Investor Update – March 2024

Maiden Holdings, Ltd.Fo urth Quart e r 2023 In vestor Pr esen ta tionMar ch 2024~PAGE-BREAK~Invest or Disclosur es2Forward Looking StatementsThispresentationcontains"forward-lookingstatements"whicharemadepursuanttothesafeharbor provisionsofthePrivateS ecurities LitigationReformActof1995.Theforward-lookingstatementsarebasedonMaidenH oldings, Ltd.'s(theCompan y")futuredevelopmen tsandtheirpotentialeffectsontheCompany.Therecanbenoassurancethatactualdevelopmen tswillbethoseanticipatedbytheCompany.Actualresultsmaydiffermateriallyfromthoseprojectedasaresultof signific antrisksanduncertainties, includingnon-receiptoftheexpectedpayments,changesininterestrates,effectoftheperf ormance offinancial marketsoninvestmentincomeandfairvaluesofinvestments,developmentsofclaims andtheeffectonlossreserves,accuracyinprojectinglossreserves,theimpactofcompetitionandpricingenvironments, changesinthedemand forthe Compan y'sproducts,theeffectofgeneraleconomicco nditions and unusual fr equency ofstormactivity,adversestateandfederallegislation,regula tionsandregulatoryinvestigationsintoindustrypr actices, developmen tsrelatingtoexistingagr eemen ts,heightenedcompetition,changesinpricingenvironments,andchangesinassetvalua tions.Additionalinformationabout theserisksanduncertainties,aswellasothersthatmaycause actualresultstodiffermateriallyfromthoseprojectediscontainedinItem1A,RiskFactorsintheCompany'sAnnual ReportonForm10-Kfortheyearended December31, 2023,filedwiththeSEConMarch12,2024.The Companyundertakesnoobligationto publicly updateanyforward-lookingstatements,exceptasmayberequiredbylaw.Anydiscrepancies betweentheamounts included inthispresentationandamounts included intheCompany'sForm10-KforthethreeandtwelvemonthsendedD ecember 31, 2023, filedwiththeSECareduetorounding.Non-GAAP FinancialM easuresIn additionto theS ummary Consolidat ed BalanceS heetsa nd Co nsolidat ed Stat em en ts of Inco me,m anag em entu sesc erta inkeyf inancial me asures,s omeofw hich aren on-GAAP me asures,toeva luatet he Compan y'sf inancial perf ormancea nd theov er allgrowthinv aluege neratedf or theC ompany's commons hare hold er s.Manage ment believ es that these measur es,wh ichmay be de finedd ifferent ly by otherc ompanies,ex plaint he Company'sr esultsto invest orsina manner that allowsforamorecom plete underst andingofthe under ly ingtre nds in theCom pany's business.T he non-GAAPmeas ures should notbev ew das asubstitu efo thos ede ermine di nacco danc ewit hU.S .GAAP .Seeth eAppend xo fth spresen atio nfo are concilia tion of theC ompany's non-GAAP measur esto then earest GAAP measur e.~PAGE-BREAK~Maiden Holdings Financial Ov er vie w3• Adjusted book v a lue incr eased t• $3.19 per share as of December 31, 2023, and cont inues t• bestable and represen ts true economic v alue of MaidenoReport ed book v a lue per common shar e decr ease to $2.48 per shar e as of December 31, 2023, reflectsGAAP P&L v olatility fr om loss deve lopmen t mostly subject t• LPT/ADC• See Q4 and YTD r esults recap starting on slide 9• Nearly 67% of the total PPD in YTD 2023 expected to retuas futur e GAAP income fr omLPT/ADC• Nearly 65% of the total PPD in Q4 2023 expected to retuas futur e GAAP income fr om LPT /ADCoDeferred ga in of $70.9m at 12/31/2023 expect ed to be recogniz ed as GAAP income ov er time as LPT /ADCre coveries ar e re ceived subject t• reinsurance contra ct and r elevant GAAP accoun ting rules• Current estimate is re ceipt of LPT/ADC recoveries expect ed to commence la te in 2024• Investment re sults signific antly stronger in 2023 - $53.1m vs. $24.7m• Higher yields on collateral asse ts and streng thening re turns on alt ernative assetsoAlternative asse t returns in 2023 of 8.0% now in excess of cost of debt capit al• Deferredta x asse t of $1.19 per shar e not y et re cogniz ed in book v alue• $337.4m in NOL carry forwards at 12/31/2023 - $151.2m or 44.8% have no ex piry dateoFo cus on curr en t income pr oducing asse ts targets to offset cont inuing r eserve deve lopmen t* Please see the definition of non-GAAP financial measures in the Appendix of this presentation for additional important information regarding certain terms used herein~PAGE-BREAK~Maiden Holdings Business Str ategy4• We create shar eholder value by active ly mana ging and alloca ting our assets and capit aloWe leverage our deep knowledg e of the insur ance and related financial ser v ices indus tries intoowners hip and manag ement of businesses and asse ts with the opportunity f or incr eased r eturns• Our strate gy allow s us to more flex ibly alloca te capital to activities we believe will pr oduce thegreatest returns fo r our common shar eholder s• Our strategy curren tly has two principal ar eas of focus• Asse t manag ement-inves ting in asse ts and asset cl asses in a pruden t but expansiv e manner in or derto ma ximize investment returns• We limit the insur a nce risk w e assume relative to the asse ts we hold and main tain required regulatory capital atvery strong levels to manage our aggregate risk pr ofile• Capita l manag ement-effective ly managing capit al a nd when appr opriate, repur chasing securities orre turning capital to enhance common shar eholder returns• Strategic focus cont inues t oevolve -leg acy under w riting now in run-offoDeve loping mor e predictable ar eas of r evenue and pr ofit a priority -activ ely ex ploring opportunitiesto ex pand in f ee-base d and insur a nce distributio n an ar ea of fo cus, possibly supplemen ted bydeploying limit ed reinsura nce capacity• Capita l commitmen t to GLS has been comple ted a nd no additional capit a l commitmen ts to newlegacy deals will occur -w ill run-off exis ting deals• We believe these ar eas of strategic focus will enhance our profit abilityoWe believe our strategy incr eases the lik elih ood of fully utilizing the significan t tax NOLcarryf orwardsw hich would cr eate additional common shar eholder v alue• Expect ed re turns fr om each strate gic pillar are ev aluated relative to our cos t of debt capit al~PAGE-BREAK~Asse t Manag e men t Upda te5*Please see the definition of non-GAAP financial measures in the Appendix of this presentation foradditional important information regarding certain terms used herein~PAGE-BREAK~Asse t Manag e men t Upda te6* Please see the definition of non-GAAP financial measures in the Appendix of this presentation foradditional important information regarding certain terms used herein Alternative Investments• Alternativeinvestmentsincr eased by 13.4%to$309. 0mat 12/31/2023 comparedto $272.5m at 12/31/2022,withacon tinuing incr eased focus oncont ributing tocurrentincome pro ducing assetsoCont ributions to Private Cr edit & Alt ernative Investmentsrepresented 48.8% of all cont ributions YTD 2023, with privatecredit at 22.9% and alt ernative investments at 26.8%• YTDtotalgrossreturns onalternativeinvestmentsfor2023of $23.6m vs. $5.0mfor2022oRe turns bene fited fromrealized & unrealized gainsfromincr eases in net asse t values in cert ain privat e equityinvestments, which incr eased $10.7m in 2023• ver 2022oReturns further bene fited fr om unr ealized gains fromincr eases in net asse t values on cert ain private creditinvestment s, which incr eased $4.2m year over yearoCurren t income on cert ainprivatecredit & realestateinvestmentsincr eased re turns $2.0m y ear over yearoRe duction of exposure to the hedg e fund asset class in2023 incr eased re turns $5.1m y ear over year• AnnualizedYTD2023grossreturnofthealternativeportfolioof8.1%oStill on track to ex ceed long-t erm benchmark returns - seeslide 7 fo r additional retudata• Numerousalternativeandrealestateinvestmentsnotmarkedtofairvalueyet-tooearlyinlifecycleofinvestments-expectedtoproducefuturereturns andgainsFixe d Income• FixedIncomereturns primarily drivenby higher income fromAmTrustloanandAFS securities• Short portfolio duration of 1.2 years well positioned forcurre nt credit marke t volatility• Higher yields on cash equivale nts and floating rate CLOs areoffsetting the impact of sh rinking fixed income portfolio• F xedincomeportfo iocon inuestodecreaseinsizeasAmTrust liabilities continuetorunoff• Payments now being made from Funds Withheld• Floatingratesecuritiescompose $246.8m or40.8%offixedincome investmentswhichisreducinginterestraterisko$78. 8m or 13.0% are CLOs which may be credit sensitive• Average CLO rating is AA+ with 94.7% rated AAA• EUR CLOs of $77.8m yield is 5.6%• USD CLOs of $0.9m yield is 9.6%o$168.0m or 27.8% is floating rate loan to related party and ispriced at Fed Funds rate + 200 basis points• Current yield of related party loan remains at 7.3%• Effective YTD 2023 yield of related party loan is 7.0%Performance of Investable AssetsFor the Three Months Ended December 31 2023 2022 2023 2022Gross Returns 1.6%1.1% 3.2%-0.4%Net Returns 1.6%1.1% 3.1%-0.1%For the Year Ended December 31 2023 2022 2023 2022Gross Returns 4.8%-0.3%8.1%2.0%Net Returns 4.8%-0.4%8.0%2.0%2.Alternative investments include other investments, equity securities, and equity method investments.4.Average invested assets is the average of the amounts disclosed in our quarterly U.S. GAAP consolidated FS3.Change in accumulated other comprehensive income ("AOCI") excludes unrealized FX gains and losses.Fixed Income Alternative Investments1.Fixed income includes AFS securities, cash, restricted cash, funds withheld, and loan to related party.~PAGE-BREAK~Asse t Manag e men t Upda te7*Please see the definition of non-GAAP financial measures in the Appendix of this presentation foradditional important information regarding certain terms used herein Alternative Investment Highligh ts• Ex cluding the 2022 saleofafundinvestmentfocused ondebtinstrumentsintherealestatesector,thecurrentportfolioofprivatecreditinvestmentsproducedaninternalrateofreturnof8.7%andamultipleoninvested capitalof1.02x• Through2023,realizedgainsof$4.8milliononthesaleoftheCompany'sstakeinBetterviewi ncluding aQ4 2023cashandstocksaletra nsaction -todateourinvestmentinBetterviewhasproduced aninternalrateofreturnof 28.9% anda multiple oninvested capitalof2.63x• 38.5% ofourtotalalternativeassetsasof 12/31/2023, primarily intheAlternativesandRealEstateassetclasses,donotreflectanyreturnstodatebasedonthedeve lopment stageoftheseinves tments,whichweexpecttoincr easeinfutureasinvestmentsdevelop• Inception todate,alternativedirectinvestmentsonrealassetshavepr oduced aninternalrateofreturnof37.8% anda multiple oninvested capitalof1.36x• SeeForm 10-Kfor further importantdetailsonalternativeinvestmentportfolio andrelatedreturns~PAGE-BREAK~Capit a l Manag emen t Upda te• Maiden con t inued active but disciplined long-t erm capital manag ement in Q4 2023• Our subsidiary Maiden R einsurance Ltd. (" MRL") r epur chased 619,470 common shar es in openmarket at an average price of $1.69 per shar e in Q4 2023• 2023 YTD r epur chases tota led 1,439,575 c• mmon shar es at $1.83 per shar e• MRL repur chased 5,567 senior notes in open mark et in 2023 at an average price of $17.10 per shar e• Maiden e x pects t• mainta in activ e but prude nt and long-t erm appr oach t• balance sheetmanag ement as part of its ov erall strategy• Significan t Boar d authoriz ation re mains f• r both co mmon shar es and senior notes tocove r both openmarket pur chases and priv at ely neg otiated trades• $71.6 million and $99.9 million in authoriz ation av ailable for common share and seniornoterepur chases, r e spectiv ely• MRL owns 29.9% of Maiden common shar es, but is limit ed to 9.5% v oting powerperMaiden bye-laws• Common shar es owne d by MRL elimina ted for accoun ting and f inancial re porting purposes on theCompan y'sc onsolida ted financial s tatemen ts and pr esented as tr easury sharesoPer share comput ations re flect elimina tion of MHLD common shar es owned b y MRL of 42,878,9238* Please see the definition of non-GAAP financial measures in the Appendix of this presentation foradditional important information regarding certain terms used herein~PAGE-BREAK~Maiden Holdings - Q 4 2023 R e sults R ecap9* Please see the definition of non-GAAP financial measures in the Appendix of this presentation foradditional important information regarding certain terms used herein CommentsQ4 2022Q4 2023($ millions, exce pt per share amounts) Net Income and Per Share Data• Net income available tocommon sharehol ders in Q4 2022 includes $87.2m of gainsfrom exchange of preference shares• Summa ry GAAP and Non-GAAP Financial Measures in Appendix$36.2  $0.41$(20.8)  $(0.21)GAAP Net (Loss) Income   (Attributable) Availablet• Common SharesPer comm on share• Improvement driven by stronger investme nt results, lower underwriting loss andlowerforeign exchange and other losses$(51.0) $(20.8)GAAP Net Loss (excl. preference share gains) Key Income Statement Details• Decline in underwriting loss in quarter, AmTrust segment had unde rwriting loss of$19.6m while Diversified Reinsurance  segment had unde rwriting loss of $1.5m• See slide 10 for detail on under w riting results and prior period loss developm ent$(35.5) $(21.1)Underwriting Loss• Net investment income 10.1% lower at $8.3m in Q4 2023 vs. $9.2m in Q4 2022 due tolower income from fixed income securities & Funds Withheld assets as asset balance scontinue to decrease• Realized and unrealized gains of $5.5m in Q4 2023 vs.losses of $(8.0)m in Q42022 mainly attributa ble to gains on equity securities & other investments, furtheraided by decrea sed losses on sales of AFS securities• Income from equity method investments of $0.9m vs. income of$1.9m in Q42022 mainly attributable to investments in the alterna tive & private equity assetclasses$3.1$14.6Investment Results• Operat ing expenses increased slightly, by $0.8m or 12.5% vs. Q4 2022 due to increasein legal, audit and tax fees$6.3$7.1Operat ing Expenses• Primarily due to reserve revaluation due to we akening of U.S. dollar relative to Euroand British pound$(10.9) $(4.9)Foreign Exchange/ OtherLosses~PAGE-BREAK~Q4 2023 UW R e sults and Loss Dev e lopmen t• Underwriting loss of $21.1m in Q4 2023 vs.$35.5m inQ4 2022oLower adverse prior year loss deve lopmen t of $22.2m inQ4 2023 compar ed to $38.1m of advers e prior y ear lossdeve lopmen t in Q4 2022• AmTrus t had low er adverse loss dev e lopmen t of$21.7m in Q4 2023 compar ed to $31.6m in Q4 2022• Net adverse prior year loss development inQ42023wasp rimarily due to unf avorable development inAIUL program business of $14. 8m, Hospital Liability of $4.4mandC LD Auto and Gene ral Liability of $4.2m partly offset bycontinued f avorable developm ent in Workers' Compensationof $6.4m• $14. 4m or 66.4% of adverse lo ss development experienced in   the AmTrust segmentin Q4 2023 is covered by the Enstar   LPT/ADC and is expected to be  recognized  as future GAAP   income over time as LPT/ADC recove ri es are receiv ed s ubj ect to relevant GAAP accounting rules• Recoveries from Enstar LPT/ ADC presently anticipated to   commence in late 2024o Divers ified had lowe r advers e loss deve lopmen t of   $0.5m in Q4 2023 compar ed to  advers e deve lopmen t of   $6.5m in Q4 2022• Adverse prior year developmen tm ostly due to GLS and IISpartly offset by Motorsreduc tion in credit loss reserve.  10~PAGE-BREAK~

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Maiden Holdings Ltd. published this content on 12 March 2024 and is solely responsible for the information contained therein. Distributed by Public, unedited and unaltered, on 12 March 2024 20:39:44 UTC.