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UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, DC 20549 FORM 8-K Current Report Pursuant to Section 13 OR 15(d) of the Securities Exchange Act of 1934 Date of Report (Date of earliest event reported): April 21, 2016 ASPEN INSURANCE HOLDINGS LIMITED (Exact name of registrant as specified in its charter) Bermuda 001-31909 Not Applicable (State or other jurisdiction of incorporation) (Commission File Number) (I.R.S. Employer Identification No.) 141 Front Street Hamilton HM 19 Bermuda (Address of principal executive offices) (Zip Code) Registrant’s telephone number, including area code: (441) 295-8201 Not Applicable (Former name or former address, if changed since last report) Check the appropriate box below if the Form 8-K filing is intended to simultaneously satisfy the filing obligation of the registrant under any of the following provisions: Written communications pursuant to Rule 425 under the Securities Act (17 CFR 230.425) Soliciting material pursuant to Rule 14a-12 under the Exchange Act (17 CFR 240.14a-12) Pre-commencement communications pursuant to Rule 14d-2(b) under the Exchange Act (17 CFR 240.14d-2(b)) Pre-commencement communications pursuant to Rule 13e-4(c) under the Exchange Act (17 CFR 240.13e-4(c)) Section 2 - Financial Information Item 2.02 - Results of Operations and Financial Condition On April 21, 2016, Aspen Insurance Holdings Limited (“Aspen” or the “Company”) issued a press release announcing results for the quarter ended March 31, 2016, which is attached hereto as Exhibit 99.1. In addition, a copy of the Aspen Insurance Holdings Limited Earnings Release Supplement for the quarter ended March 31, 2016 is attached hereto as Exhibit 99.2. Section 7 - Regulation FD Item 7.01 - Regulation FD Disclosure On April 21, 2016, Aspen issued a press release announcing results for the quarter ended March 31, 2016, which is attached hereto as Exhibit 99.1. A copy of the Aspen Insurance Holdings Limited Earnings Release Supplement for the quarter ended March 31, 2016 is attached hereto as Exhibit 99.2. In addition, the information about Aspen described in the slides attached hereto as Exhibit 99.3, to be used for reference during the earnings call to be held on April 22, 2016, will be presented by the Chief Executive Officer, the Chief Financial Officer and other members of senior management to various investors throughout the second quarter of 2016. Safe Harbor for Forward-Looking Statements Some of the statements in Exhibit 99.3 include forward-looking statements which reflect Aspen’s current views with respect to future events and financial performance. Such statements may include forward-looking statements both with respect to Aspen in general and the insurance and reinsurance sectors specifically. Statements that include the words “expect,” “assume,” “objective,” “intend,” “plan,” “believe,” “do not believe,” “aim,” “project,” “anticipate,” “seek,” “will,” “likely,” “estimate,” “may,” “continue,” “guidance,” “outlook,” “trends,” “future,” “could,” “would,” “should,” “target,” “on track” and similar statements of a future or forward-looking nature identify forward-looking statements in Exhibit 99.3 for purposes of the U.S. federal securities laws or otherwise. We intend these forward-looking statements to be covered by the safe harbor provisions for forward-looking statements in the Private Securities Litigation Reform Act of 1995. All forward-looking statements address matters that involve risks and uncertainties. Accordingly, there are or may be important factors that could cause actual results to differ from those indicated in the forward-looking statements. See slide 2 of the attached presentation on Exhibit 99.3 for such factors as well as our Annual Report on Form 10-K filed with the United States Securities and Exchange Commission. Forward-looking statements speak only as of the date on which they are made or as otherwise indicated, and we undertake no obligation publicly to update or revise any forward-looking statement, whether as a result of new information, future developments or otherwise. Section 9 - Financial Statements and Exhibits Item 9.01- Financial Statements and Exhibits (d) The following exhibits are furnished under Items 2.02 and 7.01 as part of this report: 99.1 99.2 99.3 Press Release of the Registrant, dated April 21, 2016. Earnings Release Supplement for the quarter ended March 31, 2016. First Quarter 2016 Slide Presentation. The information furnished under Item 2.02 “Results of Operations and Financial Condition” and Item 7.01 “Regulation FD Disclosure” shall not be deemed “filed” for purpose of Section 18 of the Securities Exchange Act of 1934, as amended (the “Exchange Act”), or incorporated by reference in any filing under the Securities Act of 1933, as amended, or the Exchange Act, except as shall be expressly set forth by specific reference in such a filing. 2 SIGNATURES Pursuant to the requirements of the Securities Exchange Act of 1934, the registrant has duly caused this report to be signed on its behalf by the undersigned hereunto duly authorized. ASPEN INSURANCE HOLDINGS LIMITED (Registrant) Dated: April 21, 2016 By: Name: Title: 3 /s/ Scott Kirk Scott Kirk Chief Financial Officer Exhibit 99.1 PRESS RELEASE ASPEN REPORTS RESULTS FOR QUARTER ENDED MARCH 31, 2016 Annualized Net Income Return on Equity of 14.4% Annualized Operating Return on Equity of 11.2% Diluted Book Value Per Share of $48.22 , up 4.8% from December 31, 2015 Hamilton, Bermuda, April 21, 2016 - Aspen Insurance Holdings Limited (“Aspen”) (NYSE: AHL) reported today net income after tax of $114.4 million , or $1.68 per diluted share, and operating income after tax of $89.9 million , or $1.29 per diluted share, for the first quarter of 2016 . Chris O’Kane, Chief Executive Officer, commented, “Aspen has started the year well, with solid first quarter underwriting results from our Insurance and Reinsurance businesses contributing to an annualized operating return on equity of 11.2% and 4.8% growth in diluted book value per share. Our Insurance teams are successfully executing our global products line strategy and delivered growth in targeted lines of business. At the same time, we continued to pull back from areas where we do not feel returns are adequate or are historically more volatile. Within Aspen Re, our teams had successful January and April renewals, again demonstrating our ability to maintain relevance with clients while navigating a challenging and changing market. We also welcomed our colleagues from AgriLogic. In addition, we continue to move closer to our clients, recently announcing the opening of our Dubai office to serve as our hub for the Middle East and Africa. As we move forward, we remain focused on consistently delivering value for our shareholders.” (1) _____________________ Non-GAAP financial measures are used throughout this release as defined at the end of this press release. (1) Refer to "Forward-looking Statements Safe Harbor" at the end of this press release. 1 Operating highlights for the quarter ended March 31, 2016 • Gross written premiums increased by 6.1% to $975.7 million in the first quarter of 2016 compared with $919.2 million in the first quarter of 2015 • Combined ratio of 91.6% for the first quarter of 2016 compared with 88.9% for the first quarter of 2015 . Net favorable development on prior year loss reserves of $21.6 million , or 3.3 combined ratio points, for the first quarter of 2016 compared with $27.5 million , or 4.6 combined ratio points, in the comparable period • Pre-tax catastrophe losses, net of reinsurance recoveries, totaled $18.7 million , or 2.8 combined ratio points, in the first quarter of 2016 compared with $13.5 million , or 2.3 combined ratio points, of pre-tax catastrophe losses, net of reinsurance recoveries, in the first quarter of 2015 Financial highlights for the quarter ended March 31, 2016 • Annualized net income return on average equity of 14.4% and annualized operating return on average equity of 11.2% for the quarter ended March 31, 2016 compared with 16.4% and 12.4% , respectively, for the first quarter of 2015 • Net income per diluted share of $1.68 for the quarter ended March 31, 2016 compared with net income per diluted share of $1.87 for the quarter ended March 31, 2015 • Operating income per diluted share of $1.29 for the quarter ended March 31, 2016 compared with operating income per diluted share of $1.39 for the quarter ended March 31, 2015 • Diluted book value per share of $48.22 as at March 31, 2016 up 4.8% from December 31, 2015 Segment Highlights Insurance Operating highlights for Insurance for the quarter ended March 31, 2016 include: • Gross written premiums of $458.1 million , an increase of 5.5% compared with $434.4 million in the first quarter of 2015 • Combined ratio of 92.0% compared with 93.5% for the first quarter of 2015 • Prior year favorable reserve development of $3.4 million , or 0.9 combined ratio points, compared with prior year favorable reserve development of $14.3 million , or 4.2 combined ratio points, for the first quarter of 2015 Growth in the Financial and Professional Lines, and Property and Casualty sub-segments was offset by a decline in the Marine, Aviation and Energy sub-segment, which includes a number of lines that continue to be impacted by rate pressures. The combined ratio of 92.0% for the first quarter of 2016 included $8.0 million , or 2.1 percentage points, of pre-tax catastrophe losses, net of reinsurance recoveries, from weather-related events in the U.S. The combined ratio for the first quarter of 2015 included $5.8 million , or 1.7 percentage points, of pre-tax catastrophe losses net of reinsurance recoveries. For the quarter ended March 31, 2016 , the Insurance accident year loss ratio excluding catastrophes was 57.0% compared with 60.8% a year ago. Mario Vitale, CEO of Insurance, commented, “Aspen Insurance started the year with a solid quarter of profitable growth. The growth in the quarter was largely driven from businesses in which we have selectively chosen to expand, including contributions from Global Accident and Health, Management Liability, and our new European Property business. We continue to focus on growing our business in those areas that are strongest and offer us the most consistent returns which, we believe, will further improve our loss ratios over time. Our global insurance product line strategy is progressing well, most recently with the appointment of Lorraine Seib as Global head of Excess Casualty.” (1) 2 Reinsurance Operating highlights for Reinsurance for the quarter ended March 31, 2016 include: • Gross written premiums of $517.6 million , an increase of 6.8% from $484.8 million in the first quarter of 2015 . Adjusting for $45.2 million of premiums from AG Logic Holdings, LLC (“AgriLogic”) in the first quarter of 2016 and the negative impact of year-over-year foreign currency movements, gross written premiums in the first quarter of 2016 increased by 4.2% compared to the first quarter of 2015 • Combined ratio of 84.9% compared with 76.7% for the first quarter of 2015 • Prior year favorable reserve development of $18.2 million , or 6.5 combined ratio points, compared with $13.2 million prior year favorable reserve development, or 5.3 combined ratio points, for the first quarter of 2015 • General and administrative expense ratio in first quarter of 2016 increased by 2.7 percentage points compared to the first quarter of 2015 primarily due to expenses associated with AgriLogic Growth in the Specialty and Casualty sub-segments was offset by a decline in the Property Catastrophe and Other Property sub-segments. Growth in the Specialty sub-segment primarily reflects the first-time inclusion of AgriLogic in Aspen's financial results. The combined ratio of 84.9% for the first quarter of 2016 included $10.7 million , or 3.8 percentage points, of pre-tax catastrophe losses, net of reinsurance recoveries, primarily as a result of weather-related events in the U.S. and an earthquake in Taiwan. The combined ratio of 76.7% for the first quarter of 2015 included $7.7 million , or 3.1 percentage points, of pre-tax catastrophe losses, net of reinsurance recoveries. For the quarter ended March 31, 2016 , the Reinsurance accident year loss ratio excluding catastrophes was 50.7% compared with 44.5% a year ago. Of the total increase in the accident year loss ratio excluding catastrophes, approximately half was due to the inclusion of AgriLogic, with the balance due to unfavorable foreign currency movements and change in business mix. Allowing for the impact of the above factors, the underlying performance of the Reinsurance segment is broadly in line with the first quarter of last year. Stephen Postlewhite, CEO of Reinsurance, commented, “Aspen Re started the year well. We had successful January and April renewals as we continue to identify opportunities in a challenging market. We achieved premium growth in our Specialty and Casualty sub-segments and continued to carefully manage down our Property Cat book given ongoing pressures in that market. We also welcomed the AgriLogic team and are very pleased with the integration progress and prospects for this business. Additionally, we continue to seek further opportunities for future profitable growth and develop our regional expansion strategy, most recently announcing the opening of an office in Dubai to serve as a hub for the business in the Middle East and Africa.” (1) Investment performance Investment income of $49.5 million in the first quarter of 2016 increased by 4.4% compared to $47.4 million in the first quarter of 2015 , as a significant portion of dividend income on the equity portfolio is concentrated in the first quarter. Aspen’s investment portfolio continues to be comprised primarily of high quality fixed income securities with an average credit quality of “AA-”. The average duration of the fixed income portfolio was 3.63 years as at March 31, 2016 excluding the impact of interest rate swaps, or 3.56 years including the impact of interest rate swaps. The total return on Aspen’s aggregate investment portfolio was 2.08% for the three months ended March 31, 2016 and reflected gains in the fixed income and equity portfolios. Book yield as at March 31, 2016 on the fixed income portfolio was 2.56% compared to 2.59% as at December 31, 2015. 3 Capital Total shareholders’ equity was $3.6 billion as at March 31, 2016 . During the first quarter of 2016 , Aspen repurchased 568,239 ordinary shares at an average price of $44.00 per ordinary share for a total cost of $25.0 million . Aspen had $391.3 million remaining under its current share repurchase authorization as at April 20, 2016. Earnings conference call and webcast Aspen will host a conference call to discuss the results at 8:00 am (ET) on Friday, April 22, 2016. To participate in the April 22 conference call by phone Please call to register at least 10 minutes before the conference call begins by dialing: +1 (844) 378 6481 (US toll free) or +1 (412) 542 4176 (international) Conference ID 10082504 To listen live online Aspen will provide a live webcast on Aspen’s website at www.aspen.co. To download the materials The earnings press release and a detailed financial supplement will also be published on Aspen’s website at www.aspen.co . To listen later A replay of the call will be available approximately two hours after the end of the live call for 14 days via phone and internet. To listen to the replay by phone please dial: +1 (877) 344 7529 (US toll free) or +1 (412) 317 0088 (international) Replay ID 10082504 The recording will be also available at www.aspen.co on the Event Calendar page within the Investor Relations section. For further information please contact Investors Mark Jones, Senior Vice President, Investor Relations, Aspen [email protected] +1 (646) 289 4945 Media Karen Green, Office of the CEO [email protected] +44 20 7184 8110 International - Citigate Dewe Rogerson Caroline Merrell or Jos Bieneman [email protected] [email protected] +44 20 7638 9571 North America - Sard Verbinnen & Co Paul Scarpetta or Jamie Tully +1 (212) 687 8080 4 Aspen Insurance Holdings Limited Summary consolidated balance sheet (unaudited) $ in millions, except per share data As at March 31, 2016 ASSETS Total investments Cash and cash equivalents Reinsurance recoverables Premiums receivable Other assets Total assets 7,916.3 903.1 609.6 1,339.1 737.3 11,505.4 $ $ $ 5,011.5 1,804.0 479.0 104.5 549.3 7,948.3 SHAREHOLDERS’ EQUITY Total shareholders’ equity Total liabilities and shareholders’ equity Book value per share Diluted book value per share (treasury stock method) LIABILITIES Losses and loss adjustment expenses Unearned premiums Other payables Silverton loan notes Long-term debt Total liabilities $ As at December 31, 2015 $ $ $ 7,712.2 1,099.5 523.7 1,115.6 597.8 11,048.8 $ 4,938.2 1,587.2 451.3 103.0 549.2 7,628.9 $ 3,557.1 11,505.4 $ 3,419.9 11,048.8 $ $ 49.45 48.22 $ $ 46.99 46.00 5 Aspen Insurance Holdings Limited Summary consolidated statement of income (unaudited) $ in millions, except ratios Three Months Ended March 31, 2016 UNDERWRITING REVENUES Gross written premiums Premiums ceded $ March 31, 2015 975.7 (176.0 ) $ 919.2 (156.0 ) 799.7 (136.6 ) 763.2 (169.6 ) Net earned premiums 663.1 593.6 UNDERWRITING EXPENSES Losses and loss adjustment expenses 357.4 306.1 Amortization of deferred policy acquisition costs 130.2 119.3 General, administrative and corporate expenses 119.8 102.2 Total underwriting expenses Net written premiums Change in unearned premiums 607.4 527.6 Underwriting income including corporate expenses 55.7 66.0 OTHER OPERATING REVENUE Net investment income Interest expense Other (expense) 49.5 (7.4 ) (3.0 ) 47.4 (7.4 ) (1.6 ) Total other operating revenue 39.1 38.4 OPERATING INCOME BEFORE TAX 94.8 104.4 Net realized and unrealized exchange (losses) Net realized and unrealized investment gains (20.1 ) 42.2 (11.0 ) 39.7 INCOME BEFORE TAX Income tax expense 116.9 (2.5 ) 133.1 (5.1 ) NET INCOME AFTER TAX Dividends paid on ordinary shares Dividends paid on preference shares Proportion due to non-controlling interest 114.4 (12.8 ) (9.5 ) 0.2 128.0 (12.4 ) (9.5 ) — Retained income Components of net income (after tax) Operating income Net realized and unrealized exchange (losses) after tax Net realized investment gains after tax NET INCOME AFTER TAX Loss ratio Policy acquisition expense ratio General, administrative and corporate expense ratio Expense ratio Combined ratio $ 92.3 $ $ 89.9 (16.9 ) 41.4 $ $ 114.4 $ 53.9 19.6 18.1 37.7 91.6 % % % % % 106.1 98.0 (9.8 ) 39.8 128.0 51.6 20.1 17.2 37.3 88.9 % % % % % 6 Aspen Insurance Holdings Limited Summary consolidated financial data (unaudited) $ in millions, except number of shares Three Months Ended March 31, March 31, 2016 2015 Basic earnings per ordinary share Net income adjusted for preference share dividend and non-controlling interest $1.73 $1.91 $1.33 $1.43 $1.68 $1.87 $1.29 $1.39 Weighted average number of ordinary shares outstanding (in millions) 60.868 62.159 Weighted average number of ordinary shares outstanding and dilutive potential ordinary shares (in millions) 62.484 63.533 Book value per ordinary share $49.45 $47.14 Diluted book value per ordinary share (treasury stock method) $48.22 $46.02 Ordinary shares outstanding at end of the period (in millions) 60.675 61.723 Ordinary shares outstanding and dilutive potential ordinary shares at end of the period (treasury stock method) (in millions) 62.213 63.227 Operating income adjusted for preference share dividend and non-controlling interest Diluted earnings per ordinary share Net income adjusted for preference share dividend and non-controlling interest Operating income adjusted for preference share dividend and non-controlling interest 7 Aspen Insurance Holdings Limited Summary consolidated segment information (unaudited) $ in millions, except ratios Three Months Ended March 31, 2016 Reinsurance Gross written premiums $ 517.6 Insurance $ 458.1 Three Months Ended March 31, 2015 Total $ 975.7 Reinsurance $ 484.8 Insurance $ 434.4 Total $ 919.2 Net written premiums 449.5 350.2 799.7 442.1 321.1 763.2 Gross earned premiums 306.8 445.6 752.4 265.8 415.1 680.9 Net earned premiums Losses and loss adjustment expenses Policy acquisition expenses General and administrative expenses Underwriting income 280.3 382.8 663.1 249.4 344.2 593.6 134.5 222.9 357.4 105.5 200.6 306.1 59.4 70.8 130.2 53.4 65.9 119.3 44.1 58.6 102.7 32.4 55.3 87.7 $ 42.3 $ 30.5 $ Net investment income Net realized and unrealized investment gains (1) Corporate expenses Other (expense) (2) Interest expense Net realized and unrealized foreign exchange (losses) (3) Income before tax Income tax expense Net income Ratios Loss ratio Policy acquisition expense ratio General and administrative expense ratio (4) Expense ratio Combined ratio 72.8 $ 58.1 $ 22.4 $ 80.5 49.5 47.4 42.2 (17.1 ) (3.0 ) (7.4 ) (20.1 ) 39.7 (14.5 ) (1.6 ) (7.4 ) (11.0 ) $ 116.9 (2.5 ) $ 133.1 (5.1 ) $ 114.4 $ 128.0 48.0% 21.2% 58.2% 18.5% 53.9 % 19.6 % 42.3% 21.4% 58.3% 19.1% 51.6 % 20.1 % 15.7% 36.9% 84.9% 15.3% 33.8% 92.0% 18.1 % 37.7 % 91.6 % 13.0% 34.4% 76.7% 16.1% 35.2% 93.5% 17.2 % 37.3 % 88.9 % Includes realized and unrealized capital gains and losses and realized and unrealized gains and losses on interest rate swaps Other (expense) in the first quarter of 2016 and first quarter of 2015 included $4.4 million and $2.9 million , respectively, related to a change in the fair value of loan notes issued by Silverton Re (3) Includes realized and unrealized foreign exchange gains and losses and realized and unrealized gains and losses on foreign exchange contracts (4) The total group general and administrative expense ratio includes the impact from corporate expenses (1) (2) 8 About Aspen Insurance Holdings Limited Aspen provides reinsurance and insurance coverage to clients in various domestic and global markets through wholly-owned subsidiaries and offices in Australia, Bermuda, Canada, France, Germany, Ireland, Singapore, Switzerland, the United Arab Emirates, the United Kingdom and the United States. For the year ended December 31, 2015, Aspen reported $11.0 billion in total assets, $4.9 billion in gross reserves, $3.4 billion in total shareholders’ equity and $3.0 billion in gross written premiums. Its operating subsidiaries have been assigned a rating of “A” by Standard & Poor’s Financial Services LLC (“S&P”), an “A” (“Excellent”) by A.M. Best Company Inc. (“A.M. Best”) and an “A2” by Moody’s Investor Service, Inc. (“Moody’s”). For more information about Aspen, please visit www.aspen.co . (1) Forward-looking Statements Safe Harbor This press release contains, and Aspen’s earnings conference call will contain, written or oral “forward-looking statements” within the meaning of the US federal securities 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,” “believe,” “do not believe,” “aim,” “project,” “anticipate,” “seek,” “will,” “likely,” “assume,” “estimate,” “may,” “continue,” “guidance,” “objective,” “outlook,” “trends,” “future,” “could,” “would,” “should,” “target,” “on track” and similar expressions of a future or forward-looking nature. All forward-looking statements rely on a number of assumptions, estimates and data concerning future results and events and are subject to a number of uncertainties and other factors, many of which are outside Aspen’s control that could cause actual results to differ materially from such statements. 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: our ability to successfully implement steps to further optimize the business portfolio, ensure capital efficiency and enhance investment returns; 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 or material loss events, than our underwriting, reserving, reinsurance purchasing or investment practices have anticipated; the assumptions and uncertainties underlying reserve levels that may be impacted by future payments for settlements of claims and expenses or by other factors causing adverse or favorable development, including our assumptions on inflation costs associated with long-tail casualty business which could differ materially from actual experience; a vote by the U.K. electorate in favor of a U.K. exit from the European Union in a forthcoming in-or-out referendum; the reliability of, and changes in assumptions to, natural and man-made catastrophe pricing, accumulation and estimated loss models; decreased demand for our insurance or reinsurance products and cyclical changes in the insurance and reinsurance industry; the models we use to assess our exposure to losses from future natural catastrophes contain inherent uncertainties and our actual losses may differ significantly from expectations; our capital models may provide materially different indications than actual results; increased competition from existing insurers and reinsurers and from alternative capital providers and insurance-linked funds and collateralized special purpose insurers on the basis of pricing, capacity, coverage terms, new capital, binding authorities to brokers or other factors and the related demand and supply dynamics as contracts come up for renewal; 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; our acquisition strategy; changes in market conditions in the agriculture industry, which may vary depending upon demand for agricultural products, weather, commodity prices, natural disasters, and changes in legislation and policies related to agricultural products and producers; termination of, or changes in, the terms of the U.S. Federal Multiple Peril Crop Insurance Program or the U.S. Farm Bill, including modifications to the Standard Reinsurance Agreement put in place by the Risk Management Agency of the U.S. Department of Agriculture; the recent consolidation in the (re)insurance industry; loss of one or more of our senior underwriters or key personnel; changes in our ability to exercise capital management initiatives (including our share repurchase program) or to arrange banking facilities as a result of prevailing market conditions or changes in our financial position; changes in the availability, cost or quality of reinsurance or retrocessional coverage; changes in general economic conditions, including inflation, deflation, foreign currency exchange rates, interest rates and other factors that could affect our financial results; the risk of a material decline in the value or liquidity of all or parts of our investment portfolio; the risks associated with the management of capital on behalf of investors; evolving issues with respect to interpretation of coverage after major loss events; our ability to adequately model 9 and price the effects of climate cycles and climate change; any intervening legislative or governmental action and changing judicial interpretation and judgments on insurers’ liability to various risks; the risks related to litigation; the effectiveness of our risk management loss limitation methods, including our reinsurance purchasing; changes in the total industry losses, or our share of total industry losses, resulting from past events 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 modeling techniques, changes in rulings on flood damage or other exclusions as a result of prevailing lawsuits and case law; the impact of one or more large losses from events other than natural catastrophes or by an unexpected accumulation of attritional losses and deterioration with loss estimates; the impact of acts of terrorism, acts of war and related legislation; any changes in our reinsurers’ credit quality and the amount and timing of reinsurance recoverables; the continuing and uncertain impact of the current depressed lower growth economic environment in many of the countries in which we operate; our reliance on information and technology and third-party service providers for our operations and systems; the level of inflation in repair costs due to limited availability of labor and materials after catastrophes; a decline in our operating subsidiaries’ ratings with S&P, A.M. Best or Moody’s; the failure of our reinsurers, policyholders, brokers or other intermediaries to honor their payment obligations; our reliance on the assessment and pricing of individual risks by third parties; our dependence on a few brokers for a large portion of our revenues; the persistence of heightened financial risks, including excess sovereign debt, the banking system and the Eurozone crisis; changes in government regulations or tax laws in jurisdictions where we conduct business; changes in accounting principles or policies or in the application of such accounting principles or policies; increased counterparty risk due to the credit impairment of financial institutions; and Aspen or Aspen Bermuda Limited becoming subject to income taxes in the United States or the United Kingdom. For a more detailed description of these uncertainties and other factors, please see the “Risk Factors” section in Aspen’s Annual Report on Form 10-K as filed with the U.S. Securities and Exchange Commission on February 19, 2016. 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. The actuarial range of reserves and management’s best estimate represents a distribution from our internal capital model for reserving risk based on our then current state of knowledge and explicit and implicit assumptions relating to the incurred pattern of claims, the expected ultimate settlement amount, inflation and dependencies between lines of business. 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 within the stated amount. 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 financial 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 in the financial supplement, which can be obtained from the Investor Relations section of Aspen’s website at www.aspen.co . Annualized Operating Return on Average Equity (“Operating ROE”) is a non-GAAP financial measure. Operating ROE is calculated using operating income, as defined below, and average equity is calculated as the arithmetic average on a monthly basis for the stated periods of shareholders’ equity excluding the aggregate value of the liquidation preferences of our preference shares net of issuance costs and the total amount of non-controlling interest. Aspen presents Operating ROE as a measure that is commonly recognized as a standard of performance by investors, analysts, rating agencies and other users of its financial information. See page 21 of Aspen’s financial supplement for a reconciliation of operating income to net income and page 7 for a reconciliation of average ordinary shareholders’ equity to average shareholders’ equity. Aspen’s financial supplement can be obtained from the Investor Relations section of Aspen’s website at www.aspen.co. 10 Operating Income is a non-GAAP financial measure. Operating income is an internal performance measure used by Aspen in the management of its operations and represents after-tax operational results excluding, as applicable, after-tax net realized and unrealized gains or losses, including net realized and unrealized gains and losses on interest rate swaps, after-tax net foreign exchange gains or losses, including net realized and unrealized gains and losses from foreign exchange contracts and certain non-recurring items. Aspen excludes the items above from its calculation of operating income because they are either not expected to recur and therefore are not reflective of underlying performance or the amount of these gains or losses is heavily influenced by, and fluctuates in part, according to the availability of market opportunities. Aspen believes these amounts are largely independent of its business and underwriting process and including them would distort the analysis of trends in its operations. In addition to presenting net income determined in accordance with GAAP, Aspen believes that showing operating income enables investors, analysts, rating agencies and other users of its financial information to more easily analyze Aspen’s results of operations in a manner similar to how management analyzes Aspen’s underlying business performance. Operating income should not be viewed as a substitute for GAAP net income. Please see page 21 of Aspen’s financial supplement for a reconciliation of operating income to net income. Aspen’s financial supplement can be obtained from the Investor Relations section of Aspen’s website at www.aspen.co . Diluted Book Value per Ordinary Share is not a non-GAAP financial measure. Aspen has included diluted book value per ordinary share as it illustrates the effect on basic book value per share of dilutive securities thereby providing a better benchmark for comparison with other companies. Diluted book value per share is calculated using the treasury stock method, defined on page 20 of Aspen’s financial supplement, which can be obtained from the Investor Relations section of Aspen’s website at www.aspen.co . Diluted Operating Earnings per Share and Basic Operating Earnings per Share are non-GAAP financial measures. Aspen believes that the presentation of diluted operating earnings per share and basic operating earnings per share supports meaningful comparison from period to period and the analysis of normal business operations. Diluted operating earnings per share and basic operating earnings per share are calculated by dividing operating income by the diluted or basic weighted average number of shares outstanding for the period. See page 21 of Aspen’s financial supplement for a reconciliation of diluted and basic operating earnings per share to basic earnings per share. Aspen’s financial supplement can be obtained from the Investor Relations section of Aspen’s website at www.aspen.co . Accident Year Loss Ratio Excluding Catastrophes is a non-GAAP financial measure. Aspen believes that the presentation of loss ratios excluding catastrophes and prior year reserve movements supports meaningful comparison from period to period of the underlying performance of the business. Accident year loss ratios excluding catastrophes are calculated by dividing net losses excluding catastrophe losses, net expenses and prior year reserve movements by net earned premiums excluding catastrophe-related reinstatement premiums. Aspen has defined catastrophe losses in the first quarter of 2016 as losses associated with weather-related events in the U.S. and an earthquake in Taiwan. Catastrophe losses in the comparable period of 2015 were defined as losses associated with storms in Europe, Australia and the U.S. See pages 9 and 10 of Aspen’s financial supplement for a reconciliation of loss ratios to accident year loss ratios excluding catastrophes. 11 xhibit 99.2 FINANCIAL SUPPLEMENT As of March 31, 2016 Aspen Insurance Holdings Limited This financial supplement is for information purposes only. It should be read in conjunction with other documents filed or to be filed by Aspen Insurance Holdings Limited with the United States Securities and Exchange Commission. www.aspen.co Investor Contact: Aspen Insurance Holdings Limited Mark Jones, Senior Vice President, Investor Relations T: +1 646 289 4945 email: [email protected] 1 ASPEN INSURANCE HOLDINGS LIMITED Table Of Contents Page Basis of Presentation Financial Highlights Consolidated Statements of Operations - Quarterly Results Consolidated Statements of Operations - Year to Date Results Consolidated Balance Sheets Earnings Per Share and Book Value Per Share Return on Average Equity Consolidated Underwriting Results by Operating Segment Operating Segment - Quarterly Results Written and Earned Premiums by Segment and Lines of Business Consolidated Statements of Changes in Shareholders' Equity Consolidated Statements of Comprehensive Income Condensed Consolidated Statements of Cash Flows Reserves for Losses and Loss Adjustment Expenses Reserves by Operating Segment Prior Year Reserve Releases Consolidated Investment Portfolio Investment Analysis Book Value Per Ordinary Share Operating Income Reconciliation 1 2 3 4 5 6 7 8 9 - 10 11 12 13 14 15 16 17 18 19 20 21 ASPEN INSURANCE HOLDINGS LIMITED Basis of Presentation Definitions and presentations : All financial information contained herein is unaudited except for information for the fiscal year ended December 31, 2015. Unless otherwise noted, all data is in U.S. dollar millions, except for per share amounts, percentages and ratio information. 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 in this financial supplement. Operating income (a non-GAAP financial measure): Operating income is an internal performance measure used by Aspen in the management of its operations and represents after-tax operational results excluding, as applicable, after-tax net realized and unrealized gains or losses, including net realized and unrealized gains and losses on interest rate swaps, after-tax net foreign exchange gains or losses, including net realized and unrealized gains and losses from foreign exchange contracts and certain non-recurring items. Aspen excludes these items above from its calculation of operating income because they are either not expected to recur and therefore are not reflective of underlying performance or the amount of these gains or losses is heavily influenced by, and fluctuates in part, according to the availability of market opportunities. Aspen believes these amounts are largely independent of its business and underwriting process and including them would distort the analysis of trends in its operations. In addition to presenting net income determined in accordance with GAAP, Aspen believes that showing operating income enables investors, analysts, rating agencies and other users of its financial information to more easily analyze Aspen's results of operations in a manner similar to how management analyzes Aspen's underlying business performance. Operating income should not be viewed as a substitute for GAAP net income. Please see page 21 for a reconciliation of operating income to net income. Annualized operating return on average equity (“Operating ROE”) (a non-GAAP financial measure): Operating ROE is calculated using operating income, as defined above, and average equity is calculated as the arithmetic average on a monthly basis for the stated periods of shareholders' equity excluding the aggregate value of the liquidation preferences of our preference shares net of issuance costs and the total amount of non-controlling interest. Aspen presents Operating ROE as a measure that is commonly recognized as a standard of performance by investors, analysts, rating agencies and other users of its financial information. See page 21 for a reconciliation of operating income to net income and page 7 for a reconciliation of average ordinary shareholders' equity to average shareholders' equity. Diluted operating earnings per share and basic operating earnings per share (non-GAAP financial measures): Aspen believes that the presentation of diluted operating earnings per share and basic operating earnings per share supports meaningful comparison from period to period and the analysis of normal business operations. Diluted operating earnings per share and basic operating earnings per share are calculated by dividing operating income by the diluted or basic weighted average number of shares outstanding for the period. See page 21 for a reconciliation of diluted and basic operating earnings per share to basic earnings per share. Diluted book value per ordinary share (not a non-GAAP financial measure): Aspen has included diluted book value per ordinary share as it illustrates the effect on basic book value per share of dilutive securities thereby providing a better benchmark for comparison with other companies. Diluted book value per share is calculated using the treasury stock method as defined on page 20. Accident year loss ratio excluding catastrophes (a non-GAAP financial measure): Aspen believes that the presentation of loss ratios excluding catastrophes and prior year reserve movements supports meaningful comparison from period to period of the underlying performance of the business. Accident year loss ratios excluding catastrophes are calculated by dividing net losses excluding catastrophe losses, net expenses and prior year reserve movements by net earned premiums excluding catastrophe-related reinstatement premiums. Aspen has defined catastrophe losses in the first quarter of 2016 as losses associated with weather-related events in the U.S. and an earthquake in Taiwan and in the first quarter of 2015 as losses predominantly associated with storms in Europe, Australia and the U.S. See pages 9 and 10 for a reconciliation of loss ratios to accident year loss ratios excluding catastrophes. Underwriting ratios (GAAP financial measures): Aspen, along with others in the industry, uses underwriting ratios as measures of performance. The loss ratio is the ratio of net claims and claims adjustment expenses to net premiums earned. The acquisition expense ratio is the ratio of underwriting expenses (commissions, premium taxes, licenses and fees, as well as other underwriting expenses) to net premiums earned. The general and administrative expense ratio is the ratio of general and administrative expenses to net premiums earned. The combined ratio is the sum of the loss ratio, the acquisition expense ratio and the general and administrative expense ratio. These ratios are relative measurements that describe for every $100 of net premiums earned, the cost of losses and expenses, respectively. The combined ratio presents the total cost per $100 of earned premium. A combined ratio below 100% demonstrates underwriting profit; a combined ratio above 100% demonstrates underwriting loss. GAAP combined ratios differ from U.S. statutory combined ratios primarily due to the deferral of certain third-party acquisition expenses for GAAP reporting purposes and the use of net premiums earned rather than net premiums written in the denominator when calculating the acquisition expense and the general and administrative expense ratios. 1 ASPEN INSURANCE HOLDINGS LIMITED Financial Highlights Three Months Ended March 31, (in US$ millions except for percentages, share and per share amounts) 2016 2015 Change Gross written premium $ 975.7 $ 919.2 6.1 % Net written premium $ 799.7 $ 763.2 4.8 % Net earned premium $ 663.1 $ 593.6 11.7 % Net income after tax $ 114.4 $ 128.0 (10.6)% Operating income after tax $ 89.9 $ 98.0 (8.3)% Net investment income $ 49.5 $ 47.4 4.4 % Underwriting income $ 55.7 $ 66.0 (15.6)% $ 1.73 $ 1.91 (9.4)% $ 1.33 $ 1.43 (7.0)% Net income adjusted for preference share dividend and non-controlling interest $ 1.68 $ 1.87 (10.2)% Operating income adjusted for preference share dividend and non-controlling interest $ 1.29 $ Earnings Per Share and Book Value Per Share Basic earnings per ordinary share Net income adjusted for preference share dividend and non-controlling interest Operating income adjusted for preference share dividend and non-controlling interest Diluted earnings per ordinary share Weighted average number of ordinary shares outstanding (in millions of shares) 60.868 Diluted weighted average number of ordinary shares outstanding (in millions of shares) 62.484 Book value per ordinary share $ Diluted book value per ordinary share $ 49.45 $ 48.22 $ 1.39 (7.2)% 62.159 (2.1)% 63.533 (1.7)% 47.14 4.9 % 46.02 4.8 % Ordinary shares outstanding at March 31, 2016 and March 31, 2015 (in millions of shares) 60.675 61.723 (1.7)% Diluted ordinary shares outstanding at March 31, 2016 and March 31, 2015 (in millions of shares) 62.213 63.227 (1.6)% Underwriting Ratios Loss ratio Policy acquisition expense ratio General, administrative and corporate expense ratio Expense ratio Combined ratio Return On Equity 53.9 % 19.6 % 18.1 % 37.7 % 91.6 % Average equity (1) Return on average equity Net income adjusted for preference share dividend and non-controlling interest Operating income adjusted for preference share dividend and non-controlling interest Annualized return on average equity Net income Operating income See pages 7 and 21 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. (1) Average equity excludes preference shares. 2 $ 2,931.5 51.6 % 20.1 % 17.2 % 37.3 % 88.9 % $ 2,886.3 3.6% 2.8% 4.1 % 3.1 % 14.4 % 11.2 % 16.4 % 12.4 % ASPEN INSURANCE HOLDINGS LIMITED Consolidated Statements of Operations - Quarterly Results (in US$ millions except for percentages and per share amounts) Q1 2016 Q4 2015 Q3 2015 Q2 2015 Q1 2015 UNDERWRITING REVENUES Gross written premiums $ 975.7 $ (176.0 ) Premiums ceded 634.8 $ 720.5 $ 722.8 (48.0 ) (68.7 ) (78.4 ) 651.8 644.4 (11.2 ) (35.0 ) $ 919.2 (156.0 ) 799.7 586.8 (136.6 ) 42.9 663.1 629.7 640.6 609.4 593.6 Losses and loss adjustment expenses 357.4 334.0 365.6 360.5 306.1 Amortization of deferred policy acquisition costs 130.2 118.2 132.0 114.1 119.3 General, administrative and corporate expenses 119.8 125.9 100.5 95.4 102.2 Total underwriting expenses 607.4 578.1 598.1 570.0 527.6 55.7 51.6 42.5 39.4 66.0 Net investment income 49.5 46.4 45.0 46.7 47.4 Interest expense (7.4 ) (7.4 ) (7.4 ) (7.3 ) (7.4 ) Other (expense) (3.0 ) (5.4 ) (10.6 ) (2.7 ) (1.6 ) Total other operating revenue 39.1 33.6 27.0 36.7 38.4 OPERATING INCOME BEFORE TAX 94.8 85.2 69.5 76.1 104.4 (20.1 ) 6.1 4.5 (9.4 ) (11.0 ) 42.2 31.9 (44.0 ) (15.5 ) 39.7 116.9 123.2 30.0 51.2 133.1 (1.8 ) (2.2 ) Net written premiums Change in unearned premiums Net earned premiums 763.2 (169.6 ) UNDERWRITING EXPENSES Underwriting income including corporate expenses OTHER OPERATING REVENUE AND EXPENSES Net realized and unrealized exchange (losses)/gains (1) Net realized and unrealized investment gains/(losses) (2) INCOME BEFORE TAX (2.5 ) Income tax expense (5.3 ) (5.1 ) NET INCOME AFTER TAX 114.4 117.9 28.2 49.0 Dividends paid on ordinary shares (12.8 ) (12.8 ) (12.7 ) (13.0 ) (12.4 ) (9.5 ) (9.4 ) (9.5 ) (9.4 ) (9.5 ) Dividends paid to non-controlling interest — (0.1 ) — — — Proportion due to non-controlling interest 0.2 — (0.3 ) (0.5 ) — Dividends paid on preference shares Retained income $ 92.3 $ 95.6 $ 5.7 $ 26.1 128.0 $ 106.1 Components of net income after tax Operating income Net realized and unrealized exchange (losses)/gains after tax (1) 84.0 67.2 72.2 98.0 5.7 1.4 (7.5 ) (9.8 ) 41.4 Net realized and unrealized investment gains/(losses) after tax (2) NET INCOME AFTER TAX 89.9 (16.9 ) $ 114.4 28.2 $ 117.9 (40.4 ) $ 28.2 (15.7 ) $ 49.0 39.8 $ 128.0 53.9 % 53.0 % 57.1 % 59.2 % 51.6 % Policy acquisition expense ratio 19.6 % 18.8 % 20.6 % 18.7 % 20.1 % General, administrative and corporate expense ratio 18.1 % 20.0 % 15.7 % 15.7 % 17.2 % Expense ratio 37.7 % 38.8 % 36.3 % 34.4 % 37.3 % Combined ratio 91.6 % 91.8 % 93.4 % 93.6 % 88.9 % Loss ratio Basic earnings per share (3) $ 1.73 $ 1.78 $ 0.30 $ 0.64 $ 1.91 Diluted earnings per share (3) $ 1.68 $ 1.75 $ 0.30 $ 0.62 $ 1.87 Annualized return on average equity Net income 14.4 % 15.2 % 2.8 % 5.6 % 16.4 % Operating income 11.2 % 10.4 % 8.4 % 8.8 % 12.4 % See pages 7 and 21 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. (1) Includes the net realized and unrealized gains/(losses) from foreign exchange contracts. (2) Includes the net realized and unrealized gains/(losses) from interest rate swaps. (3) Adjusted for preference share dividends and non-controlling interest. 3 ASPEN INSURANCE HOLDINGS LIMITED Consolidated Statements of Operations - Year To Date Results Three Months Ended March 31, 2016 2015 UNDERWRITING REVENUES $ Gross written premiums 975.7 $ (176.0 ) Premiums ceded 919.2 (156.0 ) 799.7 763.2 (136.6 ) (169.6 ) 663.1 593.6 Losses and loss adjustment expenses 357.4 306.1 Amortization of deferred policy acquisition costs 130.2 119.3 General, administrative and corporate expenses 119.8 102.2 Total underwriting expenses 607.4 527.6 55.7 66.0 Net investment income 49.5 47.4 Interest expense (7.4 ) (7.4 ) Other (expense) (3.0 ) (1.6 ) Total other operating revenue 39.1 38.4 OPERATING INCOME BEFORE TAX 94.8 104.4 Net written premiums Change in unearned premiums Net earned premiums UNDERWRITING EXPENSES Underwriting income including corporate expenses OTHER OPERATING REVENUE AND EXPENSES (20.1 ) Net realized and unrealized exchange (losses) (1) Net realized and unrealized investment gains (2) INCOME BEFORE TAX (11.0 ) 42.2 39.7 116.9 133.1 (2.5 ) Income tax expense (5.1 ) NET INCOME AFTER TAX 114.4 128.0 Dividends paid on ordinary shares (12.8 ) (12.4 ) (9.5 ) (9.5 ) Dividends paid on preference shares — 0.2 Proportion due to non-controlling interest $ Retained income 92.3 $ 106.1 Components of net income after tax 89.9 Operating income 98.0 (16.9 ) Net realized and unrealized exchange (losses) after tax (1) (9.8 ) 41.4 Net realized and unrealized investment gains after tax (2) $ NET INCOME AFTER TAX 114.4 39.8 $ 128.0 53.9 % 51.6 % Policy acquisition expense ratio 19.6 % 20.1 % General, administrative and corporate expense ratio 18.1 % 17.2 % Expense ratio 37.7 % 37.3 % Combined ratio 91.6 % 88.9 % Loss ratio See pages 7 and 21 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. (1) Includes the net realized and unrealized gains/(losses) from foreign exchange contracts. (2) Includes the net realized and unrealized gains/(losses) from interest rate swaps. 4 ASPEN INSURANCE HOLDINGS LIMITED Consolidated Balance Sheets March 31, 2016 (in US$ millions except for per share amounts) December 31, 2015 September 30, 2015 $ $ June 30, 2015 March 31, 2015 Investments Fixed income securities $ 6,960.5 757.8 Equity securities 6,739.1 736.4 6,496.4 $ 696.3 6,407.4 $ 729.3 6,339.2 719.0 Other investments 8.9 8.9 9.5 9.5 9.5 Catastrophe bonds 46.1 55.4 36.7 32.3 32.8 143.0 172.4 183.2 185.2 180.9 7,916.3 7,712.2 7,422.1 7,363.7 7,281.4 903.1 1,099.5 1,196.7 1,148.4 1,225.9 Unpaid losses 366.0 354.8 348.7 337.3 360.1 Ceded unearned premiums 243.6 168.9 224.6 257.1 276.4 1,339.1 1,115.6 1,208.4 1,249.9 1,264.8 Other 117.9 94.3 108.7 108.1 92.1 Funds withheld 39.6 36.0 39.0 44.5 46.1 407.7 361.1 346.8 349.0 333.8 10.9 9.2 9.2 4.1 2.1 Short-term investments Total investments Cash and cash equivalents Reinsurance recoverables Receivables Underwriting premiums Deferred policy acquisition costs Derivatives at fair value Receivable for securities sold Office properties and equipment Taxation Other assets Intangible assets and goodwill Total assets 1.9 0.6 6.7 5.5 0.3 83.2 70.6 68.7 65.6 61.9 — 3.7 — 0.9 — 1.8 4.1 5.9 1.9 18.2 74.3 18.2 18.2 18.2 18.2 $ 11,505.4 $ 11,048.8 $ 11,003.7 $ 10,954.2 $ 10,981.3 $ 5,011.5 $ 4,938.2 $ 4,913.9 $ 4,815.9 $ 4,698.9 LIABILITIES Insurance reserves Losses and loss adjustment expenses Unearned premiums 1,804.0 1,587.2 1,686.9 1,702.8 1,665.1 Total insurance reserves 6,815.5 6,525.4 6,600.8 6,518.7 6,364.0 148.9 92.7 135.6 164.5 171.5 19.2 10.8 22.7 32.1 34.8 293.3 343.8 237.7 242.7 308.6 17.6 4.0 1.9 7.2 11.5 479.0 451.3 397.9 446.5 526.4 Loan notes issued by variable interest entities, at fair value 104.5 103.0 84.5 76.2 76.0 Long-term debt 549.3 549.2 549.2 549.2 549.1 7,948.3 7,628.9 7,632.4 7,590.6 7,515.5 Ordinary shares 0.1 0.1 0.1 0.1 0.1 Non-controlling interest 1.1 1.3 1.3 1.0 0.5 — — — — — Additional paid-in capital 1,055.9 1,075.3 1,068.3 1,061.7 1,106.0 Retained earnings 2,375.9 2,283.6 2,188.0 2,182.3 2,156.2 124.1 59.6 113.6 118.5 203.0 Payables Reinsurance premiums Taxation Accrued expenses and other payables Liabilities under derivative contracts Total payables Total liabilities SHAREHOLDERS’ EQUITY Preference shares Accumulated other comprehensive income, net of taxes 3,557.1 Total shareholders’ equity 3,419.9 3,371.3 3,363.6 3,465.8 $ 11,505.4 $ 11,048.8 $ 11,003.7 $ 10,954.2 $ 10,981.3 Book value per ordinary share $ 49.45 $ 46.99 $ 46.30 $ 46.18 $ 47.14 Book value per diluted ordinary share $ 48.22 $ 46.00 $ 45.28 $ 45.16 $ 46.02 Total liabilities and shareholders’ equity See pages 7 and 21 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. 5 ASPEN INSURANCE HOLDINGS LIMITED Earnings Per Share and Book Value Per Share Three Months Ended (in US$ except for number of shares) March 31, 2016 March 31, 2015 Basic earnings per ordinary share Net income adjusted for preference share dividend and non-controlling interest $ 1.73 $ 1.91 Operating income adjusted for preference share dividend and non-controlling interest $ 1.33 $ 1.43 $ 1.68 $ 1.87 $ 1.29 $ 1.39 Diluted earnings per ordinary share Net income adjusted for preference share dividend and non-controlling interest Operating income adjusted for preference share dividend and non-controlling interest Weighted average number of ordinary shares outstanding (in millions) Weighted average number of ordinary shares outstanding and dilutive potential ordinary shares (in millions) Book value per ordinary share Diluted book value per ordinary share 60.868 62.159 62.484 63.533 $ 49.45 $ 47.14 $ 48.22 $ 46.02 Ordinary shares outstanding at end of the period (in millions) 60.675 61.723 Ordinary shares outstanding and dilutive potential ordinary shares at end of the period (in millions) 62.213 63.227 See pages 7 and 21 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. 6 ASPEN INSURANCE HOLDINGS LIMITED Return On Average Equity Three Months Ended (in US$ millions except for percentages) March 31, 2016 March 31, 2015 Average shareholders' equity Average non-controlling interest Average preference shares $ 3,488.5 (1.2 ) (555.8 ) $ 3,442.6 (0.5 ) (555.8 ) Average ordinary shareholders' equity $ 2,931.5 $ 2,886.3 Return on average equity: Net income adjusted for preference share dividend and non-controlling interest Operating income adjusted for preference share dividend and non-controlling interest Annualized return on average equity: Net income Operating income Components of return on average equity: Return on average equity from underwriting activity (1) Return on average equity from investment and other activity (2) Pre-tax operating income return on average equity (3) Post-tax operating income return on average equity (4) See page 21 for a reconciliation of non-GAAP financial measures to their most directly comparable GAAP financial measures. (1) Calculated by using underwriting income. (2) Calculated by using total other operating revenue and other income/(expense) adjusted for preference share dividends and non-controlling interest. (3) Calculated by using operating income before tax adjusted for preference share dividends and non-controlling interest. (4) Calculated by using operating income after-tax adjusted for preference share dividends and non-controlling interest. 7 3.6 % 2.8 % 4.1 % 3.1 % 14.4 % 11.2 % 16.4 % 12.4 % 1.9 % 1.0 % 2.9 % 2.8 % 2.3 % 1.0 % 3.3 % 3.1 % ASPEN INSURANCE HOLDINGS LIMITED Consolidated Underwriting Results by Operating Segment Three Months Ended March 31, 2016 (in US$ millions except for percentages) Gross written premiums Reinsurance $ 517.6 Insurance $ 458.1 Three Months Ended March 31, 2015 Total $ 975.7 Reinsurance $ 484.8 Insurance $ 434.4 Total $ 919.2 Net written premiums 449.5 350.2 799.7 442.1 321.1 763.2 Gross earned premiums 306.8 445.6 752.4 265.8 415.1 680.9 Net earned premiums 280.3 382.8 663.1 249.4 344.2 593.6 Losses and loss adjustment expenses 134.5 222.9 357.4 105.5 200.6 306.1 59.4 70.8 130.2 53.4 65.9 119.3 Amortization of deferred policy acquisition costs General and administrative expenses Underwriting income 44.1 $ 42.3 58.6 $ 30.5 102.7 $ Net investment income Net realized and unrealized investment gains (1) Corporate expenses Other (expense) Interest expense Net realized and unrealized foreign exchange (losses) (2) 72.8 32.4 $ 58.1 55.3 $ 22.4 87.7 $ 80.5 49.5 47.4 42.2 (17.1) (3.0) (7.4) 39.7 (14.5) (1.6) (7.4) (20.1) (11.0) Income before tax Income tax expense $ 116.9 (2.5) $ 133.1 (5.1) Net income $ 114.4 $ 128.0 Ratios Loss ratio Policy acquisition expense ratio General and administrative expense ratio (3) Expense ratio Combined ratio 48.0% 21.2% 15.7% 36.9% 84.9% 58.2 % 18.5 % 15.3 % 33.8 % 92.0 % (1) Includes the net realized and unrealized gains/(losses) from interest rate swaps. (2) Includes the net realized and unrealized gains/(losses) from foreign exchange contracts. (3) The total group general and administrative expense ratio includes the impact from corporate expenses. 8 53.9% 19.6% 18.1% 37.7% 91.6% 42.3% 21.4% 13.0% 34.4% 76.7% 58.3 % 19.1 % 16.1 % 35.2 % 93.5 % 51.6% 20.1% 17.2% 37.3% 88.9% ASPEN INSURANCE HOLDINGS LIMITED Reinsurance Segment - Quarterly Results (in US$ millions except for percentages) Q1 2016 Q4 2015 Q3 2015 Q2 2015 Q1 2015 $ 517.6 $ 186.8 $ 316.6 $ 260.7 $ 484.8 Net written premiums 449.5 178.5 294.7 238.2 442.1 Gross earned premiums 306.8 295.9 304.6 287.2 265.8 Net earned premiums 280.3 270.3 284.6 268.3 249.4 Net losses and loss adjustment expenses 134.5 99.9 169.9 116.3 105.5 Amortization of deferred policy acquisition costs 59.4 56.1 64.8 50.4 53.4 General and administrative expenses 44.1 44.0 34.7 35.4 32.4 Gross written premiums $ Underwriting income Ratios Loss ratio Policy acquisition expense ratio General and administrative expense ratio Expense ratio Combined ratio Accident Year Ex-cat Loss Ratio Loss ratio Prior year loss development Catastrophe losses Accident year ex-cat loss ratio 42.3 48.0 21.2 15.7 36.9 84.9 $ % % % % % 48.0 % 6.5 % (3.8 )% 50.7 % 9 70.3 37.0 20.8 16.3 37.1 74.1 $ % % % % % 37.0 % 13.8 % (8.4)% 42.4 % 15.2 59.7 22.8 12.2 35.0 94.7 $ % % % % % 59.7 % 5.7 % (5.9 )% 59.5 % 66.2 43.3 18.8 13.2 32.0 75.3 $ % % % % % 43.3 % 9.0 % (0.9)% 51.4 % 58.1 42.3 21.4 13.0 34.4 76.7 % % % % % 42.3 % 5.3 % (3.1 )% 44.5 % ASPEN INSURANCE HOLDINGS LIMITED Insurance Segment - Quarterly Results (in US$ millions except for percentages) Q1 2016 Q4 2015 Q3 2015 Q2 2015 Q1 2015 $ 458.1 $ 448.0 $ 403.9 $ 462.1 $ 434.4 Net written premiums 350.2 408.3 357.1 406.2 321.1 Gross earned premiums 445.6 436.0 429.0 423.2 415.1 Net earned premiums 382.8 359.4 356.0 341.1 344.2 Net losses and loss adjustment expenses 222.9 234.1 195.7 244.2 200.6 Amortization of deferred policy acquisition costs 70.8 62.1 67.2 63.7 65.9 General and administrative expenses 58.6 61.8 51.3 45.2 55.3 Gross written premiums $ Underwriting income/(loss) Ratios Loss ratio Policy acquisition expense ratio General and administrative expense ratio Expense ratio Combined ratio Accident Year Ex-cat Loss Ratio Loss ratio Prior year loss development Catastrophe losses Accident year ex-cat loss ratio 30.5 58.2 18.5 15.3 33.8 92.0 $ % % % % % 58.2 % 0.9 % (2.1)% 57.0 % 10 1.4 65.1 17.3 17.2 34.5 99.6 $ % % % % % 65.1 % 6.0 % (6.5 )% 64.6 % 41.8 55.0 18.9 14.4 33.3 88.3 $ (12.0 ) % % % % % 55.0 % 6.4 % (0.6)% 60.8 % 71.6 18.7 13.3 32.0 103.6 % % % % % 71.6 % 2.1 % (2.8)% 70.9 % $ 22.4 58.3 19.1 16.1 35.2 93.5 % % % % % 58.3 % 4.2 % (1.7 )% 60.8 % ASPEN INSURANCE HOLDINGS LIMITED Written and Earned Premiums by Segment and Lines of Business (in US$ millions) Gross Written Premiums Q1 2016 Q4 2015 Q3 2015 Q2 2015 Q1 2015 Reinsurance Property Catastrophe Reinsurance $ 127.6 67.3 $ 153.8 Other Property Reinsurance 103.0 $ 61.2 4.1 $ 105.2 49.1 $ 84.0 109.9 Casualty Reinsurance 127.1 45.9 77.9 49.0 114.7 Specialty Reinsurance Total Reinsurance 159.9 75.6 84.4 60.4 106.4 $ 517.6 $ 186.8 $ 316.6 $ 260.7 $ 484.8 Insurance $ 226.3 $ 213.9 $ 208.5 $ 254.8 $ 213.4 Marine, Aviation and Energy Insurance 117.7 107.1 85.3 103.2 131.7 Financial and Professional Lines Insurance 114.1 127.0 110.1 104.1 89.3 $ 458.1 $ 448.0 $ 403.9 $ 462.1 $ 434.4 $ 975.7 $ 634.8 $ 720.5 $ 722.8 $ 919.2 $ $ $ $ Property and Casualty Insurance Total Insurance Total Gross Written Premiums Net Written Premiums Reinsurance Property Catastrophe Reinsurance 92.1 53.5 $ 126.1 92.9 59.9 100.1 80.6 98.8 Casualty Reinsurance 125.6 41.5 76.8 46.7 113.8 Specialty Reinsurance 138.9 72.3 84.0 57.4 103.4 $ 449.5 $ 178.5 $ 294.7 $ 238.2 $ 442.1 $ 180.5 $ 185.2 $ 172.9 $ 222.1 $ 156.7 Other Property Reinsurance Total Reinsurance 4.8 33.8 Insurance Property and Casualty Insurance 106.6 99.7 76.1 82.5 120.5 63.1 123.4 108.1 101.6 43.9 $ 350.2 $ 408.3 $ 357.1 $ 406.2 $ 321.1 $ 799.7 $ 586.8 $ 651.8 $ 644.4 $ 763.2 $ $ $ $ $ Marine, Aviation and Energy Insurance Financial and Professional Lines Insurance Total Insurance Total Net Written Premiums Net Earned Premiums Reinsurance Property Catastrophe Reinsurance 47.3 58.1 54.0 53.8 57.1 Other Property Reinsurance 87.3 79.4 91.5 78.9 77.5 Casualty Reinsurance 67.0 63.7 68.6 71.2 57.8 Specialty Reinsurance 78.7 69.1 70.5 64.4 57.0 $ 280.3 $ 270.3 $ 284.6 $ 268.3 $ 249.4 $ 189.7 $ 172.0 $ 171.8 $ 162.9 $ 159.8 93.9 94.9 94.1 97.3 99.4 Total Reinsurance Insurance Property and Casualty Insurance Marine, Aviation and Energy Insurance 99.2 92.5 90.1 80.9 85.0 Total Insurance $ 382.8 $ 359.4 $ 356.0 $ 341.1 $ 344.2 Total Net Earned Premiums $ 663.1 $ 629.7 $ 640.6 $ 609.4 $ 593.6 Financial and Professional Lines Insurance 11 ASPEN INSURANCE HOLDINGS LIMITED Consolidated Statements of Changes in Shareholders' Equity Three Months Ended March 31, (in US$ millions) 2016 2015 Ordinary shares $ Beginning and end of period 0.1 $ 0.1 Preference shares Beginning and end of period — — 1.3 0.5 Non-controlling interest Beginning of period (0.2 ) — 1.1 0.5 Beginning of period 1,075.3 1,134.3 New shares issued 1.5 3.5 (25.0 ) (36.5 ) 4.1 4.7 1,055.9 1,106.0 2,283.6 2,050.1 Net income for the period 114.4 128.0 Dividends paid on ordinary and preference shares (22.3 ) (21.9 ) Net change for the period End of period Additional paid-in capital Ordinary shares repurchased Share-based compensation End of period Retained earnings Beginning of period Proportion due to non-controlling interest End of period 0.2 — 2,375.9 2,156.2 Accumulated other comprehensive income: Cumulative foreign currency translation adjustments, net of taxes: 0.6 72.7 Change for the period (11.0 ) (26.1 ) End of period (10.4 ) 46.6 Beginning of period (1.2 ) (3.8 ) Net change from current period hedged transactions (1.4 ) (2.4 ) End of period (2.6 ) (6.2 ) Beginning of period Loss on derivatives: Unrealized appreciation/(depreciation) on available for sale investments, net of taxes: Beginning of period 60.2 Change for the period 76.9 End of period Total accumulated other comprehensive income $ Total shareholders' equity 12 165.4 (2.8 ) 137.1 162.6 124.1 203.0 3,557.1 $ 3,465.8 ASPEN INSURANCE HOLDINGS LIMITED Consolidated Statements of Comprehensive Income Three Months Ended March 31, (in US$ millions) 2016 Net income adjusted for non-controlling interest $ 114.4 2015 $ 128.0 Other comprehensive income, net of taxes: Available for sale investments: Reclassification adjustment for net realized (gains) included in net income (3.7) (31.9) Change in net unrealized gains on available for sale securities held Net change from current period hedged transactions Change in foreign currency translation adjustment 80.6 (1.4) (11.0) 29.1 (2.4) (26.1) 64.5 (31.3) Other comprehensive income/(loss) Comprehensive income $ 13 178.9 $ 96.7 ASPEN INSURANCE HOLDINGS LIMITED Condensed Consolidated Statements of Cash Flows Three Months Ended March 31, (in US$ millions) 2016 Net cash from operating activities $ Net cash (used in)/from investing activities Net cash (used in) financing activities Effect of exchange rate movements on cash and cash equivalents 47.3 2015 $ (106.2 ) (133.2 ) (4.3 ) Decrease in cash and cash equivalents (196.4 ) Cash at beginning of period 47.4 1,099.5 Cash at end of period $ 14 903.1 66.2 120.9 (119.8 ) (19.9) 1,178.5 $ 1,225.9 ASPEN INSURANCE HOLDINGS LIMITED Reserves for Losses and Loss Adjustment Expenses For the Twelve Months Ended December 31, 2015 For the Three Months Ended March 31, 2016 (in US$ millions) Provision for losses and loss adjustment expenses at the start of the period Reinsurance recoverables $ Net loss and loss adjustment expenses at the start of the period Net loss and loss adjustment expenses assumed Provision for losses and loss adjustment expenses for claims incurred 4,938.2 (354.8 ) $ 4,750.8 (350.0 ) 4,583.4 4,400.8 5.7 — Current period Prior period release 379.0 (21.6) 1,522.7 (156.5 ) Total incurred 357.4 1,366.2 (294.5 ) (1,108.5 ) (6.4) (75.1 ) Losses and loss adjustment expenses payments for claims incurred Foreign exchange (gains) Net loss and loss adjustment expenses reserves at the end of the period Reinsurance recoverables on unpaid losses at the end of the period Gross loss and loss adjustment expenses reserves at the end of the period $ 15 4,645.5 4,583.4 366.0 354.8 5,011.5 $ 4,938.2 ASPEN INSURANCE HOLDINGS LIMITED Reserves by Operating Segment (in US$ millions) Reinsurance Insurance Total losses and loss adjustment expense reserves Gross $ 2,472.5 As at March 31, 2016 Reinsurance Recoverables $ 2,539.0 $ 5,011.5 (39.5 ) Net $ (326.5 ) $ (366.0 ) 16 As at December 31, 2015 Reinsurance Gross Recoverables 2,433.0 $ 2,212.5 $ 4,645.5 2,441.9 $ 2,496.3 $ 4,938.2 (32.4 ) $ (322.4 ) $ (354.8 ) Net 2,409.5 2,173.9 $ 4,583.4 ASPEN INSURANCE HOLDINGS LIMITED Prior Year Reserve Releases (in US$ millions) Reinsurance Three Months Ended March 31, 2016 Reinsurance Gross Recoverables Net $ Insurance Release in reserves for prior years during the period 20.3 $ (2.1 ) 2.8 $ 23.1 $ 0.6 $ (1.5 ) 17 18.2 Three Months Ended March 31, 2015 Reinsurance Gross Recoverables Net $ 3.4 $ 21.6 14.5 $ 21.2 $ 35.7 (1.3 ) $ (6.9 ) $ (8.2 ) 13.2 14.3 $ 27.5 ASPEN INSURANCE HOLDINGS LIMITED Consolidated Investment Portfolio Fair Market Value (in US$ millions) March 31, 2016 December 31, 2015 September 30, 2015 June 30, 2015 March 31, 2015 1,138.1 $ 1,074.6 $ 1,041.8 Marketable Securities - Available For Sale U.S. government securities $ 1,111.7 U.S. agency securities $ 1,123.1 $ 149.9 158.7 162.0 182.0 182.9 Municipal securities 32.9 26.6 28.5 29.5 30.7 Corporate securities 2,680.9 2,660.6 2,496.7 2,420.8 2,333.6 674.5 644.2 628.4 661.7 637.7 Asset-backed securities 76.3 76.0 132.5 138.7 140.9 Bonds backed by foreign government 72.5 82.1 77.0 78.3 68.2 1,265.0 1,179.8 1,041.3 1,044.1 1,104.0 6,063.7 5,951.1 5,704.5 5,629.7 5,539.8 135.3 162.9 176.3 184.1 180.2 $ 5,813.8 $ 5,720.0 $ $ Foreign government securities Mortgage-backed securities Total fixed income securities Short-term investments Total Available For Sale $ 6,199.0 $ 6,114.0 $ 5,880.8 $ $ 27.3 $ 13.5 Marketable Securities - Trading U.S. government securities 42.1 3.4 9.0 — — — — 0.2 Municipal securities 4.0 0.5 0.5 0.5 0.5 Corporate securities 615.2 558.2 547.2 540.1 554.1 Foreign government securities 198.5 179.5 128.9 133.8 133.7 Asset-backed securities 19.6 20.5 18.7 19.7 16.0 Mortgage-backed securities 17.4 — — — — U.S. agency securities Bank loans Total fixed income securities Short-term investments Equity securities Catastrophe bonds — 2.0 83.1 80.2 85.9 896.8 788.0 791.9 777.7 799.4 7.7 9.5 6.9 1.1 0.7 757.8 736.4 696.3 729.3 719.0 36.7 32.3 32.8 Total Trading $ 1,708.4 $ 1,589.3 $ 1,531.8 $ 1,540.4 $ 1,551.9 Other Investments $ $ 8.9 $ 9.5 $ $ Cash 46.1 8.9 903.1 55.4 1,099.5 1,196.7 9.5 1,148.4 9.5 1,225.9 ASPEN INSURANCE HOLDINGS LIMITED Investment Analysis (in US$ millions except for percentages) Q1 2016 Net investment income from fixed income investments and cash $ 42.6 Q4 2015 Q3 2015 $ 42.8 $ 40.5 Q2 2015 $ 40.9 Q1 2015 $ 41.2 Net investment income from equity securities Net investment income 6.9 3.6 4.5 5.8 6.2 49.5 46.4 45.0 46.7 47.4 Net realized and unrealized investment gains/(losses) excluding the interest rate swaps 45.0 30.5 (41.2) (15.3 ) 42.9 Net realized investment (losses)/gains from the interest rate swaps (2.8 ) 1.4 (2.8) (0.2 ) (3.2) — — — — — Net realized and unrealized investment gains/(losses) 42.2 31.9 (44.0) (15.5 ) 39.7 Change in unrealized (losses)/gains on available for sale investments (gross of tax) 85.0 (33.4) 17.3 (77.5 ) — $ 18.3 $ (46.3 ) $ 87.1 Other-than-temporary impairment charges Total return/(loss) on investments (1) $ 176.7 Portfolio Characteristics Fixed income portfolio book yield (excluding the impact of the interest rate swaps) Fixed income portfolio duration (excluding the impact of the interest rate swaps) 19 2.56 % 3.6 years $ 44.9 2.59 % 3.7 years 2.50 % 3.4 years 2.57 % 3.5 years 2.56 % 3.5 years ASPEN INSURANCE HOLDINGS LIMITED Book Value Per Ordinary Share (in US$ millions except for number of shares and per share amounts) March 31, 2016 December 31, 2015 September 30, 2015 June 30, 2015 March 31, 2015 Net assets Less: Preference shares Less: Non-controlling interest $ 3,557.1 (555.8 ) (1.1 ) $ 3,419.9 (555.8 ) (1.3) $ 3,371.3 (555.8 ) (1.3) $ 3,363.6 (555.8 ) (1.0 ) $ 3,465.8 (555.8 ) (0.5) Total $ 3,000.2 $ 2,862.8 $ 2,814.2 $ 2,806.8 $ 2,909.5 Ordinary shares outstanding (in millions) 60.675 60.918 60.782 60.778 61.723 Ordinary shares and dilutive potential ordinary shares (in millions) 62.213 62.240 62.147 62.149 63.227 Book value per ordinary share $ 49.45 $ 46.99 $ 46.30 $ 46.18 $ 47.14 Diluted book value per ordinary share $ 48.22 $ 46.00 $ 45.28 $ 45.16 $ 46.02 The dilutive effect of options has been calculated using the treasury stock method. The treasury stock method assumes that the proceeds received from the exercise of options will be used to purchase the Company's ordinary shares at the average market price during the period of calculation. 20 ASPEN INSURANCE HOLDINGS LIMITED Operating Income Reconciliation Net income is adjusted to exclude after-tax change in net foreign exchange gains and losses, realized gains and losses in investments and non-recurring items. Three Months Ended (in US$ millions except where stated) March 31, 2016 March 31, 2015 Net income as reported $ $ Net change attributable to non-controlling interest Preference share dividends 114.4 — (9.5) 0.2 (9.5 ) Net income available to ordinary shareholders Add (deduct) after tax income: Net foreign exchange losses Net realized (gains) on investments Operating income after tax available to ordinary shareholders Tax expense on operating income Operating income before tax available to ordinary shareholders 128.0 105.1 118.5 16.9 (41.4 ) 9.8 (39.8) 80.6 88.5 4.9 6.4 $ 85.5 $ 94.9 $ 1.73 $ 1.91 Basic earnings per ordinary share Net income adjusted for preference share dividends and non-controlling interest Add (deduct) after tax income: Net foreign exchange losses Net realized (gains) on investments 0.28 (0.68 ) Operating income adjusted for preference shares dividends and non-controlling interest 0.16 (0.64) $ 1.33 $ 1.43 $ 1.68 $ 1.87 Diluted earnings per ordinary share Net income adjusted for preference share dividends and non-controlling interest Add (deduct) after tax income: Net foreign exchange losses Net realized (gains) on investments 0.27 (0.66 ) Operating income adjusted for preference shares dividends and non-controlling interest 21 $ 1.29 0.15 (0.63) $ 1.39 Aspen Insurance Holdings Limited INVESTOR PRESENTATION FIRST QUARTER 2016 Exhibit 99.3 AHL: NYSE 2 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 or to be filed shortly 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 financial 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.co. 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 securities 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,” “assume,” “objective,” “intend,” “plan,” “believe,” “do not believe,” “aim,” “project,” “anticipate,” “seek,” “will,” “likely,” “estimate,” “may,” “continue,” “guidance,” “outlook,” “trends,” “future,” “could,” “would,” “should,” “target,” "on track" 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: our ability to successfully implement steps to further optimize the business portfolio, ensure capital efficiency and enhance investment returns; 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 or material loss events, than our underwriting, reserving, reinsurance purchasing or investment practices have anticipated; the assumptions and uncertainties underlying reserve levels that may be impacted by future payments for settlements of claims and expenses or by other factors causing adverse or favorable development, including our assumptions on inflation costs associated with long-tail casualty business which could differ materially from actual experience; a vote by the U.K. electorate in favor of a U.K. exit from the European Union in a forthcoming in-or-out referendum; the reliability of, and changes in assumptions to, natural and man-made catastrophe pricing, accumulation and estimated loss models; decreased demand for our insurance or reinsurance products and cyclical changes in the insurance and reinsurance industry; the models we use to assess our exposure to losses from future natural catastrophes contain inherent uncertainties and our actual losses may differ significantly from expectations; our capital models may provide materially different indications than actual results; increased competition from existing insurers and reinsurers and from alternative capital providers and insurance linked funds and collateralized special purpose insurers on the basis of pricing, capacity, coverage terms, new capital, binding authorities to brokers or other factors and the related demand and supply dynamics as contracts come up for renewal; 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; our acquisition strategy; changes in market conditions in the agriculture industry, which may vary depending upon demand for agricultural products, weather, commodity prices, natural disasters, and changes in legislation and policies related to agricultural products and producers; termination of, or changes in, the terms of the U.S. Federal Multiple Peril Crop Insurance Program or the U.S. Farm Bill, including modifications to the Standard Reinsurance Agreement put in place by the Risk Management Agency of the U.S. Department of Agriculture; the recent consolidation in the (re)insurance industry; loss of one or more of our senior underwriters or key personnel; changes in our ability to exercise capital management initiatives (including our share repurchase program) or to arrange banking facilities as a result of prevailing market conditions or changes in our financial position; changes in the availability, cost or quality of reinsurance or retrocessional coverage; changes in general economic conditions, including inflation, deflation, foreign currency exchange rates, interest rates and other factors that could affect our financial results; the risk of a material decline in the value or liquidity of all or parts of our investment portfolio; the risks associated with the management of capital on behalf of investors; evolving issues with respect to interpretation of coverage after major loss events; our ability to adequately model and price the effects of climate cycles and climate change; any intervening legislative or governmental action and changing judicial interpretation and judgments on insurers’ liability to various risks; the risks related to litigation; the effectiveness of our risk management loss limitation methods, including our reinsurance purchasing; changes in the total industry losses, or our share of total industry losses, resulting from past events 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 modeling techniques, changes in rulings on flood damage or other exclusions as a result of prevailing lawsuits and case law; the impact of one or more large losses from events other than natural catastrophes or by an unexpected accumulation of attritional losses and deterioration with loss estimates; the impact of acts of terrorism, acts of war and related legislation; any changes in our reinsurers’ credit quality and the amount and timing of reinsurance recoverables; the continuing and uncertain impact of the current depressed lower growth economic environment in many of the countries in which we operate; our reliance on information and technology and third- party service providers for our operations and systems; the level of inflation in repair costs due to limited availability of labor and materials after catastrophes; a decline in our operating subsidiaries’ ratings with S&P, A.M. Best or Moody’s; the failure of our reinsurers, policyholders, brokers or other intermediaries to honor their payment obligations; our reliance on the assessment and pricing of individual risks by third parties; our dependence on a few brokers for a large portion of our revenues; the persistence of heightened financial risks, including excess sovereign debt, the banking system and the Eurozone crisis; changes in government regulations or tax laws in jurisdictions where we conduct business; changes in accounting principles or policies or in the application of such accounting principles or policies; increased counterparty risk due to the credit impairment of financial institutions; and Aspen or Aspen Bermuda Limited becoming subject to income taxes in the United States or the United Kingdom. For a more detailed description of these uncertainties and other factors, please see the “Risk Factors” section in Aspen's Annual Report on Form 10-K as filed with the U.S. Securities and Exchange Commission on February 19, 2016. 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. The actuarial range of reserves and management's best estimate represents a distribution from our internal capital model for reserving risk based on our then current state of knowledge and explicit and implicit assumptions relating to the incurred pattern of claims, the expected ultimate settlement amount, inflation and dependencies between lines of business. 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 within the stated amount. SAFE HARBOR DISCLOSURE heightened financial risks, including excess sovereign debt, the banking system and the Eurozone crisis; changes in government regulations or tax laws in jurisdictions where we conduct business; changes in accounting principles or policies or in the application of such accounting principles or policies; increased counterparty risk due to the credit impairment of financial institutions; and Aspen or Aspen Bermuda Limited becoming subject to income taxes in the United States or the United Kingdom. For a more detailed description of these uncertainties and other factors, please see the “Risk Factors” section in Aspen's Annual Report on Form 10-K as filed with the U.S. Securities and Exchange Commission on February 19, 2016. 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. The actuarial range of reserves and management's best estimate represents a distribution from our internal capital model for reserving risk based on our then current state of knowledge and explicit and implicit assumptions relating to the incurred pattern of claims, the expected ultimate settlement amount, inflation and dependencies between lines of business. 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 within the stated amount. SAFE HARBOR DISCLOSURE AHL: NYSE 3 Specialty Other Property Casualty Property Cat 30% 28% 23% 19% Property and Casualty Financial and Professional Lines Marine, Aviation and Energy 51% 26% 23% Reinsurance Insurance 42% 58% ASPEN OVERVIEW • Global specialty insurer and reinsurer with long-term track record of shareholder value creation • $3.1bn gross written premiums for the last twelve months ended March 31, 2016 • Underwriting focused company with industry-leading underwriting expertise and collaborative culture with team-based decision making • Well-run, risk aware business building value in a controlled way • Clear strategy to create superior value through well- balanced business portfolio, enhancing investment returns and capital efficiency • Proven management team, disciplined risk management and balance sheet strength • Ratings/Outlook of A / Stable (S&P), A2 / Stable (Moody’s) and A Excellent/ Stable (A.M. Best) for Aspen’s operating subsidiaries Q1 2016 LTM (1) INSURANCE BUSINESS LINES Q1 2016 LTM (1) REINSURANCE BUSINESS LINES Q1 2016 LTM (1) COMPANY BUSINESS MIX (1) LTM: Last Twelve Months through March 31, 2016 AHL: NYSE 4Reinsurance Insurance Lloyd's 2002 2003 2004 2005 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015 $375 $1,307 $1,587 $2,093 $1,946 $1,819 $2,002 $2,067 $2,077 $2,208 $2,583 $2,647 $2,903 $2,997 HAVE STEADILY DIVERSIFIED THE BUSINESS MIX (GWP in $m) Note: Included in Lloyd's is our Lloyd's insurance and reinsurance business as well as business written on the Lloyd's platform that is included in U.S. Insurance. 23% 77% 23% 77% 26% 74% 69% 38% 31% 37% 62% 63% 7% 37% 54% 30% 16% 47% 37% 16% 43% 41% 16% 40% 43% 17% 41% 42% 17% 11% 57% 56% 30% 14% 32% 56% AHL: NYSE 5 Diluted Book Value Per Share Accumulated Dividends per Ordinary Share Q1 2006 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015 Q1 2016 $18.95 $21.83 $27.08 $28.19 $34.14 $38.90 $38.21 $40.65 $40.90 $45.13 $46.00 $48.22 $0.87 $1.32 $1.92 $2.52 $3.12 $3.72 $4.32 $4.98 $5.70 $6.50 $7.34 $7.56 A STRONG TRACK RECORD OF CAPITAL RETURNED TO SHAREHOLDERS CAGR 10.9 %(2 ) • Built a diversified specialty insurer and reinsurer with strong track record • Average 10 year Operating ROE of 11.0%(1) • Investment in growing the business profitably is a key priority • However, will return capital to shareholders when that is financially more attractive than deploying elsewhere • Returned over $2bn to shareholders through ordinary dividends and share repurchases from inception through Q1 2016 (1) Average of annualized quarterly ROE from 04/01/06 through 03/31/06. (2) Compound Annual Growth Rate calculated to reflect total equity and accumulated dividends per ordinary share from 03/31/06 through 03/31/16. AHL: NYSE 6 ASPEN RE – AN ESTABLISHED INDUSTRY LEADER (1) LTM: Last Twelve Months through March 31, 2016 (2) 2015 premiums from APAC, LatAM and MENA (3) See "Safe Harbor Disclosure", slide 2 Q1 2016 LTM (1) GWP $1.28 billion BY BUSINESS LINE • Deep and enduring relationships with well-chosen clients, significant industry expertise and excellent track record of performance • Innovative and thoughtful solutions; utilizing multi- line capabilities and Aspen Capital Markets to leverage third-party capital • Increasingly diversified portfolio across four sub- segments • Regional structure to meet increasing demand for local market solutions • Significant long-term growth prospects in emerging markets, which accounted for 19% of total Reinsurance premiums in 2015(2) (3) • Continued focus on research and development of new products, bringing innovation, deep expertise and fresh thinking to our markets and operations • Successful 1/1 and 4/1 renewals and new business opportunities reaffirm Aspen’s relevance, strategy and broad reach in a difficult market • Acquired AgriLogic, a diversifying, growing U.S. crop insurance business and agricultural consultancy(3) Specialty Other Property Casualty Property Cat 30% 28% 23% 19% Aspen Re is a powerful contributor to ROE and has strong future prospects (3) SPECIALTY OTHER PROPERTY • Credit & Surety • Treaty Risk Excess • Agriculture • Treaty Pro Rata • Other Specialty including Aviation, Energy and Marine • Global Property Facultative CASUALTY PROPERTY CATASTROPHE • U.S. Casualty Treaty • Treaty Catastrophe • International Casualty Treaty • Global Casualty Facultative AHL: NYSE 7 ASPEN RE GROWTH & DIVERSIFICATION - AGRILOGIC ACQUISITION • U.S. crop insurance business and agricultural consultancy within the Specialty Re sub-segment • High quality, diversifying business for Aspen, excellent long-term growth opportunity(1) • Significant intellectual capital, strong analytical tools and capabilities • Enhanced marketing, combined with larger Aspen balance sheet, offers excellent growth opportunity(1) • Limited integration risk - Aspen Re has a long relationship with AgriLogic and integration progressing well • AgriLogic should be a double digit ROE business(1) • Transaction expected to be broadly neutral to operating ROE in 2016; and accretive to operating ROE in 2017(1) (1) See " Safe Harbor Disclosure" slide 2 AHL: NYSE 8 Property and Casualty Financial and Professional Lines Marine, Aviation and Energy 51% 26% 23% ASPEN INSURANCE – LEADING SPECIALTY INSURER PROPERTY & CASUALTY FINANCIAL & PROFESSIONAL LINES MARINE, AVIATION AND ENERGY • U.K. Property & Construction • Accident & Health • Aviation • U.S. Property • Crisis Management • Energy • U.K. Regional Property & Liability • Credit and Political Risk • Marine & Energy Liability • Global Excess Casualty • Professional Liability (Indemnity) • Marine Hull • U.K. Casualty • Management Liability / Directors & Officers • Specie & Fine Art • U.S. Casualty • Technology Liability & Data Protection Indemnity • U.S. Marine Energy & Construction • Environmental Liability • U.S. Surety • U.S. Programs • Financial Institutions • Railroad (1) LTM: Last Twelve Months through March 31, 2016 (2) See "Safe Harbor Disclosure", slide 2 Q1 2016 LTM (1) GWP $1.77 billion BY BUSINESS LINE • A growing force in global specialty insurance offering creative, customized solutions to complex risks, deep local knowledge and expertise, integrated claims and underwriting teams and select distribution. Built on two main specialty insurance platforms: • U.S. - Growing specialty insurance business; diversified portfolio with broadening range of product offerings; expanding network of offices throughout the U.S. • International - Highly respected lead expertise in many niche lines; portfolio comprises impressive variety of specialty products with business predominantly originating in Lloyd's and the London market; hubs in Bermuda, Zurich and Dublin Aspen Insurance continues to diversify and expand its global product offering(2) AHL: NYSE 9 ASPEN INSURANCE: ENHANCING A LEADING GLOBAL SPECIALTY INSURANCE FRANCHISE • Track record of investing for profitable organic growth: U.S. Insurance platform • Two strategies to accelerate the growth and profitability of Aspen Insurance business: (1) organize business globally for risks that are traded globally and (2) enrich targeted areas of underwriting expertise HOW: Hired David Cohen, a best in class specialty underwriting leader with a successful history of running a global specialty business ▪ Identified 13 global product lines, of which 9 global product heads appointed to date ▪ Promoted from within Aspen and hired seasoned global underwriting leaders to manage the global lines; hired a select few underwriting experts for specialties not covered and upgraded underwriting talent in key lines EXPENSE: Aspen Insurance infrastructure was built to be leveraged for greater scale ▪ Majority of costs are personnel related (along with some reorganization costs); invested $5 million in 2015; further investment of approximately $15 million anticipated in 2016(1) EXPECTED RESULTS: ▪ Short term: Decrease volatility in Insurance business by evaluating line size, exposure profile, reinsurance arrangements, and business mix under new global leadership, modest incremental GWP impact in 2016, more significant in 2017 and beyond(1) ▪ Medium term: Lower loss ratio driven by less volatility(1) (1) See " Safe Harbor Disclosure" slide 2 Anticipate larger, more profitable business, more stable outcomes and better loss ratios(1) AHL: NYSE 10 BUILT A DIVERSIFIED INTERNATIONAL INSURANCE PORTFOLIO Lloyd's UK Bermuda 55% 44% 1% Energy Physical Damage Aviation Credit and Political Risks Marine and Energy Liability Global Excess Casualty Financial and Corporate Risks Professional and Management Liability Marine Hull Specie & Fine Art Crisis Management 12% 15% 3% 21% 3% 14% 15% 8% 3% 6% Q1 2016 LTM (1) LLOYD'S GWP: $477.1m Q1 2016 LTM (1) INTERNATIONAL INSURANCE TEAM GWP: $879.5m • International Insurance teams diversified by platform and line • With a more volatile rate environment than the U.S.: ▪ Teams remain disciplined and focused on better rated opportunities ▪ We downsized some international lines in response to changing market conditions (1) LTM: Last Twelve Months through March 31, 2016 AHL: NYSE 11 2008 2009 2010 2011 2012 2013 2014 2015 $138 $230 $287 $361 $421 $439 $489 $507 LLOYD'S IS A KEY COMPONENT OF INTERNATIONAL INSURANCE BUSINESS CAGR 20% (1) See "Safe Harbor disclosure", slide 2 Note: Included above is our Lloyd's insurance and reinsurance business as well as business written on the Lloyd's platform that is included in U.S. Insurance. Premiums reported in British pounds converted to U.S. dollars at average exchange rate during the applicable year. Source: Syndicate reports ($m) • International Insurance teams generated close to $860m of premiums in 2015, with pre-eminent positions in targeted markets and offerings across a diverse range of risks and geographies • Lloyd’s of London platform increasingly fundamental for first-tier commercial insurers • Clients want access to Lloyd’s global footprint • Significant barrier to entry for new applicants; any new Syndicate business plan must be differentiated and accretive to Lloyd’s franchise to gain entry Aspen’s Lloyd’s Premium Well-established International Insurance platform, achieving strong contribution to ROE since inception(1) AHL: NYSE 12 Property Casualty Professional Lines 60%25% 15% Programs Property Professional Liability Marine Energy Casualty Environmental Liability Management Liability Surety 24% 17% 16% 4% 7% 16% 8% 4%4% BUILT A DIVERSIFIED U.S. SPECIALTY INSURANCE PORTFOLIO 2010 U.S. INSURANCE TEAMS GWP: $167m Q1 2016 LTM (1) U.S. INSURANCE TEAMS GWP: $905m • Diversified portfolio with broadening range of product offerings focused on delivering strong premium growth and solid underwriting margins • Over $250m of net operating losses carried forward; can be applied against future U.S. Insurance profits(2) (1) LTM: Last Twelve Months through March 31, 2016 AHL: NYSE 13 CAPITAL EFFICIENCY: SUSTAINED RECORD OF PROACTIVE MANAGEMENT OF CAPITAL • Continued focus on responsible capital stewardship: hold more than regulatory and risk capital models suggest; return capital to shareholders when it is financially more attractive to do so than deploying elsewhere • Aspen's franchise has generated approximately $4bn of capital since inception • Returned to shareholders over $2bn of cumulative repurchases and ordinary dividends through March 31, 2016, including all ordinary shareholder funds raised at our Initial Public and Secondary Offerings • Steadily increased dividend growth over recent years; 5% quarterly dividend increase in April 2016 • Returned a cumulative 70% of operating income to shareholders since inception through Q1 2016 ($ in mm) Cumulative Repurchases Cumulative Dividends 2004 2005 2006 2007 2008 2009 2010 2011 2012 2013 2014 2015 Q1 2016 $8 $56 $313 $467 $617 $667 $1,122 $1,172 $1,282 $1,639 $1,870 $2,005 $2,043 >$2bn of Total Capital Returned through Q1 2016 AHL: NYSE 14 CAREFUL INVESTMENT MANAGEMENT AND CONSISTENT INVESTMENT RETURNS 38% IG Credit 13% US Treasury 10% Cash & Short-Term 15% Agency MBS 9% Equities 6% Sovereign 4% Non US Agency 2% US Agency 1% ABS 1% Non US Govt Guaranteed 0.3% CMBS 1% Munis PORTFOLIO ALLOCATIONS March 31, 2016 100% = $8.6 billion(1) • Stable investment income and total return through all market cycles • Since 2011 have tactically built the risk asset portfolio and dynamically managed the positions • 12.8% of the portfolio invested in risk assets (including equities 8.8%, and BBB emerging market debt 3.6%) • Fixed income portfolio duration: 3.56 years (including swaps) (1) Excludes amounts attributable to variable interest entities; may not add to 100% due to rounding AHL: NYSE 15 CONCLUSION: FOCUSED ON SHAREHOLDER VALUE • Deep underwriting expertise and understanding of client needs and risks • Pursuing selective, profitable growth in exposures we understand, subject to market conditions • Diversified platform allows us to focus on better rated opportunities as they arise, including: • Reinsurance ▪ Agriculture, Bond, Financial, Terrorism, Marine • Insurance ▪ Enhance our global product offering in areas such as Accident and Health, Environmental, Professional Liability, Technology Liability & Data Protection Indemity, Marine, and Crisis Management (1) See “Safe Harbor Disclosure” slide 2 Deliver growth in Operating ROE and Diluted Book Value Per Share over time(1) APPENDIX AHL: NYSE 17 UNDERWRITING EXPERTISE: ASPEN’S NATURAL CATASTROPHE EXPOSURES IN MAJOR PERIL ZONES AS AT APRIL 1, 2016 100 YEAR RETURN PERIOD AS % OF TOTAL SHAREHOLDERS’ EQUITY AND IN $ MILLIONS 1 in 100 year tolerance: 17.5% of total shareholders’ equity 1 in 250 year tolerance: 25.0% of total shareholders’ equity Based on Shareholders' equity of $3,556.0 million (excluding non-controlling interest) at March 31, 2016. The estimates reflect Aspen's own view of the modelled maximum losses (“PMLs”) at the return periods shown which include input from various third party vendor models, our own proprietary adjustments to these models, and planned reinsurance purchases. The U.S. regional WS PMLs reflect the outward reinsurance structures in place. Catastrophe loss experience may materially differ from the modelled PMLs due to limitations in one or more of the models or uncertainties in the application of policy terms and limits. $0 $100 $200 $300 $400 $500 $600 250 year return period as $m of Total Shareholder Equity U.S. Eastern Quake Cascadia EQ Japan All Perils European Wind Northeast and MidAtlantic WS Texas and Gulf WS Florida and Southeast WS California EQ $304 $246 $160 $274 $405 $446 $524 $485 • PMLs are net of reinsurance and Aspen Capital Markets' third-party capital • Enhanced disclosure of regional WS exposures $0 $100 $200 $300 $400 100 year return period as $m of Total Shareholder Equity U.S. Eastern Quake Cascadia EQ Japan All Perils European Wind Northeast and MidAtlantic WS Texas and Gulf WS Florida and Southeast WS California EQ $59 $117 $133 $192 $245 $264 $359 $382 1.7% 8.5% 3.3% 3.7% 6.9% 5.4% 4.5% 6.9% 7.7% 7.4% 11.4% 10.1% 10.7% 13.6% 12.5% 14.7% 250 YEAR RETURN PERIOD AS % OF TOTAL SHAREHOLDERS’ EQUITY AND IN $ MILLIONS Aspen Insurance Holdings Limited INVESTOR PRESENTATION FIRST QUARTER 2016