Sirius Group adopted the Sirius Group Severance and Change in Control Plan (the "Executive Severance Plan"), which provides executive officers with severance and post-employment benefits in the event of (i) an involuntary termination without cause or (ii) a resignation by the executive officer for good reason. For these qualifying terminations of employment prior to a change in control, our named executive officers will receive severance benefits equal to one times base salary, any earned but unpaid bonus for the year prior to termination, a pro-rata bonus for the year of termination, based on actual performance, and medical continuation benefits for 12 months. In the event of a qualifying termination of employment following a change in control, the severance benefits are the same, except the severance pay is increased to two times base salary for the named executive officers, the medical continuation period is increased to two years for the named executive officers, and the prorated bonus for the year of the termination will be paid at the target level of performance. Additionally, the Executive Severance Plan provides that in the event of a qualifying termination within 24 months following a change in control, all outstanding equity compensation awards will become fully vested, with the attainment or deemed attainment of any applicable performance conditions determined under the terms of the applicable equity compensation plan or award agreements. In order to be eligible to receive severance payments, pursuant to the Executive Severance Plan, the executive officer must execute a release in Sirius Group's favor. The Executive Severance Plan provides that, to the extent that Mr. Waters' or Ms. Cramér Manhem's employment agreements provide additional severance protections, they will continue to receive the employment agreement severance protections, to the extent they do not result in duplicative benefits under the Executive Severance Plan.

Potential Purchases of Public Shares

        In connection with the stockholder vote to approve the proposed Merger, the Sponsor, Easterly's directors, officers or advisors, or their respective affiliates may privately negotiate transactions to

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purchase shares from stockholders who would have otherwise elected to have their shares redeemed for a per-share pro rata portion of the Trust Account in conjunction with their consideration of a proposal to approve the Merger. None of the Sponsor, Easterly's directors, officers or advisors, or their respective affiliates will make any such purchases when they are in possession of any material non-public information not disclosed to the seller or during a restricted period under Regulation M under the Exchange Act. It is expected that such a purchase would include a contractual acknowledgement that such stockholder, although still the record holder of Easterly's shares, is no longer the beneficial owner thereof and therefore agrees not to exercise its redemption rights. To the extent required to comply with applicable securities laws, Easterly expects that any purchase by the Sponsor would be reported promptly on an amendment to the Sponsor's Schedule 13D. In the event that the Sponsor, Easterly's directors, officers or advisors, or their affiliates purchase shares in privately negotiated transactions from public stockholders who have already elected to exercise their redemption rights, such selling stockholders would be required to revoke their prior elections to redeem their shares. Any such privately negotiated purchases may be effected at purchase prices that are in excess of the per-share pro rata portion of the Trust Account. There is no limit to the number of public shares that the Sponsor, Easterly's directors, officers or advisors, or their respective affiliates could purchase. The purpose of any such purchases would be to increase the likelihood of obtaining stockholder approval of the Merger.

        The purpose of any such purchases would be to increase the likelihood of obtaining stockholder approval of the Merger or, where the purchases are made by the Sponsor, Easterly's directors, officers or advisors, or their respective affiliates, to satisfy a closing condition in an agreement related to the Merger.

Total Sirius Group Common Shares to be Issued in the Merger

        Based on the number of shares of Easterly common stock and Easterly warrants outstanding on September 30, 2018, Sirius Group expects to issue or reserve for issuance to Easterly public stockholders approximately 8.6 million common shares pursuant to the Merger Agreement (excluding the estimated 6.1 million Sirius Group common shares issuable upon exercise of the converted warrants). Sirius Group also expects to issue approximately 1.0 million common shares to the Sponsor, resulting in a total of approximately 9.6 million Sirius Group common shares issued in exchange for outstanding shares of Easterly common stock pursuant to the Merger Agreement. Upon the closing of the Merger, Easterly's public stockholders are expected to own approximately 6.8% of Sirius Group. The foregoing amounts assume that (i) the Exchange Ratio is equal to 0.607, (ii) no Easterly stockholders exercise their redemption rights in connection with the Merger Proposal, (iii) Sirius Group issues 11.7 million common shares and Series B preference shares convertible into common shares in connection with the Sirius Group Private Placement (based on subscriptions received as of October 8, 2018 and inclusive of participants in the Employee Share Purchase Plan), (iv) Sirius Group redeems 14.5 million common shares from CM Bermuda for approximately $250 million pursuant to the Common Shares Redemption Agreement and (v) all of the issued and outstanding Sirius Group Series A redeemable preference shares are redeemed for $95 million in cash pursuant to the Preference Shares Redemption Agreement prior to the closing of the Merger. Further, such percentages do not take into account (x) the issuance of any Sirius Group common shares upon the exercise of the converted warrants that may remain issued and outstanding following the Merger or that are issued pursuant to the Sirius Group Private Placement or (y) the issuance of Sirius Group common shares reserved for issuance pursuant to Sirius Group's Long Term Incentive Plan and 2018 Omnibus Incentive Plan. If the facts differ from these assumptions, Easterly's stockholders may experience dilution of their ownership interest unless they elect to have their shares of Easterly common stock redeemed in connection with the Merger Proposal.

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Recent Developments Impacting the Exchange Ratio

        Late in the third quarter of 2018, there were numerous natural disasters around the world, including Typhoon Jebi in Japan, the Kerala Flood in India, Typhoons Mangkhut and Trami in Southeastern Asia, a tsunami in Indonesia, and Hurricane Florence in the eastern United States. Sirius Group has exposure to losses resulting from these and other natural disasters. Potential losses from these events take time to assess. Preliminary loss estimates are initially established based upon client information, catastrophe models, market loss data and underwriter judgement. Updated loss advices from clients are received over time as the losses develop.

        Sirius Group is in the process of evaluating available preliminary information in order to record an estimate of losses, including from these events, at September 30, 2018. It is currently estimated that the third quarter losses will likely be higher than previously estimated. Based upon this loss and other information available as of October 8, 2018, in accordance with the Merger Agreement, Sirius Group delivered to Easterly its good faith estimate of 1.05 multiplied by the Sirius Group September 30 Adjusted DBVPS, equal to $17.22, which is subject to adjustment post-closing, as more fully described herein.

Redemption Rights

        Pursuant to Easterly's charter, holders of public shares may elect to have their shares redeemed for cash at the applicable redemption price per share calculated in accordance with Easterly's charter. As of September 30, 2018, this would have amounted to approximately $10.45 per share. If a holder exercises its redemption rights, then such holder will be exchanging its shares of Easterly common stock for cash and will no longer own shares of Easterly. Such a holder will be entitled to receive cash for its public shares only if it properly demands redemption and delivers its shares (either physically or electronically) to Easterly's transfer agent in accordance with the procedures described herein. Each redemption of public shares by Easterly's public stockholders will decrease the amount in the Trust Account, which is approximately $148.5 million as of September 30, 2018. Easterly has no specified maximum redemption threshold under its charter. In no event, however, will Easterly redeem public shares in an amount that would cause Easterly's net tangible assets to be less than $5,000,001. See the section entitled "Special Meeting of Easterly Stockholders—Redemption Rights" for the procedures to be followed if you wish to redeem your shares for cash.

Appraisal Rights

        There are no appraisal rights available to Easterly's stockholders in connection with the Merger.

U.S. Federal Income Tax Considerations

        The following is a general discussion of the material U.S. federal income tax considerations of the Merger and the pre-Merger redemption to holders of Easterly common stock or Easterly warrants. The discussion is based on the Code, U.S. Treasury regulations, judicial decisions and administrative pronouncements, all as currently in effect. Such authorities are subject to change, possibly with retroactive effect. Any such change could result in U.S. federal income tax consequences that are materially different from those described below. Moreover, any subsequent change in any of the factual matters set forth in this proxy statement/prospectus may affect the considerations discussed below.

        This discussion does not address all aspects of U.S. federal income taxation that may be relevant to all holders of Easterly common stock or Easterly warrants, some of which may be subject to special rules, such as dealers in securities, traders in securities that elect mark-to-market treatment, banks, thrifts or other financial institutions, insurance companies, regulated investment companies, real estate investment trusts, S corporations, accrual basis taxpayers subject to special tax accounting rules as a result of their use of financial statements, tax-exempt organizations, qualified plans (such as 401(k)

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plans, individual retirement accounts, etc.), persons subject to the qualified small business stock rules, U.S. expatriates, non-U.S. persons who are engaged in a trade or business in the United States, persons that hold Easterly common stock or Easterly warrants as part of a straddle, conversion transaction or hedge, persons deemed to sell Easterly common stock or Easterly warrants under the constructive sale provisions of the Code, holders that are subject to the alternative minimum tax, holders whose functional currency is not the U.S. dollar, holders that are treated as partnerships for U.S. federal income tax purposes, holders that are not the beneficial owners of Easterly common stock or Easterly warrants, and holders that own, actually or under applicable constructive ownership rules, 10% or more of Easterly common stock. This discussion deals only with holders that hold Easterly common stock or Easterly warrants as a capital asset (within the meaning of Section 1221 of the Code). If an entity treated as a partnership for U.S. federal income tax purposes holds Easterly common stock or Easterly warrants, the U.S. federal income tax treatment of a partner of the partnership will depend on the status of the partner and the activities of the partnership. If you are a partner of a partnership holding Easterly common stock or Easterly warrants, you are urged to consult your own tax adviser regarding the consequences to you of the Merger and the pre-Merger redemption.

        This discussion does not address any U.S. federal tax laws other than U.S. federal income tax laws, any U.S. state or local tax laws or any non-U.S. tax laws. You are encouraged to consult your own tax advisers concerning the overall tax consequences arising in your own particular situation under U.S. federal, state, local and non-U.S. laws from the Merger and the pre-Merger redemption.

U.S. Federal Income Tax Considerations of the Merger to Holders of Easterly Common Stock or Easterly Warrants

        The following is a discussion of the U.S. federal income tax considerations to holders of Easterly common stock or Easterly warrants that receive their Sirius Group common shares or Sirius Group converted warrants in the Merger. The following does not discuss the U.S. federal income tax considerations relating to the pre-Merger redemption.

    Treatment of the Merger

        Subject to the assumptions and qualifications described below and other customary representations, assumptions and qualifications, it is the opinion of Sidley Austin LLP ("Counsel") that under current United States federal income tax law, it is more likely than not that the Merger will qualify as a "reorganization" within the meaning of Section 368 of the Code (the "Opinion"). In reaching this conclusion, Counsel has assumed, with the permission of Sirius Group and Easterly, that not more than 50% of the assets of Easterly will be used to redeem shares of common stock of Easterly in contemplation of, or in connection with, the Merger (subject to any catastrophic event covered by insurance issued by Sirius Group and its subsidiaries occurring prior to the Merger, which cannot be predicted at this time). No assurance can be given that these assumptions will be correct and the Opinion could differ if the facts on which Counsel has relied on are, become or are found to be different.

        Easterly and Sirius Group intend to report the Merger as a "reorganization" pursuant to Section 368(a) of the Code. Neither Easterly nor Sirius Group intends to request any ruling or other guidance from the IRS on the U.S. federal income tax treatment of the Merger. The qualification of the Merger as a tax-deferred reorganization is not a condition to the closing of the Merger and the Merger Agreement does not include any covenant requiring Sirius Group to ensure that the Merger qualifies as a tax-deferred reorganization. Furthermore, because of the absence of direct authorities, no assurance can be given that the IRS would not challenge such treatment in light of the specific terms of the Merger and related transactions.

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        In order to qualify as a "reorganization," in pertinent part, the Merger must either qualify as a reorganization under Section 368(a)(2)(E) of the Code (a "Reverse Triangular Reorganization") or qualify as a reorganization under Section 368(a)(1)(B) of the Code (a "'B' Reorganization").

        The qualification of the Merger as a Reverse Triangular Reorganization or a "B" Reorganization depends on meeting certain technical requirements that cannot be determined at this time. To qualify as a Reverse Triangular Reorganization, "substantially all" of Easterly's assets are required to be retained by Easterly following the Merger. If a significant number of stockholders decide to redeem their Easterly common stock, Easterly will not be able to meet this requirement and the Merger will not so qualify. For this purpose, as a condition for obtaining a ruling from the IRS, the IRS has previously required a target corporation to retain at least 90% of the fair market value of its net assets and at least 70% of the fair market value of its gross assets. To qualify either as a Reverse Triangular Reorganization or as a "B" Reorganization, Easterly will be required to either continue its historic business or continue to hold a significant portion of its historic business assets after the Merger. The treatment of the Merger as a tax-deferred reorganization would therefore depend on the extent to which stockholders of Easterly decide to exchange their Easterly common stock for common shares of Sirius Group rather than redeem them for cash. Additionally, while Sirius Group intends to repurchase common shares held by CM Bermuda with cash from sources other than Easterly's Trust Account, no assurance can be given that the IRS would not successfully recharacterize the repurchase as a distribution by Easterly to Sirius Group of the cash in the Easterly Trust Account, thereby resulting in a failure of the Merger to meet the continuity of business enterprise requirement.

        In addition, to qualify as a "B" Reorganization, no "boot" (generally cash and property which is not voting stock) is permitted to be provided in exchange for the Easterly common stock. Absent direct guidance, it is unclear whether post-closing adjustment and the Promissory Note described below would result in the former Easterly stockholders being treated as having received "boot" in the Merger.

        Under the Amendment to the Merger Agreement, in order to ensure that the former stockholders of Easterly receive the correct number of Sirius Group common shares based on the September 30 Book Value of Sirius Group, which may not be known as of the closing of the Merger and therefore may be based on an estimate, after the closing of the Merger, (A) if the September 30 Book Value of Sirius Group was lower than the estimate, CM Bermuda may be required to either surrender Sirius Group common shares to Sirius Group for no consideration or make a capital contribution to Sirius Group of the difference, or (B) if the value was greater than the estimate, Sirius Group may be required to issue to CM Bermuda additional Sirius Group common shares for not consideration or pay to CM Bermuda the difference. A post-closing adjustment could therefore result in an increase in the former Easterly stockholders' proportionate share ownership in Sirius Group as a result the dilution of CM Bermuda's interests in Sirius Group, and an argument could be made that such value is "boot" to the stockholders. This adjustment, however, does not result in any former stockholder of Easterly receiving any cash or other property (other than common shares in Sirius Group) in the Merger in return for their shares in Easterly.

        As part of the transaction, Easterly issued a Promissory Note in favor of Sirius Group pursuant to which Sirius Group has agreed to lend Easterly $0.03 per month for every public share of Easterly common stock outstanding as of June 30, 2018. While the Promissory Note increases the value of the common shares of each holder of Easterly common stock, the arrangement is economically similar to a secured termination fee in the event that the Merger does not close, and is required to be fully repaid back to Sirius Group in the event that the Merger closes. Additionally, the loan is required to be segregated in a special account under the Trust Account, it bears no interest, and all income earned on the proceeds of the loan is also required to be returned to Sirius Group in the event that the Merger closes. Under these facts, the parties have specifically agreed to treat the loan for federal income tax purposes as a mere collateral arrangement securing a termination fee, however, no assurance can be given that the IRS would agree with this treatment and not treat it as "boot".

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        If the IRS were to successfully challenge the tax-deferred reorganization treatment of the Merger, in general, a United States holder of the common stock of Easterly would recognize capital gain or loss on the exchange in an amount equal to the difference, if any, between (i) the sum of the fair market value of the Sirius Group common shares received plus the cash received in lieu of fractional shares and (ii) the United States holder's adjusted tax basis in the Easterly common stock exchanged in the Merger. Gain or loss, as well as the holding period, will be determined separately for each block of shares exchanged pursuant to the Merger. Such gain or loss will be long-term capital gain or loss provided that the United States holder has held (or is treated as having held) his or her common stock of Easterly for more than one year as of the date of the Merger. Otherwise, the recognized gain or loss generally will be a short-term capital gain or loss. The deductibility of capital losses may be subject to limitations.

        You are strongly urged to consult with your own tax advisor to determine the particular U.S. federal, state or local or foreign income or other tax consequences of the Merger to you.

Tax Consequences of the Merger Generally to Holders of Easterly Common Stock or Easterly Warrants

        For purposes of this discussion, you are a "U.S. holder" if, for U.S. federal income tax purposes, you are treated as a beneficial owner of Easterly common stock or Easterly warrants and you are:

    a citizen or resident of the United States;

    a corporation created or organized in or under the law of the United States or any state thereof (including the District of Columbia);

    an estate the income of which is subject to U.S. federal income taxation regardless of its source; or

    a trust if (1) a court within the United States is able to exercise primary supervision over the administration of the trust and one or more U.S. persons have the authority to control all substantial decisions of the trust or (2) the trust has in effect a valid election under applicable U.S. Treasury regulations to be treated as a U.S. person.

        For purposes of this discussion, you are a "Non-U.S. holder" if you are a beneficial owner of Easterly common stock or Easterly warrants, you are not a U.S. holder and you are not treated as a partnership for U.S. federal income tax purposes.

        Assuming the Merger is treated as a "reorganization" within the meaning of Section 368(a) of the Code, the tax consequences for holders of Easterly common stock and Easterly warrants who receive Sirius Group common shares or Sirius Group warrants in exchange for shares of Easterly common stock or Easterly warrants pursuant to the Merger are as follows:

    no gain or loss will be recognized (except with respect to cash received instead of fractional Sirius Group common shares);

    the aggregate basis of the Sirius Group common shares received in the Merger (including any fractional Sirius Group common shares deemed received and sold for cash as described below) will be the same as the aggregate basis of the shares of Easterly common stock for which they are exchanged;

    the aggregate basis of the Sirius Group converted warrants received in the Merger will be the same as the aggregate basis of the Easterly warrants for which they are exchanged; and

    the holding period of the Sirius Group common shares and warrants received in the Merger (including any fractional Sirius Group common shares deemed received and sold for cash as described below) will be the same as the holding period of the shares of Easterly common stock and warrants for which they are exchanged.

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Cash Received Instead of a Fractional Sirius Group Common Share

        A holder of Easterly common stock who receives cash instead of a fractional Sirius Group common share will generally be treated as having received the fractional share pursuant to the Merger and then as having sold that fractional Sirius Group common share for cash. As a result, a U.S. holder of Easterly common stock will generally recognize gain or loss equal to the difference between the amount of cash received and the basis in his or her fractional share interest as set forth above. This gain or loss will generally be capital gain or loss, and will be long-term capital gain or loss if, as of the effective date of the Merger, the holding period for such shares is greater than one year. The deductibility of capital losses is subject to limitations. For the tax consequences to Non-U.S. holders, see the section entitled "Material Tax Consequences—Material U.S. Tax Consequences—Taxation of Non-U.S. Holders" beginning on page 155.

Information Reporting and Gain Recognition Agreement

        A U.S. holder of Easterly common stock or Easterly warrants who receives Sirius Group common shares or converted warrants as a result of the Merger will be required to retain records pertaining to the Merger. Each U.S. holder of Easterly common stock or Easterly warrants who is required to file a U.S. federal income tax return and who is a "significant holder" that receives Sirius Group common shares or converted warrants in the Merger will be required to file a statement with such U.S. federal income tax return in accordance with U.S. Treasury regulations Section 1.368-3 setting forth such holder's basis (determined immediately prior to the exchange) in the Easterly common stock or Easterly warrants surrendered and the fair market value (determined immediately prior to the exchange) of the Sirius Group common shares or converted warrants that are exchanged by such significant holder. A "significant holder" is a holder of Easterly common stock who, immediately before the Merger, owned at least 5% of the outstanding stock of Easterly or securities of Easterly with a basis for federal income taxes of at least $1 million.

        A U.S. Holder who is a five-percent transferee shareholder is generally required to enter into a gain recognition agreement with the IRS with respect to the Sirius Group common shares and Sirius Group converted warrants received in the Merger as a condition to obtaining the tax deferred treatment described above with respect to the Merger. For this purpose, a five-percent transferee shareholder is a person that owns at least 5% of the total voting power or value of the Sirius Group common shares immediately after the Merger. After the Closing of the Merger, Sirius Group is permitted and is likely to engage in restructuring transactions that may constitute a triggering event requiring five-percent transferee shareholders to either recognize gain on the Merger or file a gain recognition agreement reflecting the internal restructuring as a condition to the continued deferral of the tax on the Merger. Five-percent transferee shareholders should therefore contact Sirius Group prior to filing their tax returns to obtain the necessary information on such post-closing restructuring transactions.

        You are strongly urged to consult with your own tax advisor to determine the particular U.S. federal, state or local or foreign income or other tax consequences of the Merger to you.

U.S. Federal Income Tax Considerations of Redeeming Easterly Common Stock

        The following is a discussion of the U.S. federal income tax considerations to holders of Easterly common stock that elect to have their Easterly common stock redeemed for cash upon the closing of the Merger. The following does not discuss the U.S. federal income tax considerations relating to the ownership and disposition of Sirius Group common shares following the Merger. No advance ruling has been or will be sought from the IRS regarding the pre-Merger redemption nor will any opinion be sought.

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U.S. Holders

        This subsection is addressed to U.S. holders of Easterly common stock that elect to have their Easterly common stock redeemed for cash as described in the section entitled "The Special Meeting of Easterly Stockholders—Redemption Rights." For purposes of this discussion, a "Redeeming U.S. Holder" is a U.S. holder that so redeems its Easterly common stock.

        The U.S. federal income tax treatment of a Redeeming U.S. Holder will depend upon whether the redemption is treated as a sale or distribution for U.S. federal income tax purposes. The redemption of Easterly common stock generally will be treated as a sale or exchange (rather than a corporate distribution) if the receipt of cash pursuant to the redemption (i) is "substantially disproportionate" with respect to the holder, (ii) results in a "complete termination" of the holder's interest in Easterly, or (iii) is "not essentially equivalent to a dividend" with respect to the holder. In order to meet the substantially disproportionate test, the percentage of Easterly voting stock actually and constructively owned by the Redeeming U.S. Holder immediately following the redemption must, among other requirements, be less than 80 percent of the percentage of Easterly outstanding voting stock actually and constructively owned by such holder immediately before the redemption. There will be a complete termination of a Redeeming U.S. Holder's interest if either (a) all of the shares of Easterly stock actually and constructively owned by the Redeeming U.S. Holder are redeemed or (b) all of the shares of Easterly stock actually owned by the Redeeming U.S. Holder are redeemed and such holder is eligible to waive, and effectively waives in accordance with specific rules, the attribution of stock owned by certain family members and such holder does not constructively own any other shares of Easterly stock. The redemption of Easterly common stock will not be "essentially equivalent to a dividend" if the redemption results in a "meaningful reduction" of the Redeeming U.S. Holder's proportionate interest in Easterly. Whether the redemption will result in a meaningful reduction in a Redeeming U.S. Holder's proportionate interest will depend on the particular facts and circumstances. However, if a Redeeming U.S. Holder has a relatively minimal stock interest and, such percentage interest is reduced by any amount as a result of the redemption, the Redeeming U.S. Holder should generally be regarded as having incurred a meaningful reduction in interest. For example, the IRS has ruled that any reduction in a stockholder's proportionate interest is a "meaningful reduction" if the stockholder's relative interest in the corporation was minimal and the stockholder did not have management control over the corporation.

        In determining whether any of the foregoing tests are satisfied, a Redeeming U.S. Holder will take into account not only shares of Easterly stock actually owned by such holder, but also shares of Easterly stock that are constructively owned by it. A Redeeming U.S. Holder may constructively own, in addition to shares of Easterly stock owned directly, shares of Easterly stock owned by certain related individuals and entities in which such holder has an interest or that have an interest in such holder, as well as any shares of Easterly stock the holder has a right to acquire by exercise of an option, which would generally include Easterly common stock which could be acquired pursuant to the exercise of the warrants.

        If the redemption qualifies as a sale of Easterly common stock by the U.S. holder under Section 302 of the Code, the Redeeming U.S. Holder will generally recognize capital gain or loss equal to the difference between the amount realized on the redemption and such holder's adjusted tax basis in the Easterly common stock exchanged therefor. Such gain or loss will be long-term capital gain or loss if the holding period of such stock is more than one year at the time of the exchange. The deductibility of capital losses is subject to limitations. U.S. holders who hold different blocks of Easterly common stock (generally, shares of Easterly common stock purchased or acquired on different dates or at different prices) should consult their own tax advisors to determine how the above rules apply to them.

        If the redemption does not qualify as a sale of Easterly common stock by the Redeeming U.S. Holder under Section 302, the Redeeming U.S. Holder will be treated as receiving a corporate

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distribution. Any such distribution will be treated as dividend income for U.S. federal income tax purposes to the extent of Easterly's current or accumulated earnings and profits. However, for the purposes of the dividends-received deduction and "qualified dividend" treatment, due to the redemption right, a Redeeming U.S. Holder may be unable to include the time period prior to the redemption in such holder's "holding period." Any distribution in excess of Easterly's current and accumulated earnings and profits will reduce the Redeeming U.S. Holder's basis in the Easterly common stock (but not below zero), and any remaining excess will be treated as gain realized on the sale or other disposition of the Easterly common stock.

        U.S. holders of Easterly common stock considering exercising their redemption rights should consult their own tax advisors as to whether the redemption will be treated as a sale or as a distribution under the Code.

        Redeeming U.S. Holders of Easterly common stock who are individuals, estates or trusts may be required to pay a 3.8% tax on all or a portion of their "net investment income" or "undistributed net investment income" (as applicable), which may include all or a portion of their capital gain or dividend income from their redemption of Easterly's common stock. Non-corporate Redeeming U.S. Holders of Easterly common stock should consult their own tax advisors regarding the effect, if any, of the net investment income tax.

    Backup Withholding

        In general, proceeds received from the exercise of redemption rights will be subject to backup withholding at a rate of 24% for a non-corporate U.S. holder that:

    fails to provide an accurate taxpayer identification number;

    is notified by the IRS regarding a failure to report all interest or dividends required to be shown on his or her federal income tax returns; or

    in certain circumstances, fails to comply with applicable certification requirements.

        Any amount withheld under these rules will be creditable against such holder's U.S. federal income tax liability or refundable to the extent that it exceeds this liability, provided that the required information is timely furnished to the IRS and other applicable requirements are met.

Non-U.S. Holders

        This subsection is addressed to non-U.S. holders of Easterly common stock that elect to have their Easterly common stock redeemed for cash as described in the section entitled "The Special Meeting of Easterly Stockholders—Redemption Rights." For purposes of this discussion, a "Redeeming Non-U.S. Holder" is a non-U.S. holder that so redeems its Easterly common stock.

        Except as discussed in the following paragraph, a Redeeming Non-U.S. Holder who elects to have its Easterly common stock redeemed will generally be treated in the same manner as a Redeeming U.S. Holder for U.S. federal income tax purposes. See the discussion above under "Proposal No. 1—The Merger Proposal—U.S. Federal Income Tax Considerations of Redeeming Easterly Common Stock—U.S. Holders."

        Any Redeeming Non-U.S. Holder will not be subject to U.S. federal income tax on any capital gain recognized as a result of the exchange unless (i) such holder is an individual who is present in the United States for 183 days or more during the taxable year in which the redemption takes place and has a "tax home" in the United States (in which case such holder will be subject to a 30% tax on his or her net capital gain for the year) or (ii) such holder is engaged in a trade or business within the United States and any gain recognized in the exchange is treated as effectively connected with such trade or business (in which case such holder will generally be subject to the same treatment as a Redeeming U.S. Holder with respect to the exchange). In addition, with respect to any redemption treated as a

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distribution rather than a sale, any amount treated as dividend income to a Redeeming Non-U.S. Holder will generally be subject to U.S. withholding tax at a rate of 30%, unless the Redeeming Non-U.S. Holder is entitled to a reduced rate of withholding under an applicable income tax treaty.

        Non-U.S. holders of Easterly common stock considering exercising their redemption rights should consult their own tax advisors as to whether the redemption of their Easterly common stock will be treated as a sale or as a distribution under the Code.

        Under the Foreign Account Tax Compliance Act ("FATCA") and U.S. Treasury regulations and administrative guidance thereunder, a 30% United States federal withholding tax may apply to any dividends paid to (i) a "foreign financial institution" (as specifically defined in FATCA), whether such foreign financial institution is the beneficial owner or an intermediary, unless such foreign financial institution agrees to verify, report and disclose its United States "account" holders (as specifically defined in FATCA) and meets certain other specified requirements or (ii) a non-financial foreign entity, whether such non-financial foreign entity is the beneficial owner or an intermediary, unless such entity provides a certification that the beneficial owner of the payment does not have any substantial United States owners or provides the name, address and taxpayer identification number of each such substantial United States owner and certain other specified requirements are met. In certain cases, the relevant foreign financial institution or non-financial foreign entity may qualify for an exemption from, or be deemed to be in compliance with, these rules. Non-U.S. holders of Easterly common stock should consult their own tax advisors regarding this legislation and whether it may be relevant to the redemption of their Easterly common stock.

Approval of the Merger

        Pursuant to the Merger, among other things:

    Merger Sub will merge with and into Easterly, with Easterly surviving the Merger as a wholly owned subsidiary of Sirius Group.

    Upon the effectiveness of the Merger, all shares of Easterly common stock (other than (i) shares of Easterly common stock with respect to which an Easterly stockholder has validly exercised its redemption rights, and that will be redeemed as provided for by Easterly's charter, (ii) shares of Easterly common stock held by Easterly as treasury stock or owned by Easterly, Sirius Group or Merger Sub and (iii) shares of Easterly common stock held by the Sponsor that will be cancelled pursuant to the Sponsor Letter) will be converted into Sirius Group common shares at the Exchange Ratio.

    The Exchange Ratio will be determined prior to the closing of the Merger and will be equal to a fraction determined by dividing (i) the estimated amount of cash per public share of Easterly common stock in the Trust Account immediately prior to the closing of the Merger by (ii) (x) 1.05 multiplied by (y) the Sirius Group September 30 Adjusted DBVPS. The Sirius Group September 30 Adjusted DBVPS is calculated by dividing (a) the book value of Sirius Group determined based on GAAP on a consolidated basis, based on the final, Sirius Group board of directors approved, unaudited GAAP consolidated financial statements of Sirius Group for the nine months ended September 30, 2018, decreased by the $7 million deferred underwriting fee payable by Easterly to Citigroup Global Markets Inc. as underwriter of the IPO, and as adjusted by the GAAP accounting effect of the redemption of the Sirius Group Series A redeemable preference shares by (b) the sum of (x) the fully diluted number of Sirius Group common shares issued and outstanding as of September 30, 2018 and (y) 593,000 Sirius Group common shares. If an estimate of the Sirius Group September 30 Adjusted DBVPS is used to determine the Exchange Ratio at the closing of the Merger, then the Merger Agreement provides for a post-closing adjustment if such estimate is different than the actual Sirius Group September 30 Adjusted DBVPS as finally determined after the closing of the Merger. Such

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      adjustment will result in either (x) the issuance of new Sirius Group common shares or a payment of cash by Sirius Group to CM Bermuda, if the Exchange Ratio is greater than it would have been using the actual Sirius Group September 30 Adjusted DBVPS or (y) the surrender to Sirius Group of Sirius Group common shares owned by CM Bermuda or a payment of cash to Sirius Group from CM Bermuda if the Exchange Ratio is less than it would have been using the actual Sirius Group September 30 Adjusted DBVPS.

    Each issued and outstanding public warrant to acquire shares of Easterly common stock will cease to represent a right to acquire shares of Easterly common stock and will be converted into a converted warrant. The number of Sirius Group common shares subject to each converted warrant will be equal to the number of shares of Easterly common stock subject to each Easterly warrant immediately prior to the closing of the Merger multiplied by the Exchange Ratio, and such converted warrant will have an exercise price per Sirius Group common share equal to the exercise price per share of Easterly common stock subject to such Easterly warrant immediately prior to the closing of the Merger divided by the Exchange Ratio.

        By approving the Merger Agreement and the Merger, you will be approving, among other transactions contemplated by the Merger Agreement, each of the transactions set forth above.

        Easterly's charter requires that it provide all holders of its public shares with the opportunity to have their public shares redeemed upon the consummation of Easterly's initial business combination in conjunction with either a tender offer or a stockholder vote. For business and other reasons, Easterly has elected to provide Easterly stockholders with the opportunity to have their public shares redeemed in connection with a stockholder vote rather than pursuant to a tender offer. Therefore, Easterly is seeking to obtain approval of Easterly's stockholders of the Merger Proposal in order to provide its public stockholders with the opportunity to redeem their public shares in connection with the closing of the Merger. Because Easterly is holding a stockholder vote on the Merger, Easterly's charter provides that it may consummate the Merger only if it is approved by the affirmative vote of the holders of a majority of the shares of Easterly common stock that are voted at the Easterly special meeting of stockholders.

Vote Required for Approval

        Approval of this proposal is a condition to the completion of the Merger. If this proposal is not approved, the Merger will not occur.

        The Merger Agreement and the Merger will be approved if the holders of at least a majority of the outstanding shares of Easterly common stock vote "FOR" the Merger Proposal. Broker non-votes, abstentions or the failure to vote on this Merger Proposal will have the same effect as a vote "AGAINST" the approval of this proposal.

        As of the record date, Easterly's founders have agreed to vote the Founder Shares and any other shares held by them in favor of the Merger. The founders have not purchased any public shares.

Recommendation of the Board

        EASTERLY'S BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS THAT EASTERLY'S STOCKHOLDERS VOTE "FOR" THE MERGER PROPOSAL.

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PROPOSAL NO. 2—THE ADJOURNMENT PROPOSAL

        The Adjournment Proposal, if adopted, will allow Easterly's board of directors to adjourn the Easterly special meeting of stockholders to a later date or dates to permit further solicitation of proxies. The Adjournment Proposal will only be presented to Easterly's stockholders in the event that, based on the tabulated votes, there are not sufficient votes at the time of the Easterly special meeting of stockholders to approve the Merger Proposal presented at the Easterly special meeting. In no event will Easterly's board of directors adjourn the Easterly special meeting of stockholders or consummate the Merger beyond the date by which it may properly do so under Easterly's charter and Delaware law.

Consequences if the Adjournment Proposal is Not Approved

        If the Adjournment Proposal is not approved by Easterly's stockholders, Easterly's board of directors may not be able to adjourn the Easterly special meeting of stockholders to a later date in the event that, based on the tabulated votes, there are not sufficient votes at the time of the Easterly special meeting of stockholders to approve the Merger Proposal.

Vote Required for Approval

        The affirmative vote of the holders of a majority of the shares of Easterly common stock cast on this proposal is required to approve the Adjournment Proposal. Broker "non-votes", abstentions or the failure to vote on this Proposal No. 2 will have no effect on the approval of this proposal.

Recommendation of the Board

EASTERLY'S BOARD OF DIRECTORS UNANIMOUSLY RECOMMENDS THAT STOCKHOLDERS
VOTE "FOR" THE APPROVAL OF THE ADJOURNMENT PROPOSAL.

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USE OF PROCEEDS

        As of September 30, 2018, funds held in the Trust Account aggregated to approximately $148.5 million. If the Merger is consummated, the funds held in the Trust Account will be released to (i) the surviving company for general corporate purposes, including making loans or contributing cash to other affiliates for working capital, organic growth and future potential acquisitions, (ii) pay unpaid franchise and income taxes of Easterly, (iii) Easterly stockholders who properly exercise their redemption rights, and (iv) pay up to $2 million of Easterly's liabilities, fees, costs and expenses and the $7 million deferred underwriting fee. The total amount of cash to be made available to Sirius Group as a result of the consummation of the Merger will depend on, among other things, the total number of public shares of Easterly to be redeemed by its stockholders.

        Following the consummation of the Merger, the combined company will be entitled to use the funds in the Trust Account. Other than the foregoing uses, the combined company does not have specific plans for any funds remaining from the Trust Account and will have broad discretion regarding how to use the funds that remain. These funds could be used in a manner with which you may not agree or applied in ways that do not improve the combined company's results of operations or increase the value of your investment.


ACCOUNTING TREATMENT

        The Merger is a capital transaction in substance whereby Easterly will be treated as the "acquired" company for financial reporting purposes. This determination was primarily based on the following: Sirius Group will own the majority of the outstanding common shares of the combined company, the current executive officers of Sirius Group will manage the combined company, the board of directors of the combined company will be comprised of the current members of the board of directors of Sirius Group, and Sirius Group's operations will be the operations of the combined company. Accordingly, for accounting purposes, the Merger will be treated as the equivalent of Sirius Group issuing shares for the net assets of Easterly, which are comprised of cash and cash equivalents. The net assets of Easterly will be stated at historical cost, with no goodwill or other intangible assets recorded. All the expenses incurred by Sirius Group related to the Merger will be charged to Additional paid-in surplus.

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SELECTED CONSOLIDATED HISTORICAL FINANCIAL DATA OF SIRIUS GROUP

        The following table sets forth selected consolidated historical financial information derived from Sirius Group's (i) audited financial statements included elsewhere in this proxy statement/prospectus as of December 31, 2017 and 2016 and for each of the three years ended December 31, 2017, (ii) unaudited financial statements not included elsewhere in this proxy statement/prospectus as of December 31, 2015, 2014 and 2013 and for the years ended December 31, 2014 and 2013 and (iii) unaudited interim financial statements included elsewhere in this proxy statement/prospectus as of June 30, 2018 and 2017 and for the six months ended June 30, 2018 and 2017. You should read the following selected financial information in conjunction with the section entitled "Management's Discussion and Analysis of Financial Condition and Results of Operations of Sirius Group" and Sirius Group's audited and unaudited interim financial statements appearing elsewhere in this proxy statement/prospectus.

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  Six Months Ended
June 30,
  Years Ended December 31,  
 
  2018   2017   2017   2016