Aspen Insurance Holdings Limited Macquarie Bermuda in Boston Conference Richard Houghton Chief Financial Officer Brian Boornazian CEO, Aspen Reinsurance September 21, 21 1
Safe Harbor Disclosure This slide presentation is for information purposes only. It should be read in conjunction with our financial supplement posted on our website on the Investor Relations page and with other documents filed by Aspen Insurance Holdings Limited (the Company or Aspen ) with the U.S. Securities and Exchange Commission. Non-GAAP Financial Measures In presenting Aspen's results, management has included and discussed certain "non-gaap financial measures", as such term is defined in Regulation G. Management believes that these non-gaap measures, which may be defined differently by other companies, better explain Aspen's results of operations in a manner that allows for a more complete understanding of the underlying trends in Aspen's business. However, these measures should not be viewed as a substitute for those determined in accordance with GAAP. The reconciliation of such non-gaap financial measures to their respective most directly comparable GAAP financial measures in accordance with Regulation G is included herein or in the financial supplement, as applicable, which can be obtained from the Investor Relations section of Aspen's website at www.aspen.bm. Application of the Safe Harbor of the Private Securities Litigation Reform Act of 1995 This presentation contains written or oral forward-looking statements within the meaning of the U.S. federal laws. These statements are made pursuant to the safe harbor provisions of the Private Securities Litigation Reform Act of 1995. Forward-looking statements include all statements that do not relate solely to historical or current facts, and can be identified by the use of words such as expect, intend, plan, do not believe, aim, project, anticipate, seek, will, estimate, may, continue, guidance, and similar expressions of a future or forward-looking nature. All forward-looking statements address matters that involve risks and uncertainties. Accordingly, there are or will be important factors that could cause actual results to differ materially from those indicated in these statements. Aspen believes these factors include, but are not limited to: changes in insurance and reinsurance market conditions that could adversely impact execution of the business plan; the continuing and uncertain impact of the current lower growth economic environment in many of the countries in which we operate; the risk of a material decline in the value or liquidity of all or parts of our investment portfolio; changes in our ability to exercise capital management or strategic initiatives or to arrange banking facilities as a result of prevailing market changes or changes in our financial position; our ability to execute our business plan to enter new markets, introduce new products and develop new distribution channels, including their integration into our existing operations; increased counterparty risk due to the impairment of financial institutions; changes in the total industry losses, or our share of total industry losses, resulting from past events such as Hurricanes Ike and Gustav and, with respect to such events, our reliance on loss reports received from cedants and loss adjustors, our reliance on industry loss estimates and those generated by modelling techniques, changes in rulings on flood damage or other exclusions as a result of prevailing lawsuits and case law, any changes in our reinsurers credit quality and the amount and timing of reinsurance recoverables; the impact of acts of terrorism and related legislation and acts of war; the possibility of greater frequency or severity of claims and loss activity, including as a result of natural or man-made (including economic and political risks) catastrophic events, than our underwriting, reserving, reinsurance purchasing or investment practices have anticipated; evolving interpretive issues with respect to coverage after major loss events; the level of inflation in repair costs due to limited availability of labor and materials after catastrophes; the effectiveness of our loss limitation methods; changes in the availability, and any new intervening legislative or governmental action, cost or quality of reinsurance or retrocessional coverage; the reliability of, and changes in assumptions to, natural and man-made catastrophe pricing, accumulation and estimated loss models; loss of key personnel; a decline in our operating subsidiaries ratings with Standard & Poor s ( S&P ), A.M. Best or Moody s Investors Service ( Moody s ); changes in general economic conditions, including inflation, foreign currency exchange rates, interest rates and other factors that could affect our investment portfolio; the number and type of insurance and reinsurance contracts that we wrote at the January 1st and other renewal periods and the premium rates available at the time of such renewals within our targeted business lines; increased competition on the basis of pricing, capacity, coverage terms or other factors and the related demand and supply dynamics as contracts come up for renewal; decreased demand for our insurance or reinsurance products and cyclical changes in the insurance and reinsurance sectors; changes in government regulations or tax laws in jurisdictions where we conduct business; and Aspen or its Bermudian subsidiary becoming subject to income taxes in the United States or the United Kingdom; and the effect on insurance markets, business practices and relationships of ongoing litigation, investigations and regulatory activity by insurance regulators and prosecutors. For a more detailed description of these uncertainties and other factors, please see the "Risk Factors" section in Aspen's Annual Reports on Form 1-K as filed with the U.S. Securities and Exchange Commission on February 26, 21. Aspen undertakes no obligation to publicly update or revise any forward-looking statements, whether as a result of new information, future events or otherwise. Readers are cautioned not to place undue reliance on these forward-looking statements, which speak only as of the dates on which they are made. In addition, any estimates relating to loss events involve the exercise of considerable judgment and reflect a combination of ground-up evaluations, information available to date from brokers and cedants, market intelligence, initial tentative loss reports and other sources. Due to the complexity of factors contributing to the losses and the preliminary nature of the information used to prepare these estimates, there can be no assurance that Aspen s ultimate losses will remain with the stated amount. 2
Summary Who we are What we do The Aspen approach How it all adds up Our investment proposition Appendix 3
Who We Are Bermuda domiciled Specialty Insurer and Reinsurer Founded 22; IPO 23; $2.1bn market cap 21* $2.1bn GWP in 29; estimate $2.1bn +/- 5% GWP for 21** STRONG BALANCE SHEET MULTI-PLATFORM APPROACH WELL DIVERSIFIED PORTFOLIO $3.3bn of total capital, as of June 3, 21 Ratings of A (S&P), A2 (Moody s) and A (AM Best) Diluted BVPS 17% CAGR over four years 3 main underwriting locations: London, Bermuda and US Branch offices in Paris, Zurich, Cologne, Singapore, Dublin and 3 main locations in the US Focus on Specialty Lines Insureds tend to be more unusual or higher risk Typically requires high degree of individual risk underwriting expertise 58% Reinsurance, 42% Insurance*** 53% Property, 47% Casualty*** Underwriting Led, Diversified Specialty Insurer and Reinsurer Underpinned by Strong Risk Management Culture * As at August 23, 21 **Estimated as at July 28, 21 *** LTM to June 3, 21 4
What We Do 23 LTM** June 21 Insurance vs. Reinsurance* Insurance 23% 77% Reinsurance 42% Insurance 42% 42% 58% 58% Reinsurance Property vs. Casualty* Casualty 39% 61% Property Casualty 47% 53% Property GWP by Core Platform Bermuda 4% US 2% 94% UK Bermuda 18% US 18% 19% 64% UK Global Footprint 176 employees 4 offices, 3 countries 66+ employees 17 offices, 8 countries Balanced Business Lines, Diversified Production Sources and Increased Global Presence * By GWP **Last Twelve Months 5
What We Do Our strategy has 6 key elements: Diversified underwriting platform (product, peril and geography) Measured expansion where Aspen has a competitive advantage consistent with market conditions = continuous investment in our franchise Execution framework underpinned by strong risk management infrastructure and culture Focus on spreading risk and lowering volatility Prudent stewardship of capital People - hiring and development of talent Creating Franchise Value 6
What We Do Setting our Risk Return Profile Risk appetite statement core component of our Risk Management framework Risk preferences Risks inside and outside of core mission and strategy Return objective Sets the levels of return on capital we seek to achieve, subject to risk constraints Volatility constraint Limit on earnings volatility Capital constraint Minimum level of risk adjusted capital Integrated Risk Management Underpinning Everything We Do 7
What We Do The Specialty Approach Underwriting Risk Profiles by Segment (21e) UW Loss ($M) Insurance Reinsurance Diversification Total StDev 12 185 13.9% 146 1 in 25 382 663 19.6% 84 1 in 1 297 575 17.8% 717 1 in 1 98 125 23.8% 17 Probability Insurance Lower average return, less tail risk, more normally distributed Reinsurance Higher average return, significant tail, skewed distributed Combined Insurance and Reinsurance -119-119 -19-19 -99m -99-89m -89-79m -79-69m -69-59m -59-49m -49-39m -39-29m -29-19m -19-9m -9 1m 1 11m 11 21m 21 31m 31 41m 41 51m 51 61m 61 Underwriting Profit ($m) Combined book (insurance and reinsurance) benefits from diversification between the two risk profiles Specialty Approach Results in Lower Earnings Volatility 8
What We Do Risk Profile As At January 1, 21 Net Income* Mean 11.5% ROE Probability of under-performing mean by 5% or more = 24% Median 13% ROE Probability Probability of negative income 11% 1-in-1-27% ROE 1-in-25-36% ROE -1,5, -1,3, -1,1, -9, -7, -5, -3, -1, 1, 3, 5, 7, 9, 1,1, Return $m Return Profile Consistent with Risk Appetite Disclaimer: The above graph is based on the 21 plan without adjustment for H2 21 actual performance. The risk profile is the result of numerous assumptions within our Economic Capital Model. Results may vary significantly from those shown. (*) Return periods shown relate to total annual net income 9
What We Do Reinsurance: Overview and Strategy 12 underwriting units in 4 divisions GWP LTM* to June 3, 21: $1,239m Aspen Approach Established market leader Presence in major market hubs allowing close proximity to customers Deep expertise and understanding of client needs and risks Focus on smaller, specialized companies and risks to maintain portfolio diversity Focus on clients where reinsurance and reinsurance relationships are a vital part of their business need 24% 24% 29% 23% Property Catastrophe Reinsurance Other Property Reinsurance Casualty Reinsurance Specialty Reinsurance Property Catastrophe Reinsurance Property Other Casualty Reinsurance Specialty Reinsurance Treaty Catastrophe Treaty Risk Excess Treaty Pro Rata Global Property Facultative Risk Solutions US Casualty Treaty International Casualty Treaty Global Casualty Facultative Credit & Surety Reinsurance Agriculture Specialty Reinsurance Structured *Last Twelve Months 1
What We Do Insurance: Overview and Strategy 13 underwriting units in 4 divisions GWP LTM * to June 3, 21: $95m Aspen Approach Specialist E&S type approach to underwriting within Insurance operations Bias towards complex risks 18% 2% 14% 48% Diverse portfolio of disparate insurance risks Divisional focus compliments in-house underwriting expertise Marine, Energy and Transportation Financial and Professional Lines Property Insurance Casualty Insurance Marine, Energy and Transportation Financial and Professional Lines Property Insurance Casualty Insurance MEC Liability Energy Property Marine Hull Specie Aviation Financial Institutions Professional Liability (including Management and Technology Liability) Financial & Political Risks UK Commercial Property & Construction US Property (E&S) UK Commercial Liability Excess Casualty US Casualty (E&S) *Last Twelve Months 11
The Aspen Approach Managing Growth Growth Continuum Hiring of individual underwriters Establishment of new underwriting units Bolt on acquisitions Transformational M&A Key Evaluation Criteria Strategic fit Financially attractive Manageable execution risk Consistent with our risk management appetite Regular Evaluation of Opportunities Consistent with Market Conditions in Accordance with Strict Criteria 12
The Aspen Approach Investing in our Franchise Products Platforms Specialty RI (Aviation & Marine) US Casualty Re US E&S lines US based reinsurance lines - Property (including Fac) - Casualty (including Fac) Aviation Insurance Marine Insurance Energy Insurance 3 4 5 International Property Facultative Reinsurance Financial & Political Risk Insurance Financial Institutions Insurance Non-US Management Technology and Liability Insurance Non-US Professional Liability Insurance Non-US Excess Casualty Transportation related Liability Insurance Specie Insurance International Casualty Faculative Reinsurance Credit & Surety Reinsurance 6 7 8 9 1 Non-US Agriculture Reinsurance US Professional Liability Insurance US Directors & Officers Insurance US Excess Casualty Insurance Bermuda London US Paris Zurich Dublin Lloyd s Singapore Miami Cologne Development of GWP GWP $m 2 15 1 5 22 23 24 25 26 27 28 29 Year 29 Lines 28 Lines 27 Lines 26 Lines 25 Lines 24 Lines 23 Lines Original Lines Incremental Expansion into Adjacent Business Lines Consistent with Diversification Strategy and Market Conditions 13
The Aspen Approach Testing Conventional Wisdom Aviation Insurance Political and Financial Risk Insurance Credit & Surety Reinsurance Inception 25 GWP $113m; combined ratio 92% (29) 29 third consecutive loss-making year for industry; industry sector loss ratio estimated at >11% including Air France loss Aspen 29 result likely to be comfortably in the top quartile for the industry Inception 28 GWP $33m; combined ratio 81.1% (29) GWP $39m; combined ratio 83.% (28) Building reputation as a market leader while sustaining core principle of underwriting profitability Quantitative credit analysis Fundamental analysis Structural analysis Policy documentation Inception 29 29: GWP $49m; combined ratio 89.6% Well positioned to benefit from rating improvements in 21 in response to global financial crisis Focus is primarily European and ex-us; US Surety business excluded Very Strong Performance in Selected Lines Despite Challenging Market Conditions Reflecting Specialist Approach 14
The Aspen Approach 21 and Beyond Business Key Elements Insurance Build out US Insurance platform Addition of Admitted Market capability Round out London Market portfolio Addition of selected lines Development of UK regional platform Establishment of foothold in Swiss insurance market Build out of non-us operations Reinsurance Establishment of Miami office targeting Latin America Continued selective build out for Continental Europe and Asian operations Watching brief on Middle East Measured Growth in Exposures We Know and Understand Subject to Market Conditions 15
The Aspen Approach Key Focus Areas 21 / 211 Macro economic environment Pricing adequacy Cycle management Investment returns Capital deployment 16
The Aspen Approach Shareholder Value Creation: Pulling the Financial Levers Shareholder Value Creation 27-29 3% Value Creation (%) 25% 2% 15% 1% 26.1% 2.% 3.1% 1.2% 23.% 1.9% 1.2% 17.% 3.6% 14.9% 8.% 5.9% 9.6%.8% 1.7% 5% % 9.1% 27 2.1% 1.9% 28 5.7% 8.1% 29 3.2% 3.9% 21 Dividends Other Currency Unrealised Investment Returns Year Investment Income & Realised Gains/Losses Underwriting & Operating Contribution Capital Management Efficient Management of Financial Levers Crucial to Value Creation 17
The Aspen Approach Business Performance and Market Outlook Q2 21* Performance 1 Absolute Pricing 2 Relative Price Movement 3 Terms & Conditions 4 Volume change 5 Outlook 6 Reinsurance Q3'9 Q4'9 Q1'1 Q2'1 Q3'9 Q4'9 Q1'1 Q2'1 Q3'9 Q4'9 Q1'1 Q2'1 Q3'9 Q4'9 Q1'1 Q2'1 Q3'9 Q4'9 Q1'1 Q2'1 Q3'9 Q4'9 Q1'1 Q2'1 Property Catastrophe Reinsurance Treaty Catastrophe Other Property Reinsurance Treaty Risk Excess Treaty Pro Rata Property Facultative Casualty Reinsurance International Casualty Treaty US Casualty Treaty Casualty Facultative Specialty Reinsurance Credit Surety & Political Risk RI Specialty Reinsurance Insurance Property Insurance UK Commercial Property & Construction Ins US Property E&S Insurance Casualty Insurance UK Liability Insurance Excess Casualty Insurance US Casualty E&S Insurance Marine, Energy & Transportation Insurance MEC Liability Insurance Energy Property Insurance Marine Hull Insurance Aviation Insurance Specie Financial & Professional Lines Insurance Financial Institutions Insurance Professional Lines Insurance Political & Financial Risks Insurance * As at June 3, 21. Key located on final page of presentation. 18
The Aspen Approach Managing the Cycle UK Liability US Casualty Re 25 2 223.2 212.5 171.2 25 2 25 2 261. 237.3 222.3 219.7 3 25 RRV index 21=1 15 1 75.7 124.8 92.2 75.1 15 1 GWP $m RRV index 21=1 15 1 17.5 181.2 163.1 14.5 2 15 1 GWP $m 5 21 22* GWP $m (LH scale) 23 24 25 26 27 45.4 44.6 28 29 21e** 5 RRV index (RH scale) 5 4.9 Proactive Management of Cycle 21 22* GWP $m (LH scale) 23 24 25 26 27 28 29 21e** 5 RRV index (RH scale) * Since inception June 22 ** Estimated GWP for 21 (full year) *** Renewal Rate Variation Report (RRV) monitors the change in rate for the risk from one year to the next 19
The Aspen Approach Investment Philosophy and Current Appetite Likes High quality credit Active management of problem issues Simplicity Input from multiple money managers Freedom to optimise investments over the yield curve Quality of investment decisions shown in total returns Dislikes High volatility Concentrated big bets Constriction on flexibility Exclusive focus on income statement Impairment charges X Current approach Maintain fixed income credit quality at AA or better Maintain duration between 3. and 3.5 years driven by yield curve sweet spot Incrementally add to A rated or better corporate bonds at 4%+ Add to Agency MBS at 4% and better Put cash to work in rising rate environment Hygienic actions on limited lower quality portion of portfolio Focus on Long Term Holdings of Liquid High Quality Credit Instruments 2
The Aspen Approach Prudent Investment Management Growth and stability in Aspen s book yield since 23 5.5% 5.% 4.5% 4.% 3.5% 3.% 2.5% 2.% 1.5% 1.%.5% Consistent investment approach to deliver stable investment income focused on Credit quality & liquidity Interest rate tactics Yield curve management Sector rotation opportunities.% 23 24 25 26 27 28 29 21 21 Aspen FI Book Yield 3YR Treas Mkt Yield Proactive Management of Investment Portfolio to Build Long Term Value Through all Market Cycles; $293m in Unrealized Investment Gains at Q2 21 21
The Aspen Approach Delivering Strong Investment Returns Fixed Income Portfolio Credit Ratings 3 Year Total Return vs. Peers* -5% % 5% 1% 15% 2% $6.784bn** as at June 3, 21 J Aspen 17.8% 16.7% 2% 3% 1% B I C E 16.7% 16.5% 16.% 14.% M 12.5% A 11.9% 1% 66% K L G 11.8% 11.8% 11.1% F 1.6% D 9.9% H 9.7% AAA AA A BBB BIG*** N 7.7% Significant Outperformance vs. Peers; Aspen Rated #2 out of 15 * Total investment return at June 3, 21 ** Includes cash and short term securities in managed fixed income portfolios *** Below Investment Grade Peers include ACE, ACGL, AWH, AXS, ENH, MRH, MXGL, PRE, PTP, RE, RNR, TRH, VR, XL 22
The Aspen Approach Pro-active Management of Capital HARD MARKET Shareholder Equity Development 23 Q2 21 4,5 354 4, 726 Adequate Return on Capital 3,5 3, 185 925 334 $ms Inadequate Return on Capital 2,5 2, 1,5 1299 1, SOFT MARKET 23 Ordinary Shareholders Funds Retained Earnings (Ex Ordinary Divs) New shares issued Net preference shareholder funds Return of capital to ordinary shareholders Q2 21 Total Shareholders Funds Continued Commitment to Capital Management; Returned $1bn* from 23 to Date** * Includes preference dividends and $2m share repurchase entered into in Q1 21 ** End of Q2 21 23
The Aspen Approach History Issued $2m of preference shares Issued $23m of Debt & Hybrids Capital Issued $25m of 6% 1- year Senior Notes PIERS Repurchased $67m of preference shares 3 4 5 6 7 8 9 1 Common Equity IPO Issued $6m of ordinary shares Entered into 2 * $5m accelerated share repurchases Completed $1m private placement with Candover Issued $25m as condition of preference share repurchase Entered into $2m accelerated share repurchase Leverage.% 3.% 14.4% 19.6% 25.7% 22.2% 22.4% 19.9% 19.% 17.7% 17.2% 18.1% 17.2% 4, 3,5 3, 2,5 249 25 25 25 43 43 363 25 363 25 363 25 363 25 363 25 363 $ mil 2, 1,5 1, 5 837 249 28 385 1,91 1,96 249 43 1,442 1,533 2 971 1,73 1,29 147 1,13 457 1,693 1,53 1,417 1,336 1,396 1,41 1,47 1,41 1,565 1,728 1,212 1,213 22 23 24 25 26 27 28 Q1 29 Q2 29 Q3 29 Q4 29 Q1 21 Q2 21 Common share capital Retained earnings inc OCI and issue costs Preference shares Debt Active, Prudent Capital Management Key to Financial Performance 24
How It All Adds Up Growth in Book Value Per Share Aspen vs. Peers* B C Aspen E I M J K D A H L F G 19.1% 17.9% 16.% 15.6% 14.7% 14.6% 14.6% 14.6% 12.8% 11.6% 11.% 1.7% 9.4% 8.3% -22.6% N -25% -2% -15% -1% -5% % 5% 1% 15% 2% 25% 26-29 CAGR BVPS Top Quartile Performance vs. Peers * Source: Company data, SNL * Peers include ACE, AWH, ACGL, AXS, ENH, RE, MXGL, PRE, PTP, TRH, XL, RNR, MRH, VR (*) Note: See Aspen's quarterly financial supplement for a reconciliation of diluted book value per share to basic book value per share in the Investor Relations section of Aspen's website at www.aspen.bm 25
How It All Adds Up Growth in Book Value Per Share and ROE 4 4% 35 3% $ Diluted BV Per Share 3 25 2 15 1 Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Q2 Q3 Q4 Q1 Q2 2% 1% % -1% Annualized ROE% 5-2% 26 27 28 29 21-3% BVPS(LH Scale) Annualized ROE (RH Scale)* Diluted Book Value per Share up 21% since June 3, 29 (*) Note: See Aspen's quarterly financial supplement for a reconciliation of diluted book value per share to basic book value per share and reconciliation of average equity to closing shareholders equity in the Investor Relations section of Aspen's website at www.aspen.bm 26
How It All Adds Up Delivering Growth with Low Volatility Aspen vs. Peers* 14. 12. F I C Standard Deviation 1. 8. 6. 4. L A D K J M E ASPEN B 2. G H. % 5% 1% 15% 2% 25% CAGR % BVPS** 26-29 Strong Growth in Diluted BVPS and Low Volatility vs. Peers, by Managing all of our Levers Source: Company data, SNL * Peers include ACE, AWH, ACGL, AXS, ENH, RE, MXGL, PRE, PTP, TRH, RNR, MRH, VR (*) Note: See Aspen's quarterly financial supplement for a reconciliation of diluted book value per share to basic book value per share and reconciliation of average equity to closing shareholders equity in the Investor Relations section of Aspen's website at www.aspen.bm 27
Our Investment Proposition The Embedded Value in Our Franchise Underwriting Excellence Operational Effectiveness Talent Management Agility Right business model Niche focused Expert based Appropriately diversified (Insurance/Reinsurance, Property/Casualty, Geography) Right Tools Significant investment in integrated risk management, actuarial and other quantitative techniques to enhance our business Right People Motivation Experience Appetite to succeed Alignment with shareholders (i.e., the right compensation structures) Right size and speed of response Sufficient scale to withstand shock losses and compete effectively in all phases of the cycle Ability to respond rapidly to changes in market conditions Aspen Well Positioned for Future Success 28
Appendix 29
Appendix Return Objective The Aspen Group aims to generate 1 year average ROEs which exceed the 3 year risk free rate by an average of at least 8% with a target of 1.5% Spread over the risk free rate rather than an absolute value of ROE Time weighted averaging over 1 years rather than the more usual over the cycle Key Features Reported ROE with an average of 8.5% over the risk free rate since inception* Aim not to fall below 8% Believe that if we perform at higher target level of 1.5%, then more likely to achieve our valuation objective Motivated By Shareholder Return and Valuation Aspirations, But Subject to Constraints to Limit Downside Risk * 7 years excluding part year 22 3
Appendix Volatility Constraint Limiting the chance of an ROE which is 5 percentage points worse than plan to a probability less than 25% (i.e. 1 in 4 years) Constraint seeks to limit volatility of earnings near to the mean Fluctuations of up to 5 points likely to occur reasonably often Key Features Volatility calibrated at level exhibited by top quartile performers in our peer group Applied prospectively based on the volatility measured by our Economic Capital Model Excessive Earnings Volatility Detrimental to Long Term Shareholder Value Growth 31
Aspen s Modelled Worldwide Natural Catastrophe Exposures Major Peril Zones Appendix US Eastern EQ 1.6% US Pacific NW EQ 6.8% US Pacific NW EQ 3.6% US Eastern EQ 7.% Japanese EQ & Typhoon 8.3% Japanese EQ & Typhoon 1.8% California EQ 9.4% California EQ 11.% European Wind 9.8% European Wind 12.8% US All Wind 12.3% US All Wind 18.1% % 2% 4% 6% 8% 1% 12% 14% 1 year return period as % of Total Shareholders' Equity % 2% 4% 6% 8% 1% 12% 14% 16% 18% 2% 25 year return period as % of Total Shareholders' Equity 1 in 1 Year Tolerance: 17.5% of Total Shareholders Equity 1 in 25 Year Tolerance: 25% of Total Shareholders Equity Source: Aspen analysis using RMS v9. occurrence exceedance probability as at July 1, 21 and Shareholders Equity of $3,33.9 million 32
Appendix 21 Guidance Actual 29 Results Initial Guidance February 9, 21 Revised Guidance April 28, 21 Revised Guidance July 28, 21 Gross Written Premium $2.1 billion $2.2 billion ± 5% $2.2 billion ± 5% $2.1 billion ± 5% % Premium Ceded 11.3% of GEP 8% - 12% of GEP 8% - 12% of GEP 8% - 1% of GEP Combined Ratio 84.1% 88% - 94% 92% - 98% 92% - 98% Tax Rate 11.4% 1% to 14% 9% to 13% 9% to 13% Cat-Load $12 million $17 million (assuming normal loss experience) $14 million (assuming normal loss experience for the remainder of 21) $11 million (assuming normal loss experience for the remainder of 21) 33
Appendix Financial Highlights: Q2 21 (US$ in millions, except per share data) Quarter Ended June 3 21 29 Change Gross Written Premiums 545.4 534.3 2.1% Net Written Premiums 538.8 484.7 11.2% Net Earned Premiums 479.9 428.6 12.% Underwriting Income 62.8 53.2 18.% Net Investment Income 57.5 72.2 (2.4%) Net Income after Tax 18.9 11.4 (1.4%) Financial Ratios Loss Ratio 57.7% 54.8% Expense Ratio 29.2% 32.9% Combined Ratio 86.9% 87.7% Annualized Operating ROE* 15.6% 16.4% Operating EPS* 1.23 1.14 7.9% Diluted Book Value per Share* 36.96 3.46 21.3% (*) Note: See Aspen's quarterly financial supplement for a reconciliation of operating income to net income, average equity to closing shareholders equity and diluted book value per share to basic book value per share in the Investor Relations section of Aspen's website at www.aspen.bm 34
Appendix Financial Highlights: H1 21 (US$ in millions, except per share data) Year Ended June 3 21 29 Change Gross Written Premiums 1,248.2 1,171.1 6.6% Net Written Premiums 1,118.9 991.3 12.9% Net Earned Premiums 947.5 875.9 8.2% Underwriting Income 14.6 122.6 (88.1%) Net Investment Income 116.9 131.4 (11.%) Net Income after Tax 127.2 21.8 (37.%) Financial Ratios Loss Ratio 69.2% 55.4% Expense Ratio 29.2% 3.6% Combined Ratio 98.4% 86.% Annualized Operating ROE* 7.8% 17.% Operating EPS* 1.24 2.32 (46.6%) Diluted Book Value per Share* 36.96 3.46 21.3% (*) Note: See Aspen's quarterly financial supplement for a reconciliation of operating income to net income, average equity to closing shareholders equity and diluted book value per share to basic book value per share in the Investor Relations section of Aspen's website at www.aspen.bm 35
Appendix Financial Highlights: Group Summary Q2 21 6 Total 534 545 GWP $m 4 2 277 262 257 283 Q2 29 Q2 21 Aspen Re Aspen Insurance GWP $m $m Reinsurance 283 257 3 25 46 6 2 47 51 15 1 86 81 5 78 91 Q2 29 Q2 21 Property Catastrophe Other Property Casualty Specialty GWP $m Insurance 277 262 3 25 2 3 2 149 118 15 1 53 45 5 55 69 Q2 29 Q2 21 Property Casualty Marine, Energy and Transportation Financial and Professional Lines 36
Appendix Financial Highlights: Group Summary H1 21 Total GWP $m 14 12 1 8 6 4 2 1,171 1,248 461 475 71 773 H1 29 H1 21 Aspen Re Aspen Insurance GWP $m Reinsurance 1 71 773 8 156 118 6 222 226 4 175 154 2 195 237 H1 29 H1 21 Property Catastrophe Other Property Casualty Specialty GWP $m Insurance 5 461 475 42 58 4 3 244 229 2 95 82 1 8 16 H1 29 H1 21 Property Casualty Marine, Energy and Transportation Financial and Professional Lines 37
Appendix Financial Highlights: Group Summary Q2 21 Underwriting Revenues Expenses $m 8 7 6 5 4 3 2 1 534 GWP 545 49 6 Premiums Ceded 485 NWP 539 429 NEP 48 $m $m 5 4 3 2 1 234 277 Loss & Loss Expenses 81 78 Acquisition Exp 5 52 Operating Admin Expenses 1 1 Corporate Expenses 375 417 Total Underw riting Expenses $m 14 12 1 8 6 4 2 122 Operating Income Before Tax Income 13 118 121 Income Before Tax 11 19 Income After Tax 8 7 92 92 6 5 4 3 2 1 Retained Income Q2 29 Q2 21 $m Contribution 63 53 Underw riting Income 72 57 Net Investment Income H1 29 H1 21 38
Appendix Financial Highlights: Group Summary H1 21 $m 14 12 1 8 6 4 2 1171 GWP 1248 Underwriting Revenues 18 129 Premiums Ceded 991 NWP 1119 876 NEP 948 $m 1 8 6 4 2 486 656 Loss & Loss Expenses 159 162 Acquisition Exp Expenses 89 95 Operating Admin Expenses 19 2 Corporate Expenses 753 933 Total Underwriting Expenses $m 3 2 1 244 238 124 Income 141 22 127 165 92 $m 14 12 1 8 6 4 2 123 Contribution 15 131 117 Operating Income Before Tax Income Before Tax Income After Tax Retained Income Underwriting Income Net Investment Income H1 29 H1 21 39
Appendix Key Performance Metrics: Q2 21 and H1 21 1 1 Ratio Analysis 12 Ratio Analysis 9 9 8 8 7 7 6 6 58 58 55 55 88 87 1 8 69 86 98 % 5 5 % 6 56 4 4 3 3 4 2 2 1 1 19 19 16 16 14 13 2 18 17 12 12 Loss Ratio Acquisition Expense Ratio Operating Expense Ratio * Combined Ratio Loss Ratio Acquisition Expense Ratio Operating Expense Ratio Combined Ratio Q2 29 Q2 21 H1 29 H1 21 4
Appendix Results by Business Segment: Q2 21 GWP Underwriting Income * 32 28 24 257 283 277 262 9 8 7 78 67 2 6 $m 16 12 $m 5 4 3 8 2 4 1 6 Reinsurance Insurance -1-2 Q2 29 Q2 21 Reinsurance (15) Insurance (*) Underwriting income is calculated as underwriting revenues, less underwriting expenses. 41
Appendix Results by Business Segment: H1 21 GWP Underwriting Income * 9 8 7 71 773 18 16 14 161 6 12 5 461 475 1 $m 4 3 $m 8 6 2 4 27 1 2 8 Reinsurance Insurance -2 (19) -4 Reinsurance Insurance H1 29 H1 21 (*) Underwriting income is calculated as underwriting revenues, less underwriting expenses. 42
Appendix Key Performance Metrics: Q2 21 Total Combined Ratio 1% 8% 6% 4% 2% % -2% 87.7% 86.9% 88.2% 89.1% (.5)% (2.2)% Q2 29 Q2 21 Prior year adj. Adj. AY Combined Ratio Reinsurance Insurance Combined Ratio 1% 8% 6% 4% 2% % -2% 69.5% 76.8% 76.1% 83.8% * (6.6)% (7.)% Q2 29 Q2 21 Combined Ratio 14% 12% 1% 8% 6% 4% 2% % 18.7% 96.9% 13.9% 91.6% 4.8% 5.3% Q2 29 Q2 21 Prior year adj. Adj. AY Combined Ratio Prior year adj. Adj. AY Combined Ratio 43
Appendix Key Performance Metrics: H1 21 Total Combined Ratio 12% 1% 8% 6% 4% 2% % -2% 98% 86% 12% 9% 9% (4.1)% (3.3)% H1 29 H1 21 Prior year adj. Adj. AY Combined Ratio Chilean Earthquake Combined Ratio 12% 1% 8% 6% 4% 2% % -2% Reinsurance 95% 7% 2% 78% 83% * (8.7)% (6.9)% H1 29 H1 21 Combined Ratio 12% 1% 8% 6% 4% 2% % -2% Insurance 16% 98% 13% 95.4% 2% 2% H1 29 H1 21 Prior year adj. Adj. AY Combined Ratio Chilean Earthquake Prior year adj. Adj. AY Combined Ratio 44
Appendix Total Investment Return Q2 21 18 14 119 146 $m 1 6 72 58 42 82 2 8 6-2 (3) -6 Net Investment Income Realized Investment Gains/Losses Other-Than- Temporary Impairment Charges Movement in Unrealized Investment Gains/Losses Total Investment Return Q2 29 Q2 21 Annualized Investment Return for the Quarter of 8.7% 45
Appendix Total Investment Return H1 21 37 32 27 243 $m 22 17 12 7 2 131 117 11 18 45 18 169-3 -8 Net Investment Income Realized Investment Gains/Losses (18) Other-Than- Temporary Impairment Charges Movement in Unrealized Investment Gains/Losses Total Investment Return H1 29 H1 21 Annualized Investment Return for the Year to Date of 7.2% 46
Appendix Fixed Income Portfolio by Asset Type (US$ in millions) ASSETS : INVESTMENT PORTFOLIO JUNE 3, 21 TOTAL INVESTMENT PORTFOLIO AT MARKET VALUE $6,823.4 Cash, Short-Term Securities and FOHF Government/Agency Structured Securities Unsecured Credit Short-term Securities 34.3 U.S. Government 74.3 Asset-backed securities 82.7 Corporate bonds 1,829.8 Agency Rated Mortgagebacked securities (GNMA, FDIC Guaranteed Corporate Cash and Cash Equivalents 726.1 Agency Debentures 346.7 FNMA, FHLB) 1,149.3 bonds 136.7 Non-Agency Rated Mortgagebacked Other Investments (Iris Re) 27.8 Foreign Governments 549. securities Foreign corporates 45.8 Funds Receivable 11.6 Bonds backed by foreign - CMBS 157.3 government 234.5 - RMBS 4.7 Municipal bonds 35.8 Q2 21 1,69.8 1,636. 1,43. 2,687.6 Q1 21 992.4 1,575.5 1,479.7 2,66.6 47
Managing Risk 2% 1.9% Property Reinsurance Loss Event Market Share* 1.5% 1.4% Market Share 1% 1.%.7%.6%.4%.3%.2%.1%.1%.1%.1%.1%.1%.1% % Hurricane Katrina (25) Hurricane Ike (28) Hurricane Gustav (28) Windstorm Kyrill (27) June UK Floods (27) Windstorm Emma (28) Windstorm Klaus (29) Chilean Earthquake (21) US UK / Europe Latin America Gross Net Significant Reduction in Peak Zone Nat Cat Exposure Post 25 * Data pre-tax as at March 31, 21. Net is net of reinstatement premium and reinsurance 48
Natural Catastrophe Exposure vs. Peers: Hurricanes Gustav / Ike 45 4 35 A D Post-tax loss $m 3 25 2 15 L N F I Aspen C K J M 1 B E H 5 G % 2% 4% 6% 8% 1% 12% 14% Post-tax loss as % June 3, 28 Shareholders' Equity Gustav / Ike Loss in Line with our Business Model Source: Dowling & Partners, Aspen Analysis Peers include ACE, ACGL, AWH, AXS, ENH, MRH, MXGL, PRE, PTP, RE, RNR, TRH, XL, VR 49
Natural Catastrophe Exposure vs. Peers: Chile Earthquake 35 I M 3 F Post-tax loss $m 25 2 15 A N D K 1 L Aspen J H 5 C E B G % 1% 2% 3% 4% 5% 6% 7% 8% 9% Post-tax loss as % December 31, 29 Shareholders' Funds Chile Loss in Line with Our Business Model Source: Dowling & Partners, Aspen Analysis Peers include ACE, ACGL, AWH, AXS, ENH, MRH, MXGL, PRE, PTP, RE, RNR, TRH, XL, VR 5
Appendix Business Performance and Market Outlook: Key Key Performance Absolute Pricing Relative Price Movement Terms and Conditions Volume change Outlook 1 2 3 4 5 6 Excellent Excellent Significantly Up Excellent Significantly Up Excellent Good Good Up Good Up Good Satisfactory Satisfactory Flat Satisfactory Flat Satisfactory Of Concern Of Concern Down Of Concern Down Of Concern Unsatisfactory Unsatisfactory Significantly Down Unsatisfactory Significantly Down Unsatisfactory 51