Greenlight Capital Re: Q3 2026 Investor Presentation

Q3 2026

NASDAQ: GLRE

Greenlight Re: Introduction

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Open Market Reinsurance Underwriting

Innovations Underwriting & Investments

Value Oriented Investments

Capture capital appreciation from early-stage investments

Maintain a highly diversified book with the flexibility to adjust line concentration based on market conditions

Use investment to gain optionality in both insurance and reinsurance opportunities

Provide reinsurance globally, on both proportional and non-proportional bases

Designed to achieve higher rates of return over the long term than more traditional fixed income investment strategies

Low correlation to underwriting

Target ability to influence strategic direction and future participation rights in each deal

Business is primarily sourced through global reinsurance brokers

Long-short strategy reduces market exposure

Liquid portfolio

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Our strategic focus is driving underwriting excellence with respect to each and every decision we make

Property 10%

$754M

Gross Premiums Written2

$2.3B

Q3 2026

Total assets

$695M

Q3 2026

Shareholders' Equity

Specialty 23%

Multiline 42%

Health 1%

Casualty 9%

3

Offices in Strategic International Locations

$30.5M

Value of shares repurchased in 20264

"A" (Excellent)

AM Best Financial Strength Rating (Stable Outlook)

48.5%

2022-2026

Cumulative Book Value Growth3

20+ Years

Operating History

1%

Total Debt Leverage5

Financial 15%

1. Multiline includes our Funds at Lloyd's and Syndicate 3456 business.

2. Gross premiums written is for the trailing 12 months. Business mix chart represents gross premiums written by line of business for trailing twelve months.

3. Refers to fully diluted BVPS growth. Fully diluted BVPS is a non-GAAP measure. See Appendix for non-GAAP measure rationale and reconciliation to the most comparable GAAP measure. Period measured: December 31, 2021 through September 30, 2026.

4. During the third quarter of 2026, we repurchased 504,829 ordinary shares at an aggregate cost of $8.0 million at an average price of $15.77 per share. Also, during October 2026, we repurchased a further 220,352 ordinary shares at an aggregate cost of $3.3 million at an average cost of $14.95.

5. Debt leverage (calculated as total debt divided by shareholders' equity) has significantly decreased in recent years from 12% at year-end 2023 to 1% as of Q3 2026 close.

Greenlight Capital Re, Ltd.

NASDAQ: "GLRE"

Gross Premiums Written

($ in millions)

CAGR: 10.0%

1

$565 $563 $637

$698 $773

$612 $593

2021 2022 2023 2024 2025 9M 2025 9M 2026

Combined Ratio

3.9%

28.5%

69.0%

94.5% 101.4% 94.6%

95.4% 95.6%

69.5%

67.4%

3.8%

29.0%

61.7%

4.3%

28.0%

62.3%

4.6%

28.0%

62.8%

5.2%

29.1%

61.3%

2021 2022 2023 2024 2025 9M 2025 9M 2026

Underwriting Expense Ratio

Acquisition Cost Ratio

Loss Ratio

1. CAGR in the chart is calculated from full-year 2020 gross premiums written ($479.8M) through full-year 2025.

Net Income

($ in millions)

$87

$75

$18 $25

$43

$9

2021 2022 2023 2024 2025 9M 2026

$17.95

$20.43

$13.99

$14.33

$16.74

Fully Diluted Book Value Per Share

CAGR: 8.8%

1

$20.78

2021 2022 2023 2024 2025 9M 2026

1. CAGR in the chart is calculated from December 31, 2020 ($13.42) through year-end 2025.

Shareholders'

Equity

($ in millions)

$476 $503

$596 $636 $708

$695

2021 2022 2023 2024 2025 Q3 2026

Debt Leverage

17% 16%

12%

9%

1% 1%

2021 2022 2023 2024 2025 Q3 2026

Financial Strength Rating Upgrade: In November 2025, AM Best upgraded the financial strength rating of Greenlight Reinsurance, Ltd. and Greenlight Reinsurance (Ireland), dac to "A" (Excellent) with a Stable outlook - reflecting strengthened capitalization, improved operating performance, and a more diversified earnings profile.

Third Quarter Highlights

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"We are pleased to report strong underwriting income in the third quarter, aided by a relatively benign catastrophe and large loss environment. The conservative reserving approach we took on Middle East-related exposures last quarter has developed favorably, and our year-to-date underwriting result is now trending in line with our expectations."

- Greg Richardson, Chief Executive Officer

Q3 2025

Q3 2026

9M 2025

9M 2026

(expressed in millions U.S. dollars, except percentages and per share amounts)

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Segment Results

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($ in millions)

$528

Casualty 6%

94.4% 94.6%

$471

Specialty 25%

Financial 14%

84.5% 87.9%

3.8%

3.6%

4.2%

$155 $139

Q3 2025 Q3 2026 9M 2025 9M 2026

Property 12%

Multiline 43%

Q3 2025 Q3 2026 9M 2025 9M 2026

Underwriting Expense Ratio

Acquisition Cost Ratio

Loss Ratio

($ in millions)

$122

Specialty 14%

Casualty 23%

96.8% 98.2% 99.6% 96.7%

10.1%

$29

$43

$84

Multiline 43%

Financial 17%

Health 3%

Underwriting Expense Ratio

Acquisition Cost Ratio

Loss Ratio

Q3 2025 Q3 2026 9M 2025 9M 2026

Q3 2025 Q3 2026 9M 2025 9M 2026

Key Highlights

Gross premiums written increased 46.4% to $43 million in Q3 2026 compared to $29 million in Q3 2025

2.9 point combined ratio improvement in YTD 2026 versus prior year period

Maintain a whole account quota share on the segment's underwriting portfolio, providing rated third-party capacity and validation

We invest early in innovative insurance and MGA start-ups, gaining preferential access to underwriting business as partners scale

Generally early-stage only -

$250K-$2M checks

Every deal must stand on its own underwriting merits - we do not subsidize unprofitable business to maintain relationships

Every investment assessed on value proposition, people, technology, and market access

Low concentration risk, with diverse portfolio (by geography, platform and class of business) across active programs

Increasing use of third-party capital to manage growth

Three highly rated (re)insurance platforms: Syndicate 3456 ("A+" FSR), Greenlight Reinsurance, Ltd. (Cayman) ("A" FSR), and Greenlight Reinsurance (Ireland), dac ("A" FSR)

Often act as lead market, setting terms that align MGA incentives; commercial (re)insurance agreements in most deals

Provides fee generating opportunities for the Group

Innovations maximum limit exposure is

low (net limits < $2m for 95%+ of segment GWP) through a combination of line size, third-party capital and reinsurance

Currently over 45 active portfolio companies GWP CAGR of 18% (2023-2025)

Investment portfolio carried value of ~$65M

Composite ratios (loss + acquisition) of 94% (2023), 92% (2024) and 91% (2025)

First investment in 2018

Recently announced strategic partnership with Hippo (NYSE: HIPO) for additional US admitted aligned capacity and co-investments

Solasglas Investments Update

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A Differentiated Investment Strategy

Solasglas Investments, LP is the dedicated investment fund managed by DME

Advisors, for the benefit of Greenlight Re and its affiliates, into which Greenlight Re allocates its investment assets

DME Advisors serves as general partner and owns approximately 18% of Solasglas

Investment Portfolio is currently 70% of Greenlight Re's adjusted surplus

Investment Approach

Greenlight Capital, Inc., an affiliate of DME Advisors, Solasglas' investment advisor, was founded in 1996 by our Chairman David Einhorn and is recognized for its disciplined, research-driven investment strategy

DME Advisors conducts deep fundamental analysis of financials, strategy, and prospects to identify both undervalued and overvalued securities

Greenlight Re has employed this value-oriented approach since its inception

Objective is to maximize total risk-adjusted returns supporting long-term book value growth

25.3%

9.4% 9.8%

7.5%

7.5%

10.2%

5.8%

0.0%

2021 2022 2023 2024 2025

*Investment returns stated in this presentation reflect the total returns, net of fees and expenses. Investment returns are calculated monthly and compounded to calculate the quarterly and annual returns. The monthly investment return is calculated by dividing the investment income/loss (net of fees and expenses) by the Investment Portfolio. Actual investment income may vary depending on cash flows into and out of the investment account. Past performance is not necessarily indicative of future results. Annual average returns since 2021 is calculated from January 2021 through October 2026 and annual average returns since inception is calculated from August 2004 through October 2026. Monthly investment returns are posted on the Investor section of our corporate website.

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Investing in Greenlight Re

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Focused on underwriting culture and results-driven decision-making

Specialty property and casualty reinsurance portfolio with a diversified risk profile

Now a distinct reporting segment with strong momentum and disciplined growth

Designed to continue to generate strong returns in volatile markets

Supported by a recent upgrade from A.M. Best and very low debt leverage ratio

Repurchased 5.4% of outstanding shares for

$30.5 million in 2026 (as of October 30)

Greg Richardson

Chief Executive Officer

Joined 2024

(formerly TransRe)

AVERAGE INDUSTRY EXPERIENCE: 20+ Years

Our Executive Team

Is Focused on Executing Five Core Values

• Nimble • Innovative • Excellence

• Accountable • Collaborative

Executive Team Comprised of Significant Greenlight Re Tenure and Fresh Perspectives

Patrick O'Brien

CEO Ireland & COO

Joined 2016 (formerly Liberty)

Brian O'Reilly

Head of Innovations

Joined 2013 (formerly ICW Group)

Regan Cairns

CUO, Cayman Islands

Joined 2018 (formerly KPMG)

Faramarz Romer Chief Financial Officer Joined 2007

(formerly KPMG)

David Sigmon

General Counsel

Joined 2023 (formerly Everest)

Tom Curnock

Group CUO

Joined 2009 (formerly Aon)

Kagabo Ngiruwonsanga

CUO, Innovations

Joined 2011 (formerly Liberty)

Richard Strommer

Chief Actuary

Joined 2017 (formerly EY)

Finbar Griffin CUO, Ireland Joined 2018

(formerly Travelers)

Ian McGuire

Martin Vezina

Head of Underwriting Analytics

Joined 2025 (formerly Allianz)

Active Underwriter, Syndicate 3456

Joined 2026 (formerly Argenta)