# EDGAR Filing Document

**Accession Number:** 0001363829
**File Stem:** 0001104659-25-065357
**Filing Date:** 2025-7
**Character Count:** 62306
**Document Hash:** 1518eb6292e4504b25e1568984426c88
**Contains OCR:** False
**Source Format:** 

## Filing Content

## Filing Summary
**0001104659-25-065357.hdr.sgml**: 20250702

**ACCESSION NUMBER**: 0001104659-25-065357

**CONFORMED SUBMISSION TYPE**: SC 13E3/A

**PUBLIC DOCUMENT COUNT**: 2

**FILED AS OF DATE**: 20250702

**DATE AS OF CHANGE**: 20250702

**GROUP MEMBERS**: DOMINIC F. SILVESTER

**GROUP MEMBERS**: ELK BIDCO LTD

**GROUP MEMBERS**: ELK CYPRESS INVESTMENTS, LLC

**GROUP MEMBERS**: ELK EVERGREEN INVESTMENTS, LLC

**GROUP MEMBERS**: ELK PARENT LTD

**GROUP MEMBERS**: ELK TOPCO, LLC

**GROUP MEMBERS**: TSSP SUB-FUND HOLDCO, LLC

**SUBJECT COMPANY**: 

**COMPANY DATA:**
- **COMPANY CONFORMED NAME:** Enstar Group LTD
- **CENTRAL INDEX KEY:** 0001363829
- **STANDARD INDUSTRIAL CLASSIFICATION:** FIRE, MARINE & CASUALTY INSURANCE [6331]
- **ORGANIZATION NAME:** 02 Finance
- **EIN:** 999999999
- **STATE OF INCORPORATION:** D0
- **FISCAL YEAR END:** 1231

**FILING VALUES:**
- **FORM TYPE:** SC 13E3/A
- **SEC ACT:** 1934 Act
- **SEC FILE NUMBER:** 005-83620
- **FILM NUMBER:** 251102046

**BUSINESS ADDRESS:**
- **STREET 1:** P.O. BOX HM 2267, A.S. COOPER BUILDING
- **STREET 2:** 26 REID STREET
- **CITY:** HAMILTON
- **STATE:** D0
- **ZIP:** HM 11
- **BUSINESS PHONE:** 441-292-3645

**MAIL ADDRESS:**
- **STREET 1:** P.O. BOX HM 2267, A.S. COOPER BUILDING
- **STREET 2:** 26 REID STREET
- **CITY:** HAMILTON
- **STATE:** D0
- **ZIP:** HM 11

**FORMER COMPANY:**
- **FORMER CONFORMED NAME:** Castlewood Holdings LTD
- **DATE OF NAME CHANGE:** 20060523
**FILED BY**: 

**COMPANY DATA:**
- **COMPANY CONFORMED NAME:** Enstar Group LTD
- **CENTRAL INDEX KEY:** 0001363829
- **STANDARD INDUSTRIAL CLASSIFICATION:** FIRE, MARINE & CASUALTY INSURANCE [6331]
- **ORGANIZATION NAME:** 02 Finance
- **EIN:** 999999999
- **STATE OF INCORPORATION:** D0
- **FISCAL YEAR END:** 1231

**FILING VALUES:**
- **FORM TYPE:** SC 13E3/A

**BUSINESS ADDRESS:**
- **STREET 1:** P.O. BOX HM 2267, A.S. COOPER BUILDING
- **STREET 2:** 26 REID STREET
- **CITY:** HAMILTON
- **STATE:** D0
- **ZIP:** HM 11
- **BUSINESS PHONE:** 441-292-3645

**MAIL ADDRESS:**
- **STREET 1:** P.O. BOX HM 2267, A.S. COOPER BUILDING
- **STREET 2:** 26 REID STREET
- **CITY:** HAMILTON
- **STATE:** D0
- **ZIP:** HM 11

**FORMER COMPANY:**
- **FORMER CONFORMED NAME:** Castlewood Holdings LTD
- **DATE OF NAME CHANGE:** 20060523

**UNITED STATES**

**SECURITIES AND EXCHANGE COMMISSION**

**WASHINGTON, D.C. 20549**

**SCHEDULE 13E-3**

**RULE 13E-3 TRANSACTION STATEMENT UNDER SECTION 13(E) OF THE SECURITIES EXCHANGE ACT OF 1934**

**Amendment No. 4**

**Enstar Group Limited**

(Name of the Issuer)

**Enstar Group Limited** 

**Elk Evergreen Investments, LLC<br> Elk Cypress Investments, LLC**

**TSSP Sub-Fund HoldCo, LLC<br> Dominic F. Silvester**

**Elk Topco, LLC**

**Elk Parent Limited**

**Elk Bidco Limited** 

**(Names of Persons Filing Statement)**

**Ordinary Shares, par value $1.00 per share**

**Depositary Shares, each representing a 1/1,000th Interest in a 7.00% Fixed-to-Floating Rate Perpetual Non-Cumulative Preference Shares, Series D, par value $1.00 per share**

**Depositary Shares, each representing a 1/1,000th 7.00% Perpetual Non-Cumulative Preference Shares, Series E, par value $1.00 per share**

**(Title of Class of Securities)**

**G3075 P101 (Ordinary Shares)**

**G3075P119\***

**G30759200\*\***

**(CUSIP Number of Class of Securities)**

---

| | | |
|:---|:---|:---|
| **Enstar Group Limited** | **Elk Evergreen Investments, LLC** | **Dominic F. Silvester** |
| **Deer Ltd.** | **Elk Cypress Investments, LLC** |  |
| **Deer Merger Sub Ltd.** | **TSSP Sub-Fund Holdco, LLC** | **A.S. Cooper Building, 4th Floor** |
|  | **Elk Bidco Limited** | **26 Reid Street** |
| **A.S. Cooper Building, 4th Floor** | **Elk Merger Sub Limited** | **Hamilton HM11** |
| **26 Reid Street** |  | **Bermuda** |
| **Hamilton HM11** | **c/o Sixth Street Partners, LLC** |  |
| **Bermuda** | **2100 McKinney Avenue, Suite 1500** |  |
|  | **Dallas, Texas 75201** |  |

---

**(Name, Address, and Telephone Numbers of Person Authorized to Receive Notices and Communications on Behalf of the Persons Filing Statement)**

 

*With copies to*

---

| | |
|:---|:---|
| **Krishna Veeraraghavan** | **Katherine M. Krause** |
| **Benjamin M. Goodchild** | **Elizabeth A. Cooper** |
| **Paul, Weiss, Rifkind, Wharton & Garrison LLP** | **Louis H. Argentieri** |
| **1285 Avenue of the Americas** | **Simpson Thacher & Bartlett LLP** |
| **New York, New York 10019** | **425 Lexington Avenue** |
| **(212) 373-3000** | **New York, NY 10017** |
|  | **(212) 455-2000** |

---

This statement is filed in connection with (check the appropriate box):

&nbsp;&nbsp;&nbsp;&nbsp;a. x The filing of solicitation materials or an information statement subject to Regulation 14A (§§ 240.14a-1 through 240.14b-2),
Regulation 14C (§§ 240.14c-1 through 240.14c-101) or Rule 13E-3(c) (§ 240.13e-3(c)) under the Securities Exchange Act
of 1934.

&nbsp;&nbsp;&nbsp;&nbsp;b. ¨ The filing of a registration statement under the Securities Act of 1933.

&nbsp;&nbsp;&nbsp;&nbsp;c. ¨ A tender offer.

&nbsp;&nbsp;&nbsp;&nbsp;d. ¨ None of the above.

Check the following box if the soliciting materials or information statement referred to in checking box (a) are preliminary copies: ☐

Check the following box if the filing is a final amendment reporting the results of the transaction: ☒

\* CUSIP number for Depositary Shares, each representing a 1/1,000th interest in a 7.00% Fixed-to-Floating Rate Perpetual Non-Cumulative Preference Shares, Series D, par value $1.00 per share.

\*\* CUSIP number for Depositary Shares, each representing a 1/1,000th interest in a 7.00% Perpetual Non-Cumulative Preference Shares, Series E, par value $1.00 per share.

NEITHER THE SECURITIES AND EXCHANGE COMMISSION NOR ANY STATE SECURITIES COMMISSION HAS APPROVED OR DISAPPROVED THIS TRANSACTION, PASSED ON THE MERITS OR THE FAIRNESS OF THE TRANSACTION OR PASSED UPON THE ADEQUACY OR ACCURACY OF THE INFORMATION CONTAINED IN THIS DOCUMENT. ANY REPRESENTATION TO THE CONTRARY IS A CRIMINAL OFFENSE.

**TABLE OF CONTENTS**

---

| | | |
|:---|:---|:---|
| SCHEDULE 13E-3 ITEMS | SCHEDULE 13E-3 ITEMS | 3 |
|  | [Item 15. Additional Information](#S_001) | [4](#S_001) |
|  | [Item 16. Exhibits](#S_002) | [5](#S_002) |

---

**INTRODUCTION**

This Amendment No. 4 (this "**Final Amendment**") to the Rule 13e-3 Transaction Statement on Schedule 13E-3, together with the exhibits hereto (as amended, this "**Transaction Statement**"), is being filed with the Securities and Exchange Commission (the "**SEC**") pursuant to Section 13(e) of the Securities Exchange Act of 1934, as amended (the "**Exchange Act**"), by: (i) Enstar Group Limited, an exempted company limited by shares existing under the laws of Bermuda (the "**Company**") and the issuer of the ordinary shares representing ownership interests in the Company, par value $1.00 per share (the "**Enstar Ordinary Shares**"), the depositary shares, each representing a 1/1,000th Interest in a 7.00% Fixed-to-Floating Rate Perpetual Non-Cumulative Preference Shares, Series D, par value $1.00 per share (the "**Series D Preferred Shares**") and the depositary shares, each representing a 1/1,000th 7.00% Perpetual Non-Cumulative Preference Shares, Series E, par value $1.00 per share (the "**Series E Preferred Shares**", together with the Series D Preferred Shares, the "**Depositary Shares**"), that are subject to the Rule 13E-3 transaction; (ii) Elk Evergreen Investments, LLC, a Delaware limited liability company; (iii) Elk Cypress Investments, LLC, a Delaware limited liability company; (iv) TSSP Sub-Fund HoldCo, LLC, a Delaware limited liability company; (v) Dominic F. Silvester, a natural person; (vi) Elk Topco, LLC, a limited liability company existing under the laws of Bermuda; (vii) Elk Parent Limited, an exempted company limited by shares existing under the laws of Bermuda; and (viii) Elk Bidco Limited, an exempted company limited by shares existing under the laws of Bermuda ("**Parent**").

The Transaction Statement relates to the Agreement and Plan of Merger, dated as of July 29, 2024 (as it may be amended from time to time, the "**Merger Agreement**"), by and among Parent, Elk Merger Sub Limited, an exempted company limited by shares existing under the laws of Bermuda and direct wholly owned subsidiary of Parent ("**Parent Merger Sub**"), the Company, Deer Ltd., an exempted company limited by shares existing under the laws of Bermuda ("**New Company Holdco**") and Deer Merger Sub Ltd., an exempted company limited by shares existing under the laws of Bermuda and a direct wholly owned subsidiary of New Company Holdco ("**Company Merger Sub**"). Pursuant to the Merger Agreement, (i) Company Merger Sub merged with and into the Company (the "**First Merger**"), with the Company surviving the merger as a direct wholly owned subsidiary of New Company Holdco (the "**First Surviving Company**"); (ii) New Company Holdco merged with and into the Company (the "**Second Merger**"), with the Company surviving such merger (the "**Second Surviving Company**"); and (iii) Parent Merger Sub merged with and into the Company (the "**Third Merger**" and, together with the First Merger and Second Merger, the "**Mergers**"), with the Company surviving such merger (the "**Third Surviving Company**"), so that as of immediately following such Mergers, Parent directly owns all Enstar Ordinary Shares. As a result of the Mergers, Company Merger Sub, New Company Holdco and Parent Merger Sub ceased to exist as independent entities and, therefore, are no longer Filing Persons.

This Final Amendment is being filed pursuant to Rule 13e-3(d)(3) under the Exchange Act to report the results of the transaction that is the subject of the Transaction Statement.

Except as otherwise set forth herein, the information set forth in the Transaction Statement remains unchanged and is incorporated by reference into this Final Amendment. All information set forth in this Final Amendment should be read together with the information contained in or incorporated by reference in the Transaction Statement.

While each of the Filing Persons acknowledges that the Mergers may be deemed to constitute a "going private" transaction for purposes of Rule 13e-3 under the Exchange Act, the filing of this Final Amendment and the Transaction Statement shall not be construed as an admission by any Filing Person, or by any affiliate of a Filing Person, that, prior to the Mergers, the Company was "controlled" by any of the Filing Persons or their respective affiliates.

Pursuant to General Instruction F to Schedule 13E-3, the information contained in the definitive proxy statement filed under Regulation 14A of the Exchange Act with the SEC pursuant to which the Company solicited proxies from the Company's shareholders in connection with the Merger (as amended, the "**Proxy Statement**"), including all annexes thereto, is incorporated herein by reference in its entirety. Responses to each item herein are qualified in their entirety by the information contained in the Proxy Statement and the annexes thereto. The cross-references below are being supplied pursuant to General Instruction G to Schedule 13E-3 and show the location in the Proxy Statement of the information required to be included in response to the items of Schedule 13E-3. Terms used but not defined in this Transaction Statement shall have the meanings given to them in the Proxy Statement.

All information concerning the Company contained in, or incorporated by reference into, this Transaction Statement was supplied by the Company. Similarly, all information concerning each other Filing Person contained in, or incorporated by reference into, this Transaction Statement was supplied by such Filing Person.

**Item 15. Additional Information**

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(c) ***Other material information***. Item 15(c) is hereby amended and supplemented as follows:

On November 6, 2024, at a special general meeting of the Company's shareholders, the Company's shareholders voted to approve, among other things, (1) a proposal to adopt the Merger Agreement, the Statutory Merger Agreements and the Mergers and (2) on a non-binding, advisory basis, the compensation that will or may become payable by the Company to its named executive officers in connection with the Mergers.

In addition, on July 2, 2025, Parent, Elk Evergreen Investments, LLC and Elk Cypress Investments, LLC entered into rollover and support agreements ("**New Rollover and Support Agreements**") with each of David Ni, Nazar Alobaidat and Audrey Taranto (the "**New Reinvesting Shareholders**"). Under the New Rollover and Support Agreements, the New Reinvesting Shareholders agreed to contribute certain of the ordinary shares of the Second Surviving Company owned by the New Reinvesting Shareholder to an indirect parent company of Parent in exchange for equity interests in such indirect parent company of Parent, which contribution and exchange happened immediately after the Second Effective Time and prior to the Third Effective Time. The New Reinvesting Shareholders, in the aggregate, will indirectly own less than 1% of Parent through such indirect parent company following such contribution and exchange. As a result of the Mergers and the transactions contemplated by the New Rollover and Support Agreements, the Enstar Ordinary Shares held by the New Reinvesting Shareholders immediately prior to the First Merger corresponding to the ordinary shares of the Second Surviving Company that were subject to such contribution and exchange were cancelled and extinguished without any conversion thereof or consideration paid therefor.

On July 2, 2025, each of the First Merger, the Second Merger and the Third Merger became effective pursuant to the Certificates of Merger that were issued by the Registrar of Companies in Bermuda in connection with the First Merger, the Second Merger and the Third Merger, respectively. As a result of the Mergers and the other transactions contemplated by the Merger Agreement (collectively, the "**Transactions**"), Parent directly owns all Enstar Ordinary Shares.

As a result of the Transactions, (i) each holder of Enstar Ordinary Shares issued and outstanding immediately prior to the First Effective Time (other than (a) Enstar Ordinary Shares owned by Parent, Parent Merger Sub, the Company or their respective wholly owned subsidiaries, (b) all Reinvesting Shares, (c) all Enstar Ordinary Shares subject to the Company's equity awards (other than Company Restricted Shares) and (d) all Ordinary Shares that were Dissenting Shares) was entitled to the right to receive a total of $338 in cash, without interest, for each Enstar Ordinary Share, and (ii) the Company's shareholders holding each class of preferred shares of the Company (the "**Enstar Preferred Shares**") received a corresponding class of preferred shares of the Company, as the Third Surviving Company, and the dividend and all other preferences and privileges, relative rights, terms and conditions of each such Enstar Preferred Shares remained unchanged. Following consummation of the Transactions, holders of the Enstar Ordinary Shares no longer directly own any shares of the Company, which is the Third Surviving Company following the Mergers, and the holders of the Enstar Preferred Shares hold preferred shares of the Company (as the Third Surviving Company following the Mergers).

In addition, by virtue of the Mergers, each Company Restricted Share, Company RSU Award and Company PSU Award was converted into the right to receive the consideration for such award set forth in the Merger Agreement.

As a result of the Transactions, the Enstar Ordinary Shares and the Depositary Shares will no longer be listed on any security exchange or quotation system, including the NASDAQ Stock Market LLC ("**Nasdaq**"), and the Company will cease to be a publicly traded company. On July 2, 2025, the Company notified Nasdaq that the Mergers had been completed, and Nasdaq halted trading of Enstar Ordinary Shares prior to the opening of trading on July 3, 2025. The Company requested that Nasdaq file with the SEC a notification of removal from listing and registration on Form 25 (the "**Ordinary Shares Form 25**") with respect to the delisting of all Enstar Ordinary Shares from Nasdaq and the deregistration of such shares under Section 12(b) of the Exchange Act.

On July 2, 2025, the Company notified representatives of Nasdaq of its determination to voluntarily withdraw the Depositary Shares from listing on Nasdaq and registration pursuant to Section 12(b) of the Exchange Act, and its intention to file a Form 25 Notification of Delisting with the SEC (the "**Depositary Shares Form 25**" and together with the Ordinary Shares Form 25, the "**Form 25s**") on or about July 14, 2025 relating to delisting and deregistering of the Depositary Shares.

Following the effectiveness of the Form 25s, the Company intends to file with the SEC a certification on Form 15 requesting the termination of registration of Enstar Ordinary Shares and the Depositary Shares under Section 12(g) of the Exchange Act and the suspension of reporting obligations under Sections 13 and 15(d) of the Exchange Act. Such deregistration of the Enstar Ordinary Shares and the Depositary Shares will become effective 90 days after the filing of the applicable Form 25 or such shorter period as may be determined by the SEC. The Company's reporting obligations under the Exchange Act will be suspended immediately upon the filing of Form 15.

In addition, on July 2, 2025, the Company issued a press release announcing the closing of the Mergers. The press release is attached as Exhibit 99.1 to the Company's Current Report on Form 8-K, filed concurrently with the SEC, and is incorporated by reference herein as Exhibit (a)(5)(i) hereto.

**Item 16. Exhibits**

The following exhibits are filed herewith:

---

| | |
|:---|:---|
| **Exhibit<br> No.** | **Description** |
| [(a)(2)(i)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924108102/tm2420342-21_defm14a.htm) | [Definitive Proxy Statement of Enstar Group Limited (the "**Proxy Statement**") (included in the Schedule 14A filed on October 11, 2024 and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924108102/tm2420342-21_defm14a.htm) |
| [(a)(2)(ii)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924108102/tm2420342-21_defm14a.htm) | [Form of Proxy Card (included in the Proxy Statement and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924108102/tm2420342-21_defm14a.htm) |
| [(a)(2)(iii)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924108102/tm2420342-21_defm14a.htm) | [Letter to Shareholders (included in the Proxy Statement and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924108102/tm2420342-21_defm14a.htm) |
| [(a)(2)(iv)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924108102/tm2420342-21_defm14a.htm) | [Notice of Special Meeting of Shareholders (included in the Proxy Statement and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924108102/tm2420342-21_defm14a.htm) |
| [(a)(2)(v)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924083290/tm2420342-2_defa14a.htm) | [Current Report on Form 8-K, dated July 29, 2024 (included in Schedule 14A filed on July 29, 2024 and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924083290/tm2420342-2_defa14a.htm) |
| [(a)(2)(vi)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924083603/tm2420342d3_defa14a.htm) | [Form of Email to Regulators, dated July 29, 2024 (included in Schedule 14A filed on July 29, 2024 and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924083603/tm2420342d3_defa14a.htm) |
| [(a)(2)(vii)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924083605/tm2420342d5_defa14a.htm) | [Email to Employees, dated July 29, 2024 (included in Schedule 14A filed on July 29, 2024 and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924083605/tm2420342d5_defa14a.htm) |
| [(a)(2)(viii)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924083606/tm2420342d6_defa14a.htm) | [Email to Brokers, dated July 29, 2024 (included in Schedule 14A filed on July 29, 2024 and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924083606/tm2420342d6_defa14a.htm) |
| [(a)(2)(ix)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924083608/tm2420342d4_defa14a.htm) | [Email to Investors, dated July 29, 2024 (included in Schedule 14A filed on July 29, 2024 and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924083608/tm2420342d4_defa14a.htm) |
| [(a)(2)(x)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924083610/tm2420342d7_defa14a.htm) | [Email to Investors, dated July 29, 2024 (included in Schedule 14A filed on July 29, 2024 and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924083610/tm2420342d7_defa14a.htm) |
| [(a)(2)(xi)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096635/tm2420342d12_defa14a.htm) | [Press Release, dated September 4, 2024 (included in Schedule 14A filed on September 4, 2024 and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096635/tm2420342d12_defa14a.htm) |
| [(a)(5)(i)](https://www.sec.gov/Archives/edgar/data/1363829/000110465925065337/tm2519642d2_ex99-1.htm) | [Press Release, dated July 2, 2025 (included in the Company's Current Report on Form 8-K filed on July 2, 2025 and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465925065337/tm2519642d2_ex99-1.htm) |
| [(a)(5)(ii)](https://www.sec.gov/ix?doc=/Archives/edgar/data/1363829/000110465925065337/tm2519642d2_8k.htm) | [Current Report on Form 8-K, dated July 2, 2025 (filed by Enstar Group Limited on July 2, 2025 and incorporated herein by reference).](https://www.sec.gov/ix?doc=/Archives/edgar/data/1363829/000110465925065337/tm2519642d2_8k.htm) |
| [(b)(i)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096659/tm2420342d8_ex99-bi.htm) | [Equity Commitment Letter dated as of July 29, 2024, by and among Elk Bidco Limited and the persons set forth on Schedule A thereto.+](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096659/tm2420342d8_ex99-bi.htm) |
| [(b)(ii)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096659/tm2420342d8_ex99-bii.htm) | [Limited Guarantee dated as of July 29, 2024, by and among Enstar Group Limited and the persons set forth on Schedule A thereto.+](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096659/tm2420342d8_ex99-bii.htm) |
| [(b)(iii)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096659/tm2420342d8_ex99-biii.htm) | [Facilities Commitment Letter dated as of July 29, 2024, by and between Elk Bidco Limited and Barclays Bank PLC.+](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096659/tm2420342d8_ex99-biii.htm) |
| [(b)(iv)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096659/tm2420342d8_ex99-biv.htm) | [Preferred Equity Commitment Letter dated as of July 29, 2024, by and between Elk Bidco Limited and Stone Point Credit Adviser LLC.+](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096659/tm2420342d8_ex99-biv.htm) |
| [(c)(i)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXL) | [Opinion of Goldman Sachs & Co. LLC, dated July 29, 2024 (included as Annex L to the Proxy Statement and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXL) |
| [(c)(ii)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096659/tm2420342d8_ex99-cii.htm) | [Discussion Materials of Goldman Sachs & Co. LLC, dated March 26, 2024.+](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096659/tm2420342d8_ex99-cii.htm) |
| [(c)(iii)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096659/tm2420342d8_ex99-ciii.htm) | [Discussion Materials of Goldman Sachs & Co. LLC, dated April 4, 2024.\*+](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096659/tm2420342d8_ex99-ciii.htm) |
| [(c)(iv)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096659/tm2420342d8_ex99-civ.htm) | [Discussion Materials of Goldman Sachs & Co. LLC, dated April 8, 2024.+](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096659/tm2420342d8_ex99-civ.htm) |
| [(c)(v)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096659/tm2420342d8_ex99-cv.htm) | [Discussion Materials of Goldman Sachs & Co. LLC, dated April 10, 2024.+](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096659/tm2420342d8_ex99-cv.htm) |
| [(c)(vi)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096659/tm2420342d8_ex99-cvi.htm) | [Discussion Materials of Goldman Sachs & Co. LLC, dated July 28, 2024.\*+](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096659/tm2420342d8_ex99-cvi.htm) |
| [(d)(i)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXA) | [Agreement and Plan of Merger dated as of July 29, 2024, by and among Elk Bidco Limited, Elk Merger Sub Limited, Enstar Group Limited, Deer Ltd. and Deer Merger Sub Ltd. (included as Annex A to the Proxy Statement and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXA) |
| [(d)(ii)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXB) | [Form of First Statutory Merger Agreement to be entered into by and among Deer Ltd., Deer Merger Sub Ltd. and Enstar Group Limited (included as Annex B to the Proxy Statement and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXB) |
| [(d)(iii)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXC) | [Form of Second Statutory Merger Agreement to be entered into by and among Deer Ltd. and Enstar Group Limited (included as Annex C to the Proxy Statement and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXC) |

---

---

| | |
|:---|:---|
| [(d)(iv)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXD) | [Form of Third Statutory Merger Agreement to be entered into by and among Elk Bidco Limited, Elk Merger Sub Limited, and Enstar Group Limited (included as Annex D to the Proxy Statement and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXD) |
| [(d)(v)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXE) | [Rollover and Support Agreement dated as of July 29, 2024, by and among Elk Topco, LLC, Elk Evergreen Investments, LLC, Elk Cypress Investments, LLC and Dominic Silvester (included as Annex E to the Proxy Statement and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXE) |
| [(d)(vi)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXK) | [Rollover and Support Agreement dated as of July 29, 2024, by and among Elk Topco, LLC, J.C. Flowers & Co. LLC, Elk Evergreen Investments, LLC, Elk Cypress Investments, LLC and David Walsh (included as Annex K to the Proxy Statement and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXK) |
| [(d)(vii)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXH) | [Rollover and Support Agreement dated as of July 29, 2024, by and among Elk Topco, LLC, J.C. Flowers & Co. LLC, Elk Evergreen Investments, LLC, Elk Cypress Investments, LLC and Frazer Holdings (included as Annex H to the Proxy Statement and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXH) |
| [(d)(viii)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXI) | [Rollover and Support Agreement dated as of July 29, 2024, by and among Elk Topco, LLC, J.C. Flowers & Co. LLC, Elk Evergreen Investments, LLC, Elk Cypress Investments, LLC and Hyman 2018 Family Trust (included as Annex I to the Proxy Statement and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXI) |
| [(d)(ix)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXG) | [Rollover and Support Agreement dated as of July 29, 2024, by and among Elk Topco, LLC, J.C. Flowers & Co. LLC, Elk Evergreen Investments, LLC, Elk Cypress Investments, LLC and J. Christopher Flowers (included as Annex G to the Proxy Statement and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXG) |
| [(d)(x)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXJ) | [Rollover and Support Agreement dated as of July 29, 2024, by and among Elk Topco, LLC, J.C. Flowers & Co. LLC, Elk Evergreen Investments, LLC, Elk Cypress Investments, LLC and John J. Oros 1998 Family Trust (included as Annex J to the Proxy Statement and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXJ) |
| [(d)(xi)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXF) | [Rollover and Support Agreement dated as of July 29, 2024, by and among Elk Topco, LLC, J.C. Flowers & Co. LLC, Elk Evergreen Investments, LLC, Elk Cypress Investments, LLC and Steven D. Arnold (included as Annex F to the Proxy Statement and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXF) |
| [(d)(xii)](https://www.sec.gov/Archives/edgar/data/1363829/000136382923000201/exhibit103-shareholderrigh.htm) | [Shareholder Rights Agreement, dated as of November 8, 2023, by and among Enstar Group Limited, Elk Evergreen Investments, LLC and Elk Cypress Investments, LLC (incorporated by reference to Exhibit 10.3 to the Company's Form 8-K filed on November 13, 2023).](https://www.sec.gov/Archives/edgar/data/1363829/000136382923000201/exhibit103-shareholderrigh.htm) |
| [(d)(xiii)](https://www.sec.gov/Archives/edgar/data/1363829/000136382923000201/exhibit104-registrationrig.htm) | [Registration Rights Agreement, dated as of November 8, 2023, by and among Enstar Group Limited, Elk Evergreen Investments, LLC and Elk Cypress Investments, LLC (incorporated by reference to Exhibit 10.4 to the Company's Form 8-K filed on November 13, 2023).](https://www.sec.gov/Archives/edgar/data/1363829/000136382923000201/exhibit104-registrationrig.htm) |
| [(d)(xiv)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096659/tm2420342d8_ex99-dxiv.htm) | [Purchase Agreement, dated November 8, 2023, between Canada Pension Plan Investment Board, Elk Evergreen Investments, LLC and Elk Cypress Investments, LLC.+](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096659/tm2420342d8_ex99-dxiv.htm) |
| [(d)(xv)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096659/tm2420342d8_ex99-dxv.htm) | [Assignment and Assumption Agreement, dated November 8, 2023, between Canada Pension Plan Investment Board, Elk Evergreen Investments, LLC, Elk Cypress Investments, LLC, Flexpoint Asset Opportunity Fund II-A, L.P. and Flexpoint Asset Opportunity Fund II-B, L.P.+](https://www.sec.gov/Archives/edgar/data/1363829/000110465924096659/tm2420342d8_ex99-dxv.htm) |
| [(d)(xvi)](https://www.sec.gov/Archives/edgar/data/1363829/000136382923000068/exhibit101-cppibpurchaseag.htm) | [Purchase Agreement, dated March 23, 2023, between Enstar Group Limited and Canada Pension Plan Investment Board (incorporated by reference to Exhibit 10.1 to the Company's Form 8-K filed on March 28, 2023).](https://www.sec.gov/Archives/edgar/data/1363829/000136382923000068/exhibit101-cppibpurchaseag.htm) |
| [(d)(xvii)](https://www.sec.gov/Archives/edgar/data/1363829/000136382923000201/exhibit101-cppibandcppiblp.htm) | [Purchase Agreement, dated as of November 7, 2023, by and among Enstar Group Limited, Canada Pension Plan Investment Board, and CPPIB Epsilon Ontario Limited Partnership (incorporated by reference to Exhibit 10.1 to the Company's Form 8-K filed on November 13, 2023).](https://www.sec.gov/Archives/edgar/data/1363829/000136382923000201/exhibit101-cppibandcppiblp.htm) |
| [(d)(xviii)](https://www.sec.gov/Archives/edgar/data/1363829/000136382923000201/exhibit102-eglxtridentpurc.htm) | [Purchase Agreement, dated as of November 7, 2023, by and between Enstar Group Limited and Trident Public Equity L.P. (incorporated by reference to Exhibit 10.2 to the Company's Form 8-K filed on November 13, 2023).](https://www.sec.gov/Archives/edgar/data/1363829/000136382923000201/exhibit102-eglxtridentpurc.htm) |
| [(d)(xix)](tm2519642d1_ex99-dxix.htm) | [Form of New Rollover and Support Agreements.](tm2519642d1_ex99-dxix.htm) |
| [(f)](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXM) | [Section 106 of the Bermuda Companies Act (included as Annex M to the Proxy Statement and incorporated herein by reference).](https://www.sec.gov/Archives/edgar/data/1363829/000110465924104026/tm2420342-13_prer14a.htm#tANXM) |

---

[107](https://www.sec.gov/Archives/edgar/data/1363829/000110465924108117/tm2420342-22_ex107.htm) [Filing Fee Table#](https://www.sec.gov/Archives/edgar/data/1363829/000110465924108117/tm2420342-22_ex107.htm)

---

| | |
|:---|:---|
| \* | Certain portions of this exhibit have been redacted and separately filed with the SEC pursuant to a request for confidential treatment. |
| + | Previously filed with the Transaction Statement on the Schedule 13E-3 filed with the SEC on September 4, 2024. |
| # | Previously filed with the Transaction Statement on the Schedule 13E-3 filed with the SEC on October 11, 2024. |

---

**SIGNATURES**

After due inquiry and to the best of each of the undersigned's knowledge and belief, each of the undersigned certifies that the information set forth in this statement is true, complete and correct.

Dated as of July 2, 2025

---

| | | |
|:---|:---|:---|
| **ENSTAR** **GROUP LIMITED** | **ENSTAR** **GROUP LIMITED** | **ENSTAR** **GROUP LIMITED** |
| By: | /s/ Audrey B. Taranto | /s/ Audrey B. Taranto |
|  | Name: | Audrey B. Taranto |
|  | Title: | General Counsel |

---

---

| | | |
|:---|:---|:---|
| **ELK EVERGREEN INVESTMENTS, LLC** | **ELK EVERGREEN INVESTMENTS, LLC** | **ELK EVERGREEN INVESTMENTS, LLC** |
| By: | /s/ Joshua Peck | /s/ Joshua Peck |
|  | Name: | Joshua Peck |
|  | Title: | Vice President |

---

---

| | | |
|:---|:---|:---|
| **ELK CYPRESS INVESTMENTS, LLC** | **ELK CYPRESS INVESTMENTS, LLC** | **ELK CYPRESS INVESTMENTS, LLC** |
| By: | /s/ Joshua Peck | /s/ Joshua Peck |
|  | Name: | Joshua Peck |
|  | Title: | Vice President |

---

---

| | | |
|:---|:---|:---|
| **TSSP SUB-FUND HOLDCO, LLC** | **TSSP SUB-FUND HOLDCO, LLC** | **TSSP SUB-FUND HOLDCO, LLC** |
| By: | /s/ Joshua Peck | /s/ Joshua Peck |
|  | Name: | Joshua Peck |
|  | Title: | Vice President |

---

[*Signature Page to Schedule 13E-3*]

---

| | | |
|:---|:---|:---|
| **ELK BIDCO LIMITED** | **ELK BIDCO LIMITED** | **ELK BIDCO LIMITED** |
| By: | /s/ A. Michael Muscolino | /s/ A. Michael Muscolino |
|  | Name: | A. Michael Muscolino |
|  | Title: | Authorized Signatory |

---

---

| | | |
|:---|:---|:---|
| **DOMINIC F. SILVESTER** | **DOMINIC F. SILVESTER** | **DOMINIC F. SILVESTER** |
|  | /s/ Dominic F. Silvester | /s/ Dominic F. Silvester |
|  | Name: | Dominic F. Silvester |

---

[*Signature Page to Schedule 13E-3*]

## Ex-99.(D)(Xix)

**Exhibit 99.(d)(xix)**

***Form***

Elk Topco LLC

C/O Walkers Corporate (Bermuda) Limited

Park Place, 55 Par-la-Ville Road

Hamilton, HM11, Bermuda

July 2, 2025

[*NAME*]

[*ADDRESS*]

Re: <u>Rollover and Support Agreement ([*NAME*])</u>

To whom it may concern:

This rollover and support agreement, dated as of the date first written above (as amended, restated, modified or supplemented from time to time, and together with all schedules, annexes and exhibits hereto, this "***Agreement***") is being entered into by and among Elk Topco, LLC, a Bermuda limited liability company ("***Topco***"), Elk Coinvest, L.P., a Bermuda limited partnership ("***Elk Coinvest***"), Elk Evergreen Investments, LLC, a Delaware limited liability company, Elk Cypress Investments, LLC, a Delaware limited liability company, and the Person identified on the signature pages hereto under the heading "Rollover Investor" (the "***Rollover Investor***"). This Agreement relates to the Agreement and Plan of Merger, dated as of July 29, 2024 (as amended, restated, modified or supplemented from time to time, the "***Merger Agreement***"), by and among Elk Bidco Limited, an exempted company limited by shares existing under the laws of Bermuda ("***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 wholly owned Subsidiary of the Company ("***New Company Holdco***") and Deer Merger Sub Ltd., an exempted company limited by shares existing under the laws of Bermuda and a direct wholly owned Subsidiary of New Company Holdco ("***Company Merger Sub***"), pursuant to which, among other things, upon the terms and subject to the conditions set forth therein, (i) Company Merger Sub will be merged with and into the Company, with the Company being the surviving company as a wholly owned subsidiary of New Company Holdco, (b) New Company Holdco will be merged with and into the Company, with the Company being the surviving company, and (c) Parent Merger Sub will be merged with and into the Company, with the Company being the surviving company as a wholly owned Subsidiary of Parent (such mergers, collectively, the "***Mergers***"). Capitalized or other terms used and not defined herein but defined in the Merger Agreement shall have the meanings ascribed to them in the Merger Agreement.

In consideration of the mutual covenants and conditions as hereinafter set forth, each of the parties hereto hereby agree as follows:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;1. **<u>Rollover Contribution</u>.**

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(a) <u>Certain Definitions</u>. As used in this Agreement the following terms have the following meanings:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(i) *"**Coinvest Units**"* means the limited partnership interests in Elk Coinvest designated as "CIV Member Units".

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(ii) "***Ordinary Share***" means a voting ordinary share, par value $1.00 per share, of the Company.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(iii) "***Rollover Documents***" means, collectively, (A) this Agreement, (B) the amended and restated limited partnership agreement of Elk Coinvest (C) the Accredited Investor Questionnaire attached hereto as <u>Exhibit A</u> (an "***Accredited Investor Questionnaire***"), (D) if applicable, the Consent of Spouse attached hereto as <u>Exhibit B</u> (the "***Consent of Spouse***"), and (E) any other document that may be entered into pursuant to this Agreement.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(iv) "***Rollover Shares***" means an aggregate number of Ordinary Shares held by the Rollover Investor as of immediately prior to the Rollover Closing that have a total value equal to the Value; <u>provided</u> that the number of Rollover Shares shall be rounded down to the nearest whole number. Such number of Rollover Shares is set forth on <u>Exhibit C</u>.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(v) "***Value***" means the value set forth on <u>Exhibit C</u>, calculated (A) with respect to each Rollover Share, based on the price per Ordinary Share payable as Total Cash Consideration under the Merger Agreement and (B) with respect to each Topco Interest, based on the same price per Topco Interest paid by the Equity Investors.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(b) <u>Rollover Contribution</u>.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(i) Subject to, and conditioned only upon, the satisfaction or waiver of the conditions set forth in <u>Section 1(d)</u>, and without any further action on behalf of the Rollover Investor, the Rollover Investor agrees to transfer, contribute and deliver to Topco the Rollover Shares (as such shares may be first converted in the First Merger and in the Second Merger in accordance with the Merger Agreement) (the "***Rollover***") in exchange for the issuance (whether directly or indirectly) by Topco to the Rollover Investor of a number of participating non-voting interests of Topco set forth on <u>Exhibit C</u> (each, a "***Topco Interest***"), having an aggregate Value equal to the aggregate Value of the Rollover Shares (subject to rounding down the number of Rollover Shares to the nearest whole number in accordance with the definition thereof and the corresponding adjustment to Value) in accordance with this Agreement, the Merger Agreement and applicable Law. In accordance with Section 2.7(b) of the Merger Agreement, each Ordinary Share held by the Rollover Investor immediately prior to the First Merger shall, by virtue of the First Merger, be converted into the right to receive, per Ordinary Share, a New Ordinary Share of the First Surviving Company, and in accordance with Section 2.8(b) of the Merger Agreement, each such New Ordinary Share shall, by virtue of the Second Merger, be converted into the right to receive, per New Ordinary Share, one Ordinary Share of the Second Surviving Company. The Rollover shall occur, with respect to the Ordinary Shares of the Second Surviving Company held by the Rollover Investor, conditioned upon the Third Closing and as of immediately prior to the Third Effective Time (the "***Rollover Closing***"). Topco and the Rollover Investor agree to report the Rollover in a manner consistent with such allocation for U.S. federal, state and local income tax purposes.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(ii) Immediately upon receiving the Topco Interest, without any further action on behalf of the Rollover Investor, the Rollover Investor agrees to transfer, contribute and deliver the Topco Interest to Elk Coinvest in exchange for the issuance by Elk Coinvest to the Rollover Investor of a number of Coinvest Units equal to the number of participating non-voting interests of Topco comprising the Topco Interest.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(c) <u>No Certificates</u>. The Rollover Investor acknowledges and agrees that it is not entitled to any certificate representing the issued Topco Interests or the Coinvest Units, unless and to the extent Topco or Elk Coinvest determines to issue certificates in its sole discretion.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(d) <u>Conditions</u>.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(i) The obligations of Topco, Elk Coinvest and the Rollover Investor to consummate the transactions contemplated by <u>Section 1(b)</u> are subject to (A) the satisfaction or waiver by the applicable parties to the Merger Agreement on or prior to the Rollover Closing of all of the conditions to each Closing set forth in Article IX of the Merger Agreement (other than those conditions which by their terms or nature are to be satisfied at such Closing (or following Rollover Closing and prior to such Closing) all of which have been acknowledged to be satisfied immediately following the Rollover Closing) and (B) each party to the Merger Agreement being ready, willing and able to consummate each of the Merger immediately following the Rollover Closing.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(ii) The obligations of Topco and Elk Coinvest to consummate the transactions contemplated by <u>Section 1(b)</u> are subject to (A) the representations and warranties set forth on <u>Annex A</u> being true and correct (x) as of the date hereof and (y) as of the Rollover Closing and (B) receipt by Topco from the Rollover Investor of complete copies of (x) the Accredited Investor Questionnaire, duly executed by the Rollover Investor, (y) if applicable, the Consent of Spouse, duly executed by the Rollover Investor's spouse, and (z) the amended and restated limited partnership agreement of Elk Coinvest, duly executed by the Rollover Investor.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(iii) The obligations of the Rollover Investor to consummate the transactions contemplated by <u>Section 1(b)</u> are subject to the representations and warranties set forth on <u>Annex B</u> being true and correct (x) as of the date hereof and (y) as of the Rollover Closing.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(e) <u>Other Matters</u>. The Rollover Investor agrees that (i) the Rollover Shares will be contributed to Topco and/or exchanged for Topco Interests, free and clear of all Liens, and (ii) the TopCo Interests will be contributed to Elk Coinvest and/or exchanged for Coinvest Units, free and clear of all Liens.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;2. **<u>Transfer Restrictions; Agreement to Vote Shares</u>.** 

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(a) Except as otherwise expressly provided by and in accordance with <u>Section 11(b)</u>, the Rollover Investor agrees not to directly or indirectly transfer, encumber, gift, pledge, convert, exercise, assign, exchange, grant an option with respect to (or otherwise enter into any derivative or hedging arrangement with respect to), or otherwise dispose (by merger, by testamentary disposition, by operation of law or otherwise) of any of such Rollover Investor's Shares (as defined below) during the time period between the execution of this Agreement and the Rollover Closing other than pursuant to the transactions contemplated by this Agreement, without the prior written consent of Topco.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(b) The Rollover Investor shall not enter into any agreement or understanding with any Person to vote or give instructions in any manner inconsistent with the terms of this <u>Section 2</u>.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(c) The Rollover Investor hereby irrevocably and unconditionally waives, and agrees to cause to be waived and to prevent the exercise of, any rights of appraisal, any dissenters' rights and any similar rights relating to the Mergers or any other Transactions that such Rollover Investor may have by virtue of, or with respect to, any Shares.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;3. **<u>Effectiveness and Termination</u>.** This Agreement will become effective immediately upon execution and delivery by each of the parties hereto. If the Merger Agreement is terminated for any reason prior to the Closing, this Agreement will automatically terminate at such time and none of the Rollover Investor, Topco, Elk Coinvest or any of their respective Affiliates or representatives will have any liability or obligation under this Agreement.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;4. **<u>Representations and Warranties</u>.**

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(a) The Rollover Investor hereby makes the representations and warranties set forth on <u>Annex A</u>.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(b) Topco and Elk Coinvest each hereby make the representations and warranties set forth on <u>Annex B</u>.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;5. **<u>Interests Unregistered</u>.** The Rollover Investor hereby acknowledges and represents that the Rollover Investor has been advised by Topco that:

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(a) The offer and exchange of Topco Interests and Coinvest Units pursuant to or in connection with this Agreement have not been registered under the Securities Act.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(b) The Rollover Investor must continue to bear the economic risk of the investment in the Topco Interests and/or Coinvest Units unless the offer and sale of such Topco Interests and/or Coinvest Units are subsequently registered under the Securities Act and all applicable state securities laws or an exemption from such registration is available.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(c) There is no established market for the Topco Interests and/or Coinvest Units and it is not anticipated that there will be any public market for the Topco Interests and/or Coinvest Units in the foreseeable future.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;(d) A notation shall be made in the appropriate records of Topco and Elk Coinvest indicating that the Topco Interests and/or Coinvest Units (as applicable) are subject to restrictions on transfer and, if Topco or Elk Coinvest (as applicable) should at some time in the future engage the services of a securities transfer agent, appropriate stop-transfer instructions will be issued to such transfer agent with respect to the Topco Interests and/or Coinvest Units (as applicable).

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;6. **<u>Tax Matters</u>.** Unless otherwise determined by the Voting Member (as defined in the Amended and Restated Limited Liability Company Operating Agreement of Topco, dated as of the date hereof), Topco will be classified as a partnership for U.S. federal tax purposes (as well as for any analogous state or local tax purposes). Elk Coinvest will be classified as a partnership for U.S. federal tax purposes (as well as for any analogous state or local tax purposes). The parties intend that the transactions contemplated by Section 1(b) be treated for U.S. federal income tax purposes as contributions pursuant to Section 721 of the Code.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;7. **<u>Entire Agreement</u>.** This Agreement and the other instruments and other agreements specifically referred to herein or delivered pursuant hereto constitute the entire agreement between the parties with respect to the subject matter of this Agreement and supersede all prior agreements and understandings, both oral and written, between the parties with respect to the subject matter hereof and thereof.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;8. **<u>Waiver</u>.** Any agreement on the part of a party to any such extension or waiver shall be valid only if set forth in an instrument in writing signed on behalf of such party. No failure or delay by any party in exercising any right, power or privilege hereunder shall operate as a waiver thereof nor shall any single or partial exercise thereof preclude any other or further exercise thereof or the exercise of any other right, power or privilege. The rights and remedies herein provided shall be cumulative and not exclusive of any rights or remedies provided by Law.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;9. **<u>Assignment</u>.** The provisions of this Agreement shall be binding upon, inure to the benefit of and be enforceable by the parties and their respective successors and assigns; <u>provided</u>, <u>however</u>, that no party may assign, delegate or otherwise transfer any of its rights or obligations under this Agreement without the prior written consent of the other party and no such assignment shall relieve the party of its obligations under this Agreement.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;10. **<u>Binding Effect; No Third Party Beneficiaries</u>.** No provision of this Agreement or any other agreement contemplated hereby is intended to confer any rights or remedies on any Person other than the parties hereto, except that the Company is an express third party beneficiary under Section 2(b).

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;11. **<u>Amendment</u>**. Any provision of this Agreement (including the schedules, annexes and exhibits hereto) may be amended or waived prior to the Rollover Closing if, and only if, such amendment or waiver is in writing and signed, in the case of an amendment, by the Topco and the Rollover Investor, or in the case of a waiver, by the party against whom the waiver is to be effective.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;12. **<u>Specific Performance</u>.** The parties agree that irreparable damage would occur and that the parties would not have any adequate remedy at law in the event that any provision of this Agreement were not performed in accordance with its specific terms or were otherwise breached, and that money damages or other legal remedies would not be an adequate remedy for any such failure to perform or breach. Accordingly, the parties acknowledge and hereby agree that, prior to any termination of this Agreement, in the event of any breach or threatened breach by a party of any of its respective obligations, covenants and agreements under this Agreement, the other party shall be entitled to an injunction or injunctions to prevent or restrain breaches or threatened breaches of this Agreement by such party and to specific performance by the other party of the terms and provisions of this Agreement to prevent breaches or threatened breaches of, or to enforce compliance with, the obligations, covenants and agreements of the other party under this Agreement, without proof of actual harm or the inadequacy of a legal remedy and without bond or other security being required. The pursuit of specific enforcement or other equitable remedies by any party will not be deemed an election of remedies or waiver of the right to pursue any other right or remedy (whether at law or in equity) to which such party may be entitled at any time. Each party hereby agrees not to raise objections to the availability of the equitable remedy of specific performance or an injunction or temporary restraining order to prevent or restrain breaches or threatened breaches of this Agreement by the other party and to specifically enforce the terms and provisions of this Agreement to prevent breaches or threatened breaches of, or to enforce compliance with, the obligations covenants and agreements. Each party further agrees that by seeking the remedies provided for in this <u>Section 14</u>, a party shall not in any respect waive its right to seek at any time any other form of relief that may be available to a party under this Agreement.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;13. **<u>Survival of Representations and Warranties</u>.** All representations and warranties contained herein shall survive the execution and delivery of this Agreement and the consummation of the transactions contemplated hereby.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;14. **<u>Further Assurances</u>.** Each party hereto shall cooperate and shall take such further action and shall execute and deliver such further documents as may be reasonably requested by the other party hereto in order to carry out the provisions and purposes of this Agreement.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;15. **<u>Stop Transfer Instructions</u>.** At all times commencing with the execution and delivery of this Agreement and continuing until the Rollover Closing, in furtherance of this Agreement, the Rollover Investor hereby authorizes the Company or its counsel to notify the Company's transfer agent that there is a stop transfer order with respect to all of the Shares (and that this Agreement places limits on the voting and transfer of such Shares). The Rollover Investor hereby authorizes Parent to direct the Company to impose stop orders to prevent the Transfer of any Shares on the books of the Company in violation of this Agreement.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;16. **<u>Severability</u>.** If any term, provision, covenant or restriction of this Agreement is held by a court of competent jurisdiction or other authority to be invalid, void or unenforceable, the remainder of the terms, provisions, covenants and restrictions of this Agreement shall remain in full force and effect and shall in no way be affected, impaired or invalidated so long as the economic or legal substance of the transactions contemplated by this Agreement is not affected in any manner materially adverse to any party.

&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;&nbsp;17. **<u>Miscellaneous</u>.** Each of Sections 11.6 (*Counterparts; Effectiveness*) and 11.5 (*Governing Law; Venue; Waiver of Jury Trial*) of the Merger Agreement is incorporated herein by reference *mutatis mutandis*.

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|:---|:---|
| Very truly yours, | Very truly yours, |
| **ELK TOPCO, LLC** | **ELK TOPCO, LLC** |
| By: | Elk Holdings, LLC, its sole member |
| By: | By: Elk Insurance Holdings, LLC, its managing member |

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By:  <br> Name: <br> Title:

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| | |
|:---|:---|
| **ELK COINVEST, L.P.** | **ELK COINVEST, L.P.** |
| By: | Elk Coinvest GP, LLC, its general partner |

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By:  <br> Name: <br> Title:

[Rollover Agreement Signature Page]

Acknowledged and agreed as of the date first written above:

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| |
|:---|
| **ROLLOVER INVESTOR** |
| [*NAME*] |

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[Rollover Agreement Signature Page]

Acknowledged and agreed as of the date first written above:

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| |
|:---|
| **Elk Evergreen Investments, LLC** |
| By: |
| Name: |
| Title: |

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| |
|:---|
| **Elk Cypress Investments, LLC** |
| By: |
| Name: |
| Title: |

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[Rollover Agreement Signature Page]