GREENLIGHT CAPITAL RE, LTD. (GLRE)

ITEM 2. MANAGEMENT’S DISCUSSION AND ANALYSIS OF FINANCIAL CONDITION AND RESULTS OF OPERATIONS

References to “we,” “us,” “our,” “our company,” or “the Company” refer to Greenlight Capital Re, Ltd. (“GLRE”) and its wholly-owned subsidiaries unless the context dictates otherwise.

The following discussion should be read in conjunction with the condensed consolidated financial statements (herein referred to as “financial statements”) and accompanying notes included in Item 1 of this report and the audited consolidated financial statements and accompanying notes, which appear in our 2025 Form 10-K.

The following is management’s discussion and analysis (“MD&A”) of our results of operations for the three and six months ended June 30, 2026 and 2025 and the Company’s financial condition at June 30, 2026 and December 31, 2025.

All amounts are reported in U.S. dollars, unless otherwise noted. Tabular dollars are presented in thousands, with the exception of per share amounts or as otherwise noted. Due to rounding, numbers and percentages presented in the tables included in this MD&A may not add up precisely to the totals provided.

Page

28

Return to table of contents

Overview

Business Overview

We are a global specialty property and casualty reinsurer headquartered in the Cayman Islands, with an underwriting and investment strategy that we believe differentiates us from most of our competitors. Our goal is to build long-term shareholder value by providing risk management solutions to the insurance, reinsurance, and other risk marketplaces.

For the three months ended June 30, 2026 (“Q2 2026”), we reported a net loss of $29.6 million, compared to $0.3 million net income for the three months ended June 30, 2025 (“Q2 2025”). The net loss was mainly attributable to CAT losses from underwriting and negative investment returns from Solasglas.

The following is a summary of our financial performance for Q2 2026, compared to Q2 2025:

•Gross premiums written was $183.1 million, an increase of 1.9%;

•Net premiums earned was $161.8 million, an increase of 0.1%;

•Net underwriting loss was $0.2 million, compared to net underwriting income of $8.1 million;

•Total investment loss was $23.8 million, compared to investment loss of $7.8 million;

•Diluted EPS loss was $0.89, compared to diluted EPS of $0.01; and

•Fully diluted book value per share was $20.61, a decrease of 3.7% since last quarter.

Fully diluted book value per share is a non-GAAP financial measure. See “Key Financial Measure and Non-GAAP Measures” section of this MD&A.

Outlook and Trends

Reinsurance market conditions

We continue to see an increasingly competitive market, predominantly in our Open Market segment. This is putting pressure on headline rates across various classes with some modest but increasing pressure appearing on attachment points and other terms and conditions. Our focus remains on maintaining a diversified portfolio that is resilient to market supply-demand pressures.

General economic conditions

There are many factors contributing to an uncertain global economic outlook, and in particular, the current Middle East conflict. With the recent volatility in oil price driven by this conflict, we believe that inflationary trends of recent years could persist. We continue to consider the potential impact of relevant economic factors on our underwriting portfolio.

On the investment side, DME Advisors regularly monitors and re-positions Solasglas’ investment portfolio to manage the impact of inflation on its underlying investments and holds macro positions to benefit from a rising inflationary environment. DME Advisors remains conservatively positioned as it believes the equity markets are very expensive.

In addition to the geopolitical uncertainty, the U.S. Administration continues to adopt trade policies that have increased uncertainty and volatility in financial markets. These policies continue to complicate the near-term outlook for economic growth and inflation. We remain vigilant for economic data and additional policies that may impact our business.

29

Return to table of contents

Key Financial Measures and Non-GAAP Measure

There have been no changes to our key financial measures, including non-GAAP financial measure, as described in the MD&A of our 2025 Form 10-K.

Fully Diluted Book Value Per Share

The following table presents a reconciliation of the fully diluted book value per share to basic book value per share (the most directly comparable U.S. GAAP financial measure):

(1) Assuming net exercise by the grantee.

30

Return to table of contents

Consolidated Results of Operations

The table below summarizes our consolidated operating results.

1 The net financial impact associated with changes in the estimate of losses incurred in prior years, which incorporates earned reinstatement premiums assumed and ceded, adjustments to assumed and ceded acquisition costs, and deposit interest income

31

Return to table of contents

and expense, was a gain of $1.2 million and a loss of $2.6 million for three months ended June 30, 2026 and 2025, respectively, and a gain of $2.8 million and a loss of $6.1 million for the six months ended June 30, 2026 and 2025, respectively.

Consolidated Results of Operations for Q2 2026 compared to Q2 2025

Basic book value per share decreased by $0.78 per share, or 3.5%, to $21.22 per share from $22.00 per share at March 31, 2026. Fully diluted book value per share decreased by $0.79 per share, or 3.7%, to $20.61 per share from $21.40 per share at March 31, 2026.

Net loss for Q2 2026 was $29.6 million, compared to a negligible net income for Q2 2025. This was driven mainly by the following:

•Investment loss: Increased by $16.0 million primarily driven by:

◦Our investment in Solasglas reported a loss of $27.9 million (net loss of 5.4%) during Q2 2026, compared to a loss of $18.3 million (net loss of 4.0%) for the same period in 2025; and

◦Lower net investment income from (i) interest earned on funds at Lloyds due to partially replacing it with the unsecured Citibank LC (see Note 10 of the financial statements), and (ii) with lower interest income earned from restricted cash and cash equivalents due to the interest rate cuts by central banks in 2025. Additionally, we recognized $0.4 million of unrealized losses on the fixed maturity investment portfolio and a $1.5 million impairment charge relating to the Innovations’ private equity portfolio for Q2 2026, which are included in net investment income in the financial statements.

•Underwriting loss: Unfavorable change of $8.3 mi

[Excerpt truncated for page length; source filing is linked above.]

ITEM 7. MANAGEMENT’S DISCUSSION AND ANALYSIS OF FINANCIAL CONDITION AND RESULTS OF OPERATIONS

The following is management’s discussion and analysis (“MD&A”) of the financial condition and results of operations for the years ended December 31, 2025, and 2024. Comparisons between 2024 and 2023 have been omitted from this Annual Report, but may be found in “Management’s Discussion and Analysis of Financial Condition and Results of Operations” in Part II, Item 7 of our Annual Report on Form 10-K for the year ended December 31, 2024 filed with the SEC. Accordingly, this information is incorporated by reference.

This discussion and analysis should be read in conjunction with our audited consolidated financial statements and notes thereto presented in “Part II, Item 8. Financial Statements and Supplementary Data” of this Annual Report. Unless otherwise noted, tabular dollars are in thousands, except per share amounts. Amounts may not reconcile due to rounding differences.

Page

54

Return to table of contents

Overview

Business Overview

We are a global specialty property and casualty reinsurer headquartered in the Cayman Islands, with an underwriting and investment strategy that we believe differentiates us from most of our competitors. Our goal is to build long-term shareholder value by providing risk management solutions to the insurance, reinsurance, and other risk marketplaces. Refer to “Part 1, Item 1. Business” for additional information.

We earned a net income of $74.8 million for the year ended December 31, 2025, an increase of $32.0 million, or 74.8% compared to the prior year, predominantly due to strong underwriting results and favorable foreign exchange movement in 2025, partially offset by lower net investment income from Innovations and lower yields on restricted cash and cash equivalents.

The following is a summary of our financial performance for the year ended December 31, 2025, compared to the prior year:

•Gross premiums written was $773.3 million, an increase of 10.7%;

•Net premiums earned was $661.1 million, an increase of 6.6%;

•Net underwriting income was $35.7 million, compared to net underwriting loss of $8.2 million;

•Total investment income was $60.2 million, a decrease of 24.4%;

•Foreign exchange gains were $8.5 million, compared to foreign exchange losses of $5.6 million;

•Diluted EPS was $2.17, compared to $1.24, an increase of 75.0%; and

•Fully diluted book value per share was $20.43, an increase of $2.48, or 13.8%.

Outlook and Trends

Reinsurance market conditions

At the January 1, 2026 renewals, we experienced greater opportunities owing to our stronger balance sheet and the upgrade of our A.M. Best Rating to A (Excellent), but we also faced a more competitive market. Rate changes for Open Market business varied significantly by line of business: property and specialty rates experienced downward pressure, whereas casualty rates increased. Attachment points and other terms and conditions mostly held firm.

Although January 1st, is not historically a significant renewal date for our Innovations portfolio, we observed more opportunities with rate holding up well. In the current market conditions, we see increasing opportunities to leverage retrocession coverage, and we will take advantage of these opportunities where they enhance our economics and risk profile.

General economic conditions

There are many factors contributing to an uncertain global economic outlook, and in particular, we believe that inflationary trends of recent years could persist. We continue to consider the potential impact of relevant economic factors on our underwriting portfolio. On the investment side, DME Advisors regularly monitors and re-positions Solasglas’ investment portfolio to manage the impact of inflation on its underlying investments and holds macro positions to benefit from a rising inflationary environment. DME Advisors remains conservatively positioned as it believes the equity markets are very expensive.

We believe trade policies will continue to cause uncertainty and volatility. In February 2026, the U.S. Supreme Court struck down the Administration’s tariffs enacted under the International Emergency Economic Powers Act (IEEPA) of 1977, but the Administration stated it will enact new tariffs under several other legislative acts.

Revenues and Expenses

Revenues

We derive our revenues from two principal sources:

•premiums from reinsurance on property and casualty business assumed (net of any premiums ceded) - see “Critical Accounting Estimates” section of this MD&A; and

•income from investments, including:

55

Return to table of contents

•income (or loss) generated from our investment in Solasglas, net of management fee and performance compensation;

•gains (or losses) from our other investments, including Innovations-related investments; and

•interest income on our cash and cash equivalents, fixed maturities investment portfolio and FAL.

In addition, we may from time to time derive other income from foreign exchange gains (or losses) relating to underwriting balances, net investment income from Lloyd’s syndicates, fees generated from advisory services, and fees relating to overrides, profit commissions, and fees due upon the early termination of contracts.

Expenses

Our expenses consist primarily of the following:

The extent of our net losses and LAE incurred is a function of the amount and type of reinsurance contracts we write and the loss experience of the underlying coverage. Refer to “Critical Accounting Estimates” section of this MD&A.

Acquisition costs consist primarily of brokerage fees, ceding commissions, premium taxes, profit commissions, letters of credit and trust fees, and federal excise taxes. We amortize deferred acquisition costs relating to successfully bound reinsurance contracts over the related contract term.

Underwriting expenses consist primarily of compensation costs related to our underwriting activities, in addition to an allocation of corporate overhead costs.

Corporate and other expenses consist primarily of compensation costs related to non-underwriting activities, including Innovations related investments and corporate personnel. Additionally, these also include professional fees (non-claim related), director compensation, travel and entertainment, information technology, rent, and other general operating costs, net of an allocation to underwriting expenses.

Deposit interest expense relates to the accretion costs for deposit-accounted contracts that did not meet the risk transfer condition for reinsurance accounting under U.S. GAAP.

Interest expense consists of interest paid and accrued on our debt and the amortization of the related deferred financing costs.

Key Financial Measures and Non-GAAP Measures

Management uses certain key financial measures, some of which are not prescribed under U.S. GAAP rules and standards (“non-GAAP financial measures”), to evaluate our financial performance, financial position, and the change in shareholder value. Generally, a non-GAAP financial measure, as defined in SEC Regulation G, is a numerical measure of a company’s historical or future financial performance, financial position, or cash flows that either excludes or includes amounts that are not normally excluded or included in the most directly comparable measure calculated and presented under U.S. GAAP. We believe that these measures, which may be calculated or defined differently by other companies, provide consistent and comparable metrics of our business performance to help shareholders understand performance trends and facilitate a more thorough understanding of the Company’s business. Non-GAAP financial measures should not be viewed as substitutes for those determined under U.S. GAAP.

We use the following non-GAAP financial measure in this Annual Report.

56

Return to table of contents

Fully Diluted Book Value Per Share

Our primary financial goal is to increase fully diluted book value per share over the long term. We use fully diluted book value as a financial measure in our incentive compensation plan.

We believe that long-term growth in fully diluted book value per share is the most relevant measure of our financial performance because it provides management and investors a yardstick to monitor the shareholder value generated. Fully diluted book value per share may also help our investors, shareholders, and other interested parties form a basis of comparison with other companies within the property and casualty reinsurance industry. Fully diluted book value per share should not be viewed as a substitute for the most comparable U.S. GAAP measure, which in our view is the basic book value per share.

We calculate basic book value per share as (a) ending shareholders' equity, divided by (b) the total ordinary shares issued and outstanding, as reported in the consolidated financial statements.

Fully diluted book value per share represents basic book value per share combined with any dilutive impact of in-the-money stock options and all outstanding restricted stock units, or “RSUs”. We believe these adjustments better reflect the ultimate dilution to our shareholders.

The following table presents a reconciliation of the fully diluted book value per share to basic book value per share (the most directly comparable U.S. GAAP financial measure):

(1) Assuming net exercise by the grantee.

57

Return to table of contents

Consolidated Results of Operations

The table below summarizes our consolidated operating results.

[Excerpt truncated for page length; the complete text is on the linked full-MD&A page.]