0001104659-24-096659 Sample Contracts

PURCHASE AGREEMENT among CANADA PENSION PLAN INVESTMENT BOARD, ELK EVERGREEN INVESTMENTS, LLC and ELK CYPRESS INVESTMENTS, LLC November 8, 2023 PURCHASE AGREEMENT
Purchase Agreement • September 4th, 2024 • Enstar Group LTD • Fire, marine & casualty insurance • Delaware

This Purchase Agreement (this “Agreement”) is dated as of November 8, 2023 by and among Canada Pension Plan Investment Board, a Canadian federal Crown corporation (“CPPIB”), Elk Evergreen Investments, LLC, a Delaware limited liability company (“Evergreen Purchaser”), and Elk Cypress Investments, LLC (“Cypress Purchaser” and together with Evergreen Purchaser, the “Purchasers”).

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ASSIGNMENT AND ASSUMPTION AGREEMENT
Assignment and Assumption Agreement • September 4th, 2024 • Enstar Group LTD • Fire, marine & casualty insurance

This ASSIGNMENT AND ASSUMPTION AGREEMENT is dated as of November 8, 2023 (this “Agreement”) by and among (i) Elk Evergreen Investments, LLC (“Evergreen Assignor”) and Elk Cypress Investments, LLC (“Cypress Assignor” and together with Evergreen Assignor, the “Assignors”), (ii) Flexpoint Asset Opportunity Fund II-A, L.P. (“Flexpoint Assignee A”) and Flexpoint Asset Opportunity Fund II-B, L.P. (“Flexpoint Assignee B” and together with Flexpoint Assignee A, the “Assignees”) and (iii) solely for the purposes of Section 1(b) and Sections 5-8 of this Agreement, Canada Pension Plan Investment Board (“CPPIB”). Capitalized terms used but not defined herein shall have the meanings ascribed to such terms in the Purchase Agreement (as defined below).

LIMITED GUARANTEE
Limited Guarantee • September 4th, 2024 • Enstar Group LTD • Fire, marine & casualty insurance • Delaware

LIMITED GUARANTEE, dated as of July 29, 2024 (this “Limited Guarantee”), by each of the persons set forth on Schedule A (each, a “Guarantor” and, collectively, the “Guarantors”), in favor of Enstar Group Limited, an exempted company limited by shares existing under the laws of Bermuda (the “Guaranteed Party”).

July 29, 2024 Elk Bidco Limited 2100 McKinney Ave Suite 1500 Dallas, TX 75201 Ladies and Gentlemen:
Letter Agreement • September 4th, 2024 • Enstar Group LTD • Fire, marine & casualty insurance • Delaware

This letter agreement (this “Letter Agreement”) sets forth the commitments of each of the persons set forth on Schedule A (each, a “Fund” and, collectively, the “Funds”), subject to the terms and conditions set forth herein, to purchase, directly or indirectly, certain equity interests of Elk Bidco Limited, an exempted company limited by shares existing under the laws of Bermuda (“Parent”). It is contemplated that, pursuant to that certain Agreement and Plan of Merger (as amended, restated, supplemented or otherwise modified from time to time, the “Merger Agreement”), dated as of the date hereof, by and among Parent, Elk Merger Sub Limited, an exempted company limited by shares existing under the laws of Bermuda and a direct wholly owned Subsidiary of Parent (“Parent Merger Sub”), Enstar Group Limited, an exempted company limited by shares existing under the laws of Bermuda (the “Company”), Deer Ltd., an exempted company limited by shares existing under the laws of Bermuda and a direct

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