Presentation to Board of Directors Project Wilson August 14, 2020

Discussion Framework Within this presentation, we have examined a broad set of options available to Watford and the benefits and considerations associated with each of the options As a standalone ongoing companyRun-off and M&A alternatives Standalone ongoing optionsUsing management’s projections of financial standalone ongoing results, and management guidance on potential alterations to the base plan, have explored the value of the business on a go-forward basis at its current cost of equity and multiples, as well as across a range of sensitivitiesKey question: will changes outlined under various scenarios, if achieved, drive a re-rating of the company’s cost of equity and multiples?Run-off / M&A alternativesHave analyzed management’s projections in a run-off scenario Provide perspectives on potential sale and merger alternatives 2

Potential Alternatives for Watford Multiple potential paths forward exist for WatfordMany standalone paths are not mutually exclusive (i.e., could pursue several options together) 3 Standalone / Organic Run-Off / M&A Status Quo Renegotiation of Service Agreements De-risk Investment Portfolio Arch Sidecar & De-risk Investment Portfolio Run-off Sale Merger 1 4 3 2 6 7 8 Establish Non-Arch (Re)insurance Business 5

Assessment of Standalone / Organic Alternatives 4 Benefits Consideration Description Status Quo Benefit from hardening reinsurance marketInitiatives in place to improve underwriting returns Unclear catalyst to improve valuationUnlikely to address shareholder concernsMay elevate risk of shareholder activism 1 Ongoing operation of the business plan without significant changes Renegotiation of Service Agreements 2 Could result in improved return profile, more in line with broader reinsurance peer groupBoth Arch and HPS motivated to see Watford succeed Potential lack of negotiating leverageExisting agreements limit ability to terminate contractsRun-off key threatDoes not address broader strategic challenges Ability to adjust key terms of service agreements, including fees paid to both Arch and HPS De-risk Investment Portfolio 3 Ability to return capitalEnhances comparability to traditional reinsurersMay improve cost of equity which is elevated vs. traditional reinsurers, likely in part due to higher risk / volatility investment strategy Lower returns / more difficult to achieve targeted returnsPotentially offset by capital returnDependent on support of HPS Shift of investment portfolio from high-yield assets managed by HPS to investment grade bondsShift drives reduced capital requirements, providing opportunity to return capital Arch Sidecar &De-risk Investment Portfolio May improve cost of equity which is elevated vs. traditional reinsurersEnhance scaleFurther benefit from hard market Shareholder patience to reinvest in reinsuranceBalance of capital deployment vs. capital return, particularly at current valuation 4 Shift of investment portfolio from high-yield assets managed by HPS to investment grade bondsShift drives reduced capital requirements, providing capital to write additional reinsurance business Establish Non-Arch (Re)insurance Business 5 Create “franchise value” Would create optionality on renewal of Arch agreement Difficult to pursue under current Arch agreementDependent on finding right team / targetLikely requires multi-year ramp-up pattern to prove out business modelDifficult to pursue as a public company Build out independent insurance / reinsurance business from Arch, either via M&A or hiring

Assessment of Run-Off / M&A Alternatives 5 Benefits Consideration Description Run-Off 6 Realization of value over near-term periodReadily achievable; not dependent on external factors (other than Arch) Arch constraints may complicate ability to sell vehicle to run-off specialist (i.e., as would be financing transaction vs. providing ability to accelerate reserve releases)Contractual fees paid to Arch over run-off period (1% of reserves annually)Risk of some amount of capital becoming “stuck” until regulators release it Place business into run-offProvides ability to return capital as business runs down Sale 7 Realize immediate value for company at premium to current market price Limited universe of partnersDeterrent factor of Arch / HPS agreementsLack of true franchise may limit interestPotentially difficult for run-off company to take on given Arch constraints Sale of company to strategic or financial acquiror Merger 8 Greater scale to improve returnsOpportunity to enhance platform Limited universe of partners; other “total return” reinsurers as key candidatesAbility to reconcile existing Arch / HPS agreements with partners (large number of stakeholders)Desire to issue shares Strategic benefit / resolution of challenges? Merger with partner to create larger platform

WTRE Stock Price Performance and P/BV Multiple Stock Price ($) Since WTRE Listing (x) Source: Capital IQ, SNL Financial (08/11/2020)Notes:Total Return Peers include GLRE and TPRETraditional (Re)insurance Peers include ACGL, ARGO, AXS, RE, RNR and Y 6 Price / Book Value – WTRE vs. Peers WTRE Total Return Re. Peers (1) Traditional Reinsurance Peers (2) 0.45x 0.98x 0.63x WTRE Stock Price Performance Since Listing All-Time High: $28.90 All-Time Low: $10.86 $17.46 Volume (Shares, MM) All-Time High: 0.72x All-Time Low: 0.27x

Comparison of Key Metrics Price / Book Value (x) 2021E ROE (%) Cost of Equity (%) 7 Source: Company Filings, Capital IQ, SNL Financial (08/11/2020)Notes:Total Return Peers include GLRE and TPRETraditional (Re)insurance Peers include ACGL, AXS, RE, RNR and Y WTRE Total Return Re. Peers (1) Traditional Reinsurance Peers (2)

Overview of Management Financial Projections Projections developed by company management based on current operating model (i.e. status quo scenario)Assumed baseline combined ratio and management feesNo de-risking of portfolioNo sidecar Premiums Written ($MM) Combined Ratio (%) Net Investment Assets and Average Yield ($MM / %) Net Income and ROAE ($MM / %) 8 (0.3%) 6.0% (0.7%) 4.2% 4.1% 4.0% Net Yield: (5.9%) 5.1% (5.6%) 9.5% 11.6% 11.0% ROAE:

Dividend Discount Model Summary Projections based on Company Operating Model of status quo scenarioAssumed baseline combined ratio and management feesNo de-risking of portfolioNo sidecarDiscount rate of 10.0% based on Watford’s cost of equityExit multiple of 0.45x BVPS based on Watford’s current trading multiple(1) Notes:As of 08/11/2020Includes loss reserve equity, senior notes, contingent redeemable preferred shares less intangible assets 9 (2)

Analysis of Standalone Alternatives 10 Status Quo Renegotiate Existing Agreements De-Risk Investment Portfolio Arch Sidecar and De-Risk Inv. Portfolio Description 3 point improvement to expense ratio35 bps reduction to investment management expense Transfer $500MM from HPS to investment grade strategy Transfer $500MM to investment gradeUse incremental capital to support larger reinsurance business Baseline assumptions includingHardening marketAchievement of 10%+ ROE 1 4 3 2 Sensitivity Analysis Key Metrics (2023E) Combined Ratio: 99%ROAE: 11.0%Net Yield: 4.0% Combined Ratio: 96%ROAE: 13.9%Net Yield: 4.2% Combined Ratio: 99%ROAE: 9.8%Net Yield: 3.3% Combined Ratio: 97%ROAE: 11.9%Net Yield: 3.1%

M&A Perspectives 11 Run-off a viable potential option, with Arch’s supportHowever, may be self-administered for a period vs. immediate third-party sale given Arch relationship dynamicsArch to receive run-off economics as part of service agreementMay limit run-off buyer interest given run-off model of optimizing claims activity (vs. pure financing)Ultimately, run-off will require exit option as business becomes increasingly sub-scaleSale options may be constrained by Arch service agreementMulti-year agreement with Arch, and Arch retains right to service run-off business in event of saleFew strategics likely to step into such an arrangement absent changesOngoing interest in insurance / reinsurance platforms, though requires reaching agreement with ArchTransactions for non-franchise / run-off companies have generally ranged from ~0.6x-1.0x P/TBV; multiples for franchise transactions in reinsurance space have generally ranged from ~0.8x-1.3x P/TBVMerger option exists, though universe of partners may be somewhat limited - and will likely require Arch cooperationThird Point Re / Sirius transaction as relevant precedentPotentially motivated counterparties in Greenlight Re, ABR and Harrington Re - and in the future, SiriusPointSeveral key questions for merger transaction:Are benefits created sufficient to drive a meaningful re-rating of stock? (i.e., does it improve meaningfully positioning vs. status quo?)Achievability given service agreements with investment/insurance partners (on both sides)

Run-Off Analysis Projections based on Company Run-Off ModelAssumes business is sold after 5 years of run-offAssumes 100% asset reallocation to investment-grade assets upon run-offDiscount rate of 10.0% based on Watford’s cost of equityExit multiple of 0.80x BVPS based on precedent run-off dealsPresent discounted value of Arch run-off fees over 5 years: $42.9MM or $2.14/share Notes:Based on 50% of net reserves 12 (1)

Appendix Supporting Materials 13

Peer Trading Comparables Source: Company Filings, Capital IQ, SNL Financial (08/11/2020)Notes:Reflects median annual combined ratio over the last 10 fiscal years, or since inception as appropriateReflects standard deviation of annual combined ratios over the last 10 fiscal years, or since inception as appropriate Reflects median annual BVPS growth, including dividends, over the last 10 fiscal years, or since inception as appropriateReflects standard deviation of annual BVPS growth, including dividends, over the last 10 fiscal years, or since inception as appropriate Supporting Materials 14 (1) (2) (3) (4)

Select Precedent Transactions (1 of 2) Run-Off P&C Transactions Limited publicly available data on P&C run-off transactionsOn a recent P&C run-off transaction Morgan Stanley worked on, bids were generally in the 0.85-1.00x range of tangible book valueGreenlight Re rumored to have rejected run-off bid at around ~0.9x P/BV in late 2019 15 Select Precedent Transactions Source: Capital IQ, SNL Financial, Company Filings and MaterialsNotes:Deal value reflects implied value of 100% stake; book value and tangible book value reflect 12/31/2019 figures (nearest available) (1) (1) (1)

Select Precedent Transactions (2 of 2) 16 Select Precedent Transactions Supporting Materials Source: Capital IQ, SNL Financial, Company Filings and MaterialsNotes:Represents premium paid to public shareholders; does not incorporate value to CMIHBook value and tangible book value reflect 2Q20 figures as referenced in Third Point investor presentation, which preceded Sirius earnings announcementPartnerRe 6/30/2015 book value adjusted for $315MM breakup fee payable to AXISUtilizes 2018E EPS (instead of NTM EPS) as NTM artificially low due to 4Q’17 losses (3) (3) (2) (2) (1) (4)

17 Cost of Equity Analysis Watford Cost of Equity Analysis Supporting Materials Source: Capital IQ, SNL Financial (08/11/2020)

Third Point Re Merger with Sirius Group Transaction Overview On August 7, 2020, Third Point Re and Sirius Group announced plans to merge to create SiriusPointDeal values Sirius Group at $788MM(1)Transaction value represents ~80% of Sirius’ 2Q’20 TBVThird Point LLC to manage assets directly under the direction of SiriusPointDeal is expected to be accretive to EPS and ROE with limited book value dilutionSid Sankaran, former AIG CFO and Chief Risk Officer to be Chairman and CEO Transaction Structure Third Point to acquire 100% of Sirius GroupSirius shareholders will have ability to elect one of three options:$9.50 in cash per shareTPRe shares plus two year CVR which, taken together, guarantees that on the second anniversary of the closing date the electing shareholder will have received equity and cash of at least $13.73 per share on that datei) cash, ii) TPRe shares, iii) Series A preference shares, iv) five year warrants and v) upside share instrumentCMIH has agreed to elect option #3 and has agreed to a 9.9% voting cap and lockup agreementCMIH expected to own ~39%(2) of SiriusPointExisting excess cash and $125MM bridge loan commitment providing funding for cash consideration and other redemptionsDaniel S. Loeb, Third Point’s largest individual shareholder, to provide an equity commitment of $50MM Expected Business Mix Notes:Assumes all minority investors elect option 2 at $13.73 of value and CMIH elects option 3 based on 0.743x and TPRe share price of $8.15 (excludes warrants and upside share instrument as both are out of the money)Based on pro forma diluted shares outstanding (includes Series A preference shares)Includes cash and cash equivalents (including restricted cash) Supporting Materials 18 2Q’20 GPW LTM $2.5Bn 78% Insurance 22% Reinsurance $6.1BnTotal Invested Assets (3) Expected SiriusPoint Investment Mix Third Point attempting to shift from “hedge fund reinsurer” model to more traditional reinsurance modelAcquired more traditional reinsurance business / platformHave actively de-risked investment portfolio over time

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