2 Financial Update 3 September 30, 2019 For the Years Ended, ($ - - PowerPoint PPT Presentation

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Financial Update

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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. ($ in millions, except per share) For the Years Ended, September 30, 2019

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($ in millions) Global Property Global A&H Specialty & Casualty Runoff & Other Corporate Elimination Total Gross written premiums 153.6 $ 137.4 $ 120.6 $ 2.1 $

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413.7 $ Net written premiums 103.7 $ 104.6 $ 113.2 $ 0.8 $

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322.3 $ Net earned insurance and reinsurance premiums 159.9 $ 115.1 $ 98.7 $ 0.5 $

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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) $

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(84.8) $ ($ in millions) Global Property Global A&H Specialty & Casualty Runoff & Other Corporate Elimination Total Gross written premiums 720.5 $ 459.5 $ 338.4 $ 4.7 $

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1,523.1 $ Net written premiums 536.6 $ 360.1 $ 310.6 $ 1.5 $

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1,208.8 $ Net earned insurance and reinsurance premiums 463.9 $ 330.0 $ 261.7 $ 1.2 $

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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) $

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(66.3) $

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$350

$0 $100 $200 $300 $400 $500

Business Overview

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Executive Management Committee Group Functional Leaders

Kip Oberting| Group President & CEO Sirius Tenure: 15 | Relevant Experience: 23 Monica Cramér-Manhem| President, Global Reinsurance Gene Boxer| Chief Strategy Officer & Group General Counsel Sirius Tenure: 33 | Relevant Experience: 33 Sirius Tenure: 3 | Relevant Experience: 20 Sirius Tenure: 22 | Relevant Experience: 31 Sirius Tenure: 11 | Relevant Experience: 28 Sirius Tenure: 17 | Relevant Experience: 24 Sirius Tenure: 1 | Relevant Experience: 18 Ralph Salamone| Group Chief Financial Officer Lisa Tanzi | Deputy General Counsel, Secretary & Group Chief Compliance Officer Jeff Davis| Group Chief Actuary & Chief Risk Officer Matthew Kirk| Group Treasurer & Head of Investments and Investor Relations Edward Park| Group Tax Director Sirius Tenure: 3 | Relevant Experience: 21 Sirius Tenure: 1 | Relevant Experience: 29 Sirius Tenure: - | Relevant Experience: 27 Joseph Marcianti| Group Head of Internal Audit Beth Boucher | Group Chief Information Officer

Sirius Tenure: 12 | Experience: 23 Sirius Tenure: 11 | Experience: 16 Sirius Tenure: 19 | Experience: 33 Robert Harman| Managing Director, SIMA (Lloyd's Syndicate 1945) Simon Acland| Chief Underwriting Officer, SIMA (Lloyd's Syndicate 1945) Neal Wasserman| President, Global Runoff Solutions Sirius Tenure: 23 | Experience: 33 Sirius Tenure: 16 | Experience: 29 Sirius Tenure: 7 | Experience: 25 Dan Wilson| President, U.S. Specialty Insurance Stuart Liddell| Global Head of Life, Accident and Health Tom Leonardo | Head of U.S. Accident and Health Sirius Tenure: 36 | Experience: 36 Sirius Tenure: 36 | Experience: 41 Sirius Tenure: 34 | Experience: 34 Jan Onselius | Chief Underwriting Officer, Global Reinsurance Warren Trace | President, North America Reinsurance Patrick Chamberland| EVP, International Reinsurance Sirius Tenure: 7 | Experience: 20 Sirius Tenure: 21 | Experience: 30 Sirius Tenure: 2 | Experience: 32 Martin Hamrin| Group Underwriting Analytics & Chief Portfolio Officer Lars Andersson| Chief Financial Officer, Global Reinsurance Ian Sawyer | Head of Casualty Reinsurance

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• Various insurance and financial regulators around the globe,

primarily:

• Bermuda Monetary Authority
• Swedish Financial Services Authority
• N.Y. Department of Financial Services
• U.K. Prudential Regulation Authority
• Lloyds
• Public company governance with independent directors and

independent committees.

• Additional governance protections from a shareholders

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. Meyer (Sandy) Frucher *> Vice Chairman, Nasdaq Rachelle C. Keller *> Former Managing Director, Citibank James (Jim) B. Rogers, Jr *> International investor, author and commentator Alain Karaoglan * Former COO, Voya Robert (Rob) L. Friedman * Former CIO, the Mutual Series funds Kernan (Kip) Oberting CEO, Sirius Group Raymond Tan > CEO & CRO, CMIG International

“AM Best believes that SIIG’s listing on the Nasdaq in November 2018, and subsequent compliance with the Nasdaq listing requirements, strengthened its governance and improved its transparency, reinforcing its independence from its ultimate parent, CMIG.”

• AM Best, February 15, 2019

“The Nasdaq listing of Sirius Group in November 2018 further enhanced the group’s independence; CMIG’s ownership stake was reduced and a majority independent board was instituted … In our view, this protects the group from any upstreaming of capital to CMIG. Any extraordinary dividend payment would require approval from an independent board.”

• S&P, February 12, 2019

“Fitch views Sirius’s structural safeguards as primarily insulating the company from CMIG’s liquidity issues, although its corporate governance protections have not been tested under such a high stress event.”

• Fitch, April 23, 2019

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As of

• Sept. 30, 2019

2018 2017 2016 2015 2014

slide 4 - book value per share

GAAP common shareholders' equity 1,743 $ 1,704 $ 1,917 $ 1,988 $ 1,959 $ 1,763 $ add: Series B preference shares 236 232

• add: Earned future proceeds from stock option awards

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• Adjusted book value

1,982 $ 1,937 $ 1,917 $ 1,988 $ 1,959 $ 1,763 $ less: Goodwill and intangible assets (584) (596) (617) (5) (10) (15) add: Net deferred tax liability on intangible assets 24 26 32

• Adjusted tangible book value

1,422 $ 1,367 $ 1,332 $ 1,983 $ 1,949 $ 1,747 $ Common shares outstanding 115.299 115.151 120.000 120.000 120.000 120.000 add: Series B preference shares outstanding 11.902 11.902 add: Earned share-based compensation, excl stock optio 0.649

• add: Earned portion of stock option awards issued

0.267

• Adjusted shares outstanding

128.117 127.053 120.000 120.000 120.000 120.000 Book value per common share 15.11 $ 14.80 $ 15.98 $ 16.57 $ 16.33 $ 14.69 $ Adjusted book value per share 15.47 $ 15.24 $ 15.98 $ 16.57 $ 16.33 $ 14.69 $ Adjusted tangible book value per share 11.10 $ 10.76 $ 11.10 $ 16.53 $ 16.24 $ 14.56 $ (in millions, except per share) For the Years Ended,