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

Filed by the Registrant ☑

Filed by a party other than the Registrant ☐

Check the appropriate box:

☑

Preliminary Proxy Statement

☐

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

☐

Definitive Proxy Statement

☐

Definitive Additional Materials

☐

Soliciting Material Under Rule 14a-12

ATLAS AIR WORLDWIDE HOLDINGS, INC.

(Name of Registrant as Specified In Its Charter)

Payment of Filing Fee (Check the appropriate box):

☐

No fee required

☐

Fee paid previously with preliminary materials.

☑

Fee computed on table in exhibit required by Item 25(b) per Exchange Act Rules 14a-6(i)(1) and 0-11

PRELIMINARY PROXY SUBJECT TO COMPLETION, DATED OCTOBER 6, 2022

Atlas Air Worldwide Holdings, Inc.

2000 Westchester Avenue
Purchase, NY 10577

[      ], 2022

To our Stockholders:

You are cordially invited to attend a special meeting of stockholders of Atlas Air Worldwide Holdings, Inc., a Delaware corporation (the “Company”, “we”, “us” and “our”), on [      ], 2022 at [      ], Eastern Time (unless the special meeting is adjourned or postponed), in a virtual-only meeting format. The Company’s stockholders will be able to virtually attend and vote at the special meeting by visiting [      ]. For purposes of attendance at the special meeting, all references in the enclosed proxy statement to “present” shall mean virtually present at the special meeting.

On August 4, 2022, the Company entered into an Agreement and Plan of Merger (the “merger agreement”) with Rand Parent, LLC, a Delaware limited liability company (“Parent”), and Rand Merger Sub, Inc., a Delaware corporation and a wholly-owned subsidiary of Parent (“MergerCo”), providing for, subject to the satisfaction or (to the extent permitted by law) waiver of specified conditions, the acquisition of the Company by Parent at a price of $102.50, without interest, per share of common stock, par value $0.01 per share (“common stock”), of the Company issued and outstanding. Subject to the terms and conditions of the merger agreement, MergerCo will be merged with and into the Company (the “merger”), with the Company surviving the merger as a wholly-owned subsidiary of Parent (the “surviving corporation”). If the merger is consummated, you will be entitled to receive $102.50 in cash, without interest and less any applicable withholding taxes, in exchange for each share of common stock you own at the effective time of the merger (unless you have properly and validly exercised and do not withdraw your appraisal rights under Section 262 of the General Corporation Law of the State of Delaware).

The proxy statement accompanying this letter provides you with more specific information concerning the special meeting, the merger agreement, the merger and the other transactions contemplated by the merger agreement. We encourage you to carefully read the accompanying proxy statement and the copy of the merger agreement attached as Annex A thereto, as they contain important information about, among other things, the merger and how it affects you.

The board of directors of the Company (the “Board”) has reviewed and considered the terms and conditions of the merger agreement, the merger and the other transactions contemplated by the merger agreement. The Board unanimously (i) determined and declared that it is advisable and fair to, and in the best interests of, the Company and the Company’s stockholders, that the Company enter into the merger agreement and consummate the transactions contemplated by the merger agreement, (ii) approved and declared the advisability of the merger agreement and the consummation of the transactions contemplated by the merger agreement, including the merger, (iii) recommended that the Company’s stockholders entitled to vote adopt the merger agreement and (iv) directed that the merger agreement be submitted to the Company’s stockholders entitled to vote for adoption.

At the special meeting, you will be asked to consider and vote on (i) a proposal to adopt the merger agreement (the “merger agreement proposal”), (ii) a proposal to approve, by advisory (non-binding) vote, the compensation that may be paid or become payable to the named executive officers of the Company in connection with the consummation of the merger (the “advisory compensation proposal”) and (iii) a proposal to approve any adjournment of the special meeting, if necessary or appropriate, for the purpose of soliciting additional proxies if there are not sufficient votes at the special meeting to adopt the merger agreement (the “adjournment proposal”). The Board recommends you vote “FOR” the merger agreement proposal, “FOR” the advisory compensation proposal and “FOR” the adjournment proposal.

Your vote is important. We cannot complete the merger unless the merger agreement proposal is approved by the affirmative vote (in person or by proxy) of the holders of a majority of outstanding shares of Company common stock entitled to vote thereon at the special meeting. Whether or not you plan to attend the virtual special meeting, we want to make sure your shares are represented at the meeting. Please follow the voting instructions provided on the enclosed proxy card to submit your vote.

After reading the accompanying proxy statement, please authorize a proxy to vote your shares of common stock by completing, dating, signing and returning your proxy card or vote your shares by attending and voting at the virtual special meeting. Instructions regarding the methods of authorizing your proxy are detailed in the section of the accompanying proxy statement entitled “The Special Meeting — Voting Procedures”. If you attend the special meeting and vote thereat, your vote will revoke any proxy that you have previously submitted. If you hold common stock through an account with a brokerage firm, bank or other nominee, please follow the instructions you receive from them to vote your common stock. Your bank, broker or other nominee cannot vote on any of the proposals, including the merger agreement proposal, without your instructions. If you have any questions or need assistance voting, please contact our proxy solicitor:

Morrow Sodali LLC
333 Ludlow Street, 5th Floor, South Tower
Stamford, Connecticut 06902
Shareholders may call toll-free: (800) 662-5200
Banks and brokers may call: (203) 658-9400
Email: AAWW@investor.morrowsodali.com

On behalf of the Board, thank you for your continued support.

By Order of the Board of Directors

Sincerely,

General (Ret.) Duncan J. McNabb
Chairman of the Board of Directors

[      ], 2022

The merger has not been approved or disapproved by the Securities and Exchange Commission or any state securities commission. Neither the Securities and Exchange Commission nor any state securities commission has passed upon the merits or fairness of the merger or upon the adequacy or accuracy of the information contained in this document or the accompanying proxy statement. Any representation to the contrary is a criminal offense.

The accompanying proxy statement is dated [      ], 2022 and, together with the enclosed form of proxy card, is first being mailed to the Company’s stockholders on or about [      ], 2022.

PRELIMINARY PROXY SUBJECT TO COMPLETION, DATED OCTOBER 6, 2022

Atlas Air Worldwide Holdings, Inc.

2000 Westchester Avenue
Purchase, NY 10577

NOTICE OF SPECIAL MEETING OF STOCKHOLDERS TO BE HELD ON [      ], 2022

Notice is hereby given that a special meeting of stockholders of Atlas Air Worldwide Holdings, Inc., a Delaware corporation (the “Company”, “we”, “us” and “our”), to be held on [      ], 2022 at [      ] Eastern Time (unless the special meeting is adjourned or postponed), in a virtual-only meeting format. The Company’s stockholders will be able to virtually attend and vote at the special meeting by visiting [      ]. For purposes of attendance at the special meeting, all references in the enclosed proxy statement to “present” shall mean virtually present at the special meeting. The special meeting is being held for the purpose of acting on the following matters:

Items of Business:

1. To consider and vote on a proposal to adopt the Agreement and Plan of Merger, dated as of August 4, 2022 (the “merger agreement”), by and among the Company, Rand Parent, LLC, a Delaware limited liability company (“Parent”), and Rand Merger Sub, Inc., a Delaware corporation and a wholly-owned subsidiary of Parent (“MergerCo”), pursuant to which and subject to the terms and conditions thereof, MergerCo will be merged with and into the Company (the “merger”), with the Company surviving the merger as a wholly-owned subsidiary of Parent (the “surviving corporation”). We refer to this proposal as the “merger agreement proposal”. 2. To consider and vote on a proposal to approve, by advisory (non-binding) vote, the compensation that may be paid or become payable to our named executive officers in connection with the consummation of the merger, which proposal we refer to as the “advisory compensation proposal”. 3. To consider and vote on a proposal to approve any adjournment of the special meeting for the purpose of soliciting additional proxies if there are insufficient votes at the special meeting to adopt the merger agreement, which proposal we refer to as the “adjournment proposal”.

Record Date:

Only the Company’s stockholders of record at the close of business on [      ], 2022 — the record date for the special meeting — will be entitled to notice of, and to vote at, the special meeting and any postponement or adjournment thereof.

General:	The merger agreement proposal must be approved by the affirmative vote (in person or by proxy) of the holders of a majority of outstanding shares of Company common stock entitled to vote on the matter. Assuming a quorum is present, if you fail to authorize a proxy to vote your shares of common stock or vote at the virtual special meeting, fail to instruct your bank, broker or other nominee on how to vote, or abstain from the merger agreement proposal, it will have the same effect as a vote against the merger agreement proposal. Accordingly, your vote is very important regardless of the number of shares of common stock that you own. Whether or not you plan to attend the virtual special meeting, we request that you vote your shares of common stock. If you attend the virtual special meeting and you are a Company stockholder of record at the close of business on the record date, you may continue to have your shares of common stock voted as instructed in your proxy, or you may withdraw your proxy and vote your shares of common stock at the virtual special meeting. If you fail to authorize a proxy to vote your shares or to vote at the virtual special meeting, or fail to instruct your broker, bank or other nominee on how to vote, the effect will be that the shares of common stock that you own will not be counted for purposes of determining whether a quorum is present at the virtual special meeting and will have the same effect as a vote “AGAINST” the merger agreement proposal.
​	The approval of the advisory compensation proposal and the adjournment proposal each requires the affirmative vote (in person or by proxy) of a majority of the votes cast on the proposal. Assuming a quorum is present, if you fail to authorize a proxy to vote your shares or vote at the virtual special meeting, or fail to instruct your bank, broker or other nominee on how to vote, it will have no effect on the outcome of these proposals. Abstentions will not be considered votes cast and therefore will have no effect on the outcome of the advisory compensation proposal or the adjournment proposal. If a quorum is not present or represented at the special meeting of the stockholders, the Chairman of the board of directors of the Company (the “Board”) or the stockholders entitled to vote thereat, present in person or by proxy, may adjourn the special meeting.
​	For Company stockholders of record, any proxy may be revoked at any time prior to its exercise by delivery of a properly executed, later-dated proxy card, by submitting a written revocation of your proxy to our Corporate Secretary, or by voting at the virtual special meeting. For Company stockholders that hold their shares in “street name”, any proxy may be revoked through such stockholder’s broker, bank or other nominee and in accordance with its procedures or by voting at the virtual special meeting. Attendance at the virtual special meeting alone will not be sufficient to revoke a previously authorized proxy.
​	For more information concerning the virtual special meeting, the merger agreement, the merger and the other transactions contemplated by the merger agreement, please review the accompanying proxy statement and the copy of the merger agreement attached as Annex A thereto.
​	The Board has reviewed and considered the terms and conditions of the merger agreement, the merger and the other transactions contemplated by the merger agreement. The Board unanimously (i) determined and declared that it is advisable and fair to, and in the best interests of, the Company and

the Company’s stockholders, that the Company enter into the merger agreement and consummate the transactions contemplated by the merger agreement, (ii) approved and declared the advisability of the merger agreement and the consummation of the transactions contemplated by the merger agreement, including the merger, (iii) recommended that the Company’s stockholders entitled to vote adopt the merger agreement and (iv) directed that the merger agreement be submitted to the Company’s stockholders entitled to vote for adoption.

Accordingly, the Board recommends a vote “FOR” the merger agreement proposal, “FOR” the advisory compensation proposal and “FOR” the adjournment proposal.

Whether or not you plan to attend the virtual special meeting, we want to make sure your shares are represented at the meeting. You may cast your vote by authorizing your proxy in advance of the virtual special meeting by mail. Please sign, date and return, as promptly as possible, the enclosed proxy card in the reply envelope provided. If you attend the special meeting and vote thereat, your vote will revoke any proxy that you have previously submitted. If you hold your shares in “street name”, you should instruct your bank, broker or other nominee how to vote your shares in accordance with the voting instruction form that you will receive from your bank, broker or other nominee. Your bank, broker or other nominee cannot vote on any of the proposals, including the merger agreement proposal, without your instructions. If you sign, date and mail your proxy card without indicating how you wish to vote, your proxy will be counted as a vote “FOR” the merger agreement proposal, “FOR” the compensation proposal and “FOR” the adjournment proposal.

By Order of the Board of Directors

Sincerely,

ADAM R. KOKAS
Executive Vice President, General Counsel and Secretary

Dated: [      ], 2022

TABLE OF CONTENTS

TABLE OF CONTENTS

​	Page
SUMMARY	​	2
The Parties	​	2
The Special Meeting	​	3
Record Date and Stockholders Entitled to Vote; Vote Required to Approve Each Proposal	​	3
Voting by Company Directors, Executive Officers and Principal Securityholders	​	4
The Merger; Certain Effects of the Merger; Consideration To Be Received in the Merger	​	4
Background of the Merger	​	5
Recommendation of the Board	​	5
Opinion of the Company’s Financial Advisor	​	6
Effects on the Company if the Merger Is Not Consummated	​	6
Financing of the Merger	​	7
Limited Guarantees	​	8
Interests of the Company’s Directors and Executive Officers in the Merger	​	8
Treatment of Company Long-Term Incentive Awards	​	9
Material U.S. Federal Income Tax Consequences of the Merger	​	9
Regulatory Approvals in Connection with the Merger	​	10
Appraisal Rights	​	11
No Solicitation	​	12
Conditions of the Merger	​	12
Termination of the Merger Agreement	​	13
Termination Fees	​	16
Current Price of Common Stock	​	17
Additional Information	​	17
QUESTIONS AND ANSWERS ABOUT THE SPECIAL MEETING AND THE MERGER	​	18
CAUTIONARY STATEMENT REGARDING FORWARD-LOOKING STATEMENTS	​	27
THE PARTIES	​	29
Atlas Air Worldwide Holdings, Inc.	​	29
Parent	​	29
MergerCo	​	29
THE SPECIAL MEETING	​	31
Date, Time and Place	​	31
Purpose of the Special Meeting	​	31
Recommendation of the Board	​	31
Registering for the Special Meeting	​	31

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

TABLE OF CONTENTS

​	Page
Record Date and Stockholders Entitled to Vote	​	32
Quorum	​	32
Vote Required	​	33
Voting Procedures	​	34
Limited Voting by Foreign Owners	​	35
How Proxies Are Voted	​	35
Revocation of Proxies	​	35
Solicitation of Proxies	​	36
Adjournments	​	36
Voting by Company Directors, Executive Officers and Principal Securityholders	​	36
Appraisal Rights	​	37
Other Matters	​	38
Assistance	​	38
PROPOSAL 1: MERGER AGREEMENT PROPOSAL	​	39
PROPOSAL 2: ADVISORY COMPENSATION PROPOSAL	​	40
PROPOSAL 3: ADJOURNMENT PROPOSAL	​	41
THE MERGER	​	42
Overview	​	42
Background of the Merger	​	42
Recommendation of the Board	​	54
Reasons for the Merger	​	54
Certain Financial Forecasts	​	61
Opinion of the Company’s Financial Advisor	​	65
Certain Effects of the Merger	​	73
Effects on the Company if the Merger Is Not Consummated	​	74
Financing of the Merger	​	75
Appraisal Rights	​	78
Interests of the Company’s Directors and Executive Officers in the Merger	​	82
Material U.S. Federal Income Tax Consequences of the Merger	​	87
Regulatory Approvals in Connection with the Merger	​	90
Delisting and Deregistration of the Common Stock	​	91
THE MERGER AGREEMENT	​	92
Explanatory Note Regarding the Merger Agreement	​	92
Effects of the Merger	​	93
Closing and Effective Time of the Merger	​	93
Directors and Officers of the Surviving Corporation	​	93
Consideration To Be Received in the Merger	​	94

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

TABLE OF CONTENTS

​	Page
Excluded Shares	​	94
Treatment of Company Long-Term Incentive Awards	​	94
Treatment of Company Warrants	​	95
Payment for Stock	​	95
Transfer Books; No Further Ownership Rights	​	96
Lost, Stolen or Destroyed Certificates	​	96
Termination of Exchange Fund	​	96
No Liability	​	96
Appraisal Rights	​	97
Representations and Warranties	​	97
Covenants Regarding Conduct of Business by the Company Pending the Effective Time	​	100
No Solicitation; Change in Board Recommendation	​	105
Efforts to Obtain the Company Stockholder Approval	​	109
Reasonable Best Efforts	​	109
Financing	​	111
Indemnification and Insurance	​	113
Employee Benefits Matters	​	114
Certain Additional Covenants and Agreements	​	115
Conditions of the Merger	​	115
Termination of the Merger Agreement	​	116
Termination Fees	​	118
Fees and Expenses	​	118
Withholding Taxes	​	119
Amendment or Supplement	​	119
Extension of Time, Waiver, etc.	​	119
Governing Law; Jurisdiction	​	120
Specific Enforcement	​	120
SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS AND MANAGEMENT	​	121
HOUSEHOLDING	​	125
STOCKHOLDER PROPOSALS	​	126
WHERE YOU CAN FIND ADDITIONAL INFORMATION	​	127

Annex A Agreement and Plan of Merger, dated as of August 4, 2022, by and among Rand Parent, LLC, Rand Merger Sub, Inc. and Atlas Air Worldwide Holdings, Inc.	A-1
Annex B Opinion of Morgan Stanley & Co. LLC, dated August 3, 2022	B-1

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

TABLE OF CONTENTS

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

PROXY STATEMENT

ATLAS AIR WORLDWIDE HOLDINGS, INC.

2000 Westchester Avenue
Purchase, NY 10577

SPECIAL MEETING OF STOCKHOLDERS

TO BE HELD ON [      ], 2022

PROXY STATEMENT

This proxy statement contains information relating to a special meeting of stockholders of Atlas Air Worldwide Holdings, Inc., a Delaware corporation (the “Company”, “we”, “us” or “our”). All references to “Parent” refer to Rand Parent, LLC, a Delaware limited liability company; all references to “MergerCo” refer to Rand Merger Sub, Inc., a Delaware corporation and a wholly-owned subsidiary of Parent; all references to “Apollo” refer to certain affiliates of Apollo Global Management, Inc.; all references to the “Apollo Funds” refer collectively to certain funds managed by affiliates of Apollo; all references to “JFLCO” refer to J.F. Lehman & Company, LLC; all references to the “JFLCO Funds” refer collectively to certain investment affiliates of JFLCO through which JFLCO carries out certain of its investment activities; all references to “Hill City” refer to Hill City Capital LP; and all references to the “Hill City Fund” refer to a certain investment affiliate of Hill City through which Hill City carries out certain of its investment activities. The Apollo Funds, the JFLCO Funds and the Hill City Fund are, collectively, referred to as the “Consortium Funds”. In addition, throughout this proxy statement we refer to the Agreement and Plan of Merger, dated as of August 4, 2022, by and among Parent, MergerCo and the Company as the “merger agreement”.

The special meeting will be held on [      ], 2022 at [      ], Eastern Time (unless the special meeting is postponed or adjourned), in a virtual-only meeting format. The Company’s stockholders will be able to virtually attend and vote at the special meeting by visiting [      ]. We are furnishing this proxy statement to holders (“Company stockholders”) of common stock, par value $0.01 per share, of the Company (“Company common stock”) as part of the solicitation of proxies by the Company’s board of directors (the “Board”), for exercise at the special meeting and at any postponements or adjournments thereof. This proxy statement is dated [      ], [      ], 2022 and is first being mailed to Company stockholders on or about [      ], [      ].

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 1

SUMMARY

SUMMARY

This summary highlights selected information in this proxy statement and may not contain all of the information about the merger agreement, the merger or the other transactions contemplated by the merger agreement that is important to you. We have included page references in parentheses to direct you to more complete descriptions of the topics presented in this summary. You should carefully read this proxy statement in its entirety, including the annexes hereto and the other documents to which we have referred you, for a more complete understanding of the matters being considered at the special meeting, including, without limitation, the merger agreement attached as Annex A to this proxy statement. You may obtain, without charge, copies of documents incorporated by reference into this proxy statement by following the instructions under the section of this proxy statement entitled “Where You Can Find Additional Information” beginning on page 127.

The Parties

(page 29)

Atlas Air Worldwide Holdings, Inc.

The Company is a holding company with a wholly-owned operating subsidiary, Atlas Air, Inc. It also has a 51% economic interest and 75% voting interest in Polar Air Cargo Worldwide, Inc. In addition, the Company is the parent company of several wholly-owned subsidiaries related to the Company’s dry leasing services, collectively referred to as “Titan”.

The Company, together with its consolidated subsidiaries, is a leading global provider of outsourced aircraft and aviation operating services. The Company and its consolidated subsidiaries operate the world’s largest fleet of Boeing 747 freighters and provide customers a broad array of Boeing 747, 777, 767 and 737 aircraft for domestic, regional and international cargo and passenger operations. The Company and its consolidated subsidiaries also provide unique value to customers by giving them access to highly reliable new production freighter aircraft that deliver the lowest unit cost in the marketplace combined with outsourced aircraft operating services that the Company believes lead the industry in terms of quality and global scale. Customers of the Company and its consolidated subsidiaries include express delivery providers, e-commerce retailers, the U.S. Military Air Mobility Command (“AMC”), charter brokers, freight forwarders, direct shippers, airlines, manufacturers, sports teams and fans, and private charter customers. The Company and its consolidated subsidiaries provide global services with operations in Africa, Asia, Australia, Europe, the Middle East, North America and South America.

The Company was incorporated in Delaware in 2000. The Company’s principal executive offices are located at 2000 Westchester Avenue, Purchase, New York 10577, and its telephone number is (914) 701-8000. Shares of Company common stock are listed on the NASDAQ Global Select Market (“NASDAQ”) under the trading symbol “AAWW”.

Parent

Parent is a Delaware limited liability company that was formed by the Consortium Funds solely for the purpose of entering into the merger agreement and related agreements and consummating the transactions contemplated thereby. Parent has not conducted any business operations other than in

2 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

SUMMARY

connection with its formation and the transactions contemplated by the merger agreement (collectively, the “transactions”) and related agreements. Upon the consummation of the transactions contemplated by the merger agreement and related agreements, the Company will be a wholly-owned subsidiary of Parent.

The principal executive offices of Parent are c/o Apollo Management Holdings, L.P., 9 West 57th Street, 43rd Floor, New York, New York 10019 with a telephone number of (212) 515-3200.

MergerCo

MergerCo is a Delaware corporation and a wholly-owned subsidiary of Parent that was formed solely for the purpose of entering into the merger agreement and related agreements and consummating the transactions contemplated thereby. MergerCo has not conducted any business operations other than in connection with its formation and the transactions contemplated by the merger agreement and related agreements. Upon the consummation of the merger, MergerCo will merge with and into the Company, and MergerCo will cease to exist.

The principal executive offices of MergerCo are c/o Apollo Management Holdings, L.P., 9 West 57th Street, 43rd Floor, New York, New York 10019 with a telephone number of (212) 515-3200.

The Special Meeting

(page 31)

The special meeting of Company stockholders will be held on [     ], 2022 at [     ] Eastern Time, in a virtual-only meeting format. To access the virtual special meeting, you should visit [        ]. You will be required to enter a control number, included on your proxy card, voting instruction form or as you may otherwise receive, which will allow you to participate in the virtual meeting and vote your shares of common stock if you are a Company stockholder as of the record date. Please see the section of this proxy statement entitled “The Special Meeting” for additional information on the special meeting, including how to vote your shares of common stock.

Record Date and Stockholders Entitled to Vote; Vote Required to Approve Each Proposal

(page 32 and page 33)

Only the Company’s stockholders of record at the close of business on [     ], 2022, the record date for the special meeting, will be entitled to notice of, and to vote at, the special meeting and any postponement or adjournment thereof. As of the close of business on the record date, there were [     ] shares of common stock outstanding and entitled to vote. Each Company stockholder is entitled to one vote per share of common stock held by such stockholder on the record date on each of the proposals presented in this proxy statement.

The approval of the proposal of the Company’s stockholders to adopt the merger agreement (the “merger agreement proposal”) requires the affirmative vote (in person or by proxy) of the holders of a

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 3

SUMMARY

majority of outstanding shares of Company common stock entitled to vote on the matter (the “Company stockholder approval”). Under Delaware law and the merger agreement, the receipt of such required vote is a condition to the consummation of the merger. The approval of the proposal to approve, by advisory (non-binding) vote, the compensation that may be paid or become payable to our named executive officers in connection with the consummation of the merger (the “advisory compensation proposal”) requires the affirmative vote (in person or by proxy) of a majority of the votes cast on such proposal at the special meeting. The approval of the proposal to approve any adjournment of the special meeting, if necessary or appropriate, for the purpose of soliciting additional proxies if there are insufficient votes at the special meeting to adopt the merger agreement (the “adjournment proposal”) requires the affirmative vote of a majority of the votes cast on such proposal at the special meeting (whether or not a quorum is present). Approval of the advisory compensation proposal and the adjournment proposal is not a condition to the consummation of the merger. Note that you may vote to approve the merger agreement proposal and vote not to approve the advisory compensation proposal or adjournment proposal and vice versa.

Voting by Company Directors, Executive Officers and Principal Securityholders

(page 36)

As of October 3, 2022, the directors and executive officers of the Company beneficially owned in the aggregate 325,199 shares of Company common stock, or approximately 1.1% of the outstanding shares of Company common stock as of October 3, 2022. Although none of the directors or executive officers is obligated to vote to approve the merger agreement proposal, we currently expect that each of these individuals will vote all of his or her shares “FOR” each of the proposals to be presented at the special meeting.

The Merger; Certain Effects of the Merger; Consideration To Be Received in the Merger

(page 42, page 73 and page 94)

On August 4, 2022, the Company entered into the merger agreement with Parent and MergerCo, providing for, subject to the satisfaction or (to the extent permitted by law) waiver of specified conditions, the acquisition of the Company by Parent at a price of $102.50, without interest, per share of Company common stock issued and outstanding (the “merger consideration”). Subject to the terms and conditions of the merger agreement, MergerCo will be merged with and into the Company (the “merger”), with the Company surviving the merger as a wholly-owned subsidiary of Parent (the “surviving corporation”). A copy of the merger agreement is included as Annex A to this proxy statement.

If the merger is consummated, each share of Company common stock issued and outstanding immediately prior to the time the merger is consummated (the “effective time”) will be converted automatically into, and will thereafter represent only, the right to receive $102.50 in cash, without interest and less any applicable withholding taxes, other than shares of Company common stock that are (i) owned by the Company as treasury shares immediately prior to the effective time or held by Parent or MergerCo, which will be canceled and will cease to exist and no consideration will be delivered in exchange therefor (such shares, the “excluded shares”) and (ii) owned by the Company’s stockholders

4 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

SUMMARY

who have validly exercised their statutory rights of appraisal under Section 262 (“Section 262”) of the Delaware General Corporation Law (the “DGCL”) (such shares of the Company’s stockholders, the “appraisal shares”).

If the merger is consummated, Parent and the Company will cooperate and use their respective reasonable best efforts to cause the Company common stock to be delisted from NASDAQ and deregistered under the Securities Exchange Act of 1934, as amended (the “Exchange Act”) as promptly as practicable following the effective time, and, accordingly, the common stock will no longer be publicly traded.

Background of the Merger

(page 42)

A description of the process we undertook that led to the proposed merger, including our discussions with the representatives of the Consortium (as defined in “The Merger — Background of the Merger”), is included in this proxy statement under “The Merger — Background of the Merger”.

Recommendation of the Board

(page 54)

The Board has reviewed and considered the terms and conditions of the merger agreement, the merger and the other transactions contemplated by the merger agreement. The Board unanimously (i) determined and declared that it is advisable and fair to, and in the best interests of, the Company and Company stockholders, that the Company enter into the merger agreement and consummate the transactions, (ii) approved and declared the advisability of the merger agreement and the consummation of the transactions, including the merger, (iii) recommended that the Company stockholders entitled to vote adopt the merger agreement and (iv) directed that the merger agreement be submitted to the Company’s stockholders entitled to vote for adoption. Accordingly, the Board recommends a vote “FOR” the merger agreement proposal, “FOR” the advisory compensation proposal and “FOR” the adjournment proposal. For a discussion of the factors that the Board considered in determining to recommend the approval of the merger agreement proposal, please see the section of this proxy statement entitled “The Merger — Reasons for the Merger” beginning on page 54.

Prior to the adoption of the merger agreement by the Company’s stockholders, under certain circumstances, and in compliance with certain obligations contained in the merger agreement, the Board may effect an adverse recommendation change (as defined in the section of this proxy statement entitled “The Merger Agreement — No Solicitation; Change in Board Recommendation”), including by withdrawing or withholding the foregoing recommendation, under certain circumstances in response to an intervening event (as defined in the section of this proxy statement entitled “The Merger Agreement — No Solicitation; Change in Board Recommendation”) or in connection with a superior proposal (as defined in the section of this proxy statement entitled “The Merger Agreement — No Solicitation; Change in Board Recommendation”), if the Board complies with certain procedures in the merger agreement.

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 5

SUMMARY

Opinion of the Company’s Financial Advisor

(page 65)

Morgan Stanley & Co. LLC (“Morgan Stanley”) was retained by the Company to act as its financial advisor and to render a financial opinion in connection with a potential sale of the Company. The Company selected Morgan Stanley to act as its financial advisor based on Morgan Stanley’s experience in transactions similar to the merger, qualifications, expertise and reputation and its knowledge of the Company and its business and the industries in which the Company conducts its business. As part of this engagement, the Board requested that Morgan Stanley evaluate the fairness, from a financial point of view, of the merger consideration to be received by the holders of shares of Company common stock (other than the excluded shares and appraisal shares) pursuant to the merger agreement. On August 3, 2022, Morgan Stanley rendered its oral opinion to the Board, which was subsequently confirmed by delivery of a written opinion, dated August 3, 2022, to the effect that, as of the date of such opinion, and based upon and subject to the assumptions made, procedures followed, matters considered and qualifications and limitations on the scope of review undertaken by Morgan Stanley as set forth in Morgan Stanley’s written opinion, the merger consideration to be received by the holders of shares of the Company common stock (other than the excluded shares and appraisal shares) pursuant to the merger agreement was fair from a financial point of view to such holders of shares of the Company common stock, as set forth in such opinion as more fully described in the section of this proxy statement entitled “The Merger — Opinion of the Company’s Financial Advisor”.

The full text of Morgan Stanley’s written opinion to the Board, dated August 3, 2022, is attached as Annex B to this proxy statement and is incorporated by reference into this proxy statement in its entirety. The opinion sets forth, among other things, the assumptions made, procedures followed, matters considered and qualifications and limitations on the scope of the review undertaken by Morgan Stanley in rendering its opinion. The Company stockholders are urged to, and should, read the opinion carefully and in its entirety. Morgan Stanley’s opinion was directed to the Board, in its capacity as such, and addressed only the fairness, from a financial point of view, as of the date of the opinion, of the merger consideration to be received by the holders of shares of the Company common stock (other than the excluded shares and appraisal shares) pursuant to the merger agreement. Morgan Stanley’s opinion did not address any other term or aspect of the merger agreement or the transactions or any term or aspect of any other agreement or instrument contemplated by the merger agreement entered into or amended in connection therewith and does not address the relative merits of the merger as compared to any other alternative business transaction, or other alternatives, or whether or not such alternatives could be achieved or are available. It was not intended to, and does not, constitute an opinion or recommendation as to how the holders of Company common stock should vote at the special meeting. The summary of Morgan Stanley’s opinion set forth in this proxy statement is qualified in its entirety by reference to the full text of Morgan Stanley’s opinion.

Effects on the Company if the Merger Is Not Consummated

(page 74)

In the event that the Company stockholder approval is not obtained or if the merger is not consummated for any other reason, the Company’s stockholders will not receive any payment for their shares of Company common stock in connection with the merger. Instead, the Company will remain an

6 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

SUMMARY

independent public company, the Company common stock will continue to be listed and traded on NASDAQ, the Company common stock will continue to be registered under the Exchange Act and the Company’s stockholders will continue to own their shares of Company common stock and will continue to be subject to the same general risks and opportunities as they currently are with respect to ownership of the Company common stock.

Under certain circumstances, if the merger is not consummated, the Company may be obligated to pay to Parent a $97.5 million termination fee (the “Company termination fee”) and, under certain other specified circumstances, Parent may be required to pay the Company a termination fee of $227.4 million (the “Parent termination fee”). Please see the section of this proxy statement entitled “The Merger Agreement — Termination Fees” beginning on page 118.

Financing of the Merger

(page 75)

The consummation of the merger is not conditioned on Parent’s receipt of any financing. Parent plans to fund the merger consideration with committed equity financing and debt financing, as described below.

The Apollo Funds, JFLCO Funds and Hill City Fund have committed to contribute, or cause to be contributed, to Parent an aggregate amount in cash of up to $3.213 billion (the “equity commitment”), subject to the terms and conditions set forth in the equity commitment letters provided by such Consortium Funds to Parent, dated as of August 4, 2022 (the “equity commitment letters”), which will be used by Parent, together with the debt financing described below, and available cash on our balance sheet (if any), solely to fund each such fund’s pro rata share of (i) the cash payments required under the merger agreement to be made by Parent in connection with the closing of the merger (the “closing obligations”) and (ii) the payment of Parent’s or MergerCo’s fees, costs and expenses related to the consummation of the transactions contemplated by the merger agreement (the “expense obligations” and, together with the closing obligations, the “obligations”).

Additionally, Goldman Sachs Bank USA (“GS Bank”), Barclays Bank PLC (“Barclays”), Apollo Global Funding, LLC (“AGF”), Apollo Capital Management, L.P., on behalf of one or more investment funds, separate accounts and other entities owned (in whole or in part), controlled, managed and/or advised by it or its affiliates (in such capacity, “ACM” and, together with AGF and such funds, accounts and entities, the “Apollo Debt Commitment Funds”), Mizuho Bank, Ltd. (“Mizuho”) and Crédit Agricole Corporate and Investment Bank (“Crédit Agricole” and, together with GS Bank, Barclays, the Apollo Debt Commitment Funds, Mizuho and any additional commitment party joining the committed debt financing, the “debt financing sources”) have committed to provide Parent, severally but not jointly, upon the terms and subject to the conditions set forth in the debt commitment letter provided by the debt financing sources to Parent, dated August 4, 2022 (the “debt commitment letter” and, together with the equity commitment letters, the “commitment letters”), debt financing in an aggregate amount of $1.9 billion, consisting of a senior secured first lien term loan facility in an aggregate principal amount of $1.6 billion (the “term facility”) and a senior secured first lien revolving credit facility in an aggregate principal amount of $300 million (the “revolving credit facility” and, together with the term facility, the “credit facilities”), which credit facilities may be used (i) in the case of the term facility, to finance the merger and to repay certain existing indebtedness of the Company and its subsidiaries and (ii) in the

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 7

SUMMARY

case of the revolving credit facility, for general corporate purposes from and after the closing of the merger, to the extent that Parent does not obtain alternative financing, in lieu of such credit facilities, at or prior to the closing of the merger.

Limited Guarantees

(see page 77)

Subject to the terms and conditions set forth in the limited guarantees provided by certain of the Apollo Funds (the “Apollo Guarantors”), one of the JFLCO Funds (the “JFLCO Guarantor”) and the Hill City Fund (each of the Apollo Guarantors, the JFLCO Guarantor and the Hill City Fund a “Guarantor” and, together, the “Guarantors”), the Guarantors have guaranteed certain payment obligations of Parent under the merger agreement, subject to an aggregate maximum cap of $178,151,634 for the Apollo Guarantors, a maximum cap of $36,165,577 for the JFLCO Guarantor and a maximum cap of $18,082,789 for the Hill City Fund, for payment of (i) the Parent termination fee (to the extent payable), (ii) reasonable out-of-pocket costs and expenses of the Company or any of its subsidiaries and their respective representatives in connection with the financing of the merger and (iii) reasonable and documented costs and expenses of the Company in connection with the successful enforcement of the Parent’s obligations to pay the Parent termination fee (collectively, the “guaranteed obligations”).

Interests of the Company’s Directors and Executive Officers in the Merger

(page 82)

The Company’s directors and executive officers have financial interests in the merger that may be different from, or in addition to, the interests of the Company’s stockholders generally. The Board was aware of and considered these interests in reaching the determination to approve the execution, delivery and performance by the Company of the merger agreement and to recommend that Company stockholders approve the merger agreement proposal. These interests may include:

•

the treatment of Company long-term incentive awards provided for under the merger agreement (as described below in “The Merger Agreement — Treatment of Company Long-Term Incentive Awards”);

•

severance and other benefits payable in the case of certain qualifying terminations of employment under the terms of individual employment agreements or the Company’s benefits program;

•

vesting and payment of account balances in the Company’s 401(k) Restoration and Voluntary Deferral Plan (the “401(k) Restoration Plan”);

•

the potential to receive an annual bonus for 2022 at the greater of target or actual performance levels;

•

the potential grant of cash-based retention awards under a program established for the benefit of certain Company employees; and

•

continued indemnification and insurance coverage under the merger agreement, the organizational documents of the Company and its subsidiaries and indemnification agreements the Company and any of its subsidiaries has entered into with each of its directors and executive officers.

8 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

SUMMARY

These interests are described in more detail, and certain of them are quantified, in the section entitled “The Merger — Interests of the Company’s Directors and Executive Officers in the Merger” beginning on page 82 of this proxy statement.

Treatment of Company Long-Term Incentive Awards

(page 94)

Each long-term incentive award outstanding as of August 4, 2022 will be treated as follows:

•

each restricted stock unit with respect to shares of Company common stock subject to time-based vesting conditions (each, a “Company RSU”) outstanding immediately prior to the effective time will vest and be canceled in exchange for a lump-sum cash payment equal to the merger consideration multiplied by the number of shares subject to such Company RSU;

•

each performance-based restricted stock unit with respect to shares of Company common stock subject to both time- and performance-based vesting conditions (each, a “Company PSU”) outstanding immediately prior to the effective time will vest and be canceled in exchange for a lump-sum cash payment equal to the merger consideration multiplied by the number of shares subject to such Company PSU, assuming the maximum level of achievement of any applicable Company PSU performance criteria (such performance criteria are currently trending at or near the maximum level irrespective of the transaction); and

•

each long-term cash incentive award (each, a “Company cash award”) outstanding immediately prior to the effective time will vest and be canceled in exchange for a lump-sum cash payment equal to the amount payable under the applicable award agreement assuming all relevant conditions were met and the maximum level of achievement of any applicable Company cash award performance criteria (such performance criteria are currently trending at or near the maximum level irrespective of the transaction).

With respect to the awards described above, the payments described above will be made, subject to any applicable withholding taxes, as soon as practicable following the effective time (and in no event later than the second regular payroll date following the effective time).

With respect to awards granted following August 4, 2022, the awards will be granted in the form of cash awards (each, a “post-signing cash award”), with such post-signing cash award vesting and being paid in equal annual installments over the three-year period from the applicable grant date, with accelerated vesting terms upon a qualifying termination of employment.

See “The Merger Agreement — Treatment of Company Long-Term Incentive Awards” beginning on page 94.

Material U.S. Federal Income Tax Consequences of the Merger

(page 87)

The receipt of cash pursuant to the merger will be a taxable transaction for U.S. federal income tax purposes. Generally, for U.S. federal income tax purposes, if you are a holder of common stock who is

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 9

SUMMARY

a U.S. holder (as defined below in the section of this proxy statement entitled “The Merger — Material U.S. Federal Income Tax Consequences of the Merger”), you will recognize capital gain or loss equal to the difference between the amount of cash you receive in the merger and your adjusted tax basis in your shares of common stock converted into cash in the merger. If you are a holder of common stock who is a non-U.S. holder (as defined below in the section of this proxy statement entitled “The Merger — Material U.S. Federal Income Tax Consequences of the Merger”), the merger will generally not be taxable to you under U.S. federal income tax laws unless you have certain connections to the United States or the Company stock constitutes a USRPI (as defined below in the section of this proxy statement entitled “The Merger — Material U.S. Federal Income Tax Consequences of the Merger”) and certain other conditions are met.

You should read the section of this proxy statement entitled “The Merger — Material U.S. Federal Income Tax Consequences of the Merger” beginning on page 87 for a more complete discussion of the material U.S. federal income tax consequences of the merger. You should consult your own tax advisor for a full understanding of how the merger will affect your federal, state, local and/or non-U.S. taxes.

Regulatory Approvals in Connection with the Merger

(page 90)

The consummation of the merger is subject to the requirements of and review under the Hart-Scott-Rodino Antitrust Improvements Act of 1976 and the rules and regulations promulgated thereunder (the “HSR Act”) and the rules promulgated by the Federal Trade Commission (“FTC”). As described below in the section entitled “— Conditions of the Merger”, the obligations of the parties to effect the merger are subject to, among other things, the waiting period (and any extension thereof) applicable to the merger under the HSR Act having been terminated or expired and the receipt of certain other regulatory approvals, including regulatory approvals from the U.S. Department of Transportation (“DOT”) and the Federal Communications Commission (“FCC”), as well as antitrust approvals in the European Union, the People’s Republic of China, the Republic of Korea and Japan. Both the Company and Parent filed their respective Notification and Report Forms with the FTC and the Antitrust Division of the DOJ on August 12, 2022. On September 12, 2022, Parent withdrew its filing and refiled on September 14, 2022 in order to provide the FTC and the Antitrust Division of the DOJ with an additional 30-day period to review the filings. The waiting period applicable to the consummation of the merger under the HSR Act is scheduled to expire on October 14, 2022. The parties also made the required filings with the European Union on September 13, 2022, the People’s Republic of China on September 16, 2022, the Republic of Korea on September 26, 2022 and Japan on September 30, 2022.

The merger agreement includes covenants obligating each of the parties to use reasonable best efforts to cause the closing conditions to be satisfied as promptly as reasonably practicable and to take certain actions to resolve objections under any applicable laws.

In addition, in order to prevent the entry of, or to have vacated, lifted, reversed or overturned, any restraint (as defined in the section entitled “The Merger Agreement — Conditions of the Merger”) that would prevent, prohibit, restrict or delay the consummation of the transactions, Parent has agreed to (i) execute settlements, undertakings, consent decrees, stipulations or other agreements with any governmental authority or any other person, (ii) sell, divest or otherwise convey or hold separate particular assets or categories of assets or businesses of Parent, its subsidiaries or any controlled

10 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

SUMMARY

affiliate of the foregoing, (iii) agree to sell, divest or otherwise convey or hold separate any particular assets or categories of assets or businesses of the Company and its subsidiaries contemporaneously with or subsequent to the effective time, (iv) permit the Company to sell, divest or otherwise convey or hold separate any of the particular assets or categories of assets or businesses of the Company or any of its subsidiaries prior to the effective time, (v) terminate existing relationships, contractual rights or obligations of (A) the Company or its affiliates or (B) Parent, its subsidiaries or any controlled affiliate of the foregoing, (vi) create any relationship, contractual right or obligation of (A) the Company or its affiliates or (B) Parent, its subsidiaries or any controlled affiliate of the foregoing, or (vii) effectuate any other change or restructuring of (A) the Company or its affiliates or (B) Parent, its subsidiaries or any controlled affiliate of the foregoing, or (viii) defend through litigation any claim asserted in court or administrative or other tribunal by any person (including any governmental authority) in order to avoid the entry of, or to have vacated or terminated, any restraint that would prevent the closing prior to the outside date (as defined in the merger agreement and as it may be extended (or further extended, as applicable)) then in effect.

Appraisal Rights

(page 78)

If the merger is consummated, persons who do not wish to accept the merger consideration are entitled to seek appraisal of their shares of Company common stock under Section 262 and, if all procedures described in Section 262 are strictly complied with, to receive payment in cash for the fair value of their shares of Company common stock exclusive of any element of value arising from the accomplishment or expectation of the merger, as determined by the Delaware Court of Chancery (the “Delaware Court”), together with interest, if any, to be paid upon the amount determined to be the fair value. The “fair value” of your shares of Company common stock as determined by the Delaware Court may be more or less than, or the same as, the merger consideration that you are otherwise entitled to receive under the merger agreement. These rights are known as “appraisal rights”. This proxy statement serves as a notice of such appraisal rights pursuant to Section 262.

Persons who exercise appraisal rights under Section 262 will not receive the merger consideration they would otherwise be entitled to receive pursuant to the merger agreement. They will receive an amount determined to be the “fair value” of their shares of Company common stock following petition to, and an appraisal by, the Delaware Court. Persons considering seeking appraisal should recognize that the fair value of their shares of Company common stock determined under Section 262 could be more than, the same as or less than the merger consideration they would otherwise be entitled to receive pursuant to the merger agreement. Strict compliance with the procedures set forth in Section 262 is required. Failure to comply strictly with all of the procedures set forth in Section 262 may result in the withdrawal, loss or waiver of appraisal rights. Consequently, and in view of the complexity of the provisions of Section 262, persons wishing to exercise appraisal rights are urged to consult their legal and financial advisors before attempting to exercise such rights.

A holder of record or a beneficial owner of shares of Company common stock who (i) continuously holds such shares through the effective time, (ii) has not consented to or otherwise voted in favor of the merger or otherwise withdrawn, lost or waived appraisal rights, (iii) strictly complies with the procedures under Section 262, (iv) does not thereafter withdraw his, her or its demand for appraisal of such shares

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 11

SUMMARY

and (v) in the case of a beneficial owner, a person who (A) reasonably identifies in his, her or its demand the holder of record of the shares for which the demand is made, (B) provides documentary evidence of such beneficial owner’s beneficial ownership and a statement that such documentary evidence is a true and correct copy of what it purports to be and (C) provides an address at which such beneficial owner consents to receive notices given by the Company and to be set forth on the Chancery List (as defined in the section of this proxy statement entitled “The Merger — Appraisal Rights”), will be entitled to receive the fair value of his, her or its shares of Company common stock exclusive of any element of value arising from the accomplishment or expectation of the merger, as determined by the Delaware Court, together with interest, if any, to be paid upon the amount determined to be the fair value.

A copy of Section 262 may be accessed without subscription or cost at the following publicly available website: https://delcode.delaware.gov/title8/c001/sc09/index.html#262. The following summary is not a complete statement of the law relating to appraisal rights and is qualified in its entirety by reference to Section 262 and any amendments thereto after the date of this proxy statement. Any person who desires to exercise his, her or its appraisal rights should review carefully Section 262 and is urged to consult his, her or its legal and financial advisors before electing or attempting to exercise such rights. For more information, please see the section of this proxy statement entitled “The Merger — Appraisal Rights”.

No Solicitation

(page 105)

The merger agreement generally restricts the Company’s ability to directly or indirectly solicit takeover proposals (as defined below under the section entitled “The Merger Agreement — No Solicitation; Change in Board Recommendation”) from third parties (including by furnishing non-public information), to participate in discussions or negotiations with third parties regarding any takeover proposal, to approve or recommend any takeover proposals or to enter into agreements providing for or relating to any takeover proposal. Under certain circumstances, however, and in compliance with certain obligations contained in the merger agreement, the Company is permitted to engage in negotiations with, and provide information to, third parties that have made an unsolicited takeover proposal upon the Board’s (or an authorized Board committee’s) determination in good faith, after consultation with financial advisors and outside legal counsel, that such takeover proposal constitutes or would reasonably be expected to lead to a superior proposal (as defined below under the section entitled “The Merger Agreement — No Solicitation; Change in Board Recommendation”).

Conditions of the Merger

(page 115)

Each party’s obligations to effect the merger are subject to the satisfaction (or waiver, if permissible under applicable law), on or prior to the closing date of the merger (the “closing date”), of certain conditions, including:

•

no judgment enacted, promulgated, issued, entered, amended or enforced by any governmental authority of competent jurisdiction or any applicable law in the United States or certain agreed

12 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

SUMMARY

jurisdictions will be in effect enjoining, restraining or otherwise making illegal, preventing or prohibiting the consummation of the merger (the “restraints”);

•

the expiration or early termination of the waiting period (and any extension thereof) applicable to the consummation of the merger under the HSR Act and obtaining certain agreed regulatory consents, approvals or other clearances; and

•

receipt of the Company stockholder approval.

The obligations of Parent and MergerCo to consummate the merger is subject to the satisfaction (or written waiver by Parent, if permissible under applicable law) on or prior to the closing date of the following additional conditions:

•

the truthfulness and correctness of representations and warranties of the Company to the extent specified in the merger agreement, subject to certain materiality qualifications;

•

the Company having complied with or performed, in all material respects, the obligations required to be complied with or performed by the Company at or prior to the effective time under the merger agreement; and

•

the absence of any change, event, development, occurrence, state of facts, circumstance or effect that, individually or in the aggregate, has had or would reasonably be expected to have a Material Adverse Effect (“Material Adverse Effect”) with respect to the Company and its subsidiaries (as described below in the section entitled “The Merger Agreement — Representations and Warranties”) since August 4, 2022.

The obligations of Company to consummate the merger is subject to the satisfaction (or written waiver by the Company, if permissible under applicable law) on or prior to the closing date of the following additional conditions:

•

the truthfulness and correctness of representations and warranties of Parent and MergerCo to the extent specified in the merger agreement, subject to certain materiality qualifications; and

•

Parent and MergerCo having complied with or performed, in all material respects, the obligations required to be complied with or performed by them at or prior to the effective time under the merger agreement.

The consummation of the merger and the transactions is not conditioned upon Parent’s receipt of financing. Each party may waive any of the conditions to its obligations to consummate the merger except where waiver is not permitted by law.

Termination of the Merger Agreement

(page 116)

The merger agreement may be terminated and the transactions abandoned at any time prior to the effective time, whether before or after receipt of the Company stockholder approval, by the mutual written consent of the Company and Parent.

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 13

SUMMARY

Termination by Either the Company or Parent

In addition, the Company, on the one hand, or Parent, on the other hand, may terminate the merger agreement and abandon the transactions at any time prior to the effective time, whether before or after receipt of the Company stockholder approval, if:

•

the effective time has not occurred on or before March 4, 2023, as such date may be extended as described below (the “outside date”); provided that (i) this right to terminate the merger agreement will not be available to any party if the breach by such party of its representations and warranties set forth in the merger agreement or the failure of such party to perform any of its obligations under the merger agreement has been a principal cause of or resulted in the events specified in this right to terminate; (ii) in the event the marketing period has commenced but has not completed as of the outside date, the outside date may be extended by Parent in its sole discretion to the date that is four business days following the then-scheduled end date of the marketing period (as described under “The Merger Agreement — Financing”); (iii) if on the outside date the conditions set forth under the first bullet described above in the section entitled “— Conditions of the Merger” ​(to the extent relating to matters described in the second bullet described above in the section entitled “—​Conditions of the Merger”) or the second bullet described above in the section entitled “— Conditions of the Merger” are not satisfied but all other closing conditions have been satisfied or waived (other than those conditions that by their nature are to be satisfied at the closing of the merger, but provided that such conditions will then be capable of being satisfied if the closing of the merger were to take place on such date), then the outside date will be automatically extended to June 4, 2023; and (iv) if the outside date is extended pursuant to clause (iii), the conditions set forth under the first bullet described above in the section entitled “— Conditions of the Merger” ​(to the extent relating to matters described in the second bullet described above in the section entitled “— Conditions of the Merger”) or the second bullet described above in the section entitled “— Conditions of the Merger” are not satisfied but all other closing conditions have been satisfied or waived (other than those conditions that by their nature are to be satisfied at the closing of the merger, but provided that such conditions are then capable of being satisfied if the closing of the merger were to take place on such date), then the outside date may, at the option of either the Company or Parent, be extended to August 4, 2023;

•

any restraint having the effect set forth in the first bullet described above in the section entitled “— Conditions of the Merger” is in effect and has become final and nonappealable; provided that the party seeking to terminate the merger agreement pursuant to this right to terminate has used the required efforts to prevent the entry of and to remove such restraint in accordance with its obligations under the merger agreement; and provided further that no party may invoke this right to terminate if such party’s failure to comply with its obligations described below under the section entitled “The Merger Agreement — Reasonable Best Efforts” is the primary cause of the failure of this condition to be satisfied; or

•

the special meeting of Company stockholders (including any adjournments or postponements thereof) has concluded and Company stockholder approval has not been obtained.

Termination by Parent

Parent may also terminate the merger agreement and abandon the transactions by written notice to the Company at any time prior to the effective time, whether before or after receipt of the Company stockholder approval, if:

14 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

SUMMARY

•

the Company has breached any of its representations or warranties or failed to perform any of its covenants or agreements in the merger agreement, which breach or failure to perform (i) would give rise to the failure of any of the conditions set forth under the fourth and fifth bullets described above in the section entitled “— Conditions of the Merger” and (ii) which is incapable of being cured or, if capable of being cured by the outside date then in effect, the Company has not cured such breach or failure to perform within 35 calendar days following receipt by the Company of written notice of such breach or failure to perform from Parent stating Parent’s intention to terminate the merger agreement pursuant to this right to terminate; provided that Parent will not have the right to terminate the merger agreement pursuant to this right to terminate if Parent or MergerCo is then in material breach of any of its representations, warranties, covenants or agreements under the merger agreement; or

•

(i) the Board or a duly authorized committee thereof will have made an adverse recommendation change (as defined under the section entitled “The Merger Agreement — No Solicitation; Change in Board Recommendation”) or (ii) following a written request by Parent pursuant to this right to terminate following the date any takeover proposal or any material modification thereto is first published or communicated to Company stockholders and the Company fails to issue a press release that expressly reaffirms the Board’s recommendation that Company stockholders approve the merger agreement proposal within five business days.

Termination by the Company

The Company may also terminate the merger agreement and abandon the transactions by written notice to Parent at any time prior to the effective time, whether before or after receipt of the Company stockholder approval (except as otherwise noted), if:

•

either of Parent or MergerCo has breached any of its representations or warranties or failed to perform any of its covenants or agreements in the merger agreement, which breach or failure to perform (i) (A) would give rise to any effect, change, event or occurrence that would prevent or materially delay or materially impair the consummation by Parent or MergerCo of any of the transactions on a timely basis or the compliance by Parent or MergerCo with its obligations under the merger agreement, or (B) would give rise to the failure of any of the conditions set forth under the seventh and eighth bullets described above in the section entitled “— Conditions of the Merger” and (ii) which is incapable of being cured, or, if capable of being cured by the outside date then in effect, either Parent or MergerCo, as applicable, has not cured such breach or failure to perform within 35 calendar days following receipt by Parent of written notice of such breach or failure to perform from the Company stating the Company’s intention to terminate the merger agreement pursuant to this right to terminate; provided that the Company will not have the right to terminate the merger agreement pursuant to this right to terminate if the Company is then in material breach of any of its representations, warranties, covenants or agreements under the merger agreement;

•

prior to receipt of Company stockholder approval, in connection with entering into a Company acquisition agreement (as defined under the section entitled “The Merger Agreement — No Solicitation; Change in Board Recommendation”) in accordance with the applicable terms of the merger agreement; provided that prior to or concurrently with such termination the Company pays or causes to be paid the applicable termination fee; or

•

(i) the marketing period has ended and all of the conditions under the first, second, third, fourth, fifth and sixth bullets described above in the section entitled “— Conditions of the Merger” have been satisfied or waived (to the extent such waiver is permitted by applicable law) (other than those

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 15

SUMMARY

conditions that by their nature are to be satisfied at the closing of the merger), (ii) the Company has confirmed by notice to Parent that all conditions under the seventh and eighth bullets described above in the section entitled “— Conditions of the Merger” have been satisfied (other than those conditions that by their nature are to be satisfied at the closing of the merger) or which the Company is willing to waive to the extent unsatisfied and (iii) the merger is not consummated within two business days after the delivery of such notice (provided that no party will be permitted to terminate the merger agreement pursuant to the first bullet point described above in the section entitled “— Termination of the Merger Agreement — Termination by Either the Company or Parent” during such two business-day period).

Termination Fees

(page 118)

The Company will be required to pay to Parent the Company termination fee of $97.5 million if:

•

the Company or Parent terminates the merger agreement pursuant to the provisions described in the first or third bullet point described above in the section entitled “— Termination of the Merger Agreement — Termination by Either the Company or Parent”; provided that (i) (A) at the time of termination the Company will not have been entitled to terminate the merger agreement pursuant to the provision described in the third bullet point described above in the section entitled “— Termination of the Merger Agreement — Termination by the Company” and (B) neither Parent nor MergerCo is then in material breach of its representations, warranties, covenants or agreements under the merger agreement and none of Parent, MergerCo or any party to the equity commitment letters or limited guarantees is then in material breach of its representations, warranties, covenants or agreements under any commitment letter or limited guarantee, (ii) a bona fide takeover proposal will have been publicly made, proposed or communicated by a third party after the date of the merger agreement and not withdrawn prior to the time the merger agreement is terminated and (iii) within 12 months of the date the merger agreement is terminated, the Company executes an agreement to enter into a takeover proposal with the person, entity or group that made the takeover proposal referred to in clause (ii) and such takeover proposal is consummated (it being understood that such consummation may occur after the 12-month period after the merger agreement is terminated); provided that for purposes of clauses (ii) and (iii), the references to “20%” in the definition of “takeover proposal” are deemed to be references to “50%”);

•

(i) Parent terminates the merger agreement pursuant to the provision described in the second bullet point described above in the section entitled “— Termination of the Merger Agreement — Termination by Parent” or (ii) the Company terminates the merger agreement pursuant to the provision described in the second bullet point described above in the section entitled “— Termination of the Merger Agreement — Termination by the Company”.

Parent will be required to pay to the Company the Parent termination fee of $227.4 million if (i) the Company terminates the merger agreement pursuant to the provisions described in the third bullet point described above in the section entitled “— Termination of the Merger Agreement — Termination by the Company” or (ii) if Parent terminates the merger agreement pursuant to the provisions described in the first bullet point described above in the section entitled “— Termination of the Merger Agreement — Termination by Either the Company or Parent” and at such time the Company could

16 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

SUMMARY

have terminated the merger agreement pursuant to the provisions described in the third bullet point described above in the section entitled “— Termination of the Merger Agreement — Termination by the Company”.

Current Price of Common Stock

On [     ], [     ], the latest practicable trading day before the filing of this proxy statement, the reported closing price for shares of common stock on NASDAQ was $[     ]. You are encouraged to obtain current market quotations for shares of Company common stock in connection with voting your common stock.

Additional Information

(page 127)

You can find more information about the Company in the periodic reports and other information we file with the U.S. Securities and Exchange Commission (the “SEC”). The information is available at the website maintained by the SEC at www.sec.gov.

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 17

QUESTIONS AND ANSWERS ABOUT THE SPECIAL MEETING AND THE MERGER

QUESTIONS AND ANSWERS ABOUT THE SPECIAL

MEETING AND THE MERGER

The following questions and answers are intended to briefly address some commonly asked questions regarding the special meeting, the merger and the merger agreement. These questions and answers may not address all questions that may be important to you. You should read the more detailed information contained elsewhere in this proxy statement, the annexes to this proxy statement and the documents referred to or incorporated by reference in this proxy statement.

Q:

Why am I receiving this proxy statement?

A:

On August 4, 2022, the Company entered into the merger agreement with Parent and MergerCo. Pursuant to the terms of the merger agreement, MergerCo will be merged with and into the Company, with the Company surviving the merger as a wholly-owned, direct subsidiary of Parent.

You are receiving this proxy statement in connection with the solicitation of proxies by the Board in favor of the merger agreement proposal and the other matters to be voted on at the special meeting described below under “— What proposals will be considered at the special meeting?”

Q:

As a holder of Company common stock, what will I receive in the merger?

A:

If the merger is consummated, you will be entitled to receive $102.50 in cash, without interest and subject to any applicable withholding taxes, for each share of Company common stock that you own immediately prior to the effective time.

The receipt of cash pursuant to the merger will be a taxable transaction for U.S. federal income tax purposes. Please see the section of this proxy statement entitled “The Merger — Material U.S. Federal Income Tax Consequences of the Merger” beginning on page 87 for a more detailed description of the United States federal income tax consequences of the merger. You should consult your own tax advisor for a full understanding of how the merger will affect your federal, state, local and/or non-U.S. taxes.

Q:

When and where is the special meeting of our stockholders?

A:

The special meeting of Company stockholders will be held on [           ] at [              ], Eastern Time, in a virtual-only meeting format. In light of ongoing concerns regarding the coronavirus pandemic, and to support the health and safety of our stockholders, employees and communities, Company stockholders may only attend the special meeting virtually. The Company stockholders will not be able to physically attend the special meeting. To access the virtual special meeting, you should visit [              ]. You will be required to enter a control number, included on your proxy card, voting instruction form or as you may otherwise receive, which will allow you to participate in the virtual meeting and vote your shares of common stock if you are a Company stockholder as of the record date. We encourage you to access the special meeting before the start time of [           ], Eastern Time. Please allow ample time to log into the audio webcast and test your computer systems.

18 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

QUESTIONS AND ANSWERS ABOUT THE SPECIAL MEETING AND THE MERGER

Q:

Who is entitled to attend and vote at the special meeting?

A:

Only Company stockholders of record at the close of business on [           ], 2022, the record date for the special meeting, will be entitled to notice of, and to vote at, the special meeting and any postponement or adjournment thereof. As of the close of business on the record date, there were [           ] shares of common stock outstanding and entitled to vote. Each Company stockholder is entitled to one vote per share of common stock held by such Company stockholder on the record date on each of the proposals presented in this proxy statement.

If on [           ], 2022, you were a “record” holder of Company common stock (that is, if you held Company common stock in your own name in the stock register maintained by our transfer agent, Computershare Trust Company, N.A. (“Computershare”)), you are entitled to attend and vote at the virtual special meeting or by proxy. Whether or not you intend to attend the virtual special meeting, we encourage you to authorize a proxy to vote now, online, by phone or by proxy card to ensure that your vote is counted.

If on [           ], 2022, you were the beneficial owner of Company common stock held in “street name” (that is, if you held Company common stock through your bank, broker or other nominee), then these materials are being forwarded to you by that organization. You may direct your bank, broker or other nominee how to vote your Company common stock by following the voting instructions on the form provided by your bank, broker or other nominee. If you hold any Company common stock through your bank, broker or other nominee and wish to attend the virtual special meeting, you may attend the virtual special meeting but may not be able to vote unless you first obtain a legal proxy issued in your name from such broker, bank or other nominee. Once you have received a legal proxy issued in your name from your bank, broker or other nominee, please email a scan or image of it to Computershare at legalproxy@computershare.com with “Legal Proxy” noted in the subject line. Upon receipt of your legal proxy, Computershare will provide you with a control number by email. The cut-off time for requesting a control number is [          ], 2022, five business days prior to the date of the special meeting, at 5:00 p.m. Eastern Time.

For additional information on how to vote at the special meeting, please see the section entitled “The Special Meeting — Voting Procedures”.

For a description of certain restrictions on voting by Company stockholders who are not “U.S. citizens”, as defined by applicable laws and regulations, please see the section “The Special Meeting — Limited Voting by Foreign Owners” of this proxy statement.

At the virtual special meeting and for 10 days prior to the special meeting, the names of Company stockholders entitled to vote at the special meeting will be available for inspection for any purpose germane to the meeting, between the hours of 9:00 a.m. and 5:00 p.m. Eastern Time, at the Company’s principal executive offices located at 2000 Westchester Avenue, Purchase, New York 10577, by contacting the Secretary of the Company.

Q:

What proposals will be considered at the special meeting?

A:

At the special meeting, Company stockholders will be asked to consider and vote on the following proposals:

•

the merger agreement proposal;

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 19

QUESTIONS AND ANSWERS ABOUT THE SPECIAL MEETING AND THE MERGER

•

the advisory compensation proposal; and

•

the adjournment proposal.

Q:

How does the Board recommend that I vote?

A:

The Board recommends a vote “FOR” the merger agreement proposal, “FOR” the advisory compensation proposal and “FOR” the adjournment proposal.

For a discussion of the factors that the Board considered in determining to recommend the approval of the merger agreement proposal, please see the section of this proxy statement entitled “The Merger — Reasons for the Merger” beginning on page 54.

In addition, in considering the recommendation of the Board with respect to the merger agreement, you should be aware that some of the Company’s directors and executive officers have interests that may be different from, or in addition to, the interests of the Company stockholders generally. Please see the section of this proxy statement entitled “The Merger — Interests of the Company’s Directors and Executive Officers in the Merger” beginning on page 82.

Q:

What constitutes a quorum for purposes of the special meeting?

A:

The holders of a majority of all of the stock issued and outstanding and entitled to vote at the special meeting, present in person or represented by proxy, constitutes a quorum of Company stockholders for the transaction of business at the special meeting. Virtual attendance at the special meeting constitutes presence in person for quorum purposes at the special meeting. Abstentions will be counted as shares present for the purposes of determining the presence of a quorum. Broker non-votes will not be counted as shares present for purposes of determining the presence of a quorum unless your bank, broker or other nominee has been instructed to vote on at least one of the proposals presented in this proxy statement. If a quorum is not present or represented at the special meeting of the Company stockholders, the Chairman of the Board or the stockholders entitled to vote thereat, present in person or by proxy, may adjourn the special meeting, without notice, if the time and place of the new meeting and the means of remote communication, if any, by which Company stockholders and proxy holders may be deemed to be present and vote at such adjourned meeting, are announced at the special meeting at which the adjournment is taken. If, however, the adjournment is for more than 30 days, or if after the adjournment a new record date is fixed for the adjourned meeting, we will provide a notice of the adjourned meeting to each Company stockholder of record entitled to vote at the special meeting. In the event that a quorum is not present at the special meeting, or if there are insufficient votes to adopt the merger agreement at the time of the special meeting, we expect that the special meeting will be postponed or adjourned to solicit additional proxies.

Q:

What vote of our stockholders is required to approve each of the proposals?

A:

The approval of the merger agreement proposal requires the affirmative vote (in person or by proxy) of the holders of a majority of outstanding shares of Company common stock entitled to vote on the matter. Under Delaware law and the merger agreement, the receipt of such required vote is a condition to the consummation of the merger. Note that you may vote to approve the merger agreement proposal and vote not to approve the advisory compensation proposal or adjournment proposal and vice versa. Abstentions, failures to vote (including a failure to authorize a proxy to vote on a Company

20 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

QUESTIONS AND ANSWERS ABOUT THE SPECIAL MEETING AND THE MERGER

stockholder’s behalf) and broker non-votes will have the same effect as a vote “AGAINST” the merger agreement proposal.

The approval of the advisory compensation proposal requires the affirmative vote (in person or by proxy) of a majority of the votes cast on such proposal at the special meeting. Assuming a quorum is present at the special meeting, abstentions, failures to vote (including a failure to authorize a proxy to vote on a Company stockholder’s behalf) and broker non-votes will have no effect on the outcome of the advisory compensation proposal.

The approval of the adjournment proposal requires the affirmative vote (in person or by proxy) of a majority of the votes cast on such proposal at the special meeting. Assuming a quorum is present at the special meeting, abstentions, failures to vote (including a failure to authorize a proxy to vote on a Company stockholder’s behalf) and broker non-votes will have no effect on the outcome of the adjournment proposal. The Company does not intend to call a vote on this proposal if the merger agreement proposal is approved at the special meeting.

A broker “non-vote” occurs when a bank, broker or other nominee holding shares for a beneficial owner does not vote on a particular proposal because the nominee does not have discretionary voting power with respect to that item and has not received voting instructions from the beneficial owner, but does have discretionary voting power over other “routine” items and submits votes for those matters. The Company does not expect any broker non-votes at the special meeting because the rules applicable to banks, brokers and other nominees only provide such organization with discretionary authority to vote on proposals that are considered “routine”, whereas each of the proposals to be presented at the special meeting is considered “non-routine”. As a result, no bank, broker or other nominee will be permitted to vote your shares of Company common stock at the special meeting without receiving instructions.

Q:

How do the Company’s directors and executive officers intend to vote?

A:

As of October 3, 2022, the directors and executive officers of the Company beneficially owned in the aggregate 325,199 shares of Company common stock, or approximately 1.1% of the outstanding shares of Company common stock as of October 3, 2022. Although none of the directors or executive officers is obligated to vote to approve the merger agreement proposal, we currently expect that each of these individuals will vote all of his or her shares “FOR” each of the proposals to be presented at the special meeting.

Q:

Do any of the Company’s directors or executive officers have any interests in the merger that are different from, or in addition to, my interests as a Company stockholder?

A:

In considering the proposals to be voted on at the special meeting of Company stockholders, you should be aware that the Company’s directors and executive officers have financial interests in the merger that may be different from, or in addition to, your interests as a Company stockholder. The members of the Board were aware of and considered these interests in reaching the determination to approve and declare advisable the merger agreement and the consummation of the transactions contemplated by the merger agreement, including the merger, and to recommend that Company stockholders approve the merger agreement proposal. These interests may include:

•

the treatment of Company long-term incentive awards provided for under the merger agreement (as described below in “The Merger Agreement — Treatment of Company Long-Term Incentive Awards”);

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 21

QUESTIONS AND ANSWERS ABOUT THE SPECIAL MEETING AND THE MERGER

•

severance and other benefits payable in the case of certain qualifying terminations of employment under the terms of individual employment agreements or the Company’s benefits program;

•

vesting and payment of account balances in the 401(k) Restoration Plan;

•

the potential to receive an annual bonus for 2022 at the greater of target or actual performance levels;

•

the potential grant of cash-based retention awards under a program established for the benefit of certain Company employees; and

•

continued indemnification and insurance coverage under the merger agreement, the organizational documents of the Company and its subsidiaries and indemnification agreements the Company and any of its subsidiaries has entered into with each of its directors and executive officers.

These interests are described in more detail, and certain of them are quantified, in the section of this proxy statement entitled “The Merger — Interests of the Company’s Directors and Executive Officers in the Merger” beginning on page 82.

Q:

What will happen to outstanding Company long-term incentive awards in the merger?

A:

Each long-term incentive award outstanding as of August 4, 2022 shall be treated as follows:

•

each Company RSU outstanding immediately prior to the effective time will vest and be canceled in exchange for a lump-sum cash payment equal to the merger consideration multiplied by the number of shares subject to such Company RSU;

•

each Company PSU outstanding immediately prior to the effective time will vest and be canceled in exchange for a lump-sum cash payment equal to the merger consideration multiplied by the number of shares subject to such Company PSU, assuming the maximum level of achievement of any applicable Company PSU performance criteria (such performance criteria are currently trending at or near the maximum level irrespective of the transaction); and

•

each Company cash award outstanding immediately prior to the effective time will vest and be canceled in exchange for a lump-sum cash payment equal to the amount payable under the applicable award agreement assuming all relevant conditions were met and the maximum level of achievement of any applicable Company cash award performance criteria (such performance criteria are currently trending at or near the maximum level irrespective of the transaction).

With respect to the awards described above, the payments described above will be made, subject to any applicable withholding taxes, as soon as practicable following the effective time (and in no event later than the second regular payroll date following the effective time).

With respect to each post-signing cash award, such award will vest and be paid in equal annual installments over the three-year period from the applicable grant date, with such post-signing cash award vesting and being paid in equal annual installments over the three-year period from the applicable grant date, with accelerated vesting terms upon a qualifying termination of employment.

See “The Merger Agreement — Treatment of Company Long-Term Incentive Awards” beginning on page 94.

22 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

QUESTIONS AND ANSWERS ABOUT THE SPECIAL MEETING AND THE MERGER

Q:

What happens if I transfer my Company common stock before the special meeting?

A:

The record date for the special meeting is earlier than the date of the special meeting. If you own Company common stock on the record date and transfer your shares after the record date but prior to the special meeting, you will retain your right to vote such shares of Company common stock at the special meeting. However, the right to receive the merger consideration will pass to the person to whom you transferred your shares of Company common stock.

Q:

How do I vote if I am a Company stockholder of record or hold my shares in “street name”?

A:

If you are a Company stockholder of record, you may vote in advance by authorizing a proxy for the special meeting by completing, signing, dating and mailing the enclosed proxy card in the envelope provided. You may also vote by attending the virtual special meeting and voting during the live webcast.

If your shares of Company common stock are held in a stock brokerage account by a bank, broker or other nominee, you are considered the beneficial owner of shares held in “street name”, and these proxy materials are being forwarded to you by your bank, broker or other nominee that is considered the Company stockholder of record of those shares. As the beneficial owner, you have the right to direct your bank, broker or other nominee on how to vote your shares via the internet or by phone if the bank, broker or other nominee offers these options to you or by completing, dating, signing and returning a voting instruction form. Your bank, broker or other nominee will send you instructions on how to submit your voting instructions for your shares of Company common stock. To vote at the virtual special meeting, which will have the same effect as revoking any previously submitted voting instructions, you will need to register in advance. Please see “The Special Meeting — Registering for the Special Meeting” beginning on page 31 for information on how to register in advance.

For more detailed instructions on how to vote using one of these methods, please see the section of this proxy statement entitled “The Special Meeting — Voting Procedures” beginning on page 34.

Whether or not you plan to attend the virtual special meeting, we urge you to vote now to ensure your vote is counted. You may still attend the virtual special meeting and vote during the live webcast if you have already voted by proxy.

Q:

What will happen if I abstain from voting or fail to vote on any of the proposals?

A:

The approval of the merger agreement proposal requires the affirmative vote (in person or by proxy) of the holders of a majority of outstanding shares of Company common stock entitled to vote on the matter. If you fail to authorize a proxy to vote your shares or to vote at the virtual special meeting, or fail to instruct your broker, bank or other nominee on how to vote, the effect will be that the shares of Company common stock that you own will not be counted for purposes of determining whether a quorum is present at the special meeting and will have the same effect as a vote “AGAINST” the merger agreement proposal.

The approval of the advisory compensation proposal and the adjournment proposal each requires the affirmative vote (in person or by proxy) of a majority of the votes cast on the proposal. Assuming a quorum is present, if you fail to authorize a proxy to vote your shares or vote at the virtual special meeting, or fail to instruct your bank, broker or other nominee on how to vote, it will have no effect on the outcome of these proposals. Abstentions will not be considered votes cast and therefore will have no effect on the outcome of the advisory compensation proposal or the adjournment proposal.

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 23

QUESTIONS AND ANSWERS ABOUT THE SPECIAL MEETING AND THE MERGER

Q:

Can I change my vote after I have delivered my proxy?

A:

Yes. For the Company stockholders of record, any time after you have submitted a proxy card and before the proxy card is exercised, you may revoke or change your vote in one of three ways:

•

you may submit a new proxy card bearing a later date (which automatically revokes the earlier proxy or voting instructions) in accordance with the instructions detailed in the section of this proxy statement entitled “The Special Meeting — Voting Procedures”; or

•

you may submit a written notice of revocation to the Company’s Secretary at Atlas Air Worldwide Holdings, Inc., 2000 Westchester Avenue, Purchase, NY 10577; or

•

you may attend the virtual special meeting and vote during the live webcast. Attendance at the virtual special meeting will not, in itself, constitute revocation of a previously granted proxy.

Please note that if you want to revoke your proxy by sending a new proxy card or a written notice of revocation to the Company, you should ensure that you send your new proxy card or written notice of revocation in sufficient time for it to be received by the Company prior to the special meeting.

If you hold your shares in “street name”, you will need to revoke or resubmit your proxy through your broker, bank or other nominee and in accordance with its procedures. If your broker, bank or other nominee allows you to submit a proxy via the internet or by telephone, you may be able to change your vote by submitting a new proxy via the internet or by telephone (or by mail). To vote at the virtual special meeting, which will have the same effect as revoking any previously submitted voting instructions, you will need to register in advance. Please see “The Special Meeting — Registering for the Special Meeting” beginning on page 31 for information on how to register in advance.

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 or multiple proxy or voting instruction cards. For example, if you hold your Company common stock in more than one brokerage account, you will receive a separate voting instruction card for each brokerage account in which you hold Company common stock. Please submit each proxy and voting instruction card that you receive to ensure that all of your shares of Company common stock are voted.

Q:

If I hold my Company common stock in certificated form, should I send in my stock certificates now?

A:

No. Parent will designate a bank or trust company reasonably acceptable to the Company to act as paying agent for the payment of the merger consideration in accordance with the merger agreement. At or prior to the effective time, Parent will cause to be deposited with the paying agent an amount in cash sufficient to pay the aggregate merger consideration. Promptly after the effective time, and in any event not later than the third business day after the effective time, the surviving corporation will cause the paying agent to mail to each holder of Company common stock, who holds share certificates or book-entry shares not held through the Depository Trust Corporation (“DTC”), entitled to the merger consideration a letter of transmittal and instructions advising such Company stockholder how to surrender its Company common stock in exchange for the merger consideration. Each holder of Company common stock will be entitled to receive the merger consideration upon, in the case of holders of share certificates, the surrender of such certificates for cancelation to the paying agent or,

24 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

QUESTIONS AND ANSWERS ABOUT THE SPECIAL MEETING AND THE MERGER

in the case of holders of non-certificated book-entry shares not held through the DTC, the transfer of such book-entry shares by book receipt of an “agent’s message” in customary form by the paying agent, and, in each case, together with the associated letter of transmittal, duly completed and validly executed in accordance with the instructions thereto, and such other documents as may be reasonably required by the paying agent. You should not return your stock certificates with the enclosed proxy card, and you should not forward your stock certificates to the paying agent without a letter of transmittal. If you hold non-certificated book-entry shares of Company common stock through the DTC, you will not be required to deliver a stock certificate or letter of transmittal, and you will instead receive your cash payment after the paying agent receives the documents requested in the applicable instruction from the DTC. For more information, please see the section of this proxy statement entitled “The Merger Agreement — Payment for Stock”.

Q:

Am I entitled to exercise appraisal rights instead of receiving the merger consideration for my Company common stock?

A:

Yes. Holders of Company common stock are entitled to appraisal rights under Section 262 of the DGCL so long as they take certain actions and meet certain conditions, including that they do not vote (in person or by proxy) in favor of the merger agreement proposal. For more information regarding appraisal rights, see “The Merger — Appraisal Rights” beginning on page 78. Failure to strictly comply with Section 262 of the DGCL may result in your waiver of, or inability to exercise, appraisal rights.

Q:

When is the merger expected to be consummated?

A:

We currently expect to consummate the merger during the fourth quarter of 2022 or first quarter of 2023, subject to receipt of the Company stockholder approval and the required regulatory approvals and the satisfaction or waiver of the other conditions to the merger described in the merger agreement.

Q:

What effect will the merger have on the Company?

A:

If the merger is consummated, MergerCo will be merged with and into the Company, with the Company surviving the merger as a wholly-owned subsidiary of Parent. If the merger is consummated, Parent and the Company shall cooperate and use their respective reasonable best efforts to cause the Company common stock to be delisted from NASDAQ and deregistered under the Exchange Act as promptly as practicable following the effective time, and, accordingly, the common stock will no longer be publicly traded.

Q:

What happens if the merger is not consummated?

A:

In the event that the Company stockholder approval is not obtained or if the merger is not consummated for any other reason, Company stockholders will not receive any payment for their shares of Company common stock in connection with the merger. Instead, the Company will remain an independent public company, the Company common stock will continue to be listed and traded on NASDAQ, the Company common stock will continue to be registered under the Exchange Act and the Company stockholders will continue to own their shares of Company common stock and will continue to be subject to the same general risks and opportunities as they currently are with respect to ownership of the Company common stock.

Under certain circumstances, the Company will be required to pay Parent a termination fee equal to $97.5 million and, under certain other circumstances, Parent will be required to pay the Company a

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 25

QUESTIONS AND ANSWERS ABOUT THE SPECIAL MEETING AND THE MERGER

termination fee equal to $227.4 million. For more information, please see the section of this proxy statement entitled “The Merger Agreement — Termination Fees”.

Q:

What is householding and how does it affect me?

A:

The SEC has approved rules that permit companies and intermediaries (e.g., brokers) to satisfy the delivery requirements for proxy statements and annual reports with respect to two or more of the Company stockholders sharing the same address by delivering a single proxy statement addressed to those Company stockholders. This process, which is commonly referred to as “householding”, potentially means extra convenience for Company stockholders and cost savings for companies.

Banks, brokers or other nominees with account holders who are Company stockholders may be “householding” proxy materials. A single proxy statement will be delivered to multiple Company stockholders sharing an address unless contrary instructions have been received from the affected Company stockholders. If you have received notice from your bank, broker or other nominee that they will be “householding” communications to your address, such “householding” will continue until you are notified otherwise or until you revoke your consent. If, at any time, you no longer wish to participate in “householding” and would prefer to receive a separate proxy statement, please notify your bank, broker or other nominee and write or call us at the following address or phone number: Atlas Air Worldwide Holdings, Inc., Attention: Office of the Secretary, Atlas Air Worldwide Holdings, Inc., 2000 Westchester Avenue, Purchase, NY 10577, ((914) 701-8000). Company stockholders who currently receive multiple copies of the proxy statement at their address and would like to request “householding” of their communications should contact their banks, brokers or other nominees. We will promptly deliver an additional copy of the proxy statement to any stockholder who so requests.

Q:

Who can help answer my questions?

A:

If you need assistance in completing your proxy card or have questions regarding the special meeting, please contact our proxy solicitation agent:

Morrow Sodali LLC
333 Ludlow Street, 5th Floor, South Tower
Stamford, Connecticut 06902
Shareholders may call toll-free: (800) 662-5200
Banks and brokers may call: (203) 658-9400
Email: AAWW@investor.morrowsodali.com

26 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

CAUTIONARY STATEMENT REGARDING FORWARD-LOOKING STATEMENTS

CAUTIONARY STATEMENT REGARDING FORWARD-

LOOKING STATEMENTS

This proxy statement contains “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933, as amended, and Section 21E of the Securities Exchange Act of 1934, as amended. The Company intends such forward-looking statements to be covered by the safe harbor provisions for forward-looking statements contained in the Private Securities Litigation Reform Act of 1995 and includes this statement for purposes of complying with these safe harbor provisions. Those statements are based on management’s beliefs, plans, expectations and assumptions, and on information currently available to management. Generally, the words “will”, “may”, “should”, “could”, “would”, “expect”, “anticipate”, “intend”, “plan”, “continue”, “believe”, “seek”, “project”, “estimate”, and similar expressions used in this proxy statement that do not relate to historical facts are intended to identify forward-looking statements. Forward-looking statements include, without limitation, statements regarding the proposed merger and related matters; the expected timetable for completing the proposed merger; prospective performance and opportunities; general business outlook; filings and approvals relating to the transactions; the ability to complete the transactions considering the various closing conditions; and any assumptions underlying any of the foregoing.

Such forward-looking statements speak only as of the date as of this proxy statement. They are and will be, as the case may be, subject to many risks, uncertainties and factors relating to the operations and business environments of the Company that may cause the actual results of the Company or its subsidiaries to be materially different from any future results, express or implied, in such forward-looking statements.

Factors that could cause actual results to differ materially from these forward-looking statements include, but are not limited to, the following: (i) the risk that the merger may not be completed in a timely manner or at all; (ii) the failure to receive, on a timely basis or otherwise, the required approvals of the merger by Company stockholders; (iii) the possibility that any or all of the various conditions to the consummation of the merger may not be satisfied or waived, including the failure to receive any required regulatory approvals from any applicable governmental entities (or any conditions, limitations or restrictions placed on such approvals); (iv) the possibility that competing offers or acquisition proposals for the Company will be made; (v) the occurrence of any event, change or other circumstance that could give rise to the termination of the merger agreement relating to the merger, including in circumstances which would require the Company to pay a termination fee; (vi) the effect of the announcement or pendency of the merger on the Company’s ability to attract, motivate or retain key executives, pilots and associates, its ability to maintain relationships with its customers, including Amazon.com, Inc., vendors, service providers and others with whom it does business, or its operating results and business generally; (vii) risks related to the merger diverting management’s attention from the Company’s ongoing business operations; (viii) the risk of shareholder litigation in connection with the merger, including resulting expense or delay; and (ix) (A) any other risks discussed in the Company’s Annual Report on Form 10-K for the fiscal year ended December 31, 2021 (the “Annual Report”) and the Company’s quarterly reports on Form 10-Q for the quarters ended March 31, 2022 and June 30, 2022 (the “Quarterly Reports”) filed by the Company with the Securities and Exchange Commission (the “SEC”), and, in particular, the risk factors set forth under the headings “Risk Factors” and “Management’s Discussion and Analysis of Financial Condition and Results of Operations” in the Annual Report and the Quarterly Reports and (B) other risk factors identified from time to time in other filings with the SEC. Filings with the SEC are available on the SEC’s website at http://www.sec.gov. Given these risks and uncertainties, investors should not place undue reliance on forward-looking statements as a prediction of actual results.

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 27

CAUTIONARY STATEMENT REGARDING FORWARD-LOOKING STATEMENTS

Other factors and assumptions not identified above may also affect the forward-looking statements, and these other factors and assumptions may also cause actual results to differ materially from those discussed.

The Company assumes no obligation to update such statements contained in this proxy statement to reflect actual results, changes in assumptions or changes in other factors affecting such estimates other than as required by law and expressly disclaims any obligation to revise or update publicly any forward-looking statement to reflect future events or circumstances.

28 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

THE PARTIES

THE PARTIES

Atlas Air Worldwide Holdings, Inc.

The Company is a holding company with a wholly-owned operating subsidiary, Atlas Air, Inc. It also has a 51% economic interest and 75% voting interest in Polar Air Cargo Worldwide, Inc. In addition, the Company is the parent company of several wholly-owned subsidiaries related to the Company’s dry leasing services, collectively referred to as “Titan”.

The Company, together with its consolidated subsidiaries, is a leading global provider of outsourced aircraft and aviation operating services. The Company and its consolidated subsidiaries operate the world’s largest fleet of Boeing 747 freighters and provide customers a broad array of Boeing 747, 777, 767 and 737 aircraft for domestic, regional and international cargo and passenger operations. The Company and its consolidated subsidiaries also provide unique value to customers by giving them access to highly reliable new production freighter aircraft that deliver the lowest unit cost in the marketplace combined with outsourced aircraft operating services that the Company believes lead the industry in terms of quality and global scale. Customers of the Company and its consolidated subsidiaries include express delivery providers, e-commerce retailers, the AMC, charter brokers, freight forwarders, direct shippers, airlines, manufacturers, sports teams and fans, and private charter customers. The Company and its consolidated subsidiaries provide global services with operations in Africa, Asia, Australia, Europe, the Middle East, North America and South America.

The Company, together with its consolidated subsidiaries, believes that the scale, scope and quality of its outsourced services are unparalleled in its industry. The relative operating cost efficiency of the Company’s and its consolidated subsidiaries’ current 747-8F, 747-400F and 777-200LRF aircraft, including their superior fuel efficiency, range, capacity and loading capabilities, creates a compelling value proposition for its customers and positions it well in the markets it operates. The fleet of 767-300 and 737-800 freighter aircraft of the Company and its consolidated subsidiaries are well suited for regional and domestic operations.

The Company was incorporated in Delaware in 2000. The Company’s principal executive offices are located at 2000 Westchester Avenue, Purchase, New York 10577, and its telephone number is (914) 701-8000. Shares of Company common stock are listed on NASDAQ under the trading symbol “AAWW”.

Parent

Parent is a Delaware limited liability company that was formed by the Consortium Funds solely for the purpose of entering into the merger agreement and related agreements and consummating the transactions contemplated thereby. Parent has not conducted any business operations other than in connection with its formation and the transactions and related agreements. Upon the consummation of the transactions contemplated by the merger agreement and related agreements, the Company will be a wholly-owned subsidiary of Parent.

The principal executive offices of Parent are c/o Apollo Management Holdings, L.P., 9 West 57th Street, 43rd Floor, New York, New York 10019 with a telephone number of (212) 515-3200.

MergerCo

MergerCo is a Delaware corporation and a wholly-owned subsidiary of Parent that was formed solely for the purpose of entering into the merger agreement and related agreements and consummating the

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 29

THE PARTIES

transactions contemplated thereby. MergerCo has not conducted any business operations other than in connection with its formation and the transactions contemplated by the merger agreement and related agreements. Upon the consummation of the transactions contemplated by the merger agreement and related agreements, and MergerCo will cease to exist.

The principal executive offices of MergerCo are c/o Apollo Management Holdings, L.P., 9 West 57th Street, 43rd Floor, New York, New York 10019 with a telephone number of (212) 515-3200.

30 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

THE SPECIAL MEETING

THE SPECIAL MEETING

We are furnishing this proxy statement to the holders of Company common stock as part of the solicitation of proxies by the Board for exercise at the special meeting and at any postponements or adjournments thereof.

Date, Time and Place

The special meeting of Company stockholders will be held on [           ], 2022 at [          ] Eastern Time, in a virtual-only meeting format. To access the virtual special meeting, you should visit [           ]. All shareholders are entitled to attend the special meeting; however, you are entitled to participate, meaning you are entitled to vote and submit questions, at the special meeting only if you were a shareholder of record as of the close of business on the record date, or if you were a beneficial owner of Company shares as of the record date and you register in accordance with the instructions below.

Purpose of the Special Meeting

The special meeting is being held for the following purposes:

•

to consider and vote on the merger agreement proposal;

•

to consider and vote on the advisory compensation proposal; and

•

to consider and vote on the adjournment proposal.

A copy of the merger agreement is attached as Annex A to this proxy statement.

Recommendation of the Board

The Board has reviewed and considered the terms and conditions of the merger agreement, the merger and the other transactions. The Board unanimously (i) determined and declared that it is advisable and fair to, and in the best interests of, the Company and Company stockholders, that the Company enter into the merger agreement and consummate the transactions, (ii) approved and declared the advisability of the merger agreement and the consummation of the transactions, including the merger, (iii) recommended that the Company stockholders entitled to vote adopt the merger agreement and (iv) directed that the merger agreement be submitted to the Company’s stockholders entitled to vote for adoption. Accordingly, the Board recommends a vote “FOR” the merger agreement proposal, “FOR” the advisory compensation proposal and “FOR” the adjournment proposal. For a discussion of the factors that the Board considered in determining to recommend the approval of the merger agreement proposal, please see the section of this proxy statement entitled “The Merger — Reasons for the Merger” beginning on page 54.

Registering for the Special Meeting

Stockholders of Record

If you are a record holder of Company common stock (in other words, you held Company common stock in your own name in the stock register maintained by our transfer agent, Computershare), then you do not need to register to virtually attend and participate in the special meeting. You may attend and

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 31

THE SPECIAL MEETING

participate by accessing [           ] and selecting “I have a Control Number”. Enter the control number shown on your proxy card.

Beneficial (“Street Name”) Stockholders

If you hold your shares in “street name” (in other words, your Company common stock is held in the name of your bank, broker or other nominee), you must register in advance to attend and participate in the virtual special meeting. To register in advance, you must first obtain a legal proxy from your bank, broker or other nominee. Once you have received a legal proxy from your bank, broker or other nominee, please email a scan or image of it to our transfer agent and registrar, Computershare, at legalproxy@computershare.com with “Legal Proxy” noted in the subject line. If you request a legal proxy from your bank, broker or other nominee, you should note that the issuance of the legal proxy will invalidate any prior voting instructions you have given and will prevent you from giving any further voting instructions to your bank, broker or other nominee to vote on your behalf and, in that case, you would only be able to vote at the virtual special meeting.

Requests for registration must be received by Computershare no later than 5:00 p.m., Eastern Daylight Time, on [           ], 2022. Upon receipt of your legal proxy, Computershare will provide you with a control number by email. Once provided, you can attend and participate in the virtual special meeting by accessing [           ] and selecting “I have a Control Number”. Enter the control number provided by Computershare.

Record Date and Stockholders Entitled to Vote

Only Company stockholders of record at the close of business on [           ], 2022, the record date for the special meeting, will be entitled to notice of, and to vote at, the special meeting and any postponement or adjournment thereof. As of the close of business on the record date, there were [      ] shares of Company common stock outstanding and entitled to vote. Each Company stockholder is entitled to one vote per share of Company common stock held by such Company stockholder on the record date on each of the proposals presented in this proxy statement.

At the virtual special meeting and for 10 days prior to the special meeting, the names of stockholders entitled to vote at the special meeting will be available for inspection for any purpose germane to the meeting, between the hours of 9:00 a.m. and 5:00 p.m. Eastern Time, at the Company’s principal executive offices located at 2000 Westchester Avenue, Purchase, New York 10577, by contacting the Secretary of the Company.

Quorum

The holders of a majority of all of the Company common stock issued and outstanding and entitled to vote at the special meeting, present in person or represented by proxy, constitutes a quorum of stockholders for the transaction of business at the special meeting. Virtual attendance at the special meeting constitutes presence in person for quorum purposes at the special meeting. Abstentions will be counted as shares present for the purposes of determining the presence of a quorum. Broker non-votes will not be counted as shares present for purposes of determining the presence of a quorum unless your bank, broker or other nominee has been instructed to vote on at least one of the proposals presented in this proxy statement.

32 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

THE SPECIAL MEETING

If a quorum is not present or represented at the special meeting of the Company stockholders, the Chairman of the Board or the stockholders entitled to vote thereat, present in person or by proxy, may adjourn the special meeting, without notice, if the time and place of the new meeting and the means of remote communication, if any, by which Company stockholders and proxy holders may be deemed to be present and vote at such adjourned meeting, are announced at the special meeting at which the adjournment is taken. If, however, the adjournment is for more than 30 days, or if after the adjournment a new record date is fixed for the adjourned meeting, we will provide a notice of the adjourned meeting to each Company stockholder of record entitled to vote at the special meeting. In the event that a quorum is not present at the special meeting, or if there are insufficient votes to adopt the merger agreement at the time of the special meeting, we expect that the special meeting will be postponed or adjourned to solicit additional proxies.

Vote Required

Approval of the Merger Agreement Proposal

The approval of the merger agreement proposal requires the affirmative vote (in person or by proxy) of the holders of a majority of outstanding shares of Company common stock entitled to vote on the matter. Under Delaware law and the merger agreement, the receipt of such required vote is a condition to the consummation of the merger. Note that you may vote to approve the merger agreement proposal and vote not to approve the advisory compensation proposal or adjournment proposal and vice versa.

Abstentions, failures to vote (including a failure to authorize a proxy to vote on a Company stockholder’s behalf) and broker non-votes will have the same effect as a vote “AGAINST” the merger agreement proposal.

Approval of the Advisory Compensation Proposal

The approval of the advisory compensation proposal requires the affirmative vote (in person or by proxy) of a majority of the votes cast on such proposal at the special meeting. Assuming a quorum is present at the special meeting, abstentions, failures to vote (including a failure to authorize a proxy to vote on a Company stockholder’s behalf) and broker non-votes will have no effect on the outcome of the advisory compensation proposal.

The vote on the advisory compensation proposal is a vote separate and apart from the vote to approve the merger agreement proposal. Because the vote on the advisory compensation proposal is advisory only, it will not be binding on the Company, the Board, Parent or the surviving corporation. Accordingly, because the Company is contractually obligated to pay the compensation that may be paid or become payable to our named executive officers in connection with the consummation of the merger, if the merger is approved by our stockholders, such compensation will be payable, subject only to the conditions applicable thereto, regardless of the outcome of the vote on the advisory compensation proposal.

Approval of the Adjournment Proposal

The approval of the adjournment proposal requires the affirmative vote (in person or by proxy) of a majority of the votes cast on such proposal at the special meeting. Assuming a quorum is present at the special meeting, abstentions, failures to vote (including a failure to authorize a proxy to vote on a Company stockholder’s behalf) and broker non-votes will have no effect on the outcome of the adjournment proposal. The Company does not intend to call a vote on this proposal if the merger agreement proposal is approved at the special meeting.

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 33

THE SPECIAL MEETING

The vote on the adjournment proposal is a vote separate and apart from the vote to approve the merger agreement proposal. Accordingly, you may vote to approve the merger agreement proposal and vote not to approve the adjournment proposal and vice versa.

Approval of the advisory compensation proposal and the adjournment proposal is not a condition to the consummation of the merger.

A broker “non-vote” occurs when a bank, broker or other nominee holding shares for a beneficial owner does not vote on a particular proposal because the nominee does not have discretionary voting power with respect to that item and has not received voting instructions from the beneficial owner, but does have discretionary voting power over other “routine” items and submits votes for those matters. The Company does not expect any broker non-votes at the special meeting because the rules applicable to banks, brokers and other nominees only provide banks, brokers and other nominees with discretionary authority to vote on proposals that are considered “routine”, whereas each of the proposals to be presented at the special meeting is considered “non-routine”. As a result, no bank, broker or other nominee will be permitted to vote your shares of Company common stock at the special meeting without receiving instructions.

Voting Procedures

Whether or not you plan to attend the virtual special meeting and regardless of the number of shares of Company common stock you own, your careful consideration of, and vote on, the merger agreement is important and we encourage you to vote promptly.

If you are a record holder of Company common stock (in other words, you held Company common stock in your own name in the stock register maintained by our transfer agent, Computershare) and to ensure that your shares of Company common stock are voted at the special meeting, we recommend that you provide voting instructions promptly by proxy, even if you plan to attend the virtual special meeting. In order to vote by proxy card, please complete, sign, date and mail the enclosed proxy card in the envelope provided. For your mailed proxy card to be counted, we must receive it before [           ] Eastern Time on [           ], 2022. You may also vote by attending the virtual special meeting and voting during the live webcast.

If you hold your shares in “street name” ​(in other words, your Company common stock is held in the name of your bank, broker or other nominee), you should have received a proxy card and voting instructions with these proxy materials from that organization rather than from the Company. In order to vote, complete and mail the proxy card received from your broker, bank or other nominee to ensure that your vote is counted. Alternatively, you may vote by telephone or over the internet as instructed by your broker. To vote at the virtual special meeting, which will have the same effect as revoking any previously submitted voting instructions, you will need to register in advance. Please see “— Registering for the Special Meeting” above for information on how to register in advance. Without following the voting and/or registration instructions, your common stock held in “street name” will not be voted, which will have the same effect as a vote “AGAINST” the merger agreement proposal and will not have any effect on the advisory compensation proposal and adjournment proposal.

For additional questions about the merger, assistance in submitting proxies or voting, or to request additional copies of this proxy statement or the enclosed proxy card, please contact Morrow Sodali LLC, which is acting as the Company’s proxy solicitation agent in connection with the merger, toll free at (800) 662-5200.

34 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

THE SPECIAL MEETING

Limited Voting by Foreign Owners

To comply with restrictions imposed by federal aviation law on foreign ownership of U.S. airlines, the Company’s certificate of incorporation and by-laws restrict foreign ownership of shares of its Company common stock. The restrictions imposed by federal aviation law (49 U.S.C. §411 02) currently include a requirement that no more than 25% of the Company’s voting stock be owned or controlled, directly or indirectly, by persons who are not “Citizens of the United States”. There is a separate requirement that the Company be under the actual control of Citizens of the United States.

Pursuant to the Company’s by-laws, there is a separate stock record, designated the “Foreign Stock Record” for the registration of Voting Stock that is Beneficially Owned by aliens. “Voting Stock” means all outstanding shares of the Company’s capital stock that the Company may issue from time to time which, by their terms, may vote. “Beneficially Owned” refers to owners of the Company’s securities who, directly or indirectly, have or share voting power and/or investment power.

At no time will ownership of shares of Company common stock representing more than the Maximum Percentage be registered in the Foreign Stock Record. “Maximum Percentage” refers to the maximum percentage of voting power of Voting Stock which may be voted by, or at the direction of, aliens without violating applicable statutory, regulatory or interpretative restrictions or adversely affecting the operating certificates or authorities, in each case, of the Company, Atlas Air, Inc. or Polar Air Cargo Worldwide, Inc. If the Company finds that the combined voting power of Voting Stock then registered in the Foreign Stock Record exceeds the Maximum Percentage, the registration of such shares will be removed from the Foreign Stock Record sufficient to reduce the combined voting power of the shares so registered to an amount not in excess of the Maximum Percentage.

The enclosed proxy card contains a certification that by signing the proxy card the Company stockholder certifies that such stockholder is a “Citizen of the United States” as defined by 49 U.S.C. §40102(a)(15) or that the shares represented by the proxy card have been registered on our Foreign Stock Record.

The Company will promptly deliver a copy of our by-laws to any Company stockholder who writes or calls us at the following address or phone number: Office of the Secretary, Atlas Air Worldwide Holdings, Inc., 2000 Westchester Avenue, Purchase, NY 10577, (914) 701-8000.

How Proxies Are Voted

If you complete and submit your proxy card or voting instructions, the persons named as proxies will follow your instructions. If you are a holder of record and you submit a proxy card or voting instructions but do not direct how to vote on each item, the persons named as proxies therein will vote in favor of the merger agreement proposal, the advisory compensation proposal and the adjournment proposal.

Revocation of Proxies

For Company stockholders of record, any time after you have submitted a proxy card and before the proxy card is exercised, you may revoke or change your vote in one of three ways:

•

you may submit a new proxy card bearing a later date (which automatically revokes the earlier proxy or voting instructions) in accordance with the instructions detailed in the section of this proxy statement entitled “The Special Meeting — Voting Procedures”; or

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 35

THE SPECIAL MEETING

•

you may submit a written notice of revocation to the Company’s Secretary at Atlas Air Worldwide Holdings, Inc., 2000 Westchester Avenue, Purchase, NY 10577; or

•

you may attend the virtual special meeting and vote during the live webcast. Attendance at the virtual special meeting will not, in itself, constitute revocation of a previously granted proxy.

Please note that if you want to revoke your proxy by sending a new proxy card or a written notice of revocation to the Company, you should ensure that you send your new proxy card or written notice of revocation in sufficient time for it to be received by the Company prior to the special meeting.

If you hold your shares in “street name”, you will need to revoke or resubmit your proxy through your broker, bank or other nominee and in accordance with its procedures. If your broker, bank or other nominee allows you to submit a proxy via the internet or by telephone, you may be able to change your vote by submitting a new proxy via the internet or by telephone (or by mail). In order to attend the virtual special meeting and vote during the webcast, which will have the same effect as revoking any previously submitted voting instructions, you will need to obtain a legal proxy issued in your name from your broker, bank or other nominee, who is the Company stockholder of record.

Solicitation of Proxies

The Company will bear the cost of soliciting proxies, including the expense of preparing, printing and distributing this proxy statement. In addition to soliciting proxies by mail, telephone or electronic means, we may request brokers to solicit their customers and will, upon request, reimburse them for the reasonable, out-of-pocket costs of forwarding proxy materials in accordance with customary practice and SEC and NASDAQ regulations. We may also use the services of our directors, officers and other employees to solicit proxies, personally or by telephone, without additional compensation. In addition, the Company has retained Morrow Sodali LLC, 333 Ludlow Street, 5th Floor, South Tower, Stamford, Connecticut 06902 to solicit proxies at a total cost to the Company of approximately $45,000, plus reimbursement of customary out-of-pocket expenses.

Adjournments

Although it is not currently expected, the special meeting may be adjourned for the purpose of soliciting additional proxies. If a quorum is not present or represented at the special meeting, the Chairman of the Board or the stockholders entitled to vote thereat, present in person or by proxy, may adjourn the special meeting, without notice, provided that the time and place of the new meeting and the means of remote communication, if any, by which Company stockholders and proxy holders may be deemed to be present and vote at such adjourned meeting, are announced at the special meeting at which the adjournment is taken. If, however, the adjournment is for more than 30 days, or if after the adjournment a new record date is fixed for the adjourned meeting, we will provide a notice of the adjourned meeting to each Company stockholder of record entitled to vote at the special meeting. At any subsequent reconvening of the special meeting at which a quorum is present, any business may be transacted that might have been transacted at the special meeting.

Voting by Company Directors, Executive Officers and Principal Securityholders

As of October 3, 2022, the directors and executive officers of the Company beneficially owned in the aggregate 325,199 shares of Company common stock, or approximately 1.1% of the outstanding shares

36 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

THE SPECIAL MEETING

of Company common stock as of October 3, 2022. Although none of the directors or executive officers is obligated to vote to approve the merger agreement proposal, we currently expect that each of these individuals will vote all of his or her shares “FOR” each of the proposals to be presented at the special meeting.

The Company’s directors and executive officers have interests in the merger that may be different from, or in addition to, the interests of the Company stockholders generally. For more information, please see the section of this proxy statement entitled “The Merger — Interests of the Company’s Directors and Executive Officers in the Merger” beginning on page 82.

Appraisal Rights

If the merger is consummated, persons who do not wish to accept the merger consideration are entitled to seek appraisal of their shares of Company common stock under Section 262 and, if all procedures described in Section 262 are strictly complied with, to receive payment in cash for the fair value of their shares of Company common stock exclusive of any element of value arising from the accomplishment or expectation of the merger, as determined by the Delaware Court, together with interest, if any, to be paid upon the amount determined to be the fair value. The “fair value” of your shares of Company common stock as determined by the Delaware Court may be more or less than, or the same as, the merger consideration that you are otherwise entitled to receive under the merger agreement. These rights are known as “appraisal rights”. This proxy statement serves as a notice of such appraisal rights pursuant to Section 262.

Persons who exercise appraisal rights under Section 262 will not receive the merger consideration they would otherwise be entitled to receive pursuant to the merger agreement. They will receive an amount determined to be the “fair value” of their shares of Company common stock following petition to, and an appraisal by, the Delaware Court. Persons considering seeking appraisal should recognize that the fair value of their shares of Company common stock determined under Section 262 could be more than, the same as or less than the merger consideration they would otherwise be entitled to receive pursuant to the merger agreement. Strict compliance with the procedures set forth in Section 262 is required. Failure to comply strictly with all of the procedures set forth in Section 262 may result in the withdrawal, loss or waiver of appraisal rights. Consequently, and in view of the complexity of the provisions of Section 262, persons wishing to exercise appraisal rights are urged to consult their legal and financial advisors before attempting to exercise such rights.

A holder of record or a beneficial owner of shares of Company common stock who (i) continuously holds such shares through the effective time, (ii) has not consented to or otherwise voted in favor of the merger or otherwise withdrawn, lost or waived appraisal rights, (iii) strictly complies with the procedures under Section 262, (iv) does not thereafter withdraw his, her or its demand for appraisal of such shares and (v) in the case of a beneficial owner, a person who (A) reasonably identifies in his, her or its demand the holder of record of the shares for which the demand is made, (B) provides documentary evidence of such beneficial owner’s beneficial ownership and a statement that such documentary evidence is a true and correct copy of what it purports to be and (C) provides an address at which such beneficial owner consents to receive notices given by the Company and to be set forth on the Chancery List (as defined in the section of this proxy statement entitled “The Merger — Appraisal Rights”), will be entitled to receive the fair value of his, her or its shares of Company common stock exclusive of any element of value arising from the accomplishment or expectation of the merger, as determined by the Delaware Court, together with interest, if any, to be paid upon the amount determined to be the fair value.

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 37

THE SPECIAL MEETING

A copy of Section 262 may be accessed without subscription or cost at the following publicly available website: https://delcode.delaware.gov/title8/c001/sc09/index.html#262. The following summary is not a complete statement of the law relating to appraisal rights and is qualified in its entirety by reference to Section 262 and any amendments thereto after the date of this proxy statement. Any person who desires to exercise his, her or its appraisal rights should review carefully Section 262 and is urged to consult his, her or its legal and financial advisors before electing or attempting to exercise such rights. For more information, please see the section of this proxy statement entitled “The Merger — Appraisal Rights”.

Other Matters

Pursuant to the DGCL and the Company’s by-laws, only the matters set forth in the notice of special meeting may be brought before the special meeting.

Assistance

If you have any questions or need assistance in registering, completing your proxy card or have questions regarding the special meeting, please contact Morrow Sodali LLC, which is acting as the Company’s proxy solicitation agent in connection with the merger, toll free at (800) 662-5200. Brokers may call at (203) 658-9400.

38 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

PROPOSAL 1: MERGER AGREEMENT PROPOSAL

PROPOSAL 1: MERGER AGREEMENT PROPOSAL

We are asking holders of Company common stock to vote on a proposal to adopt the merger agreement. You are urged to carefully read this proxy statement in its entirety for more detailed information concerning the merger and the merger agreement, including the information set forth under the sections of this proxy statement captioned “The Merger” and “The Merger Agreement”. A copy of the merger agreement is attached as Annex A to this proxy statement. Approval of this proposal is a condition to the consummation of the merger. In the event this proposal is not approved, the merger cannot be consummated.

The Board recommends a vote “FOR” the approval of the merger agreement proposal.

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 39

PROPOSAL 2

PROPOSAL 2: ADVISORY COMPENSATION

PROPOSAL

Pursuant to the Dodd-Frank Wall Street Reform and Consumer Protection Act of 2010 and Rule 14a-21(c) under the Exchange Act, we are asking holders of Company common stock to approve, by advisory (non-binding) vote, the compensation that may be paid or become payable to our named executive officers in connection with the consummation of the merger. As required by those rules, the Company is asking holders of Company common stock to vote on the approval of the following resolution:

“RESOLVED, that the compensation that may be paid or become payable to the Company’s named executive officers in connection with the consummation of the merger, as disclosed in the table entitled “Potential Payments to Named Executive Officers”, including the associated narrative discussion, and the agreements, arrangements or understandings pursuant to which such compensation may be paid or become payable, are hereby APPROVED.”

The vote on executive compensation payable in connection with the consummation of the merger is a vote separate and apart from the vote to approve the merger agreement proposal. Accordingly, you may vote to approve the merger agreement proposal and vote not to approve such compensation and vice versa. Because the vote is advisory in nature only, it will not be binding on the Company or the Board; as the Company is contractually obligated to pay such compensation, such compensation will be paid or become payable, subject only to the conditions applicable thereto, if the merger is consummated and regardless of the outcome of the advisory vote.

The Board recommends a vote “FOR” the approval of the advisory compensation proposal.

40 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

PROPOSAL 3

PROPOSAL 3: ADJOURNMENT PROPOSAL

The special meeting may be adjourned to another time and place to permit further solicitation of proxies, if necessary, to obtain additional votes to approve the merger agreement proposal. The Company currently does not intend to propose adjournment of the special meeting if there are sufficient votes in favor of the merger agreement proposal.

The Company is asking you to authorize the holder of any proxy solicited by the Board to vote in favor of any adjournment of the special meeting, if necessary, to solicit additional proxies if there are not sufficient votes in favor of the merger agreement proposal at the time of the special meeting.

The Board recommends a vote “FOR” the approval of the adjournment proposal.

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 41

THE MERGER

THE MERGER

Overview

The Company is seeking the adoption by the holders of Company common stock of the merger agreement the Company entered into on August 4, 2022 with Parent and MergerCo. Under the terms of the merger agreement, subject to the satisfaction or (if permissible under applicable law) waiver of specified conditions, MergerCo will be merged with and into the Company, with the Company surviving the merger as a wholly-owned subsidiary of Parent. The Board has unanimously approved and declared advisable the merger agreement, the merger and the other transactions contemplated by the merger agreement and recommends that Company stockholders vote to adopt the merger agreement.

Background of the Merger

As part of their ongoing review of the Company’s business, in concert with financial and legal advisors, the Board and the Company’s senior management team periodically review and evaluate the Company’s business and long-term strategy, competitive position, historical performance, future prospects and opportunities to increase stockholder value. These reviews have included discussions as to whether the Company should continue to execute on its strategy as a stand-alone company, consider alternative capital allocation approaches, pursue various acquisitions or pursue a sale of the Company. As part of these reviews, the Board, together with Company management and with the assistance of the Company’s advisors, has considered from time to time potential alternatives to enhance stockholder value along with the potential benefits and risks of any potential alternative.

On June 1, 2021, the Company received an unsolicited letter from Hill City, JFLCO and Apollo (collectively, the “Consortium”), which included a non-binding proposal to acquire the Company for cash consideration of $83.50 per share, subject to satisfactory completion of due diligence, the negotiation, execution and delivery of mutually satisfactory definitive agreements, approval of definitive agreements by the Board and the Consortium’s investment committees, approval of the transaction by Company stockholders and receipt of customary regulatory and other third-party approvals (the “June 1 Offer”). The June 1 Offer represented a 11.4% premium to the Company common stock’s closing share price of $74.93 on May 28, 2021, the most recent trading day prior to the June 1 Offer.

On June 3, 2021, the Board held a telephonic meeting, with Company management and representatives of Morgan Stanley, the Company’s financial advisor, and Cravath, Swaine & Moore LLP (“Cravath”), the Company’s legal advisor, in attendance, to evaluate the June 1 Offer. Representatives of Cravath reviewed with the Board its fiduciary duties and other legal matters in the context of a review of a potential sale transaction. The Board determined at the meeting that Timothy Bernlohr, a director who had disclosed to the Board that he had a family connection to a principal of a member of the Consortium, could participate in discussions regarding strategic alternatives to the June 1 Offer but would recuse himself from discussions related to the Consortium and the June 1 Offer at the meeting and at subsequent Board meetings. Representatives of Morgan Stanley reviewed with the Board the key financial metrics underlying the June 1 Offer, the Company’s historical stock price performance and a preliminary illustrative financial analysis of the Company, and Company management provided perspectives on the Company’s recent performance and outlook. Following discussion, the Board directed that Company management reject the June 1 Offer on the basis that it did not present sufficient value to Company stockholders.

42 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

THE MERGER

On June 4, 2021, as required by the terms of the Amended and Restated Stockholders Agreement, dated as of March 27, 2019, by and between the Company and Amazon.com, Inc. (“Amazon”) (the “Amazon Stockholders Agreement”), the Company sent a notice to Amazon stating that the Company had received an acquisition proposal.

On June 7, 2021, the Company sent a letter to the Consortium rejecting the June 1 Offer and stating that the June 1 Offer was not at a value that the Board believed provided a basis for discussion with the Consortium regarding a potential transaction.

On February 25, 2022, John Dietrich, Chief Executive Officer of the Company, had a telephone call with Chip Frazier, Portfolio Manager at Hill City, at Mr. Frazier’s initiation. On the call, Mr. Frazier indicated that the Consortium remained interested in exploring a potential acquisition of the Company. Mr. Dietrich indicated that while the Company was not currently looking to pursue a sale, the Company was always open to considering how best to maximize stockholder value. Mr. Dietrich requested that the Company’s Chief Financial Officer, Spencer Schwartz, be present for further discussion on this topic. Later in the same day, Mr. Dietrich and Mr. Schwartz had a follow-up call with Mr. Frazier. Mr. Frazier shared his perspectives regarding the Company’s stock price performance and the drivers behind public investors’ valuations of the Company. Mr. Dietrich and Mr. Schwartz indicated that they would be in touch with Mr. Frazier the following week after discussing with the Board Mr. Frazier’s outreach.

On February 28, 2022, representatives from Morgan Stanley received an unsolicited phone call from a representative of Evercore Group L.L.C. (“Evercore”), the Consortium’s financial advisor. The representative from Evercore indicated that the Consortium remained interested in pursuing an acquisition of the Company and intended to deliver a written acquisition proposal to the Board in the coming days.

On March 2, 2022, the Board held a telephonic meeting, with Company management and representatives of Morgan Stanley and Cravath in attendance, to discuss, among other items, the recent unsolicited approach by the Consortium and potential responses to the approach. The Board determined at the meeting that Mr. Dietrich should convey to the Consortium that the Company was not looking to pursue a sale, but that any formal acquisition proposal submitted by the Consortium would be reviewed by the Board, and that the Board would not be likely to find any proposal of interest unless it presented compelling stockholder value and a substantial premium to the Company’s then all-time high closing share price of $95.78, reached on January 4, 2022.

Following the meeting of the Board on March 2, 2022, Mr. Dietrich and Mr. Schwartz called Mr. Frazier to convey the Board’s message.

Later on March 2, 2022, the Company received a proposal letter from the Consortium, which included a non-binding proposal to acquire the Company for cash consideration of $98.00 per share, subject to satisfactory completion of due diligence, the negotiation, execution and delivery of mutually satisfactory definitive agreements, approval of definitive agreements by the Board and the Consortium’s investment committees, approval of the transaction by Company stockholders and receipt of customary regulatory and other third-party approvals (the “March 2 Offer”). The March 2 Offer represented a 21.2% premium to the Company common stock’s closing share price of $80.84 on March 2, 2022, and a 2.3% premium to its then all-time high closing share price of $95.78.

On March 4, 2022, pursuant to the Amazon Stockholders Agreement, the Company sent notice to Amazon of its receipt of an acquisition proposal.

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 43

THE MERGER

On March 14 and 15, 2022, the Board held a regularly scheduled in-person meeting. On March 15, with Company management and representatives of Morgan Stanley and Cravath in attendance, the Board discussed, among other items, the March 2 Offer. Representatives of Cravath reviewed the Board’s fiduciary duties and other legal matters in the context of a review of a potential sale transaction. Representatives of Morgan Stanley reviewed with the Board the March 2 Offer. The representatives of Morgan Stanley also discussed the cyclical nature of the business and risks associated with an evolving macroeconomic environment, including rising inflation, supply chain challenges and geopolitical instability, along with historical trends in the Company’s business and how the Company common stock had traded relative to the Company’s peers in the freight industry. Company management then discussed with the Board management’s strategic plan, including the Base Management Case (as defined in “— Certain Financial Forecasts” beginning on page 61), key assumptions underlying the management strategic plan and key drivers of potential opportunities and risks going forward. Representatives from Morgan Stanley also presented certain preliminary financial analyses of the Company based on the Base Management Case. Following discussion, the Board determined that Mr. Dietrich should convey to the Consortium: that the Board was not looking to pursue a sale of the Company, but is always open to considering what may be in the best interests of Company stockholders; that the Board had carefully considered the March 2 Offer and determined that it was not at a high enough value for the Company to engage with the Consortium regarding a potential transaction; and that any proposal would have to be at a substantial premium to the Company’s recent all-time high stock price of $95.78 to provide a basis for further engagement.

On March 18, 2022, Mr. Dietrich and Mr. Schwartz had a call with Mr. Frazier, during which Mr. Dietrich communicated the Board’s message and determinations, including that the Board had rejected the March 2 Offer.

On March 23, 2022, the Company received a proposal letter from the Consortium, which included a non-binding proposal to acquire the Company for cash consideration of $107.00 per share, subject to satisfactory completion of due diligence, the negotiation, execution and delivery of mutually satisfactory definitive agreements, approval of definitive agreements by the Board and the Consortium’s investment committees, approval of the transaction by Company stockholders and receipt of customary regulatory and other third-party approvals (the “March 23 Offer”). The March 23 Offer represented a 23.6% premium to the Company common stock’s closing share price of $86.60 on March 23, 2022 and a 11.7% premium to its then all-time high closing share price of $95.78.

On March 25, 2022, pursuant to the Amazon Stockholders Agreement, the Company sent notice to Amazon of its receipt of an acquisition proposal.

On March 29, 2022, Mr. Dietrich and Mr. Schwartz called Mr. Frazier to inform him that the March 23 Offer was under review by the Board and Company management.

On March 30, 2022, the Board held a telephonic meeting, with Company management and representatives of Morgan Stanley and Cravath in attendance, to discuss the March 23 Offer. At the meeting, representatives from Cravath reviewed with the Board their fiduciary duties and other legal matters in the context of a review of a potential sale transaction. Representatives from Morgan Stanley reviewed with the Board the March 23 Offer, including how the March 23 Offer compared to the prior offers received from the Consortium. The Board discussed with Company management and the representatives of Morgan Stanley and Cravath various potential ways in which the Company could respond to the March 23 Offer. Following discussion, the Board determined that Mr. Dietrich should inform the Consortium that the Board was not willing to consummate a transaction at the price proposed in the

44 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

THE MERGER

March 23 Offer, but that the Board was willing to allow the Consortium to conduct limited due diligence to see if it would be prepared to offer increased value, subject to the Consortium’s agreement to a customary confidentiality agreement (the “Consortium NDA”).

On April 1, 2022, Mr. Dietrich and Mr. Schwartz had a call with Mr. Frazier, during which Mr. Dietrich communicated the Board’s message and determinations to Mr. Frazier and the parties discussed next steps regarding due diligence and the proposed entry into the Consortium NDA.

On April 4, 2022, representatives of the Company provided the Consortium with a draft of the Consortium NDA. Between April 4 and April 12, the parties exchanged drafts of and negotiated the Consortium NDA.

On April 8, 2022, the Board held a telephonic meeting, with Company management and representatives of Morgan Stanley and Cravath in attendance. At the meeting, among other things, the Board reviewed the materials that Company management prepared for a management presentation, including the Seller Case (as defined in “— Certain Financial Forecasts” beginning on page 61), to be delivered to the Consortium at a meeting scheduled for April 12, 2022. The Board also discussed the differences between the Seller Case and the Base Management Case (as described further in “— Certain Financial Forecasts” beginning on page 61).

On April 12, 2022, the Company and funds affiliated with the members of the Consortium executed the Consortium NDA, which did not contain a “don’t ask, don’t waive” provision and contained standstill provisions that would automatically terminate upon the entry by the Company into a definitive acquisition agreement with a third party.

Later on April 12, 2022, representatives of the Company, with representatives of Morgan Stanley in attendance, held a management presentation for, and provided the Seller Case to, representatives of the Consortium and Evercore.

Between April 12 and late May 2022, the Company provided due diligence materials to the Consortium, including through a virtual data room containing initial due diligence materials, and representatives of Company management and Morgan Stanley had numerous calls with representatives of the Consortium and Evercore regarding due diligence.

On May 3, 2022, the Board held a telephonic meeting, with Company management and representatives of Morgan Stanley and Cravath in attendance. Company management and representatives of Morgan Stanley reviewed with the Board the March 23 Offer, as well as the prior offers submitted by the Consortium. The Board discussed with its advisors trends in the U.S. equity and debt markets, and how the Company’s stock price, and the stock prices of its peers in the freight sector, had decreased since the March 23 Offer was submitted. After discussing various alternative approaches to continuing engagement with the Consortium, the Board determined that it was in the best interest of the Company and Company stockholders to continue facilitating the Consortium’s due diligence and to encourage the Consortium to submit an updated proposal after the Company’s earnings call for the first quarter of 2022, scheduled for May 5, 2022.

On May 6, 2022, representatives of Morgan Stanley contacted representatives of Evercore to request that the Consortium submit a revised acquisition proposal representing its best offer.

On May 12, 2022, with the Company’s permission and to facilitate the Consortium’s transaction analysis and to avoid the risk of leaks, the Consortium had a discussion with a leveraged finance team at Morgan

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 45

THE MERGER

Stanley regarding the condition of the financing markets, with the understanding that Morgan Stanley and its affiliates would not provide financing to the Consortium or any other potential buyers in a potential strategic transaction with the Company.

On May 19, 2022, the Company received a proposal letter from the Consortium, which included a reaffirmed, non-binding proposal to acquire the Company for cash consideration of $107.00 per share, subject to satisfactory completion of due diligence, the negotiation, execution and delivery of mutually satisfactory definitive agreements, approval of definitive agreements by the Board and the Consortium’s investment committees, approval of the transaction by the Company stockholders and receipt of customary regulatory and other third-party approvals (the “May 19 Offer”). As of the May 19 Offer, the U.S. equity and debt markets had experienced significant downturns since the Consortium had sent its letter containing the March 23 Offer. These downturns coincided with a period of rising interest rates and oil prices, increased inflation and geopolitical instability, resulting in a general decline in the stock prices of the Company and its industry peers in the freight sector relative to earlier periods in the year. In its letter, the Consortium noted that since the March 23 Offer had been communicated, macroeconomic conditions had changed, and that the May 19 Offer, which maintained the $107.00 per share price despite such headwinds, represented a significant increase in the premium offered per share as compared to the March 23 Offer. The May 19 Offer represented a 54.8% premium to the Company common stock’s closing share price of $69.10 on May 18, 2022, and an 11.7% premium to its then all-time high closing share price of $95.78.

On May 24, 2022, Morgan Stanley provided to the Company a disclosure statement identifying prior and current engagements and relationships between Morgan Stanley and affiliates of members of the Consortium.

Later on May 24, 2022, the Board held a telephonic meeting, with Company management and representatives of Morgan Stanley and Cravath in attendance, to discuss, among other items, the May 19 Offer. Company management and representatives of Morgan Stanley reviewed with the Board the May 19 Offer, along with current industry and macroeconomic trends, highlighting the deteriorating market conditions due to strong inflation, rising oil prices and the conflict in Ukraine, which was resulting in higher costs of capital in the U.S. debt and equity markets. Representatives of Cravath reviewed with the Board its fiduciary duties and other legal matters in the context of a review of a potential sale transaction. The Board discussed with Company management and representatives of Morgan Stanley and Cravath potentially initiating an exploratory process involving outreach to additional potential counterparties to a strategic transaction. In an executive session attended by only the Board, Company management and the representatives of Cravath, the Board concluded, following discussion, that Mr. Dietrich and Company management, together with the Company’s advisors, should (i) continue to advance more fulsome due diligence with the Consortium, while continuing to seek to obtain a higher price from the Consortium, and (ii) begin a process of soliciting proposals from a group of other potential acquirors, and to compare those proposals with that received from the Consortium and the Company’s standalone outlook. The Board then directed Company management to begin outreach to a list of potential strategic and financial counterparties identified during the meeting.

On May 25, 2022, representatives of Morgan Stanley called representatives of Evercore to convey that, while the Board was disappointed that the May 19 Offer had not improved in absolute terms upon the March 23 Offer, the Company intended to continue working with the Consortium toward a potential transaction, including by providing access to a virtual data room containing additional due diligence materials. The representatives of Morgan Stanley emphasized that the Board and Company management continued to believe that a higher price was appropriate.

46 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

THE MERGER

Between May 25 and May 29, 2022, representatives of Morgan Stanley reached out to a representative of a strategic party that we refer to as “Party A”, a representative of a strategic party that we refer to as “Party B”, a representative of a financial sponsor that we refer to as “Party C”, a representative of a financial sponsor that we refer to as “Party D”, a representative of a financial sponsor that we refer to as “Party E” and a representative of a financial sponsor that we refer to as “Party F”, in each case on behalf of the Company and on a confidential basis to determine if such party would be interested in pursuing a potential strategic transaction with the Company. Each of Party A and Party B informed Morgan Stanley that it was not interested in pursuing a strategic transaction with the Company at that time because such a transaction would not align with the applicable party’s current strategic direction.

Also during this period, Mr. Dietrich and Michael Steen, Executive Vice President and Chief Commercial Officer of the Company, reached out to a representative of a strategic party that we refer to as “Party G”, a representative of a strategic party that we refer to as “Party H” and a representative of a financial sponsor that we refer to as “Party I”, in each case, on a confidential basis to determine if such party would be interested in pursuing a potential strategic transaction with the Company.

Between May 26, 2022 and May 29, 2022, representatives of Morgan Stanley sent draft confidentiality agreements to each of Party C, Party D, Party E, Party F and Party I. Party D subsequently informed Morgan Stanley on May 28, 2022 that it was not interested in pursuing a strategic transaction with the Company, indicating that the opportunity was not the right fit at the time.

Between May 27 and June 7, 2022, the Company and its advisors negotiated and executed confidentiality agreements with Party C, Party E, Party F and Party I, each of which did not contain a “don’t ask, don’t waive” provision and contained standstill provisions that would automatically terminate upon the entry by the Company into a definitive acquisition agreement with a third party.

On May 31, 2022, the Company held its annual meeting of stockholders. At the meeting, Walter Borst, Raymond Conner and George Willis were each elected as new members of the Board, and each of Mr. Bernlohr, Carol Hallett and John Wulff retired from the Board.

Also on May 31, 2022, the Board held an in-person meeting with Company management and representatives of Morgan Stanley and Cravath in attendance via video conference to discuss the status of the ongoing bidding process and next steps.

Throughout June and into late-July 2022, the Company and its advisors provided management presentations and various due diligence materials to each of Party C, Party E, Party F and Party I. Representatives of Company management and Morgan Stanley had numerous calls with representatives of such prospective bidders and their respective financial advisors, as well as with the Consortium and Evercore, regarding due diligence. Also throughout this period, the Board received periodic updates from Company management and the Company’s financial and legal advisors.

On June 9, 2022, representatives of the Company and Morgan Stanley called representatives of each of Party C, Party E, Party F and Party I and requested that the parties each submit an initial acquisition proposal, including a proposed purchase price, by June 16, 2022. The representatives of Morgan Stanley also offered each prospective bidder the opportunity to speak with a leveraged finance team at Morgan Stanley to discuss the condition of the financing market, with the understanding that Morgan Stanley would not provide financing to any of the potential buyers in a potential strategic transaction with the Company.

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 47

THE MERGER

Also on June 9, 2022, the Company provided the Consortium access to additional due diligence materials in a virtual data room. The Company continued to provide due diligence materials to the Consortium through late July 2022.

On June 10, 2022, representatives of each of Party G and Party H informed representatives of the Company that the applicable party would not be submitting an acquisition proposal, with Party G and Party H each noting that an acquisition of the Company did not align with its current strategic direction.

On June 13, 2022, a telephonic meeting was held, with Duncan McNabb, the Chairman of the Board, Mr. Dietrich, and the Company’s three newest directors, Messrs. Borst, Conner and Willis, as well as certain members of Company management and representatives of Morgan Stanley and Cravath in attendance, for the purpose of providing the new directors with an overview of the Company’s ongoing exploratory process of soliciting proposals from potential acquirors and the acquisition proposals received to date from the Consortium, including by having the representatives of Morgan Stanley review with the directors certain preliminary financial analyses previously presented to the Board.

On June 15 and June 16, 2022, Party F and Party C, respectively, informed representatives of Morgan Stanley that neither would be submitting an acquisition proposal. Party F noted that the opportunity was not the right fit for its company. Party C noted that it did not believe it would be able to offer a competitive valuation.

Also on June 16, 2022, Party E delivered a letter to the Company that included a non-binding offer to acquire the Company for cash consideration of $100.00 per share, subject to satisfactory completion of due diligence, the execution of a definitive agreement, and approval of the definitive agreement by Party E’s investment committee (the “Party E Offer”). The letter stated that the Party E Offer was not contingent on securing any third-party equity capital commitments, and that Party E expected to fund a component of the purchase price with third-party debt.

Also on June 16, 2022, Party I delivered a letter to the Company that included a non-binding offer to acquire the Company for cash consideration within the range of $95.00 to $110.00 per share, subject to satisfactory completion of due diligence, the execution of a definitive agreement, and formal approval of the definitive agreement by Party I’s investment committee (the “Party I Offer”). The letter indicated that the price per share was presented as a range due to Party I not having completed due diligence into the Company’s contracts and not having finalized the terms of its proposed financing. The letter also expressed skepticism that Party I would be able to obtain the debt financing it required on terms it would find acceptable.

On June 16 and June 17, 2022, representatives of Morgan Stanley held calls with representatives of each of Party E and Party I to discuss the Party E Offer and Party I Offer, respectively, including the factors driving the valuation implied by the applicable offer. The representatives of Party E indicated to Morgan Stanley that the $100.00 per share valuation included in the Party E Offer assumed a fully favorable due diligence investigation based on forecasts presented by Company management and Party E’s ability to obtain acceptable financing terms. The representatives of Party I indicated that the range included in the Party I Offer was contingent upon gaining greater visibility into the Company’s contracted business, improvement in the conditions in the financing markets and its ability to obtain acceptable financing terms, and that each of these components would need to turn out favorably to justify a price at the high end of such range.

On June 18, 2022, following receipt of the Party E Offer and the Party I Offer, pursuant to the Amazon Stockholders Agreement, the Company sent notice to Amazon of its receipt of two acquisition proposals.

48 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

THE MERGER

On June 21, 2022, the Board held a telephonic meeting, with Company management and representatives of Morgan Stanley and Cravath in attendance, to discuss, among other items, updates related to the ongoing bidding process, including the Party E Offer and the Party I Offer, and corresponding next steps. Representatives of Cravath reviewed with the Board its fiduciary duties and other legal matters in the context of a review of a potential sale transaction. Company management and representatives of Morgan Stanley provided an update on the ongoing engagement with the Consortium, and representatives of Morgan Stanley reviewed with the Board the Party E Offer and the Party I Offer. Following discussion, the Board directed Company management and the Company’s advisors to: (i) invite Party E and Party I to engage with the Company on a timeline to announce any proposed transaction before the Company’s second quarter earnings release in early August, with a final bid deadline of July 26, 2022, (ii) provide Party E and Party I with the same due diligence information made available to the Consortium, (iii) deliver a draft merger agreement to each of Party E, Party I and the Consortium, (iv) communicate to the Consortium the proposed transaction timeline and July 26 final bid deadline and (v) inform the Consortium about the existence of other prospective bidders.

Later on June 21, 2022, representatives of Morgan Stanley spoke with representatives of each of the Consortium, Party E and Party I to communicate the proposed transaction timing and July 26 final bid deadline, and to discuss providing each party with access to expanded due diligence information.

On June 22, 2022, Party E and Party I were each granted access to a virtual data room containing the Seller Case and other due diligence materials that had been made available to the Consortium.

On June 23, 2022, at the request of directors of the Company, representatives of Morgan Stanley spoke to representatives of a strategic party we refer to as “Party J” to determine if such party would be interested in a potential strategic transaction with the Company. On June 28, 2022, Party J informed representatives of Morgan Stanley that it was not interested in pursuing a potential transaction with the Company at that time as the opportunity did not align with its current strategic direction.

Also on June 28, 2022, Party E informed representatives of Morgan Stanley that Party E was unlikely to increase its offer above $100 per share based on the work it had done to date.

On June 29, 2022, the Board held a telephonic meeting, with Company management and representatives of Morgan Stanley and Cravath in attendance. The Board discussed with its advisors the ongoing diligence processes conducted by the Consortium, Party E and Party I, as well as the draft merger agreement that was proposed to be provided to each prospective bidder. The Board also approved the terms of the proposed form of engagement letter providing for Morgan Stanley’s engagement as the Company’s financial advisor in connection with a potential sale of the Company, which was executed by Company management and representatives of Morgan Stanley on June 30, 2022.

Also on June 29, 2022, a draft of the merger agreement prepared by Cravath was provided to representatives of the Consortium, Party E and Party I. This draft of the merger agreement provided for, among other things: a “go-shop” period of 30 days (with an extension period of up to 15 days); a termination fee payable by the Company of (i) 0.75% of the fully diluted equity value of the Company in the event the merger agreement was terminated for the Company to enter into a superior proposal received during the go-shop period and (ii) 1.5% of the fully diluted equity value of the Company otherwise; a reverse termination fee payable by the prospective buyer of 10% of the fully diluted equity value of the Company; and a “fiduciary out” provision allowing the Board to change its recommendation that Company stockholders approve the merger agreement either upon receipt of a superior takeover

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 49

THE MERGER

proposal or if the failure to change such recommendation is inconsistent with the directors’ fiduciary duties under applicable law.

On July 1, 2022, representatives of Morgan Stanley contacted each of the Consortium, Party E and Party I to request a markup of the draft merger agreement by July 18, 2022, and to confirm the request for a final acquisition proposal by July 26, 2022.

On July 6, 2022, representatives of Morgan Stanley informed Antoine Munfakh, as a representative of the Consortium, that the Company had engaged with other prospective bidders that were exploring a potential transaction with the Company in parallel to the Consortium. Mr. Munfakh had previously requested a meeting with Mr. Dietrich to discuss the Company and its prospects. That meeting was scheduled for July 11, 2022.

Between early June and late July 2022, the Company provided its consent to the Consortium to engage in conversations with various debt financing sources to discuss financing terms.

On July 11, 2022, Mr. Dietrich and Mr. Munfakh met for lunch. Mr. Munfakh affirmed the Consortium’s continued interest in acquiring the Company, and noted that significant resources had been devoted to the potential transaction and to advancing due diligence. Mr. Munfakh noted, however, that the Consortium’s most significant challenge was obtaining acceptable financing terms. Mr. Dietrich answered questions that Mr. Munfakh had asked regarding the Company’s business and discussed certain of the Company’s business opportunities. Mr. Munfakh and Mr. Dietrich also discussed the timeline for the bidding process, and Mr. Munfakh indicated he expected the Consortium would be able to submit a draft merger agreement mark-up and final proposal on the timeline provided by the Company.

On July 13, 2022, representatives of Party I informed Morgan Stanley that Party I would not submit a final proposal to acquire the Company, citing that Party I had been unable to secure financing on acceptable terms given the current condition of the financing markets, and that it had been unable to substantiate value anywhere near the top end of the range provided in the Party I Offer. The representatives of Party I inquired as to whether the Company would be willing to delay its timeline for entering into a potential transaction to allow the conditions of the financing market to improve, but the representatives of Morgan Stanley responded, on behalf of the Board, that the Company was seeking to conclude the process prior to its earnings release for the second quarter of 2022, scheduled for early August.

On July 18, 2022, representatives of Party E had informed Morgan Stanley that Party E would not submit a final proposal to acquire the Company, citing the condition of the financing markets and that it was unable to substantiate additional value beyond the $100.00 per share amount set forth in the Party E Offer.

Also on July 18, 2022, the Company issued a press release setting August 5, 2022 as the date of its earnings call for the second quarter of 2022.

On July 19, 2022, representatives of Paul, Weiss, Rifkind, Wharton & Garrison LLP (“Paul Weiss”), the Consortium’s legal advisor, sent a revised draft of the merger agreement to representatives of Cravath on behalf of the Consortium. This draft of the merger agreement reduced the proposed “go-shop” extension period down to five days and also bracketed the go-shop provision as under consideration by the Consortium; it proposed a Company termination fee of 3.5% of the fully diluted equity value of the Company following the go-shop period; it proposed a reverse termination fee of 5% of the fully diluted equity value of the Company; it provided that the Company was to reimburse the Consortium’s transaction

50 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

THE MERGER

expenses up to an undetermined value if the deal was terminated due to the Company’s failure to obtain stockholder approval; it provided that the Company would use commercially reasonable efforts to have no less than $700 million in cash and cash equivalents at the closing of the merger; and it revised the “fiduciary out” provision to require that the Company only change its recommendation to Company stockholders with respect to approval of the merger agreement in the event of a conflict with its fiduciary duties upon the occurrence of a material event or development that was neither known nor reasonably foreseeable by the Board prior to the date of the merger agreement, and which is not related to a takeover proposal.

On July 20, 2022, the Board held a telephonic meeting, with Company management and representatives of Morgan Stanley and Cravath in attendance. Representatives of Cravath reviewed with the Board its fiduciary duties and other legal matters in the context of a review of a potential sale transaction. Representatives of Morgan Stanley and Company management updated the Board on Party E’s and Party I’s withdrawal from the bidding process, noting that Party I in particular had cited the conditions of the financing market and its inability to obtain acceptable financing terms in its decision to withdraw. The Board determined that it would continue to engage with the Consortium in advance of receipt of its final acquisition proposal the following week.

On July 22, 2022, Company management held a call with representatives of the Consortium to discuss the Company’s results for the second quarter of 2022, scheduled to be announced on August 5, 2022, and the updated forecast for the remaining quarters of 2022, which information was also provided to the Consortium as part of its due diligence.

On July 22, 2022, representatives of Cravath held a call with representatives of Paul Weiss to discuss the revised draft of the merger agreement received from Paul Weiss on July 19, 2022.

Later on July 22, 2022, representatives of Cravath sent a revised draft of the merger agreement to representatives of Paul Weiss on behalf of the Company. This version of the merger agreement increased the go-shop extension period to 15 days; it proposed a Company termination fee of 1.5% of the fully diluted equity value of the Company following the go-shop extension period; it proposed a reverse termination fee of 10% of the fully diluted equity value of the Company; it removed the Company’s obligation to reimburse the Consortium’s transaction expenses up to an undetermined value if the deal was terminated due to the Company’s failure to obtain stockholder approval; and it removed the provision requiring the Company to use commercially reasonable efforts to have no less than $700 million in cash and cash equivalents at the closing of the merger.

From July 22 until the execution of the merger agreement on August 4, 2022, representatives of Cravath and other legal advisors to the Company (including Hogan Lovells, as regulatory legal counsel to the Company (“Hogan Lovells”), and Pillsbury Winthrop Shaw Pittman LLP, as aircraft legal counsel to the Company) had calls and exchanged correspondence with Paul Weiss and other legal advisors to the Consortium (including KMA Zuckert LLC, as regulatory legal counsel to the Consortium) related to the draft merger agreement and other related draft transaction documentation.

On July 26, 2022, representatives of the Consortium informed representatives of Morgan Stanley that they would not be able to submit a final bid that day, as had been requested by the Company, as they required additional time to finalize the details of the Consortium’s financing package. The Consortium indicated, however, that it expected to submit a final bid later in the week.

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 51

THE MERGER

Between July 26 and July 28, 2022, representatives of Morgan Stanley spoke with representatives of the Consortium to communicate the importance of the Consortium providing a bid prior to the Board meeting scheduled for the morning of July 29, 2022.

On the morning of July 29, 2022, representatives of the Consortium delivered to the Board a letter which included a non-binding proposal to acquire the Company for cash consideration of $101.00 per share, subject to the negotiation, execution and delivery of mutually satisfactory definitive agreements, approval of the transaction by Company stockholders and receipt of customary regulatory and other third-party approvals (the “July 29 Offer”). The Consortium further noted in its letter that it had completed its due diligence. In advance of delivering the letter, Mr. Munfakh called Mr. Dietrich to preview the updated bid and explained the decreased bid price relative to the Consortium’s prior bid price was a result of the Consortium’s increased costs and potential inability to obtain acceptable financing terms to the extent required to maintain its previously offered price per share, as well as the Company’s actual results for the second quarter of 2022 and forecast for the remaining quarters of 2022 previously made available to the Consortium. The July 29 Offer represented a 38.0% premium to the Company common stock’s closing share price of $73.19 on July 28, 2022, and a 5.4% premium to its then all-time high closing share price of $95.78.

Also in the morning on July 29, 2022, representatives of Paul Weiss sent a revised draft of the merger agreement to representatives of Cravath on behalf of the Consortium. This draft of the merger agreement reduced the proposed go-shop extension period down to five days and bracketed the go-shop period as under consideration by the Consortium; it increased the Company termination fee to 3.5% of the fully diluted equity value of the Company following the go-shop period; it decreased the reverse termination fee of 5% of the fully diluted equity value of the Company; and it provided that the Company was to reimburse the Consortium’s transaction expenses up to an undetermined value if the deal was terminated due to the Company’s failure to obtain stockholder approval.

Later in the morning of July 29, 2022, the Board held a telephonic meeting, with members of Company management and representatives of Morgan Stanley and Cravath in attendance. Members of Company management summarized negotiations with the Consortium to date and explained to the Board that the Consortium had cited the absorption of increased costs, the difficulties in obtaining acceptable financing terms, the broader macroeconomic climate and the Company’s actual results for the second quarter of 2022 and forecast for the remaining quarters of 2022 previously made available to the Consortium as the predominant factors driving a bid that was lower than the March 23 Offer and the May 19 Offer. Representatives of Cravath reviewed with the Board its fiduciary duties and other legal matters in the context of a review of a potential sale transaction, and representatives of Morgan Stanley reviewed for the Board the terms of the July 29 Offer and presented an updated financial analysis to account for the current state of the financing market and the Company’s performance since the March 23 Offer and the May 19 Offer. Members of the Company management presented to the Board the Updated Management Case (as defined in “— Certain Financial Forecasts”). The Company’s management also discussed their views on the outlook for the Company’s business on a standalone basis. Following discussion, the Board directed that Mr. Dietrich send the Consortium a counteroffer of $105.00 per share, provided that the Consortium respond as soon as possible and that the Consortium finalize its financing commitments by August 2, 2022.

Later in the day on July 29, 2022, Mr. Dietrich talked to Mr. Munfakh on the phone and communicated the Board’s counteroffer of $105.00 per share and the Board’s other messages.

On July 30, 2022, Mr. Munfakh called Mr. Dietrich to provide a counteroffer of $102.50 per share (the “July 30 Offer”), which he confirmed was the highest bid the Consortium would be willing to offer.

52 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

THE MERGER

Later in the day on July 30, 2022, the Board held a telephonic meeting, with Company management and representatives of Morgan Stanley and Cravath in attendance. Mr. Dietrich provided the Board with a summary of his conversation with Mr. Munfakh. After discussion and careful deliberation, the Board authorized Company management and the Company’s advisors to move forward with the Consortium’s proposed acquisition price of $102.50 per share in cash, provided that all remaining deal points and documentation could be negotiated with the Consortium and finalized on terms acceptable to the Company prior to the Company’s scheduled earnings announcement date of August 5, 2022.

Later on July 30, 2022, Mr. Dietrich called Mr. Munfakh and communicated the Board’s willingness to move forward with an acquisition at $102.50 per share and agreed to remove the go-shop provision from the merger agreement in exchange for the Consortium’s agreement to certain terms in the merger agreement, including, among other items, (i) a reverse termination fee of 8% of the fully diluted equity value of the Company and (ii) a Company termination fee of 3% of the fully diluted equity value of the Company.

On July 31, 2022, Mr. Dietrich and Mr. Munfakh agreed that the merger agreement would not include a go-shop provision; would include a Company termination fee of 3% of the fully diluted equity value of the Company; and would include a reverse termination fee of 7% of the fully diluted equity value of the Company.

Between July 29, 2022 and August 3, 2022, the Company and its advisors continued to negotiate with the Consortium and its advisors the proposed terms of the merger agreement and other transaction documents, including proposed debt and equity commitment letters and limited guarantees. Throughout this period, the Board received frequent updates from Company management and the Company’s financial and legal advisors.

On August 1, 2022, pursuant to the Amazon Stockholders Agreement, the Company sent notice to Amazon of its receipt of an acquisition proposal.

On August 1, 2022, The Wall Street Journal published an article stating that a group of investors led by Apollo was in advanced talks to acquire the Company. Following the report, the Company’s stock price closed at $84.99 on August 1, 2022, compared to $75.71 on July 29, 2022 (the trading day immediately prior to the reports).

On August 2, 2022, the Consortium confirmed that it had financing commitments in hand from its debt financing sources.

On the evening of August 2, 2022, Bloomberg published an article stating that an investor group led by Apollo had agreed to acquire the Company for around $102.50 per share and a transaction might be announced as soon as later in the week. Following the Bloomberg report, the Company’s stock price closed at $96.78 on August 3, 2022, compared to $87.37 on August 2, 2022 (the trading day ended immediately prior to the Bloomberg report).

Later in the evening on August 3, 2022, the Board held a telephonic meeting, with Company management and representatives of Morgan Stanley and Cravath in attendance. Company management presented an overview of the proposed acquisition of the Company to the Board. A representative of Cravath delivered a legal presentation outlining the terms of the near-final draft of the merger agreement and the near-final drafts of the debt and equity financing documentation, and reviewing with the Board its fiduciary duties. Following the legal presentation, representatives of Morgan Stanley reviewed with the Board its financial

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 53

THE MERGER

analyses of the proposed merger consideration based on the Updated Management Case and rendered to the Board its oral opinion, which was subsequently confirmed by delivery of a written opinion, dated August 3, 2022, which is attached to this proxy statement as Annex B, that, as of that date and based on and subject to the assumptions made, procedures followed, matters considered and qualifications and limitations on the scope of review undertaken by Morgan Stanley as set forth therein, the merger consideration to be received by the holders of shares of Company common stock pursuant to the merger agreement with the Consortium was fair from a financial point of view to such holders of Company common stock. The Board also reviewed an updated disclosure statement from Morgan Stanley identifying prior or current engagements or relationships between Morgan Stanley and affiliates of the Consortium Funds.

After discussion and consideration of a variety of factors, including those discussed in “— Reasons for the Merger” beginning on page 54, the Board resolved to proceed with the proposal from the Consortium and unanimously (i) determined that it is advisable and fair to, and in the best interests of, the Company and the Company stockholders, and declared it advisable that the Company enter into the merger agreement and consummate the transactions, (ii) resolved to approve and declare the advisability of the merger agreement and the consummation of the transactions, including the merger, (iii) resolved to recommend that the Company stockholders entitled to vote adopt the merger agreement and (iv) directed that the merger agreement and the transactions be submitted to Company stockholders entitled to vote for adoption.

Following the meeting of the Board, representatives of the Company and the Consortium finalized and executed the merger agreement and the other transaction documents, including debt and equity commitment letters and limited guarantees.

The following morning, on August 4, 2022, the Company issued a press release announcing the execution of the merger agreement and the proposed terms of the acquisition by the Consortium.

Recommendation of the Board

At the special meeting of the Board on August 3, 2022, after consideration, including of the material factors described in the section below entitled “— Reasons for the Merger”, and detailed discussions with the Company’s management and its legal and financial advisors, at such meeting and prior meetings of the Board, the Board unanimously:

•

determined and declared that it is advisable and fair to, and in the best interests of, the Company and Company stockholders, that the Company enter into the merger agreement and consummate the transactions;

•

approved and declared the advisability of the merger agreement and the consummation of the transactions, including the merger;

•

recommended that the Company stockholders entitled to vote adopt the merger agreement; and

•

directed that the merger agreement be submitted to the Company’s stockholders entitled to vote for adoption.

Reasons for the Merger

As described above in the section entitled “— Background of the Merger”, prior to and in reaching its unanimous determination to (i) declare that it is advisable and fair to, and in the best interests of, the

54 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

THE MERGER

Company and Company stockholders, that the Company enter into the merger agreement and consummate the transactions, (ii) approve and declare the advisability of the merger agreement and the consummation of the transactions, including the merger, (iii) recommend that the Company stockholders entitled to vote adopt the merger agreement and (iv) direct that the merger agreement be submitted to the Company’s stockholders entitled to vote for adoption, the Board consulted with and received the advice of its financial advisors and outside legal counsel, discussed certain issues with the Company’s management and considered a variety of factors weighing positively in favor of the merger, the merger agreement and the transactions contemplated thereby, including the following non-exhaustive list of material factors (not necessarily in order of relative importance):

•

the $102.50 per share price of Company common stock to be paid in cash, which represented a premium of approximately:

•

57% over the 30-day volume-weighted average trading price per share as of July 29, 2022, the last full trading day prior to published market speculation regarding a potential sale of the Company;

•

35% over the unaffected closing stock price on July 29, 2022, the last full trading day prior to published market speculation regarding a potential sale of the Company; and

•

7% over the all-time highest closing price for shares of Company common stock on any day since July 21, 2004;

•

the Board’s understanding of the Company’s business, operations, financial condition, earnings, prospects, competitive position and the nature of the industry in which the Company competes;

•

the Board’s understanding of the risks and uncertainties in the industry in which the Company competes, and the risks that the Company would face if it continued to operate on a stand-alone public company basis, including:

•

risks relating to the air cargo services industry, including, but not limited to, the competitive market for air cargo services, the failure to comply with extensive governmental laws and regulations in the U.S. and abroad and the imposition of more stringent regulations and rules on the air cargo services industry, and the initiatives to address global climate change;

•

risks relating to the operation of the Company, including, but not limited to, the deterioration or disruption in the airfreight market, global economic conditions, financial markets or global supply chains, including the impact of geopolitical events, severe weather, natural disasters or health epidemics, the underutilization of existing aircraft, the failure to deploy or redeploy aircraft with customers at favorable rates or due to the impairment or loss of one or more aircraft, the seasonal nature of global trade flows, the fuel availability and the price volatility;

•

risks relating to the Company’s collective bargaining agreements covering the Company’s pilots and flight dispatchers of Atlas Air, Inc. and Polar Air Cargo Worldwide, Inc., which could result in higher labor costs than those faced by some of the Company’s non-unionized competitors or in a work interruption or stoppage;

•

risks relating to the Company and the customers of its dry leasing aircraft and engines services with respect to obtaining adequate insurance coverage;

•

risks relating to compliance with existing and future applicable laws and regulations, especially the rules and regulations applicable to the Company as a U.S. government contractor;

•

risks relating to ongoing lawsuits and claims related to alleged pricing practices or other legal and regulatory matters;

•

risks relating to compliance with the Company’s agreements with the U.S. Treasury under the Company’s payroll support program;

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 55

THE MERGER

•

risks relating to the Company’s agreements with Amazon.com, Inc. and Amazon Fulfillment Services, Inc. (collectively, “Amazon parties”), including that the Amazon parties may exercise their termination rights under certain agreements with the Company, which may result in the Company’s inability to realize the full benefits of the agreements, the Amazon parties may exercise their right to acquire additional shares of Company common stock pursuant to the warrants granted to the Amazon parties which may, amongst other things, entitle the Amazon parties to appoint a director to the Board, dilute the current ownership interests and adversely affect the market price of Company common stock;

•

risks that revenues from the AMC, which accounted for total operating revenue of approximately 10.5% in 2021, 15.9% in 2020 and 24.6% in 2019, may decline over time and that teaming arrangements may affect the Company’s relative share of AMC flying and the associated revenue;

•

risks relating to the Company’s dry leasing business, including the risk of failure to realize the anticipated strategic and financial benefits of the Company’s dry leasing joint venture with Bain Capital Credit, LP and the risk of default by the Company’s dry lease customers, including, but not limited to, the failure to make timely payments, the failure to maintain insurance and the failure to properly maintain the Company’s aircraft;

•

risks relating to the Company’s substantial lease and debt obligations, including aircraft leases and other obligations, which could impair the Company’s financial condition and adversely affect its ability to raise additional capital to fund its aircraft purchases, operations or other capital requirements; and

•

other risks and uncertainties, including the risk factors set forth in the Company’s Annual Report on Form 10-K for the fiscal year ended December 31, 2021 and on Form 10-Q for the fiscal quarters ended March 31, 2022 and June 30, 2022;

•

the Board’s assessment of potential risks, rewards and uncertainties associated with remaining an independent public company as a possible strategic alternative to the sale of the entire Company (including the potential value to Company stockholders based on the Company’s strategic plan that could be expected to be generated from remaining an independent public company), and the Board’s resulting determination that such alternative did not represent an attractive alternative to the merger;

•

the Board’s consideration of the current state of the economy, debt financing markets and uncertainty surrounding forecasted economic conditions in the near term and the long term, which could negatively affect the Company’s financial performance;

•

the fact that the merger consideration is all cash, which provides certainty, immediate value and liquidity to holders of Company common stock, especially when viewed against any internal or external risks and uncertainties associated with the Company’s stand-alone strategy, immediately upon the closing of the merger;

•

the financial analyses reviewed and discussed with the Board by representatives of Morgan Stanley, as well as the oral opinion of Morgan Stanley, subsequently confirmed in writing, which written opinion is attached to this proxy statement as Annex B, rendered to the Board, that as of August 3, 2022, and based upon and subject to the assumptions made, procedures followed, matters considered and qualifications and limitations on the scope of review undertaken by Morgan Stanley as set forth in Morgan Stanley’s written opinion, the merger consideration to be received by the holders of shares of the Company common stock (other than the excluded shares and appraisal shares) pursuant to the merger agreement was fair from a financial point of view to such holders of shares of the Company common stock, as set forth in such opinion as more fully described below in the section of this proxy statement entitled “— Opinion of the Company’s Financial Advisor”;

56 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

THE MERGER

•

the Board’s assessment, taking into account the other factors described herein, of the Company’s value on a stand-alone basis relative to the $102.50 per share of Company common stock to be paid in cash in connection with the merger, and the possibility that the trading price of shares of Company common stock would not reach and sustain such price, or that doing so could take a considerable period of time;

•

the Company’s operating and financial performance and its prospects, including certain prospective forecasts for the Company prepared by the Company’s senior management, which reflect an application of various assumptions of senior management, and the inherent uncertainty of achieving senior management’s prospective forecasts, as set forth below under the section entitled “— Certain Financial Forecasts”, and that as a result the Company’s actual financial results in future periods could differ materially from senior management’s forecasts;

•

the Board’s process for soliciting and responding to offers from the financial and strategic third parties that were believed to be the most willing and able to pay the highest price for the Company, which included contacting, or responding to, 11 potential acquirors, entering into non-disclosure agreements with five potential acquirors, providing management presentations to five potential acquirors, granting access to a data room containing detailed due diligence materials to three potential acquirors, receiving non-binding offers from three potential acquirors and receiving one final proposal, which was from the Consortium, as well as providing Amazon.com, Inc. with an opportunity to make an acquisition proposal by notifying Amazon.com, Inc. of the Company’s receipt of acquisition proposals from third parties as required by the terms of the Amazon Stockholders Agreement, and the fact that, although several of the potential acquirors, including Party E and Party I, had cited the amount of available financing and the terms available in the current condition of the financing markets as reasons for withdrawing from the sale process, the Consortium had obtained committed debt and equity financing for the full amount in cash necessary to fund the aggregate merger consideration, in each case as further described above under the section entitled “— Background of the Merger”;

•

the course and history of competitive arm’s-length negotiations with all three third parties that submitted non-binding offers, which negotiations the Board believed resulted in the Company obtaining the highest price that the Consortium, as the last remaining bidder, was willing to pay for the Company, as evidenced by the Company’s ability to increase the Consortium’s proposed price per share of Company common stock from $83.50 in its June 1, 2021 initial proposal to $102.50 per share in its July 30, 2022 final offer, as further described above under the section entitled “— Background of the Merger”;

•

the Board’s belief that, based on discussions with the Consortium and other potential counterparties, the final proposal submitted by the Consortium represented the best and final offer and the highest price per share of Company common stock that the Consortium or any other potential counterparty would be willing to pay, particularly given the condition of the financing market and broader macroeconomic climate, and any request for a further price increase or solicitation of additional bids from other third parties would have created a meaningful risk that the Consortium might determine not to enter into the transaction and to terminate negotiations, in which event Company stockholders would lose the opportunity to obtain the proposed $102.50 per share of Company common stock in cash being offered;

•

the consolidated financial strength and industry expertise of the Consortium, including the successful track record that Apollo and JFLCO have developed in acquiring other companies;

•

the fact that the merger is not subject to a financing condition, that the Consortium obtained committed debt financing for the merger from reputable financing sources, and that each of the Apollo Funds, the JFLCO Funds and the Hill City Fund have committed to make available and provide to Parent, pursuant to the equity commitment letters, the full amount in cash necessary, along with the committed debt

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 57

THE MERGER

financing, to fund the aggregate merger consideration, as further described below in the section entitled “— Financing of the Merger”;

•

the fact that if any portion of the debt financing for the merger becomes unavailable, Parent is required to use reasonable best efforts to obtain alternative financing in an amount sufficient to consummate the merger;

•

the fact that the Apollo Guarantors, certain of the JFLCO Funds and the Hill City Fund have provided certain limited guarantees, which support Parent’s obligation to pay Parent’s termination fee to the extent payable, in favor of the Company as described below in the section entitled “— Financing of the Merger”;

•

the provisions of the merger agreement that permit the Company (i) to seek specific performance of Parent to perform its obligations under the merger agreement, including to use its reasonable best efforts to obtain debt financing, and (ii) if the debt financing is available at closing, to force the equity financing to be funded and to cause the merger to occur;

•

the provisions of the merger agreement that permit the Company, in response to certain unsolicited takeover proposals, to furnish information to and conduct discussions and negotiations with third parties prior to the Company stockholder approval under certain circumstances and, under certain conditions, to accept a superior proposal, and the Company’s corresponding right to terminate the merger agreement (subject to the payment to Parent of the Company termination fee of $97.5 million and certain rights of Parent to match the superior proposal) in order to enter into a definitive agreement providing for the consummation of such superior proposal;

•

the provisions of the merger agreement that permit the Board, prior to obtaining stockholder approval of the merger agreement proposal, to not include, withdraw or modify (or modify, amend or qualify in a matter adverse to Parent) its recommendation in the proxy statement that our stockholders vote to adopt the merger agreement, under certain circumstances relating to a superior proposal or intervening event, subject to payment to Parent of the Company termination fee of $97.5 million if Parent elects to terminate the merger agreement in such circumstances, and that the amount of the Company termination fee is comparable to termination fees in transactions of a similar size, is reasonable, would not likely deter competing bids and would not likely be required to be paid unless the Company entered into a more favorable transaction;

•

the other terms and conditions of the merger agreement and the debt and equity financing documents, which were reviewed by the Board with the Company’s outside legal counsel and financial advisors, and the fact that such terms were the product of arm’s-length negotiations between the parties;

•

the high probability that the merger would be consummated based on, among other things, the absence of a financing contingency and the $227.4 million Parent termination fee, payable to the Company if the merger agreement is terminated in certain circumstances, which payment is guaranteed by the Apollo Guarantors, the JFLCO Funds and the Hill City Fund in accordance with their maximum caps as described in “— Financing of the Merger — Limited Guarantees”, pursuant to the limited guarantees delivered by them, the Consortium members’ ability to complete large acquisition transactions and Apollo’s experience with transactions in the airline industry;

•

the high probability that the merger would be completed in a reasonable timeframe and in an orderly manner, which could reduce the period during which the Company’s business would be subject to the potential uncertainty of closing and related disruption;

•

the fact that resolutions approving the merger were unanimously approved by the Board, which is comprised of a majority of independent directors who are not affiliated with the Company and are not employees of the Company or any of its subsidiaries;

58 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

THE MERGER

•

the fact that the merger would be subject to the approval of our stockholders, and our stockholders would be free to reject the merger by voting against the adoption of the merger agreement; and

•

the availability of appraisal rights under the DGCL to Company stockholders who comply with all of the required procedures for perfecting appraisal rights under the DGCL in connection with the merger, including the fact that such stockholders will have the right to demand appraisal and payment of the fair value of their shares as determined by the Delaware Court, as further described in the section entitled “— Appraisal Rights”.

In the course of its deliberations, the Board also considered a variety of risks and other countervailing factors related to the merger agreement and the merger, including the following material factors:

•

the potential upside in the Company’s stand-alone strategic plan;

•

the possibility that the merger might not be completed on the terms or timeline currently contemplated or at all due to a failure of certain conditions, including with respect to the required approval of the transaction by the required regulatory authorities;

•

the risks and costs to the Company if the merger does not close in a timely manner or at all, including:

•

the trading price of Company common stock may decline to the extent that the market price of the Company common stock currently reflects positive market assumptions that the merger will be consummated;

•

the potential negative impact on the Company’s ability to attract, hire and retain key employees, as current and prospective employees may experience uncertainty about their future roles with the Company following the merger;

•

the potential disruption to the Company’s business and distraction of its workforce and management team from day-to-day operations and from pursuing other opportunities that could be beneficial to the Company, in each case without realizing any of the benefits of having the merger completed; and

•

reputational harm to the Company’s relationships with investors, customers, suppliers, business partners and other third parties due to the adverse perception of any failure to successfully complete the merger.

•

the fact that holders of Company common stock will have no ongoing equity interest in the surviving corporation following the merger, meaning that the holders of Company common stock will not (by virtue of their holding Company common stock) participate in the Company’s potential future earnings or growth;

•

the restrictions on the conduct of the Company’s business prior to the consummation of the merger, which may delay or prevent the Company from undertaking certain significant financing transactions and business opportunities that may arise or any other action that it might otherwise take with respect to the operations and strategy of the Company, even if such actions would prove beneficial to the Company;

•

the risk that the parties may incur significant costs and material delays resulting from seeking regulatory approvals and other clearances, consents and approvals necessary for consummation of the merger;

•

the provisions of the merger agreement that restrict the Company’s ability to solicit or participate in discussions or negotiations regarding alternative takeover proposals with third parties, subject to specified exceptions, and that require the Company to negotiate with Parent (if Parent desires to propose revisions to the merger agreement and negotiate) prior to the Company being able to terminate the merger agreement to accept a superior proposal;

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 59

THE MERGER

•

the possibility that the Company’s obligation to pay the Company termination fee of $97.5 million to Parent upon the termination of the merger agreement under certain circumstances could discourage other potential acquirors from making an alternative proposal to acquire the Company;

•

the significant costs involved in connection with negotiating the merger agreement and consummating the merger, such as legal, accounting, financial advisory and integration costs, and the fact that if the merger is not consummated, the Company may be required to bear such costs;

•

the possibility that, although the merger provides the Company stockholders the opportunity to realize a premium to the price at which Company common stock traded prior to the public announcement of the merger, the price of Company common stock might have increased in the future to a price greater than the merger consideration;

•

the risk of litigation in connection with the execution of the merger agreement and the consummation of the merger and the other transactions contemplated therein;

•

the fact that an all-cash transaction would be taxable to the holders of common stock that are U.S. holders for U.S. federal income tax purposes; and

•

various other risks associated with the merger and the business of the Company, as more fully described above in the section entitled “Cautionary Statement Regarding Forward-Looking Statements”.

In addition, the Board was aware of and considered the fact that the Company’s directors and executive officers have financial interests in the merger that may be different from, or in addition to, those of the Company stockholders generally, as described more fully below in the section entitled “— Interests of the Company’s Directors and Executive Officers in the Merger”.

The foregoing discussion of the factors considered by the Board is not intended to be exhaustive, but rather includes the material factors considered by the Board. The Board unanimously reached the conclusion to (i) determine and declare that it is advisable and fair to, and in the best interests of, the Company and Company stockholders, that the Company enter into the merger agreement and consummate the transactions, (ii) approve and declare the advisability of the merger agreement and the consummation of the transactions, including the merger, (iii) recommend that the Company stockholders entitled to vote adopt the merger agreement and (iv) direct that the merger agreement be submitted to the Company’s stockholders entitled to vote for adoption in light of the factors described above and other factors that the Board believed were appropriate. In view of the wide variety of factors considered by the Board in connection with its evaluation of the merger and the complexity of these matters, the Board did not consider it practical, and did not attempt, to quantify, rank or otherwise assign relative weights to the specific factors it considered in reaching its decision and did not undertake to make any specific determination as to whether any particular factor, or any aspect of any particular factor, was favorable or unfavorable to the ultimate determination of the Board. Rather, the Board made its recommendation based on the totality of the information available to the Board, including discussions with, and questioning of, the Company’s management and its financial and legal advisors. In considering the factors discussed above, individual members of the Board may have given different weights to different factors.

This explanation of the Board’s reasons for its recommendations and other information presented in this section is forward-looking in nature and, therefore, should be read in light of the factors described in the section of this proxy statement entitled “Cautionary Statement Regarding Forward-Looking Statements” beginning on page 27.

60 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

THE MERGER

Certain Financial Forecasts

Other than annual guidance — including the guidance included in the Company’s press release dated February 17, 2022 and the updates of such guidance in the Company’s press release dated May 5, 2022 (the “2022 earnings guidance”), with respect to revenues, adjusted EBITDA, net income, core capital expenditures and certain other performance measures, some of which guidance the Company presents as a range — the Company does not, as a matter of course, publicly disclose forecasts as to future performance, earnings or other results due to the unpredictability of the underlying assumptions and estimates. However, the Company has included in this proxy statement certain financial forecasts of the Company that, to the extent described herein, were furnished to (i) the Board, the Company’s financial advisor and the Consortium, in connection with the discussions concerning the proposed merger and (ii) certain other parties potentially interested in a transaction with the Company.

These Financial Forecasts (as defined below) were not prepared with a view toward public disclosure or with a view toward complying with the guidelines established by the American Institute of Certified Public Accountants for preparation and presentation of prospective financial data, published guidelines of the SEC regarding forward-looking statements or generally accepted accounting principles in the United States (“GAAP”). A summary of this information is presented below.

No assurances can be made regarding future events and the estimates and assumptions underlying these financial forecasts involve judgments with respect to, among other things, future economic, competitive, regulatory and financial market conditions and future business decisions that may not be realized and that are inherently subject to significant business, economic, competitive and regulatory uncertainties and contingencies, including, among other things, the inherent uncertainty of the business and economic conditions affecting the industries in which the Company operates, and the risk and uncertainties described under “Cautionary Statement Regarding Forward-Looking Statements” beginning on page 27, all of which are difficult to predict and many of which are outside the control of the Company and, upon consummation of the merger, will be beyond the control of the Consortium and the surviving corporation. Company stockholders are urged to review the Company’s SEC filings for a description of risk factors with respect to the Company’s business. There can be no assurance that the underlying assumptions will prove to be accurate or that the projected results will be realized. Actual results likely will differ, and may differ materially, from those reflected in the Financial Forecasts, whether or not the merger is consummated. The inclusion in this proxy statement of the Financial Forecasts below should not be regarded as an indication that the Company, the Consortium, their respective boards of directors (or equivalent governing bodies) or their respective financial advisors considered, or now consider, these forecasts to be a reliable predictor of future results. The Financial Forecasts are not fact, and neither they nor any underlying assumptions should be relied upon as being indicative of future results. Readers of this proxy statement are cautioned not to place reliance on this information. The Financial Forecasts assume that the Company would continue to operate as a standalone company and do not reflect any impact of the merger, except as described below for the Seller Case.

Investors should also note that these non-GAAP financial measures presented in this proxy statement are not prepared under any comprehensive set of accounting rules or principles and do not reflect all of the amounts associated with the Company’s results of operations as determined in accordance with GAAP. Investors should also note that these non-GAAP financial measures presented in this proxy statement have no standardized meaning prescribed by GAAP and, therefore, have limits in their usefulness to investors. Because of the non-standardized definitions, the non-GAAP financial measures in this proxy statement and the accompanying footnotes may be calculated differently from, and may not be directly comparable to, similarly titled measures used by the Company’s competitors and other companies, or any similarly titled measures used by any member of the Consortium or any of their respective affiliates.

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 61

THE MERGER

Due to the inherent limitations of non-GAAP financial measures, investors should consider non-GAAP measures only as a supplement to, not as a substitute for or as a superior measure to, measures of financial performance prepared in accordance with GAAP. The footnotes to the tables below provide certain supplemental information with respect to the calculation of these non-GAAP financial measures.

The Financial Forecasts included in this document have been prepared by, and are the responsibility of, the Company’s management. PricewaterhouseCoopers LLP, the independent auditor has not audited, reviewed, examined, compiled nor applied agreed upon procedures with respect to the accompanying Financial Forecasts and, accordingly, PricewaterhouseCoopers LLP does not express an opinion or any other form of assurance with respect thereto. The PricewaterhouseCoopers LLP report incorporated by reference in this document relates to the Company’s previously issued financial statements. It does not extend to the Financial Forecasts and should not be read to do so.

The non-GAAP financial measures included in the Financial Forecasts that were approved by the Company for use by Morgan Stanley (consisting of the Updated Management Case and the Company Unlevered Free Cash Flow (as defined below)) were relied upon by Morgan Stanley for its financial analysis in connection with the preparation of its opinion and by the Board for its consideration of the merger. Financial measures provided to a financial advisor in connection with a business combination transaction are not subject to SEC rules regarding disclosures of non-GAAP financial measures. In addition, reconciliations of non-GAAP financial measures were not relied upon by the Board or Morgan Stanley in connection with their respective evaluations of the merger. Accordingly, the Company has not provided a reconciliation of the non-GAAP financial measures included in the Financial Forecasts to the relevant GAAP financial measures.

By including in this proxy statement the Financial Forecasts below, none of the Company or the Consortium members or any of their respective representatives has made or makes any representation to any person regarding the ultimate performance of the Company compared to the information contained in the Financial Forecasts. Accordingly, the Financial Forecasts should not be construed as financial guidance, nor relied upon as such, and the Financial Forecasts may differ in important respects from the 2022 earnings guidance, some of which guidance is presented as a range, and which the Company’s management prepared based on a different set of assumptions. The inclusion of the Financial Forecasts in this proxy statement does not constitute an admission or representation by the Company that the information contained therein is material. The Financial Forecasts summarized in this section reflected the opinions, estimates and judgments of the Company’s management at the time they were prepared and have not been updated to reflect any changes since such Financial Forecasts were prepared. NONE OF THE COMPANY, THE CONSORTIUM MEMBERS OR, AFTER CONSUMMATION OF THE MERGER, THE SURVIVING CORPORATION, UNDERTAKES ANY OBLIGATION, EXCEPT AS REQUIRED BY LAW, TO UPDATE OR OTHERWISE REVISE THE FINANCIAL FORECASTS TO REFLECT CIRCUMSTANCES EXISTING SINCE THEIR PREPARATION, CHANGES IN GENERAL ECONOMIC OR INDUSTRY CONDITIONS OR THE OCCURRENCE OF UNANTICIPATED EVENTS, EVEN IN THE EVENT THAT ANY OR ALL OF THE UNDERLYING ASSUMPTIONS ARE SHOWN TO BE IN ERROR.

The Company’s management prepared nonpublic, unaudited prospective financial information for fiscal years 2022 through 2026 (which we refer to as the “Base Management Case”) for the Company’s internal use, that was first reviewed by the Board at its meeting held on March 15, 2022. The Base Management Case was not made available to the Consortium or the other parties potentially interested in a transaction with the Company.

62 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

THE MERGER

The Company’s management also prepared a so-called “Seller Case” that was reviewed by the Board at its meeting held on April 8, 2022 and was also made available to the Consortium and certain other parties potentially interested in a transaction with the Company in the course of their due diligence and in connection with their review of a possible transaction with the Company. The Seller Case reflected certain assumptions with respect to yields, crew costs, crew availability and operating as a private entity.

In addition, in connection with the Company’s evaluation of a proposed transaction in July 2022, the Company’s management updated the Base Management Case (which we refer to as the “Updated Management Case”) to reflect (i) the actual results for the second quarter of 2022 and (ii) an updated forecast for the remaining quarters of 2022 and for fiscal years 2023 through 2026, which updated forecast took into account certain adjustments relating to, among other things, the developments with respect to yields, crew costs, crew availability, fuel costs (which generally impact revenue but do not result in material changes to EBITDAR) and the Company and its subsidiaries entering into new customer agreements. The Updated Management Case was relied upon by the Board in reaching its determination on August 3, 2022 to approve and declare advisable the merger agreement and the transactions contemplated thereby and to recommend that the Company’s shareholders vote to adopt the merger agreement, and was the only forecast prepared by management that was approved by the Company for use by Morgan Stanley in connection with rendering its oral opinion delivered to the Board, which was subsequently confirmed by delivery of a written opinion dated as of August 3, 2022, and performing its financial analysis in connection therewith, as summarized in the section of this proxy statement entitled “— Opinion of the Company’s Financial Advisor” beginning on page 65. The Updated Management Case was not made available in full to the Consortium or the other parties potentially interested in a transaction with the Company, but the actual results for the second quarter of 2022 and the forecast for the remaining quarters of 2022 included in the Updated Management Case were made available to the Consortium in connection with its review of a possible transaction with the Company.

The Base Management Case, the Seller Case and the Updated Management Case are collectively referred to as the “Management Financial Forecasts” and, together with the Company Unlevered Free Cash Flow, the “Financial Forecasts”.

The following table sets forth a summary of the Management Financial Forecasts; the summary of the Management Financial Forecasts is not included in this proxy statement to induce any Company stockholder to vote in favor of approving the merger agreement proposal or approving any other proposals to be voted on at the special meeting:

Base Management Case

​	Fiscal Year ending December 31,
($ millions)	2022E		2023E		2024E		2025E		2026E
Operating Revenue	​	4,353	​	4,546	​	4,611	​	4,653	​	4,700
Adjusted EBITDAR(1)	​	1,048	​	1,034	​	944	​	914	​	876
Adjusted Net Income(2)	​	477	​	431	​	362	​	357	​	333
Capital Expenditures	​	(977)	​	(536)	​	(178)	​	(179)	​	(174)

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 63

THE MERGER

Seller Case

​	Fiscal Year ending December 31,
($ millions)	2022E		2023E		2024E		2025E		2026E
Operating Revenue	​	4,373	​	4,779	​	4,855	​	4,917	​	4,971
Adjusted EBITDAR(1)	​	1,042	​	1,135	​	1,089	​	1,066	​	1,055
Adjusted Net Income(2)	​	471	​	508	​	472	​	474	​	469
Capital Expenditures	​	(977)	​	(536)	​	(178)	​	(179)	​	(174)

Updated Management Case

​	Fiscal Year ending December 31,
($ millions)	2022E		2023E		2024E		2025E		2026E
Operating Revenue	​	4,853	​	5,624	​	5,751	​	5,786	​	5,850
Adjusted EBITDAR(1)	​	1,020	​	1,073	​	958	​	881	​	875
Adjusted Net Income(2)	​	458	​	459	​	370	​	331	​	330
Capital Expenditures	​	(989)	​	(536)	​	(178)	​	(179)	​	(174)

(1)

“Adjusted EBITDAR” is defined as adjusted earnings before interest, taxes, depreciation, amortization and rent expense. Adjusted EBITDAR is a non-GAAP financial measure and should not be considered as an alternative to net income or operating income as a measure of operating performance or cash flows or as a measure of liquidity.

(2)

“Adjusted Net Income” is defined as net income, less Coronavirus Aid, Relief and Economic Security Act grant income, customer incentive asset amortization, adjustment to paid time off benefits in connection with the new five-year collective bargaining agreement between the Company and its subsidiaries and its pilots, net noncash expenses and income, unrealized loss (gain) on financial instruments, net other income and income tax effect of reconciling items. Adjusted Net Income is a non-GAAP financial measure and should not be considered as an alternative to net income or operating income as a measure of operating performance or cash flows or as a measure of liquidity.

The following table sets forth a summary of unaudited prospective unlevered free cash flows (as defined in the footnotes below) of the Company for the second half of fiscal year 2022 and fiscal years 2023 through 2026 and a terminal year (the “Company Unlevered Free Cash Flow”), as arithmetically derived by Morgan Stanley based on the Updated Management Case, which derivations were approved by the Company’s senior management for use by Morgan Stanley in connection with rendering its oral opinion delivered to the Board, which was subsequently confirmed by delivery of a written opinion dated as of August 3, 2022, and performing its financial analysis in connection therewith, as summarized in the section of this proxy statement entitled “— Opinion of the Company’s Financial Advisor” beginning on page 65. The summary of the Company Unlevered Free Cash Flow is not included in this proxy statement to induce any Company stockholder to vote in favor of approving the merger agreement proposal or approving any other proposals to be voted on at the special meeting:

Company Unlevered Free Cash Flow

​

Fiscal Year ending December 31,

Terminal Year

($ millions)

2H22E

2023E

2024E

2025E

2026E

Unlevered Free Cash Flow(3)

​

(28)

​

427

​

570

​

566

​

562

​

251

(3)

“Unlevered Free Cash Flow” is defined as Adjusted EBITDAR, less rent expense, less unlevered taxes, less capital expenditures, less (plus) increase (decrease) in net working capital, plus deferred taxes. Unlevered Free Cash Flow is a non-GAAP financial measure and should not be considered as an alternative to net income or operating income as a measure of operating performance or cash flows or as a measure of liquidity.

64 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

THE MERGER

Opinion of the Company’s Financial Advisor

Morgan Stanley was retained by the Company to act as its financial advisor and to render a financial opinion in connection with a potential sale of the Company. The Company selected Morgan Stanley to act as its financial advisor based on Morgan Stanley’s experience in transactions similar to the merger, qualifications, expertise and reputation and its knowledge of the Company and its business and the industries in which the Company conducts its business. As part of this engagement, the Board requested that Morgan Stanley evaluate the fairness, from a financial point of view, of the merger consideration to be received by the holders of shares of Company common stock (other than the excluded shares and appraisal shares) pursuant to the merger agreement. On August 3, 2022, Morgan Stanley rendered its oral opinion to the Board, which was subsequently confirmed by delivery of a written opinion, dated August 3, 2022, to the effect that, as of the date of such opinion, and based upon and subject to the assumptions made, procedures followed, matters considered and qualifications and limitations on the scope of review undertaken by Morgan Stanley as set forth in Morgan Stanley’s written opinion, the merger consideration to be received by the holders of shares of the Company common stock (other than the excluded shares and appraisal shares) pursuant to the merger agreement was fair from a financial point of view to such holders of shares of the Company common stock, as set forth in such opinion. The full text of Morgan Stanley’s written opinion to the Board, dated August 3, 2022, is attached as Annex B to this proxy statement and is incorporated by reference into this proxy statement in its entirety. The opinion sets forth, among other things, the assumptions made, procedures followed, matters considered and qualifications and limitations on the scope of the review undertaken by Morgan Stanley in rendering its opinion. Company stockholders are urged to, and should, read the opinion carefully and in its entirety. Morgan Stanley’s opinion was directed to the Board, in its capacity as such, and addressed only the fairness, from a financial point of view, as of the date of the opinion, of the merger consideration to be received by the holders of shares of the Company common stock (other than the excluded shares and appraisal shares) pursuant to the merger agreement. Morgan Stanley’s opinion does not address any other term or aspect of the merger agreement or the transactions or any term or aspect of any other agreement or instrument contemplated by the merger agreement entered into or amended in connection therewith and does not address the relative merits of the merger as compared to any other alternative business transaction, or other alternatives, or whether or not such alternatives could be achieved or are available. It was not intended to, and does not, constitute an opinion or recommendation as to how the holders of Company common stock should vote at the special meeting. The summary of Morgan Stanley’s opinion set forth in this proxy statement is qualified in its entirety by reference to the full text of Morgan Stanley’s opinion.

In arriving at its opinion, Morgan Stanley:

1)

Reviewed certain publicly available financial statements and other business and financial information of the Company;

2)

Reviewed certain internal financial statements and other financial and operating data concerning the Company;

3)

Reviewed certain financial projections prepared by the management of the Company;

4)

Discussed the past and current operations and financial condition and the prospects of the Company with senior executives of the Company;

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 65

THE MERGER

5)

Reviewed the reported prices and trading activity for the Company common stock;

6)

Compared the financial performance of the Company and the prices and trading activity of the Company common stock with that of certain other publicly-traded companies comparable with the Company, and their securities;

7)

Reviewed the financial terms, to the extent publicly available, of certain comparable acquisition transactions;

8)

Participated in certain discussions and negotiations among representatives of the Company and Parent and certain parties and their financial and legal advisors;

9)

Reviewed the merger agreement, the commitment letters from certain lenders (the “reviewed commitment letters”) and certain related documents; and

10)

Performed such other analyses, reviewed such other information and considered such other factors as Morgan Stanley deemed appropriate.

In arriving at its opinion, Morgan Stanley assumed and relied upon, without independent verification, the accuracy and completeness of the information that was publicly available or supplied or otherwise made available to Morgan Stanley by the Company, and formed a substantial basis for Morgan Stanley’s opinion. With respect to the financial projections, Morgan Stanley assumed that they had been reasonably prepared on bases reflecting the best then-currently available estimates and judgments of the management of the Company of the future financial performance of the Company. In addition, Morgan Stanley assumed that the merger will be consummated in accordance with the terms set forth in the merger agreement without any waiver, amendment or delay of any terms or conditions, including, among other things, that Parent will obtain financing in accordance with the terms set forth in the reviewed commitment letters and that the definitive merger agreement would not differ in any material respect from the draft thereof furnished to Morgan Stanley. Morgan Stanley assumed that in connection with the receipt of all the necessary governmental, regulatory or other approvals and consents required for the proposed merger, no delays, limitations, conditions or restrictions will be imposed that would have a material adverse effect on the contemplated benefits expected to be derived in the proposed merger. Morgan Stanley noted that it is not a legal, tax or regulatory advisor. Morgan Stanley is a financial advisor only and relied upon, without independent verification, the assessment of the Company and its legal, tax or regulatory advisors with respect to legal, tax or regulatory matters. Morgan Stanley expressed no opinion with respect to the fairness of the amount or nature of the compensation to any of the Company’s officers, directors, or employees, or any class of such persons, relative to the merger consideration to be received by the holders of shares of the Company common stock in the transaction. Morgan Stanley did not make any independent valuation or appraisal of the assets or liabilities of the Company, nor was Morgan Stanley furnished with any such valuations or appraisals. Morgan Stanley’s opinion was necessarily based on financial, economic, market and other conditions as in effect on, and the information made available to Morgan Stanley as of August 3, 2022. Morgan Stanley noted that its opinion is not a solvency opinion and did not in any way address the solvency or financial condition of the Company and whether other strategic alternatives existed for the Company or whether such alternatives were available. Morgan Stanley did not express any view on, and its opinion did not address, any other term or aspect of the merger agreement or the transactions contemplated thereby or any term or aspect of any other agreement or instrument contemplated by the merger agreement or entered into or amended in connection therewith. Events occurring after such date may affect Morgan Stanley’s opinion and the assumptions used in preparing it, and Morgan Stanley did not assume any obligation to update, revise or reaffirm its opinion.

66 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

THE MERGER

Summary of Financial Analyses

The following is a summary of the material financial analyses performed by Morgan Stanley in connection with its oral opinion and the preparation of its written opinion letter dated August 3, 2022 to the Board. The following summary is not a complete description of Morgan Stanley’s opinion or the financial analyses performed and factors considered by Morgan Stanley in connection with its opinion, nor does the order of analyses described represent the relative importance or weight given to those analyses. The financial analyses summarized below include information presented in tabular format. In order to fully understand the financial analyses used by Morgan Stanley, the tables must be read together with the text of each summary. The tables alone do not constitute a complete description of the financial analyses. The analyses listed in the tables and described below must be considered as a whole; considering any portion of such analyses and of the factors, without considering all analyses and factors reviewed, could create a misleading or incomplete view of the process underlying Morgan Stanley’s opinion. Except as otherwise noted, the following quantitative information, to the extent that it is based on market data, is based on market data as it existed on or before July 29, 2022, the last unaffected trading day prior to media speculation regarding a potential transaction.

In performing the financial analyses summarized below and in arriving at its opinion, Morgan Stanley, at the direction of the Board, used and relied upon certain financial projections provided by Company management on July 23, 2022 and referred to in this proxy statement as the Updated Management Case. For more information, see the section entitled “The Merger — Certain Financial Forecasts”.

Certain of the following terms are used throughout this summary of financial analyses:

•

“AAV” refers to adjusted aggregate value, calculated as fully diluted market capitalization plus total debt, including capitalized operating lease liabilities, plus preferred stock, plus non-controlling interest, less cash and cash equivalents (including marketable securities and short-term investments).

•

“AV” refers to aggregate value, calculated as fully diluted market capitalization plus total debt, excluding capitalized operating lease liabilities, plus preferred stock, plus non-controlling interest, less cash and cash equivalents (including marketable securities and short-term investments).

•

“EBIT” refers to earnings before interest and taxes.

•

“EBITDA” refers to earnings before interest, taxes, depreciation and amortization.

•

“EBITDAR” refers to earnings before interest, taxes, depreciation, amortization and rent expense.

Discounted Cash Flow Analysis.

Morgan Stanley performed a discounted cash flow analysis, which is designed to provide an implied value of a company by calculating the present value of the estimated future unlevered free cash flows and terminal value of a company. Morgan Stanley calculated a range of implied values per share of Company common stock based on estimates of future unlevered free cash flows for the second half of fiscal year 2022 and each of the fiscal years 2023 through 2026 contained in the Updated Management Case. For purposes of this analysis, unlevered free cash flows were calculated as EBITDAR, less rent expense, less unlevered cash tax expense, less change in net working capital, less capital expenditures, plus deferred taxes.

For purposes of this analysis, Morgan Stanley utilized a ratio comparing estimated AAV of the Company to the EBITDAR of the Company for fiscal year 2026, which ratio Morgan Stanley referred to as “LTM Exit AAV / EBITDAR”. Morgan Stanley calculated terminal values for the Company by applying a range of multiples of LTM Exit AAV / EBITDAR of 4.25x to 5.25x, based on Morgan Stanley’s professional

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 67

THE MERGER

judgment, to the EBITDAR of the Company for the calendar year 2026. Morgan Stanley then adjusted the terminal value for the capitalized operating leases at December 31, 2026 (based on the Updated Management Case) and discounted the unlevered free cash flows and terminal value to present value as of June 30, 2022 using mid-year convention and a range of discount rates from 6.3% to 7.3%, to reflect an estimate of the Company’s weighted average cost of capital.

Based on this analysis, Morgan Stanley derived a range of estimated implied values per share of Company common stock of $93.00 to $113.00, rounded to the nearest dollar, as compared to the consideration offered and payable pursuant to the merger agreement of $102.50 per share.

​	Implied Equity Value Per Share Range for the Company
4.25x – 5.25x LTM Exit AAV/EBITDAR	$93.00 – $113.00

Discounted Equity Value Analysis.

Morgan Stanley performed a discounted equity value analysis, which is designed to provide insight into a theoretical estimate of the future implied value of a company’s common equity as a function of that company’s estimated future earnings. The resulting equity value is subsequently discounted to arrive at an estimate of the implied present value for such company’s potential future per share equity value. In connection with this analysis, Morgan Stanley calculated a range of implied present per share equity values per share on a stand-alone basis for the Company.

To calculate the discounted per share equity value for the Company, Morgan Stanley utilized estimated EBITDAR for the next 12 months (which we refer to as “NTM”) following December 31, 2022 of $1,073 million and December 31, 2023 of $958 million based on the Updated Management Case. Based upon the application of its professional judgment and experience, Morgan Stanley applied a range of multiples of AAV to NTM EBITDAR for the 12-month periods following December 31, 2022 and December 31, 2023 of 3.5x to 4.5x, and discounted the resulting equity values to June 30, 2022 at a discount rate of 9.3% based on Morgan Stanley’s estimate of the Company’s then-current cost of equity. Based on this analysis, Morgan Stanley derived ranges of estimated implied values per share of Company common stock of $59.00 to $93.00, rounded to the nearest dollar, discounted as of December 31, 2022 and $54.00 to $82.00, rounded to the nearest dollar, discounted as of December 31, 2023, and each as compared to the consideration offered and payable pursuant to the merger agreement of $102.50 per share.

​	Implied Equity Value Per Share Range for the Company
3.5x – 4.5x NTM EBITDAR as of 12/31/2022	$59.00 – $93.00
3.5x – 4.5x NTM EBITDAR as of 12/31/2023	$54.00 – $82.00

Publicly Traded Comparable Companies Analysis.

Morgan Stanley performed a publicly traded comparable companies analysis, which attempts to provide an implied value of a company by comparing it to similar companies that are publicly traded. Morgan Stanley reviewed and compared, using publicly available information, certain future financial information for the Company with corresponding future financial information, ratios and public market multiples for other companies that shared certain similar characteristics to the Company (the “Comparable

68 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

THE MERGER

Companies”). For purposes of this analysis, Morgan Stanley analyzed the ratios comparing the AAV to EBITDAR (“AAV / EBITDAR”), for calendar years 2022 and 2023, based on consensus estimates, of the following companies:

•

The Company

•

Air Transport Services Group, Inc. (“ATSG”)

•

Heartland Express, Inc. (“Heartland”)

•

Knight-Swift Transportation Holdings Inc. (“Knight-Swift”)

•

Werner Enterprises, Inc. (“Werner”)

•

ArcBest Corporation (“ArcBest”)

•

Yellow Corporation (“Yellow”)

•

A.P. Møller — Mærsk A/S (“A.P.”)

•

Hapag-Lloyd Aktiengesellschaft (“Hapag-Lloyd”)

•

COSCO SHIPPING Holdings Co., Ltd. (“COSCO”)

•

Evergreen Marine Corporation (Taiwan) Ltd. (“Evergreen”)

Results of the analysis were presented for the Comparable Companies, as indicated in the following tables:

​	AAV / EBITDAR 2022 / 2023
ATSG	5.7x / 5.2x
Heartland	5.0x / 5.1x
Knight-Swift	5.6x / 6.3x
Werner	4.7x / 4.9x
ArcBest	3.6x / 3.9x
Yellow	4.1x / 4.2x
A.P.	1.7x / 3.7x
Hapag-Lloyd	3.3x / 7.3x
COSCO	0.8x / 1.7x
Evergreen	1.1x / 2.5x
Comparable Companies Mean	3.6x / 4.5x
Comparable Companies Median	3.8x / 4.5x
The Company	3.9x / 4.0x

Based on its analysis of the relevant metrics for each of the Comparable Companies and taking into consideration the different business, financial and operating characteristics of the Comparable Companies as compared to the Company and considering historical trading multiples of the Company and upon the application of its professional judgment, Morgan Stanley selected representative ranges of AAV / EBITDAR multiples for fiscal year 2022 of 3.5x to 4.5x and applied these ranges of multiples to estimates of fiscal year 2022 EBITDAR of $1,020 million and $1,043 million, based on the estimated EBITDAR provided by the Company management in the Updated Management Case and consensus estimates from Capital IQ as of July 29, 2022, respectively. Morgan Stanley derived a range of an implied

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 69

THE MERGER

per share price as follows, each rounded to the nearest dollar, as compared to the merger consideration payable pursuant to the Merger Agreement of $102.50 per share:

​	Implied Value Per Share Range the Company
Management 3.5x – 4.5x AAV / 2022E EBITDAR	$61.00 – $92.00
Consensus 3.5x – 4.5x AAV / 2022E EBITDAR	$64.00 – $95.00

No company utilized in the publicly traded comparable companies analysis is identical to the Company and hence the foregoing summary and underlying financial analyses involved considerations and judgments concerning differences in financial and operating characteristics and other factors that could affect the public trading or other values of the companies to which the Company was compared. In evaluating Comparable Companies, Morgan Stanley made judgments and assumptions with regard to industry performance, general business, economic, market and financial conditions and other matters, many of which are beyond the control of the Company, such as the impact of competition on the business of the Company and the industry generally, industry growth and the absence of any adverse material change in the financial condition and prospects of the Company or the industry or in the financial markets in general. Mathematical analysis is not in itself a meaningful method of using publicly traded comparable companies data.

Other Information

Morgan Stanley observed additional factors that were not considered part of Morgan Stanley’s financial analysis with respect to its opinion, but which were noted as reference data for the Board, including the following information described below under the sections entitled “— Historical Trading Range”, “— Equity Research Analysts’ Future Price Targets”, “— Illustrative Leveraged Buyout Analysis” and “— Precedent Transactions Analysis”.

Historical Trading Range.

For reference only, Morgan Stanley reviewed the range of closing prices of the Company common stock over the 52-week period ended on July 29, 2022, the last full trading day prior to media speculation regarding a potential sale of the Company. For the 52-week period reviewed, Morgan Stanley observed that the high and low closing prices of the Company common stock were $59.00 and $96.00 per share, rounded to the nearest dollar, respectively.

Equity Research Analysts’ Future Price Targets.

For reference only, Morgan Stanley reviewed future public market trading price targets for the Company common stock prepared and published by seven equity research analysts prior to July 29, 2022, the last full trading day prior to media speculation regarding a potential sale of the Company. These forward targets reflected each analyst’s estimate of the 12-month future public market trading price of the Company common stock. Morgan Stanley also discounted such 12-month future market trading price estimates by the estimated cost of equity of 9.3% for the Company. Based on the foregoing, the indicative discounted value range of the research analysts’ price targets for the Company, rounded to the nearest dollar, was $49.00 to $119.00 per share.

The public market trading price targets published by equity research analysts do not necessarily reflect current market trading prices for the Company common stock and these estimates are subject to uncertainties, including the future financial performance of the Company, and future financial market conditions.

70 Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement

THE MERGER

Illustrative Leveraged Buyout Analysis.

For reference only, Morgan Stanley performed a hypothetical leveraged buyout analysis to determine the prices at which a financial sponsor might effect a leveraged buyout of the Company. Morgan Stanley based its analysis on the Updated Management Case. Based on its professional judgment and experience, Morgan Stanley assumed (i) a transaction date of June 30, 2022 and an investment period ending December 31, 2026, (ii) a target range of annualized internal rates of return for the financial sponsor of 12.5% to 17.5%, (iii) a 50% debt-to-capitalization ratio and (iv) a range from 4.25x to 5.25x of AAV / LTM EBITDAR exit multiples. Based on these calculations, this analysis indicated a range of implied equity value per share of Company common stock, rounded to the nearest dollar, of $59.00 to $85.00 per share.

Precedent Transactions Analysis.

For reference only, Morgan Stanley performed a precedent transactions analysis, which attempts to provide an implied value of a company based on publicly available financial terms of selected precedent transactions. Based on Morgan Stanley’s professional judgment and experience, the transactions Morgan Stanley deemed most relevant and reviewed for purposes of this analysis included the acquisition of Southern Air Holdings (“Southern Air”) by the Company in April 2016 and the acquisition of Omni Air Internal LLC (“Omni”) by Air Transport Services Group (“ATSG”) in October 2018.

The selected precedent transactions varied significantly based upon company scale, business risks, growth prospects and geography, as well as the prevailing market environment at the time of such transactions. Based on its professional judgment and experience and taking into consideration, among other things, (i) the observed multiples (identified in the table below) for the precedent transactions listed above, and (ii) the prevailing market environment for the valuation and performance of the companies in the Company’s industry at the time of each transaction as compared to the current prevailing market trends, Morgan Stanley applied AV / EBITDA multiples of 5.3x and 5.8x to the Company’s average annual EBITDA for the past three years of $805 million. Based on this analysis, Morgan Stanley calculated estimated implied values per share of Company common stock of $82.00 and $93.00, each rounded to the nearest dollar, as compared to the consideration payable pursuant to the merger agreement of $102.50 per share.

​	Selected Precedent Transaction Multiple		Implied Equity Value Per Share for the Company
Acquisition of Southern Air by the Company	​	5.3x	​	$	82.00
Acquisition of Omni by ATSG	​	5.8x	​	$	93.00

No company or transaction utilized in the precedent transactions analysis is identical to the Company or the merger. In evaluating the precedent transactions, Morgan Stanley made judgments and assumptions with regard to industry performance, general business, economic, market and financial conditions and other matters, many of which are beyond the control of the Company, such as the impact of competition on the Company’s business or the industry generally, industry growth, and the absence of any adverse material change in the financial condition or prospects of the Company or the industry, or in the financial markets in general.

General

In connection with the review of the merger by the Board, Morgan Stanley performed a variety of financial and comparative analyses for purposes of rendering its opinion. The preparation of a financial opinion is

Atlas Air Worldwide Holdings, Inc.   2022 Notice & Proxy Statement 71

THE MERGER

a complex process and is not necessarily susceptible to a partial analysis or summary description. In arriving at its opinion, Morgan Stanley considered the results of all of its analyses as a whole and did not attribute any particular weight to any analysis or factor it considered. Morgan Stanley believes that selecting any portion of its analyses, without considering all analyses as a whole, would create an incomplete view of the process underlying its analyses and opinion. In addition, Morgan Stanley may have given various analyses and factors more or less weight than other analyses and factors, and may have deemed various assumptions more or less probable than other assumptions. As a result, the range of valuations res