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September
30, 2024

VIA EDGAR AND EMAIL

United States Securities and Exchange Commission

Division of Corporation Finance

Office of Merger & Acquisitions

100 F Street, N.E.

Washington, D.C. 20549-3628

Attention: Laura McKenzie and Perry Hindin

    Re:
    Enstar Group Limited

    Schedule 13E-3 filed September 4, 2024

    File No. 005-83620

    Preliminary Proxy Statement on Schedule 14A filed September 4, 2024 001-33289

Dear Ms. McKenzie and Mr. Hindin,

On behalf of Enstar Group Limited (the “Company”)
and in response to the comments of the staff (the “Staff”) of the U.S. Securities and Exchange Commission (the “Commission”)
set forth in your letter dated September 26, 2024 (the “Comment Letter”) with respect to the above-referenced Schedule
13E-3 (File No. 005-83620) (the “Schedule 13E-3”) and the preliminary proxy statement (File No. 001-33289) (the “Preliminary
Proxy Statement”), each filed with the Commission on September 4, 2024, we submit this letter containing the Company’s
response to the Comment Letter.

In connection with the submission of this
letter, the Company is filing Amendment No. 1 to the Preliminary Proxy Statement (the “Amended Preliminary Proxy
Statement”) and the Filing Persons (as defined in the Schedule 13E-3) are filing Amendment No. 1 to the Schedule 13E-3
(the “Amended Schedule 13E-3”). The Amended Preliminary Proxy Statement and the Amended Schedule 13E-3 reflect
revisions made in response to the comments of the Staff and the updating of other information.

Set forth below is our response to the Staff’s comments as
set forth in the Comment Letter. Please note that any reference to page numbers in our responses refer to the page numbers of the
Amended Preliminary Proxy Statement and the Amended Schedule 13E-3, as applicable. Capitalized terms used but not defined herein
have the meanings ascribed to such terms in the Amended Preliminary Proxy Statement and the Amended Schedule 13E-3, as
applicable.

September
30, 2024

Schedule 13E-3 and Preliminary Proxy Statement
on Schedule 14A, each filed September 4, 2024

General

 1. Exchange Act Rule 13e-3(e)(1) requires filing
                                            persons to “disclose to security holders of the class that is the subject of the transaction” the
                                            information enumerated therein. Please revised the Schedule 13E-3, including the cover page
                                            field entitled “Title of Class of Securities” to include the Series D and Series
                                            E Preferred Shares. Please also provide all required disclosure with respect to the Series
                                            D and Series E Preferred Shares. A non-exhaustive list of required disclosure that does not
                                            appear to be provided for such classes includes the benefits and detriments to unaffiliated
                                            security holders (refer to Instruction 2 to Item 1013 of Regulation M-A) and discussion of
                                            the factors described in Instruction 2 to Item 1014 of Regulation M-A (or explanation of
                                            why each factor was not deemed material or relevant to the fairness determination). In
                                            discussing the factors described in Item 1014, please refer to comment 12 below.

Response:

The
Company respectfully acknowledges the Staff’s comment and in response, the Company has revised the disclosure on pages 19, 34,
56-65, 74, 78-79 and 104 of the Amended Preliminary Proxy Statement and the Filing Persons have revised the cover page of
the Amended Schedule 13E-3 accordingly.

 2. We note the disclosure on pages 54,
                                            69 and 72 that the Board, the Sixth Street Filing Parties and Buyer Parties and the CEO Filing
                                            Party each believe “that the Mergers are fair to the [Company’s] ‘unaffiliated
                                            security holders,’ [as defined] in Rule 13e-3 under the Exchange Act.”
                                            Please supplement the disclosure to clarify that the term “unaffiliated security holders”
                                            includes the unaffiliated security holders of the ordinary shares, the Series D Preferred
                                            Shares and the Series E Preferred Shares.

Response:

The
Company respectfully acknowledges the Staff’s comment and in response, the Company has revised the disclosure on  page 15
of, and throughout,  the Amended Preliminary Proxy Statement.

 3. In your response letter, please explain
                                            why each of Alan Waxman, Elk Parent Limited, and Stone Point Capital LLC are not an
                                            affiliate of the Company engaged directly or indirectly in the Rule 13e-3 transaction, and
                                            should not be listed as a signatory to the Schedule 13E-3 signature page and included as
                                            a filing person. For guidance, refer to Questions 101.02, 201.01, 201.05, and 201.06 of the
                                            Division of Corporation Finance’s Compliance and Disclosure Interpretations for Going
                                            Private Transactions, Exchange Act Rule 13e-3 and Schedule 13E-3, available at http://www.sec.gov/divisions/corpfin/guidance/13e-3-interps.htm.
                                            We may have further comment.

Response:

 The Company respectfully acknowledges the Staff’s comment and advises the Staff that Elk Parent Limited
has been added as a filing person on Schedule 13E-3 and the proxy statement has been revised to include all information required as to
it by Schedule 13E-3. In addition, the Company has added Elk Topco, LLC, the parent company of Elk Parent Limited, as a filing person on Schedule 13E-3 and
the proxy statement has been revised to include all information required as to it by Schedule 13E-3.

    2

September
30, 2024

With respect to Alan Waxman and Stone
Point Capital LLC (“Stone Point”), the Company acknowledges the Staff’s comment and in response respectfully
advises the Staff that the filing persons set forth in the initial Schedule 13E-3 considered the issue of whether each of Mr. Waxman
and Stone Point should be a filing person for Schedule 13E-3 and concluded that neither Mr. Waxman nor Stone Point should be included
as a filing person on the basis that neither Mr. Waxman nor Stone Point is an affiliate engaged in the transaction for purposes of Rule
13e-3.

Rule 13e-3 requires that each issuer
and affiliate engaged, directly or indirectly, in a going private transaction file a Schedule 13E-3 and furnish the required disclosures.
Pursuant to Compliance and Disclosure Interpretation (“C&DI”) 201.05 and Section III of Release No. 34-17719,
there are two prongs for determining whether a person qualifies as a filing person, namely (1) whether the entities or persons are “affiliates”
of the issuer within the scope of Rule 13e-3(a)(1) under the Exchange Act and (2) whether those affiliates are deemed to be engaged,
either directly or indirectly, in the going private transaction. For purposes of Rule 13e-3, an affiliate of an issuer is a person that
directly or indirectly through one or more intermediaries controls, is controlled by, or is under common control with such issuer. It
is noted that under the Staff’s guidance in Section II.D.3. of the Current Issues and Rulemaking Projects outline dated November
14, 2000, it indicated that “affiliate” status necessarily turns on all relevant facts and circumstances of a particular
transaction, including control of a seller’s business both before and after the transaction.

The filing persons respectfully
submit that Mr. Waxman is not an “affiliate” of the Company nor is “engaged” in the pending take private
transaction within the meaning of Rule 13e-3. Elk Evergreen and Elk Cypress currently own, collectively, approximately 4.87% of the
Enstar Ordinary Shares. Mr. Waxman is the managing member of the sole member of Sub-Fund Holdco. None of Mr. Waxman, Sub-Fund
Holdco, Elk Evergreen and Elk Cypress currently “controls” the Company within the meaning of Exchange Act Rule 12b-2.
The Merger Agreement permits the Enstar Ordinary Shares held by Elk Evergreen and Elk Cypress to either be converted into the right
to receive the merger consideration and cancelled or “rolled over” into equity of Elk TopCo, LLC. It has been determined
that such Enstar Ordinary Shares held by Elk Cypress and Elk Evergreen will be converted into the right to receive the merger
consideration and cancelled, and thus, Elk Cypress and Elk Evergreen will not have any economic or beneficial interest in the
post-closing private company. Accordingly, Elk Cypress and Elk Evergreen (and, by extension, Sub-Fund Holdco and Mr. Waxman) will
not “control” the post-closing private company for purposes of Rule 13e-3. As discussed in the section “Buyer
Filing Parties”, each of Elk Parent Limited, Parent and Merger Sub is beneficially owned by three individuals: Joshua
Easterly, Anthony Michael Muscolino and Jennifer Gordon. Mr. Waxman does not have any economic or beneficial ownership interest in
such Buyer Parties. Accordingly, we respectfully submit that neither Mr. Waxman, nor Elk Cypress, Elk Evergreen or Sub-Fund Holdco
is “engaging” in the take-private transaction with the Buyer Filing Parties and the CEO Filing Party. Although we have
not removed Elk Evergreen, Elk Cypress and Sub-Fund Holdco as filing parties, we respectfully submit that Mr. Waxman is not required
to be added as a filing party.

    3

September
30, 2024

The filing persons respectfully
submit that Stone Point is neither an “affiliate” of the Company nor is “engaged” in the pending take
private transaction within the meaning of Rule 13e-3. Stone Point (through its Trident Funds) is a minority investor with a 9.5%
beneficial interest in the Company and is represented by a single seat on the Company’s 12-member board of directors. Stone
Point does not “control” the Company within the meaning of Exchange Act Rule 12b-2. Furthermore, Stone
Point did not have any direct or independent participation in the planning or negotiation with respect to the transactions
contemplated by the Merger Agreement (except for the limited purposes of negotiating the terms of the Preferred Equity Investment,
as discussed below). As discussed in the section “Background of the Mergers”, James Carey recused himself from
all meetings and information sessions of the Board related to the Board’s review of Sixth Street’s proposals and
strategic alternatives after Sixth Street expressed interest in beginning discussions with Stone Point regarding its participation
in a potential transaction until the Board meeting held on July 28, 2024, which Mr. Carey attended. Although Sixth Street had
inquired about Stone Point’s interest in participating in the transaction, Stone Point had expressed that it was not
interested in “rolling over” any of its existing equity interests into the post-closing private company. Stone
Point instead indicated interest in making, and ultimately committed to make, a debt-like preferred equity investment in the
acquisition company structure through its dedicated credit platform, Stone Point Credit Adviser LLC.
Under the terms of the Preferred Equity Financing, Stone Point does not participate in the upside of the earnings of the Company and
its preferred equity will not be convertible into common equity of the Company. In addition, Stone Point will not be entitled to any
governance rights and will not be entitled to appoint any directors to the board of the post-closing private company. The preferred
shares issued in respect of the Preferred Equity Financing will be non-voting, except as provided by mandatory applicable law.
Accordingly, Stone Point will not be in a position to “control” the surviving company within the meaning of Exchange Act
Rule 12b-2 and Stone Point is not “engaging” in the take-private transaction with the filing parties.

Based on the facts
and circumstances outlined above and consistent with the Staff’s views in applicable SEC Guidance, the filing persons respectfully
submit that neither Mr. Waxman nor Stone Point is an affiliate engaged in the proposed transaction in a manner requiring it to comply
with the disclosure, dissemination and filing requirements of Rule 13e-3 and is therefore not required to be a filing person for purposes
of Schedule 13E-3.

    4

September
30, 2024

 4. Refer to the following disclosures:

 · The
                                            first paragraph on page 39 that the Special Factors section “does not purport to be
                                            complete . . . .”

 · The
                                            first full paragraph on page 62 and penultimate paragraph on page 66 that the summary “does
                                            not purport to be a complete description of the financial analyses performed by Goldman Sachs
                                            . . . .”

 · The
                                            first paragraph on page 110 that the summary of the terms of the Merger Agreement “does
                                            not purport to be complete . . . .”

Please revise these and any similar
statements to remove the implication that the summaries are not complete. While you may include appropriate disclaimers concerning the
nature of a summary generally, it must be complete in describing all material analyses or terms.

Response:

The
Company respectfully acknowledges the Staff’s comment and in response, the Company has revised the disclosure on pages 41, 43,
66, 69, 71 and 118 of the Amended Preliminary Proxy Statement.

 5. Please
                                            explain the meaning of each defined term used in the Proxy Statement the first time that
                                            the defined term is used. For example, the defined term “AOCI,” which first appears
                                            on page 43, is not explained.

Response:

The Company respectfully
acknowledges the Staff’s comment and in response, the Company has revised the Amended Preliminary Proxy Statement
accordingly.

Background of the Merger, page 42

 6. Pages 8, 23, 73, 74, and 110 of the
                                            Proxy Statement refer to “information made available to the holders of the Company’s
                                            outstanding notes” that “is also expected to be provided to the holders
                                            of the Enstar Preferred Shares” after the consummation of the Mergers. Please
                                            provide additional disclosure regarding such information.

Response:

The
Company respectfully acknowledges the Staff’s comment and in response, the Company has revised the disclosure on pages 9, 25,
77-79 and 118-119 of the Amended Preliminary Proxy Statement.

Reasons for the Merger; Recommendation of
the Unaffiliated Committee; Fairness of the Merger, page 55

    5

September
30, 2024

 7. We note the following statement in
                                            the second full paragraph on page 3 of the Schedule 13E-3: “No Filing Person,
                                            including the Company, is responsible for the accuracy of any information supplied by any
                                            other Filing Person.” This statement is inconsistent with the disclosures in the
                                            filing, inc