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Financial Update 3
September 30, 2019 For the Years Ended, ($ in millions, except per share) YTD QTD 2018 2017 2016 2015 2014 Income Statement Data: Gross Written Premiums $ 1,523 $ 414 $ 1,821 $ 1,439 $ 1,269 $ 1,161 $ 1,137 Net Earned Premiums 1,057 374 1,262 1,035 890 847 874 Net Underwriting Income (Loss) (75) (85) (39) (79) 53 127 205 Comprehensive Income (Loss) Attributable to Sirius Group 34 (50) (80) (78) (34) 196 186 Balance Sheet Data: Total Cash and Investments $ 3,673 $ 3,542 $ 3,604 $ 3,815 $ 3,678 $ 3,290 Total Assets 6,465 6,008 5,824 5,167 5,092 5,192 Debt 670 697 723 396 403 403 Total Liabilities 4,483 4,069 3,800 2,927 2,883 3,179 Series B Preference Shares 236 232 - - - - Common Shareholders' Equity 1,743 1,704 1,917 1,988 1,959 1,763 Total Liabilities & Equity 6,465 6,008 5,824 5,167 5,092 5,192 Key Financial Indicators: GAAP Combined Ratio 107% 123% 103% 108% 94% 85% 77% Current Catastrophes on combined ratio 11% 29% 15% 25% 12% 2% 7% Book Value Per Common Share $ 15.11 $ 14.80 $ 15.98 $ 16.57 $ 16.33 $ 14.69 Adjusted Book Value Per Share (1) $ 15.47 $ 15.24 $ 15.98 $ 16.57 $ 16.33 $ 14.69 Adjusted Tangible Book Value Per Share (2) $ 11.10 $ 10.76 $ 11.10 $ 16.53 $ 16.24 $ 14.56 (1) Adjusted book value per share is derived by dividing adjusted book value (common shareholders' equity plus series B preference share amount reflected in mezzanine equity, and earned portion of future proceeds from stock option awards) by adjusted shares outstanding (common shares outstanding plus series B preference shares outstanding and earned portion of share-based compensation awards). (2) Adjusted tangible book value per share is derived by dividing adjusted tangible book value (adjusted book value less goodwill, intangible assets and net deferred tax liability on intangible assets) by adjusted shares outstanding (common shares outstanding plus series B preference shares outstanding and earned portion of share-based compensation awards). See appendix for reconciliation of non-GAAP measures. 4
Global Specialty & Runoff & Corporate ($ in millions) Global A&H Total Property Casualty Other Elimination Gross written premiums $ 153.6 $ 137.4 $ 120.6 $ 2.1 $ - $ 413.7 Net written premiums $ 103.7 $ 104.6 $ 113.2 $ 0.8 $ - $ 322.3 Net earned insurance and reinsurance premiums $ 159.9 $ 115.1 $ 98.7 $ 0.5 $ - $ 374.2 Loss and allocated LAE (184.4) (63.6) (85.5) (0.9) - (334.4) Insurance and reinsurance acquisition expenses (29.2) (32.5) (27.1) (0.1) 13.8 (75.1) Technical profit (loss) (53.7) 19.0 (13.9) (0.5) 13.8 (35.3) Unallocated LAE (5.5) (2.0) (3.0) (0.2) (3.5) (14.2) Other underwriting expenses (14.7) (6.8) (8.8) (1.4) (3.7) (35.4) Underwriting income (loss) (73.9) 10.2 (25.7) (2.1) 6.6 (84.9) Service fee revenue - 31.0 - - (14.6) 16.4 Managing general underwriter unallocated LAE - (4.3) - - 4.3 - Managing general underwriter other underwriting expenses - (3.7) - - 3.7 - General and administrative expenses, MGU + Runoff & Other - (15.1) - (1.2) (16.3) Underwriting income (loss), including net service fee income $ (73.9) $ 18.1 $ (25.7) $ (3.3) $ - $ (84.8) Global Specialty & Runoff & Corporate ($ in millions) Global A&H Total Property Casualty Other Elimination Gross written premiums $ 720.5 $ 459.5 $ 338.4 $ 4.7 $ - $ 1,523.1 Net written premiums $ 536.6 $ 360.1 $ 310.6 $ 1.5 $ - $ 1,208.8 Net earned insurance and reinsurance premiums $ 463.9 $ 330.0 $ 261.7 $ 1.2 $ - $ 1,056.8 Loss and allocated LAE (378.3) (198.6) (194.4) (4.4) - (775.7) Insurance and reinsurance acquisition expenses (82.2) (95.1) (72.2) (2.6) 36.7 (215.4) Technical profit (loss) 3.4 36.3 (4.9) (5.8) 36.7 65.7 Unallocated LAE (10.2) (5.5) (7.1) (0.9) (11.1) (34.8) Other underwriting expenses (47.9) (18.8) (23.7) (4.6) (11.2) (106.2) Underwriting income (loss) (54.7) 12.0 (35.7) (11.3) 14.4 (75.3) Service fee revenue - 97.6 - - (39.3) 58.3 Managing general underwriter unallocated LAE - (13.7) - - 13.7 - Managing general underwriter other underwriting expenses - (11.2) - - 11.2 - General and administrative expenses, MGU + Runoff & Other - (46.3) - (3.0) (49.3) Underwriting income (loss), including net service fee income $ (54.7) $ 38.4 $ (35.7) $ (14.3) $ - $ (66.3) 5
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Business Overview 8
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Executive Management Committee Kip Oberting | Group President & CEO Monica Cramér-Manhem | President, Gene Boxer | Chief Strategy Officer & Sirius Tenure: 15 | Relevant Experience: 23 Global Reinsurance Group General Counsel Sirius Tenure: 33 | Relevant Experience: 33 Sirius Tenure: 3 | Relevant Experience: 20 Group Functional Leaders Ralph Salamone | Group Chief Financial Jeff Davis | Group Chief Actuary & Matthew Kirk | Group Treasurer & Head of Lisa Tanzi | Deputy General Counsel, Officer Chief Risk Officer Investments and Investor Relations Secretary & Group Chief Compliance Officer Sirius Tenure: 22 | Relevant Experience: 31 Sirius Tenure: 11 | Relevant Experience: 28 Sirius Tenure: 17 | Relevant Experience: 24 Sirius Tenure: 1 | Relevant Experience: 18 . Edward Park | Group Tax Director Joseph Marcianti | Group Head of Internal Beth Boucher | Group Chief Information Sirius Tenure: 3 | Relevant Experience: 21 Audit Officer . Sirius Tenure: 1 | Relevant Experience: 29 Sirius Tenure: - | Relevant Experience: 27 12 .
Dan Wilson | President, U.S. Specialty Stuart Liddell | Global Head of Life, Tom Leonardo | Head of U.S. Jan Onselius | Chief Underwriting Warren Trace | President, North Patrick Chamberland | EVP, Insurance Accident and Health Accident and Health Officer, Global Reinsurance America Reinsurance International Reinsurance Sirius Tenure: 23 | Experience: 33 Sirius Tenure: 16 | Experience: 29 Sirius Tenure: 7 | Experience: 25 Sirius Tenure: 36 | Experience: 36 Sirius Tenure: 36 | Experience: 41 Sirius Tenure: 34 | Experience: 34 Martin Hamrin | Group Underwriting Lars Andersson | Chief Financial Ian Sawyer | Head of Casualty Robert Harman | Managing Director, Simon Acland | Chief Underwriting Neal Wasserman | President, Analytics & Chief Portfolio Officer Officer, Global Reinsurance Reinsurance SIMA (Lloyd's Syndicate 1945) Officer, SIMA (Lloyd's Syndicate 1945) Global Runoff Solutions Sirius Tenure: 12 | Experience: 23 Sirius Tenure: 11 | Experience: 16 Sirius Tenure: 19 | Experience: 33 Sirius Tenure: 7 | Experience: 20 Sirius Tenure: 21 | Experience: 30 Sirius Tenure: 2 | Experience: 32 . . 13 .
o Various insurance and financial regulators around the globe, Meyer (Sandy) Frucher * > Vice Chairman, Nasdaq primarily: • Bermuda Monetary Authority Rachelle C. Keller * > Former Managing Director, Citibank • Swedish Financial Services Authority James (Jim) B. Rogers, Jr * > International investor, author and • N.Y. Department of Financial Services commentator • U.K. Prudential Regulation Authority • Lloyds Alain Karaoglan * Former COO, Voya o Public company governance with independent directors and Robert (Rob) L. Friedman * Former CIO, the Mutual Series funds independent committees. Kernan (Kip) Oberting CEO, Sirius Group o Additional governance protections from a shareholders Raymond Tan > CEO & CRO, CMIG International agreement between Sirius and the Cornerstone Investors (The Carlyle Group, Bain Capital Credit, Gallatin Point Capital, and Centerbridge Partners) and CM Bermuda insulate our independent board. “ The Nasdaq listing of Sirius Group in November 2018 further enhanced the “AM Best believes that SIIG’s listing on the group’s independence ; CMIG’s ownership “ Fitch views Sirius’s structural safeguards Nasdaq in November 2018, and subsequent stake was reduced and a majority independent as primarily insulating the company from compliance with the Nasdaq listing board was instituted … In our view, this CMIG’s liquidity issues, although its corporate requirements, strengthened its governance protects the group from any upstreaming of governance protections have not been tested and improved its transparency , reinforcing its under such a high stress event.” capital to CMIG. Any extraordinary dividend independence from its ultimate parent, CMIG.” payment would require approval from an independent board.” - Fitch, April 23, 2019 - AM Best, February 15, 2019 - S&P, February 12, 2019 14
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