HAMILTON INSURANCE

GROUP

NOVEMBER 2017

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INTRODUCTION AND HIGHLIGHTS

BOARD OF DIRECTORS AND EXECUTIVE COMMITTEE

INSURANCE AND REINSURANCE OPERATIONS

TWO SIGMA

APPENDIX

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15

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Table of Contents

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Introduction and Highlights

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A Powerful Partnership

Hamilton was launched in December 2013 by a team led by insurance industry veteran Brian Duperreault.

Pina Albo will become the Chief Executive Officer of Hamilton Insurance Group on February 1, 2018.

We’re executing a strategy to leverage analytics and research to create superior underwriting and investment value for our clients and shareholders.

We’re differentiated by:

Our startup mindset coupled with a deeply experienced management

team

Our commitment to leveraging technology and data science

Our relationship with Two Sigma, a technology and investment company

No legacy (financial or systems) issues

As of September 30, 2017, Hamilton has over $1.6 billion in shareholders’ equity.

A New York-based technology and investment company with unique experience and capabilities in the area of advanced analytics which they apply to data-driven investing

Assets under management of over $47 billion

Generated positive alpha and net returns every year since inception—15 consecutive years

1,200+ employees, two thirds of whom are modelers and engineers

Has distinguished itself as an innovator and a leader in investment management

MISSION: WE’RE WRITING THE FUTURE OF RISK.We’re a Bermuda-based holding company for insurance and reinsurance

operations doing business on a worldwide basis.

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Hamilton Underwriting Limited,

a Lloyd’s Managing Agency,

controls Syndicate 3334

Approved by Lloyd’s to write

$150 million of premiums for the

2017 Year of Account

Benefits from Lloyd’s ratings

from A.M. Best “A” (Excellent);

and S&P “A+” (Strong); and

Fitch “AA-” (Very Strong);

Joint venture between Hamilton,

AIG and Two Sigma

Building a market leading,

technology-based platform in

the $150 billion Small to Medium

Enterprise (SME) market

Led by CEO James Hobson,

former COO of OnDeck Capital

Represents an unprecedented

partnership that leverages data

science, technology, brand

awareness and extensive claims

data

Partnership with Hamilton

Manages majority of Hamilton’s capital in its proprietary funds

Leverages data analytics and modeling skills to advance the science of underwriting risk

Dedicated staff at Two Sigma Insurance Quantified (TSIQ) work closely with Attune and Hamilton on data science projects

Entities affiliated with principals of Two Sigma are significant shareholders at Hamilton

Established book of business in

sixth year of growth

Shareholder’s equity over $1.5

billion at September 30, 2017

Wrote over $250 million of gross

premiums in 2016; forecast to

write approximately $290 million

in 2017

Bermuda-based Class 4

property and casualty (re)insurer

A.M. Best: “A-” (Excellent)

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Hamilton Today

A renowned Board of Directors

Pina Albo appointed Group CEO as of February 1, 2018

Commitment to our long-term strategy

Superior financial strength

Meets or exceeds profitability expectations

Expert risk management

Consistent performance through market volatility

Disciplined growth

Attracts exceptional talent

Efficient structure accessing US insurance through Attune, as well as the Bermuda market and Lloyd’s

Unique partnership with Two Sigma, a leading technology and investment company

Poised to continue to generate superior returns

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Hamilton’s Growth in BV and SE

Hamilton was funded pursuant to a private placement of fering at $10.00 per share on December 23, 2013

Certain founding shareholders exercised a $250 million greenshoe right, effective January 1, 2015

BOOK VALUE PER SHARE

$15.91 $1,621$16.22 $1,655 $1,716

30-J

UN-1

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$16.93

30-J

UN-1

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CONSOLIDATED SHAREHOLDERS EQUITY

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Board of Directors and Executive Committee

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Industry-Renowned Leadership

BOARD OF DIRECTORS

David Brown – Interim Group CEO(1), Hamilton Insurance Group; Chairman, Finance and Governance Committee

Founder & Chief Executive Officer of Flagstone Re 2005 – 2012Chief Executive Officer, Centre Solutions 1994 – 1997Former Partner, EYChairman of the Board of Bermuda Stock Exchange

Bill Freda – Chairman, Hamilton Insurance Group; Chairman, Audit Committee

Chairman of The Guardian Life Insurance Company of AmericaRetired as Vice Chairman, Deloitte LLP after a distinguished 40 year career with the firm Member of the Board of Directors of The Guardian Insurance Company of America and State Street Corporation

Tom Hill – Chairman, Investment CommitteePresident and CEO of the Hedge Funds Solutions Group, a Vice Chairman of The Blackstone Group and Member of the Board of The Blackstone Group Management

Began career at First Boston, becoming one of the co-founders of its Mergers & Acquisitions Department

Board memberships include the Council on Foreign Relations and Lincoln Center Theatre

Brad CooperSince 1990, Managing Partner and founding partner of Capital Z PartnersPrior to Capital Z, an investment banker in the Financial Institutions Group of Salomon Brothers

Board member of Make a Wish Foundation of Metro New York

Russ Fradin Lead Independent Director of Best Buy Co., Inc., and Operating Partner of private equity firm Clayton, Dubilier & RiceFormerly President and Chief Executive Officer of SunGard Data Systems; Chief Executive Officer of the BISYS Group; and Chairman and Chief Executive Officer of Aon Hewitt, where he oversaw merger between Aon Consulting and Hewitt AssociatesHeld senior positions at Automatic Data Processing and McKinsey & CompanyEarned MBA from Harvard Business School and BSc in Economics and Finance from The Wharton School at the University of Pennsylvania

Joan Lamm-TennantChief Executive Officer of Blue Marble Microinsurance, an insurance industry collaborative announced in January 2015 to provide protection to the underservedPrior to Blue Marble, served as Global Chief Economist and Risk Strategist, Guy Carpenter & Company, LLCFaculty Member of the Wharton School, University of Pennsylvania

Steve PacalaFrederick D. Petrie Professor of Ecology and Evolutionary Biology at Princeton University; Director of the Princeton Environmental InstituteRecipient of the MacArthur Award, Mercer Award and the David Starr Jordan PrizeMember of the American Academy of Arts and Sciences and the National Academy of Sciences

John Overdeck – Chairman, Underwriting and Risk CommitteeCo-founder of Two Sigma and former Managing Director, D.E. Shaw & Co.International Mathematics Olympiad Silver Medalist for the US who holds a B.S. in Mathematics (with distinction) and an M.S. in Statistics from Stanford UniversityServes on the Boards of the Robin Hood Foundation, the Institute for Advanced Study and is the Vice Chair of the National Museum of Mathematics

Pauline RichardsCOO of Armour Group Holdings LimitedFormer CFO of Lombard Odier Darier Hentsch (Bermuda)Member of the Boards of Wyndham Worldwide and Apollo Global Management and a past member of Cendant Corporation and Butterfield Bank

David Siegel – Chairman, Compensation Committee Co-founder of Two Sigma and former Chief Technology Officer and Managing Director, Tudor Investment Corporation

First Chief Information Officer, D.E. Shaw & Co.

A graduate of Princeton University who holds a PhD in computer science from the Massachusetts Institute of Technology (MIT)

Board memberships include the Scratch Foundation, NYC First, NAF, and the Cornell Tech Board of Overseers; serves as a trustee of Carnegie Hall

Mark BarrenecheaCEO, CTO and board member of OpenTextBoard member of Dick’s Sporting GoodsFormerly president, CEO and board member of Silicon Graphics International Corporation; vice president, technology and business development of Tesseract Corporation; and senior vice president of applications development of OracleNamed Top New CEO of the Year by Canadian Business magazine in 2015Earned BSc in computer science from Saint Michael’s College in Vermont

(1)Pina Albo will become the Chief Executive Officer of Hamilton Insurance Group on February 1, 2018.

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Executive Committee

Jonathan Reiss – CFO

Member of the founding management team with 24 years’ experience in the insurance industry

Insurance Practice Leader at EY Bermuda (2006 – 2012)

19 years at EY, including 12 at Partner level dedicated to serving insurance industry clients

Gemma Carreiro – General Counsel

Associate General Counsel at PartnerRe (2014 – 2017)

Associate at Conyers Dill & Pearman Limited (2007 – 2014)

Associate at Cox Hallett Wilkinson (2005 – 2007)

Dermot O’Donohoe – CEO, Hamilton Underwriting Limited

Held various positions in Torus Group (now Starstone) including Transitional Group CEO and CEO Torus International (2009 – 2013)

18 years at XL Group in various positions, including Global Head of Specialty

Former member of Council of Lloyd’s (2007 – 2009); a Chartered Insurer (ACII)

Wendy Davis Johnson – Chief Communications & Culture Officer

Over 25 years’ experience in marketing communications and brand development

For the last 10 years, has been providing communications consulting services to corporate and non-profit organizations

Former SVP, Global Communications, ACE Group

Kathleen Reardon – CEO, Hamilton Re

Member of the founding management team with more than 20 years’ experience in the insurance industry

Fellow of the Casualty Actuarial Society

CUO International of ACE Tempest Re (2005 – 2012)

Chair, Women in Reinsurance (Bermuda)

Pete Skerlj – Chief Risk Officer

Member of the founding management team with 20 years’ experience in risk and analytics

Fellow of the Casualty Actuarial Society

As a Catastrophe Modeling Consultant at Q Re, created a property retro portfolio management and pricing framework

Previous experience includes senior positions with Lancashire Insurance, Partner Re Global and Applied Research Associates

David Brown – Interim Group CEO(1)

Founder & Chief Executive Officer of Flagstone Re 2005 – 2012

Chief Executive Officer, Centre Solutions 1994 – 1997

Former Partner, EY

Chairman of the Board of Bermuda Stock Exchange

(1)Pina Albo will become the Chief Executive Officer of Hamilton Insurance Group on February 1, 2018.

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Insurance and Reinsurance Operations

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Established book of business in sixth year of growth; produced underwriting profit every year since inception

Shareholder’s equity over $1.5 billion as of September 30, 2017

Wrote over $250 million in 2016; forecast to write approximately $290 million in 2017

Maintains a conservative risk profile, limiting PML to 15% of shareholder’s equity in the US and 10% for the rest of the world

Reinsurance strategic partnership with AIG in which Hamilton Re will be provided with the opportunity to participate in an increased volume of AIG’s ceded reinsurance

Manages risk exposures through a combination of third-party models and HARP (Hamilton Analytics and Risk Platform), a proprietary risk management platform that:

• is a collection of software tools used to build, optimize and analyze Hamilton Re’s risk portfolio;

• simulates 200,000 iterations of loss scenarios over a multi-year window; and

• is fully embedded in the frontline risk selection and pricing process.

A.M. Best: “A-” (Excellent)

Bermuda-based Class 4 property and casualty (re)insurer

Hamilton Re

OVERVIEW GROSS PREMIUMS WRITTEN(1)

Kathleen ReardonCEO, Hamilton Re

(1)Pie charts reflect in-force portfolio as of June 30, 2017

Property31%

Specialty25%

Professional Liability21%

Health Care3%

Personal Motor4%

Multi-Line9%

Commercial Motor14%

Excess/Umbrella

Liability31%

General Liability18%

Casualty44%

Worldwide4%

Worldwide ex. USA3%

USA62%

Financial Lines35%

Agriculture9%

Terror/PV/Cyber3%

A&H/WC/PA Cat8%

Aviation & Space11%

Multi-Line17%

Marine & Energy17%

Japan10%

Europe & UK11%

Canada2%

Caribbean3%

Australasia5%

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Hamilton at Lloyd’s

OVERVIEW

Global licenses of Lloyd’s iconic brand

Hamilton Underwriting Limited currently manages Lloyd’s Syndicate 3334

Approved by Lloyd’s to write approximately $200 million of premiums for the 2017 Year of Account

Credit ratings:

• A.M. Best: “A” (Excellent)

• S&P: “A+” (Strong)

• Fitch: “AA-” (Very Strong)

Dermot O’Donohoe CEO, Hamilton Underwriting Limited

Whole Account41%

Energy Treaty12%

Property Treaty33%

Marine Treaty9%

Aviation Treaty3%

War and Terror Treaty2% United States

37%

Marine Liability80%

Energy Liability20%

Personal Accident46%

Financial Institutions24%

Contingency15%

War and Terror15%

Directors and Officers21%

Professional Indemnity71%

General Liability8%

In-Orbit20%

Launch and Post Separation 80%

Latam16%Chile

7%

Caribbean6%

South Africa4%

Middle East4%

Japan3%

Canada3%

New Zealand2%

Rest of World18%

2017 YEAR OF ACCOUNT

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Attune is building a market leading, technology-based platform in the $150 billion Small to Medium Enterprise (SME) market

Represents an unprecedented partnership that leverages data science, technology, brand awareness and extensive claims data

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Two Sigma

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Deploy and seek to continuously improve intelligent investment management systems first created in 2001

Manage approximately $47 billion of assets for a global, diversified client base in absolute return and benchmark-relative investment mandates(2)

Trade equities, futures, FX and derivatives in 40+ countries utilizing a highly diversified set of systematic strategies

Tap the talents of 1,200+ employees headquartered in New York with additional offices in Houston, London, and Hong Kong(2)

Operate as a Registered Investment Adviser with the SEC(3)

Computing Power & Data:

6,150+ servers in our computing environment, with 95,000 vCPUs and 1,695 terabytes of memory

35+ petabytes of data and growing

10K+ data sources including public and proprietary

Human Capital

3,300+ person years of R&D

Two thirds of staff consist of Engineers and Modelers

72% non-financial backgrounds

97% voluntary employee retention, since inception

Performance(4)

Created positive net alpha every year since inception (15 Years)

96% of investors have earned positive alpha

80% positive (net alpha) product quarters

WHAT WE DO

WHERE WE ARE TODAY

Two Sigma(1) is a process-driven, systematic investment manager primarily focused on global liquid markets. Two Sigma applies its technology and expertise in financial markets to seek to consistently generate uncorrelated alpha across a wide range of market conditions.

Note: For illustration purposes only. Not an offer to buy or sell securities. Two Sigma may modify its investment approach and portfolio parameters in the future in any manner that it believes is consistent with its fiduciary duty to its clients. There is no guarantee that Two Sigma or its products will be successful in achieving any or all of their investment objectives. Moreover, all investments involve some degree of risk, not all of which will be successfully mitigated.

(1)As referenced on this slide, “Two Sigma” or “the Firm” generally refers collectively to Two Sigma Investments, LP and Two Sigma Advisers, LP and their affiliates.(2) AuM and employee count are approximate as of June 1, 2017.(3) Two Sigma Investments, LP and Two Sigma Advisers, LP are registered with the U.S. Securities and Exchange Commission (the “SEC”). Registration does not imply review, endorsement or approval by the SEC.(4) “Net alpha” is measured against zero for absolute return products and against the applicable benchmark for beta-1 products and is net of management fees, incentive allocations and all other fund and trading expenses, in each case, to the extent applicable.  Statistics regarding investor and product performance are dollar-weighted by AuM as of December 31, 2016. Performance statistics only include performance of unaffiliated investors. “Net alpha product quarters” is an asset weighted figure derived by (i) taking the sum of the average notional AuM of each Two Sigma-managed product group by quarter and (ii) dividing the sum of the average notional AuM for the positive net alpha product quarters by (i).

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FINANCIAL HIGHLIGHTS CORPORATE ORGANIZATION CHART

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Appendix

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Hamilton Insurance Group Financial Highlights

CONSOLIDATED BALANCE SHEETS

September 30, 2017 December 31, 2016 December 31, 2015

($ in millions) Unaudited Audited Audited

Cash and investments $ 1,958 $ 1,917 $ 1,819

Premiums receivable 187 134 75

Losses and LAE recoverable 245 108 113

Intangible assets 19 39 41

Other 157 118 68

Total assets held for sale 330 — —

Total assets 2,896 2,316 2,116

Reserve for losses and LAE 589 336 226

Unearned premiums 251 209 97

Payable to related parties 20 27 158

Notes payable — 20 20

Other 100 69 50

Total liabilities held for sale 327 — —

Total liabilities 1,287 661 551

Non-controlling interest — — —

Shareholders’ equity 1,609 1,655 1,565

Total liabilities and shareholders’ equity $ 2,896 $ 2,316 $ 2,116

Book value per share $ 15.89 $ 16.22 $ 15.43

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Hamilton Re Financial Highlights

CONSOLIDATED BALANCE SHEETS

September 30, 2017 December 31, 2016 December 31, 2015

($ in millions) Unaudited Audited Audited

Cash and investments $ 1,910 $ 1,802 $ 1,746

Premiums receivable 221 137 79

Losses and LAE recoverable 215 28 11

Other 158 88 56

Total assets 2,504 2,055 1,892

Reserve for losses and LAE 617 242 124

Unearned premiums 267 182 93

Payable to related parties 15 24 154

Notes payable — 20 20

Other 40 26 16

Total liabilities 939 494 407

Non-controlling interest — 8 3

Shareholder’s equity 1,565 1,553 1,482

Total liabilities and shareholder's equity $ 2,504 $ 2,055 $ 1,892

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Corporate Organization Chart

Hamilton Insurance Group, Ltd. (Bermuda)

September 4, 2013

Hamilton Insurance Services (Bermuda), Ltd.

August 4, 2016(Lloyd’s approved coverholder)

Lloyd’s Syndicate 3334 (Managed by Hamilton Underwriting Limited)

Hamilton Underwriting Limited (U.K.)

(acquired April 1, 2015)

Turing Re, Ltd.

(Bermuda)

April 12, 2017

Hamilton Corporate Member Limited

(U.K.)

(acquired April 1, 2015)

Hamilton Re, Ltd. (Bermuda)

June 8, 2012

Hamilton UK Holdings Limited (U.K.)

September 30, 2014

Attune Insurance Services, LLC

(Delaware)

February 5, 2015

Attune Holdings, LLC (Delaware)

August 15, 2016

Hamilton U.S. Services, LLC

(Delaware)

July 18, 2017

33.3%

Hamilton U.S. Holdings II, Inc.

(Delaware)

July 18, 2017

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Wellesley House North, 1st Floor 90 Pitts Bay RoadPembroke HM08

Bermuda+1 (441) 405 5200

www.hamiltongroup.com @HamiltonInsures

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