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                                                                November 6, 2006


VIA EDGAR

Mr. Jeffrey P. Riedler
Assistant Director
Division of Corporation Finance
100 F. Street N.E.
Mail Stop 6010
Washington, D.C.  20549

Re:   Castlewood Holdings Limited
      Registration Statement on Form S-4
      File No. 333-135699

Dear Mr. Riedler:

      On behalf of Castlewood Holdings Limited, a Bermuda company (the
"Company"), we are today filing with the Securities and Exchange Commission
Amendment No. 2 to the Company's Registration Statement on Form S-4 ("Amendment
No. 2"). Amendment No. 2 revises the Registration Statement in response to the
comment letter from the Staff of the Commission to the Company dated October 20,
2006 (the "Comment Letter").

      For your convenience, we have repeated below in bold type the Staff's
comments and have set forth the Company's response immediately below the
applicable comment. References to page numbers in the responses below are to
page numbers in the version of Amendment No. 2 that is marked to indicate the
changes made from the filing of Amendment No. 1 to the Registration Statement on
September 20, 2006.

      The Company has arranged for copies of Amendment No. 2 and this letter to
be delivered to each member of the Staff referenced in the Comment Letter.

SUMMARY -- PAGE 1

1.    WE HAVE CONSIDERED YOUR RESPONSE TO COMMENT 6, BUT WE ARE UNABLE TO AGREE
      WITH YOUR CONCLUSION. PLEASE REVISE THE DISCLOSURE AS WE PREVIOUSLY
      REQUESTED. IN AN ARMS LENGTH TRANSACTION, THE PARTIES ARE DEALING FROM
      EQUAL BARGAINING POSITIONS AND NEITHER PARTY IS SUBJECT TO THE OTHER'S
      CONTROL OR DOMINANT INFLUENCE. YOU SHOULD CLEARLY AND PROMINENTLY INDICATE
      THAT THE NEGOTIATIONS WERE NOT ARMS LENGTH. ALSO DISCLOSE THAT ENSTAR'S
      BOARD DID NOT FORM AN INDEPENDENT COMMITTEE OR RETAIN A FINANCIAL ADVISOR
      TO EVALUATE THE FAIRNESS OR ADEQUACY OF THE MERGER TERMS OR CONSIDERATION.
      IF EFFORTS WERE MADE OR PROCEDURES WERE USED TO ENSURE THE FAIRNESS OF THE
      TRANSACTION, YOU SHOULD DESCRIBE THESE EFFORTS AND/OR PROCEDURES. HOWEVER,


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      NO SUCH EFFORTS OR PROCEDURES WOULD RESULT IN A TRANSACTION BETWEEN
      RELATED PARTIES BEING AN ARMS LENGTH TRANSACTION.

      The Company has clearly indicated on pages 4 and 5 and elsewhere in the
      S-4 that the parties who conducted the negotiations on behalf of Enstar
      and other Enstar directors have interests in the merger and relationships
      with Castlewood that differ from those of Enstar's public shareholders,
      and has added cautionary language to the effect that while Enstar does not
      believe that such interests or relationships adversely affected the
      efforts of Enstar's representatives to negotiate favorable merger terms or
      the terms that were ultimately negotiated, Enstar's shareholders should
      consider the possibility that such efforts or terms were adversely
      affected. The Company has also removed all references in the Registration
      Statement to the merger agreement being negotiated at arms length and
      added additional disclosure on page 5 to indicate that Enstar's board did
      not form an independent committee or retain a financial advisor to
      evaluate the fairness or adequacy of the merger terms or consideration

2.    PLEASE BRIEFLY DESCRIBE, IN CONJUNCTION WITH THE ABOVE DISCLOSURE, WHAT
      THE SPECIFIC CONFLICTS OF INTEREST ARE BY THE INDIVIDUALS WHO NEGOTIATED
      AND/OR VOTED TO APPROVE THE TRANSACTIONS AT ISSUE. CURRENTLY, DISCLOSURE
      REGARDING THESE INTERESTS DOES NOT APPEAR UNTIL PAGE 10, AND THE SPECIFIED
      INTERESTS ARE NOT QUANTIFIED AND DO NOT INCLUDE MANAGEMENT'S CURRENT
      INTERESTS IN CASTLEWOOD, SUCH AS THOSE IDENTIFIED ON PAGES 166-168. THE
      DISCLOSURE SHOULD ALSO DISCLOSE THE PERCENTAGE OF OUTSTANDING SHARES HELD
      BY THE INTERESTED INDIVIDUALS, BEFORE AND AFTER THE MERGER, AND DISCUSS
      THEIR POTENTIAL ABILITY TO CONTROL THE OUTCOME OF THE VOTE, AS WELL AS THE
      LACK OF DISSENTERS' RIGHTS.

      The Company has added additional disclosure on pages 4 and 5 to address
      the Staff's comment.

RECOMMENDATIONS OF ENSTAR'S BOARD OF DIRECTORS RELATING TO THE MERGER -- PAGE 4

3.    YOU HAVE ADDED DISCLOSURE INDICATING THAT THE BOARD "CONSIDERED THESE
      INTERESTS IN MAKING ITS RECOMMENDATION AND CONCLUDED THAT SUCH INTERESTS
      COULD BE APPROPRIATELY ADDRESSED THROUGH DISCLOSURE AND THAT NO DIRECTOR
      SHOULD RECUSE HIMSELF FROM THE DELIBERATIONS OF THE BOARD REGARDING THE
      MERGER." EXPAND THE DISCLOSURE HERE TO BRIEFLY EXPLAIN HOW DISCLOSURE
      ADDRESSES THESE PROBLEMS AND WHY IT WAS APPROPRIATE FOR THE INTERESTED
      DIRECTORS TO VOTE ON THE TRANSACTION. YOU SHOULD PROVIDE MORE DETAILED
      DISCLOSURE IN THE BODY OF THE PROSPECTUS.

      The Company has added additional disclosure on pages 5 and 48 to address
      the Staff's comment.


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REASONS FOR THE MERGER -- PAGE 4

4.    PLEASE PROVIDE, DIRECTLY FOLLOWING THIS SUBSECTION, AN EQUALLY DETAILED
      LIST OF THE FACTORS THAT MILITATE AGAINST THE MERGER.

      The Company has added additional disclosure on pages 6, 7, 51, and 52 to
      address the Staff's comment. The Company has been informed by Enstar that
      while the list of factors that militate against the merger is not as
      lengthy as the list of factors that supported the merger, the list
      represents all the material negative factors considered by Enstar's Board.
      As discussed with Suzanne Hayes and Mary K. Fraser of the Staff during a
      conference call on Friday, October 28, 2006 (the "Conference Call"),
      because Enstar's existing business is largely conducted through its
      investment in Castlewood and Enstar's management and board have monitored
      Castlewood and its business and financial condition and results of
      operation as they would those of a subsidiary since 2001 the proposed
      merger between the two companies does not present many of the typical
      risks and challenges associated with combining two distinct operating
      businesses.

OWNERSHIP OF NEW ENSTAR AFTER THE MERGER -- PAGE 5

5.    PLEASE EXPAND THE DISCLOSURE TO INCLUDE THE PERCENTAGE OF ENSTAR OWNED BY
      MANAGEMENT PRIOR TO THE MERGER.

      The Company has added additional disclosure on page 7 to address the
      Staff's comment.

6.    PLEASE TELL US, WITH A VIEW TOWARDS DISCLOSURE IN THE REGISTRATION
      STATEMENT, WHETHER ANY OF THE OWNERS OF CASTLEWOOD OR THE OTHER ENTITIES
      INVOLVED IN THIS MERGER, OTHER THAN THE PERSONS CURRENTLY IDENTIFIED IN
      THE ENSTAR OWNERSHIP TABLE, OWN SHARES OF ENSTAR. IF SO, PLEASE TELL US
      WHO THEY ARE, HOW MANY SHARES THEY OWN, AND WHY THIS INFORMATION HAS NOT
      BEEN DISCLOSED IN THE REGISTRATION STATEMENT.

      Dominic Silvester (110,239 shares), David Rocke (3,250 shares), Steve
      Aldous (1,000 shares), Alan Turner (250 shares), Michael Smellie (250
      shares) and Steve Westin (150 shares) are the only current owners of
      Castlewood or other entities involved in the merger who currently own
      shares of Enstar that were not previously identified in the Enstar
      ownership table. Mr. Silvester is the Chief Executive Officer of
      Castlewood and each of the other individuals are also officers or
      employees of Castlewood.

      The Enstar shares owned by Mr. Silvester were reflected in the number of
      shares of "New Enstar" owned by him following the merger in the table set
      forth on page 173 of Amendment No. 1 to the Registration Statement, but,
      as he is not a director or executive officer of Enstar, his ownership of
      Enstar common stock was not reflected in the Enstar ownership table.

      The other officers and employees of Castlewood who own shares of Enstar
      are not executive officers of Castlewood, so their ownership of Castlewood
      shares and Enstar shares was not previously disclosed in the Registration
      Statement.

      The Company notes that on pages 1 and 2, it has disclosed that certain
      officers and employees of Castlewood own shares of Enstar.


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7.    WE NOTE THE REVISIONS YOU MADE IN RESPONSE TO COMMENT 9. PLEASE BRIEFLY
      DISCLOSE HOW THE BOARD CONSIDERED THE FACT THAT ENSTAR'S NON-AFFILIATED
      PUBLIC SHAREHOLDERS WILL NO LONGER BE ABLE TO CONTROL THE OUTCOME OF VOTES
      AFFECTING THEIR INTEREST IN THE COMPANY. ALSO, DESCRIBE THE SPECIFIC
      ASSETS OR FINANCIAL RESOURCES THE PUBLIC SHAREHOLDERS WILL OBTAIN IN
      RETURN FOR THIS DIMINUTION OF THEIR INTERESTS, AND THE CONSIDERATION GIVEN
      TO THE WAYS IN WHICH THE RIGHTS OF ENSTAR'S SHAREHOLDERS WILL CHANGE AS A
      RESULT OF THE MERGER. IF THE BOARD DID NOT CONSIDER THESE FACTORS, SAY SO
      IN THE DOCUMENT.

      The Company has added additional disclosure on page 8 to address the
      Staff's comment.

8.    PLEASE REFER TO YOUR RESPONSE TO COMMENT 10. IT DOES NOT ADDRESS THE ISSUE
      WE RAISED. WE NOTED THAT A LARGE PROPORTION OF THE BUSINESS DONE BY
      CASTLEWOOD, NOT THE COMPANY, CURRENTLY INVOLVES TRANSACTIONS WITH
      COMPANIES AND PARTNERSHIPS MANAGED OR CONTROLLED BY MR. FLOWERS, WHO WILL
      BE A MEMBER OF THE BOARD OF DIRECTORS OF NEW ENSTAR AFTER THE MERGER. YOUR
      RESPONSE DISCUSSES BUSINESS DONE BY THE COMPANY. ALSO, IT DOES NOT ADDRESS
      THE QUESTION OF WHAT STEPS WILL BE TAKEN BY NEW ENSTAR TO ADDRESS THE
      CONFLICT OF INTEREST ISSUES INVOLVED IN TRANSACTIONS WITH RELATED PARTIES,
      INCLUDING MR. FLOWERS. PLEASE RESPOND TO THE COMMENT WE RAISED. WE MAY
      HAVE FURTHER COMMENT AFTER REVIEWING YOUR RESPONSE.

      As discussed with Ms. Hayes and Ms. Fraser during the Conference Call, the
      Company's prior response to comment 10 was referring to Castlewood.
      Transactions with affiliates of Mr. Flowers do not represent a large
      proportion of the business conducted by Castlewood. In light of the
      Staff's comment, however, the Company has modified the "Conflicts of
      Interests" risk factor on page 27 to address further the steps that will
      be taken by New Enstar to address conflict of interest issues.

EFFECTS OF THE MERGER ON THE RIGHTS OF ENSTAR SHAREHOLDERS -- PAGE 5

9.    BRIEFLY DESCRIBE THE MOST SIGNIFICANT WAYS IN WHICH THE RIGHTS OF
      SHAREHOLDERS WILL CHANGE AS A RESULT OF THE MERGER.

      The Company has added additional disclosure on page 8 to address the
      Staff's comment.



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RISK FACTORS -- PAGE 18

CONFLICTS OF INTEREST MIGHT PREVENT US FROM PURSUING DESIRABLE INVESTMENT AND
BUSINESS OPPORTUNITIES. -- PAGE 25

10.   THE RISK FACTOR YOU ADDED IN RESPONSE TO COMMENT 14 IN OUR PREVIOUS LETTER
      DOES NOT ADDRESS ALL OF THE ISSUES WE RAISED. PLEASE DISCUSS THE SPECIFIC
      STEPS YOU WILL TAKE TO ENSURE THAT FUTURE TRANSACTIONS ENTERED BY NEW
      ENSTAR ARE AT LEAST AS FAVORABLE AS COULD BE OBTAINED FROM UNAFFILIATED
      PARTIES.

      The Company has revised the "Conflict of Interest" risk factor on page 27
      to address the Staff's comment. The Company notes that while it has
      indicated additional steps that New Enstar may take to ensure that future
      transactions entered into by it with related parties are on terms at least
      as favorable as could be obtained from unaffiliated parties, as discussed
      with Ms. Hayes and Ms. Fraser during the Conference Call, the Company does
      not believe it is possible to identify all actions that New Enstar's board
      may determine are appropriate in connection with any such transaction that
      may arise in the future.

11.   YOU SAY THAT AS A RESULT OF CONFLICTS OF INTEREST, YOU "MAY NOT BE ABLE
      PURSUE TO ALL ADVANTAGEOUS TRANSACTIONS [SIC] THAT WE WOULD OTHERWISE
      PURSUE IN THE ABSENCE OF A CONFLICT." PLEASE EXPLAIN WHAT THIS STATEMENT
      MEANS.

      The Company has revised the "Conflict of Interest" risk factor on page 27
      to address the Staff's comment.

12.   PLEASE PROVIDE APPROPRIATE RISK FACTOR DISCLOSURE REGARDING THE RISKS
      INHERENT IN MR. FLOWERS' CURRENT OWNERSHIP INTERESTS IN ENSTAR, CASTLEWOOD
      AND ITS AFFILIATES AND NEW ENSTAR. WE NOTE THAT MANY OF THE TRANSACTIONS
      THAT CASTLEWOOD HAS ENTERED INTO INVOLVE ENTITIES THAT MR. FLOWERS MANAGED
      OR CONTROLLED. THE RISK FACTOR SHOULD ADDRESS THE SPECIFIC ADVERSE EFFECTS
      THE SHAREHOLDERS ARE AT RISK OF SUFFERING AS A RESULT OF MR. FLOWER'S
      COMMON OWNERSHIP OF THESE ENTITIES, THE ROLE MR. FLOWERS WILL PLAY IN NEW
      ENSTAR, AND WHETHER NEW ENSTAR WILL CONTINUE TO ENGAGE IN TRANSACTIONS
      WITH OTHER ENTITIES OWNED OR CONTROLLED BY MR. FLOWERS.

      As discussed with Ms. Hayes and Ms. Fraser during the Conference Call, the
      Company notes that Mr. Flowers does not currently own an interest in
      Castlewood other than indirectly through his ownership interest in Enstar.
      Following the merger, Mr. Flowers' sole ownership interest in New Enstar
      will be through ordinary shares of New Enstar, which are the same
      securities that will be owned by Enstar's current non-affiliated public
      shareholders. Mr. Flowers is a director and the largest individual
      shareholder of Shinsei Bank, which owns a 49.9% interest in a subsidiary
      of Castlewood, but the rights of Shinsei Bank with respect to that
      subsidiary will not be affected by virtue of the merger between Castlewood
      and Enstar.

      As also discussed with Ms. Hayes and Ms. Fraser during the Conference Call
      and as noted above in response to comment 8, the transactions that
      Castlewood has entered into with entities managed or controlled by Mr.
      Flowers do not represent a large portion of the business conducted by
      Castlewood.


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      In light of the Staff's comment, however, the Company has modified the "We
      are dependent on our executive officers..." risk factor on page 27 to
      address the role Mr. Flowers will play in New Enstar.

13.   WE DO NOT BELIEVE YOU HAVE FULLY ADDRESSED THE ISSUES WE RAISED IN
      COMMENTS 15 AND 16 OF OUR PREVIOUS LETTER. PLEASE PROVIDE MORE DETAILED
      DISCLOSURE THAT ADDRESSES EACH ISSUE WE RAISED, OR EXPLAIN TO US WHY YOU
      BELIEVE THE ISSUES HAVE BEEN SATISFACTORILY ADDRESSED.

      The Company has added additional disclosure on page 27 to address comment
      15 from the Staff's previous letter. Comment 16 from the Staff's previous
      letter was the same as comment 12 above, and the Company directs the Staff
      to the Company's response to that comment.

THE PROPOSED MERGER -- PAGE 41

14.   WE HAVE NOTED YOUR RESPONSE TO COMMENT 29. PLEASE INCLUDE DISCLOSURE
      EXPLAINING WHY ENSTAR'S CURRENT RELATIONSHIPS WITH CASTLEWOOD ARE
      UNSATISFACTORY, OR NEED IMPROVING. CURRENTLY YOUR DISCLOSURE INDICATES
      ONLY THAT "SINCE THE FORMATION OF CASTLEWOOD, SENIOR MANAGEMENT OF ENSTAR
      AND CASTLEWOOD HAVE DISCUSSED A POTENTIAL BUSINESS COMBINATION BETWEEN
      CASTLEWOOD AND ENSTAR FROM TIME TO TIME."

      The Company has added additional disclosure beginning on page 43 to
      address the Staff's comment.

15.   WE HAVE CONSIDERED YOUR RESPONSE TO COMMENT 30. YOUR DISCLOSURE INDICATES
      THAT THE TRANSACTION WAS PROPOSED, NEGOTIATED AND VOTED ON BY THE PERSONS
      WHO HAVE INTERESTS IN THESE TRANSACTIONS DIFFERENT FROM THOSE OF THE
      UNAFFILIATED PUBLIC SHAREHOLDERS. WE NOTE FURTHER THAT DISCLOSURE ON PAGE
      46 INDICATES THAT "HOLDERS OF SUBSTANTIALLY ALL OF CASTLEWOOD'S EXISTING
      SHARES WERE DIRECTLY INVOLVED IN THE NEGOTIATIONS IN RESPECT OF THE
      PROPOSED MERGER." IT APPEARS FROM BOTH THE DISCLOSURE AND YOUR RESPONSE
      THAT NO STEPS WERE TAKEN TO PROTECT THE INTERESTS OF THE UNAFFILIATED
      PUBLIC SHAREHOLDERS OF ENSTAR. YOU SHOULD CLEARLY SAY SO.

      As discussed with Ms. Hayes and Ms. Fraser during the Conference Call and
      as disclosed in the Registration Statement, steps were taken to protect
      the interests of the unaffiliated public shareholders of Enstar. Interests
      and relationships of Enstar officers and directors were disclosed to and
      discussed by the Enstar board. The board considered whether in light of
      those interests it would be advisable to convene a special committee of
      independent directors. The board also considered whether it would be
      advisable to engage a third-party financial advisor. The decisions not to
      convene a special committee or engage a financial adviser were made by the
      board with the best interests of the Enstar unaffiliated public
      stockholders in mind. The board did require that the merger be approved by
      a majority of the independent directors. The Company has added additional
      disclosure beginning on page 46 to clarify these points.


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16.   WE HEREBY REISSUE COMMENT 31 IN OUR PREVIOUS LETTER AS YOUR REVISED
      DISCLOSURE DOES NOT CONTAIN THE INFORMATION WE REQUESTED. PLEASE EXPAND
      THE DISCUSSION TO EXPLAIN HOW THE MERGER CONSIDERATION WAS DETERMINED AND
      WHAT IT IS BASED ON. CURRENTLY, NO EXPLANATION IS GIVEN AS TO HOW THESE
      TERMS WERE REACHED, OR ON WHAT BASIS THE ENSTAR BOARD HAS DETERMINED THAT
      THE CONSIDERATION IS FAIR AND IN THE BEST INTERESTS OF ENSTAR AND ITS
      SHAREHOLDERS AS STATED IN THE LAST FULL PARAGRAPH ON PAGE 44.

      The Company has added additional disclosure beginning on page 45 to
      address the Staff's comment.

17.   PLEASE DISCLOSE AND DISCUSS THE CIRCUMSTANCES THAT LED MR. FLOWERS, "ON
      BEHALF OF ENSTAR", TO PROVIDE A LETTER TO MR. SYLVESTER ON AUGUST 29, 2005
      OUTLINING A PROPOSAL FOR THE MERGER OF ENSTAR INTO CASTLEWOOD. YOUR
      REVISED DISCLOSURE SHOULD INCLUDE THE SUBSTANCE OF THE PROPOSAL. ALSO
      CLARIFY WHETHER THE PROPOSAL WAS INITIATED BY MR. FLOWERS, OR WHETHER THE
      BOARD DETERMINED THE CONTENT OF THE PROPOSAL AND APPROVED ITS SUBMISSION
      TO CASTLEWOOD. WE ALSO NOTE THAT DISCLOSURE ON PAGE 75 INDICATES THAT MR.
      FLOWERS IS ALSO A MEMBER OF THE CASTLEWOOD BOARD OF DIRECTORS. PLEASE
      CLARIFY THE CAPACITY HE WAS ACTING IN.

      The Company has added additional disclosure on page 44 to address the
      Staff's comment.

18.   AT AN APPROPRIATE PLACE IN THE PROSPECTUS, PLEASE IDENTIFY THE CURRENT
      DIRECTORS OF BOTH ENSTAR AND CASTLEWOOD.

      The Company has added additional disclosure on page 108 to address the
      Staff's comment. The current directors of Enstar are identified on pages
      38 and 39.

19.   PLEASE INCLUDE A DISCUSSION OF THE "VARIOUS OPTIONS AND ALTERNATIVES TO
      THE PROPOSAL" DISCUSSED AT THE SEPTEMBER 13, 2005 MEETING.

      The Company has added additional disclosure on page 44 to address the
      Staff's comment.

20.   PLEASE EXPAND THE DISCUSSION OF THE NOVEMBER 6, 2005 LETTER TO INCLUDE A
      SUMMARY OF ITS SUBSTANCE, INCLUDING THE "SUGGESTIONS AND AMENDMENTS" IT
      CONTAINED.

      The Company has added additional disclosure on page 45 to address the
      Staff's comment.

21.   PLEASE PROVIDE SIMILARLY EXPANDED DISCLOSURE FOR EACH MEETING AND/OR
      PROPOSAL REFERENCED IN THIS SECTION. ALL DISCLOSURE SHOULD BE QUANTIFIED
      TO THE EXTENT PRACTICABLE.

      The Company has added additional disclosure on pages 45 through 49 to
      address the Staff's comment.



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22.   THE REVISED DISCLOSURE IN THE LAST PARAGRAPH OF PAGE 42 REFERS TO A
      "WATERFALL DISTRIBUTION." PLEASE EXPLAIN, IN REASONABLE DETAIL, WHAT THIS
      IS. ALSO, QUANTIFY THE DISCLOSURE IN THIS PARAGRAPH.


      The Company has added additional disclosure beginning on page 43 to
      address the Staff's comment.


23.   IN THAT SAME PARAGRAPH YOU STATE THAT THE BOARD DETERMINED THAT IT WOULD
      NOT BE IN THE BEST INTERESTS OF ENSTAR AND ITS STOCKHOLDERS TO ENGAGE AN
      OUTSIDE FINANCIAL ADVISER. PLEASE DISCLOSE THE BASIS FOR THIS DECISION,
      INCLUDING THE FACTORS CONSIDERED IN REACHING IT.

      The Company has added additional disclosure on page 46 to address the
      Staff's comment.

24.   WE NOTE THAT YOU NOW DISCLOSE, AT THE BOTTOM OF PAGE 42, THAT THE COMPANY
      RECEIVED ADVICE FROM BOTH ITS "OUTSIDE LEGAL COUNSEL," AND ITS "SPECIAL
      LEGAL COUNSEL." PLEASE IDENTIFY THE FUNCTIONS PERFORMED BY EACH OF THESE
      COUNSEL. PLEASE ALSO TELL US WHY THE CONSENT OF PARKER, HUDSON, RAINER &
      DOBBS HAS NOT BEEN INCLUDED AS AN EXHIBIT TO THE REGISTRATION STATEMENT.

      The Company has added additional disclosure on page 46 to address the
      Staff's comment.

      The consent of Parker, Hudson, Rainer & Dobbs has not been included as an
      exhibit to the Registration Statement because no report or opinion of
      Parker, Hudson, Rainer & Dobbs is quoted or summarized in the Registration
      Statement.

25.   PLEASE REFER TO THE SECOND FULL PARAGRAPH ON PAGE ON PAGE 43. YOU SAY THAT
      MANAGEMENT PRESENTED A FINANCIAL ANALYSIS TO THE BOARD. EXPAND THE
      DISCLOSURE TO INCLUDE A SUMMARY OF THE FINANCIAL ANALYSIS AS WELL AS ALL
      OF THE OTHER INFORMATION PRESENTED TO OR CONSIDERED BY THE BOARD. THE
      INFORMATION SHOULD BE QUANTIFIED TO THE EXTENT PRACTICABLE.


      The Company has added additional disclosure on page 46 to address the
      Staff's comment.


26.   PLEASE DISCLOSE WHO PREPARED THE FINANCIAL ANALYSES MANAGEMENT PRESENTED
      TO THE BOARD AT THE APRIL 6 AND APRIL 26, 2006 MEETINGS.


      The Company has added additional disclosure on page 46 to address the
      Staff's comment.


27.   PLEASE EXPAND THE THIRD FULL PARAGRAPH ON PAGE 44 TO EXPLAIN WHY THE
      "CONTINUED VALIDITY OF THE FINANCIAL ANALYSIS" WAS AN ISSUE, HOW THE
      PROPOSED SHARE ALLOCATION WAS CHANGED FROM THE INITIAL PROPOSALS AND HOW
      THE NEGOTIATION PROCESS CHANGED THE PROPOSALS. ALSO, IDENTIFY ANY
      MODIFICATIONS TO THE MERGER AGREEMENT MADE BY THE "OFFICERS EXECUTING THE
      MERGER AGREEMENT." IT APPEARS THAT THE BOARD HAS GIVEN THE OFFICERS OF THE
      COMPANY THE AUTHORITY TO MODIFY THE MERGER AGREEMENT. YOUR REVISED
      DISCLOSURE SHOULD ALSO IDENTIFY AND DISCUSS THE EXTENT OF THE OFFICERS'
      AUTHORITY TO REVISE OR MODIFY THE AGREEMENT. WE MAY HAVE FURTHER COMMENT.


      The Company has added additional disclosure on page 46 to address how the
      proposed share allocation changed from the initial proposals. The Company
      has deleted the statement on page 49 to the effect that the board's
      approval was subject to changes approved by officers.



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ENSTAR'S REASONS FOR THE MERGER -- PAGE 44

28.   WE NOTE YOUR RESPONSE TO COMMENT 33. THE REVISED DISCLOSURE DOES NOT
      CONTAIN THE INFORMATION WE REQUESTED. AS WE PREVIOUSLY REQUESTED, EXPAND
      THE DISCLOSURE IN THIS SECTION TO EXPLAIN HOW EACH IDENTIFIED FACTOR
      CONTRIBUTED TO THE BOARD'S CONCLUSION THAT THE TRANSACTION WAS "ADVISABLE
      AND FAIR TO AND IN THE BEST INTERESTS OF ENSTAR AND ITS SHAREHOLDERS."
      YOUR REVISED DISCLOSURE SHOULD INCLUDE A REASONABLY DETAILED EXPLANATION
      OF HOW EACH OF THE BULLETED FACTORS CONTRIBUTED TO THE CONCLUSION THAT THE
      TRANSACTION WAS "ADVISABLE AND FAIR TO AND IN THE BEST INTERESTS OF ENSTAR
      AND ITS SHAREHOLDERS." THE INFORMATION SHOULD ALSO BE QUANTIFIED TO THE
      EXTENT PRACTICABLE.


      As disclosed on page 52 and discussed with Ms. Hayes and Ms. Fraser during
      the Conference Call, in reaching its decision to approve the merger
      agreement and the transactions contemplated by the merger agreement, the
      Enstar board did not view any single factor as determinative and did not
      find it necessary or practicable to assign any relative or specific
      weights to the various factors considered. In addition, individual
      directors may have given different weights to different factors. The board
      did not make any determination as to how any specific benefit or risk
      contributed to its conclusion that the transaction was advisable and fair,
      but rather considered the benefits and risks in the aggregate.


29.   IN THE BULLET AT THE BOTTOM OF PAGE 44, PLEASE EXPLAIN HOW THE TERMS OF
      THE PROPOSED TRANSACTION "FURTHER ALIGN THE INCENTIVES OF CASTLEWOOD
      MANAGEMENT WITH THE INTERESTS OF ENSTAR'S SHAREHOLDERS."


      The Company has added additional disclosure on pages 50 and 51 to address
      the Staff's comment.


30.   IT IS STILL NOT CLEAR HOW THIS TRANSACTION BENEFITS THE UNAFFILIATED
      PUBLIC SHAREHOLDERS OF ENSTAR. PLEASE PROVIDE DISCLOSURE, QUANTIFIED TO
      THE EXTENT PRACTICABLE, SHOWING HOW THE PROPOSED MERGER TRANSACTION
      BENEFITS THEM.

      The Company has added additional disclosure on pages 44 through 52 to
      address the Staff's comment. As discussed with Ms. Hayes and Ms. Fraser
      during the Conference Call, the principal benefit of the transaction to
      the unaffiliated public shareholders of Enstar is that the transaction
      results in a significant increase in the unaffiliated public shareholders'
      percentage interest in Castlewood, which is by far Enstar's most
      significant asset.

31.   IN COMMENT 33 WE ALSO NOTED, AMONG OTHER THINGS, THAT THE LAST BULLET IN
      YOUR LIST OF FACTORS CONSIDERED IS "THE OTHER RISKS DESCRIBED IN "RISK
      FACTORS" BEGINNING ON PAGE 19." PLEASE CLARIFY WHETHER THE LIST OF RISK
      FACTORS BEGINNING ON PAGE 19 WAS PRESENTED TO THE BOARD, AND IF SO, AT
      WHICH MEETING. ALSO, DISCUSS HOW EACH SPECIFIC RISK FACTOR IDENTIFIED ON
      PAGES 18-31 CONTRIBUTED TO THE BOARD'S DECISION THAT THE TRANSACTION WAS
      ADVISABLE AND FAIR.


      The Company has revised the disclosure on pages 51 and 52 to address the
      Staff's comment.



<PAGE>


32.   YOU HAVE NOT INCLUDED ANY DISCUSSION OF ANY FACTORS THAT MILITATE AGAINST
      THE TRANSACTION, OR ARE NOT POSITIVE. PLEASE EXPAND THE DISCUSSION TO
      INCLUDE THIS INFORMATION. IN THIS REGARD, IT IS NOT CLEAR HOW YOUR
      STATEMENT THAT "THE RISK THAT THE MERGER MIGHT NOT BE COMPLETED OR THAT
      THE CLOSING MIGHT BE DELAYED" MILITATES AGAINST THE TRANSACTION. IT IS
      SIMILARLY UNCLEAR HOW THE "COSTS TO BE INCURRED IN CONNECTION WITH THE
      MERGER" MILITATES AGAINST THE MERGER SINCE YOU HAVE NOT DISCUSSED THE
      COSTS OR BALANCED THEM AGAINST THE BENEFITS.

      The Company has added additional disclosure beginning on page 51 to
      address the Staff's comment. See also the Company's response to comment 4
      above.

33.   YOU INDICATE THAT SOME OF ENSTAR'S DIRECTORS AND EXECUTIVE OFFICERS HAVE
      INTERESTS IN THE PROPOSED TRANSACTIONS THAT ARE DIFFERENT FROM, OR IN
      ADDITION TO, THOSE OF THE UNAFFILIATED SHAREHOLDERS. PLEASE REVISE THE
      DISCLOSURE TO IDENTIFY THE SPECIFIC INTERESTS OF EACH DIRECTOR AND
      OFFICER. YOUR REVISED DISCLOSURE SHOULD INCLUDE THE NAMED PERSON'S
      INTERESTS IN CASTLEWOOD AND THE OTHER AFFILIATED ENTITIES, AS WELL AS
      THOSE IN ENSTAR, BOTH BEFORE AND AFTER THE MERGER. EXPAND THE DISCUSSION
      TO DISCLOSE THE SPECIFIC CONSIDERATION THE BOARD GAVE TO THESE INTERESTS
      IN REACHING ITS CONCLUSIONS TO APPROVE THE TRANSACTIONS. IF THE BOARD DID
      NOT CONSIDER THESE INTERESTS IN REACHING ITS CONCLUSION, SAY SO AND
      EXPLAIN WHY NOT. ALSO, IT APPEARS THAT PERSONS WHO HAD THESE INTERESTS
      BOTH NEGOTIATED THE TERMS OF THE PROPOSALS AND VOTED IN FAVOR OF THE
      PROPOSALS. DISCLOSE WHETHER THE INTERESTED INDIVIDUALS VOTED ON THE
      MATTERS THEY WERE INTERESTED IN. IF SO, PLEASE INCLUDE DISCLOSURE
      EXPLAINING WHY THE PERSONS DETERMINED THAT IT WAS NOT NECESSARY OR
      APPROPRIATE FOR THEM TO ABSTAIN FROM VOTING ON THE TERMS OF THE MERGER
      PROPOSAL. IN THIS REGARD, WE NOTE THAT DISCLOSURE IN THE LAST PARAGRAPH OF
      PAGE 43 INDICATES THAT THE ENSTAR BOARD "CONSIDERED" THE INTERESTS BUT
      DOES NOT EXPLAIN WHAT THAT CONSIDERATION CONSISTED OF.

      The Company has added additional disclosure beginning on page 47 to
      address the Staff's comment. See also the Company's response to comment 15
      above.

34.   WE HAVE CONSIDERED YOUR RESPONSE TO COMMENT 35 AND WE HEREBY REISSUE IT.
      WE NOTE THAT AS PART OF THE RECAPITALIZATION AGREEMENT, ENSTAR MADE A
      PAYMENT OF $5,076,000 TO CASTLEWOOD, WHO IN TURN, PAID THIS SUM TO
      "CERTAIN" OF ITS EXECUTIVE OFFICERS AND EMPLOYEES. PLEASE IDENTIFY THE
      INDIVIDUALS WHO RECEIVED THESE PAYMENTS AND DISCUSS THE CONSIDERATION
      GIVEN TO THESE PAYMENTS IN YOUR NEGOTIATION OF THE TERMS OF THE MERGER.
      THE REVISED DISCLOSURE SHOULD EXPLAIN WHAT BENEFIT OR VALUE WAS RECEIVED
      BY ENSTAR, IF ANY, IN EXCHANGE, AND WHAT THE BOARD'S REASONS FOR APPROVING
      THIS TRANSACTION WERE. PLEASE PROVIDE SIMILAR DISCLOSURE REGARDING
      ENSTAR'S INVESTMENT OF $25 MILLION IN THE J.C. FLOWERS II LP IN JUNE OF
      2006.

      The Company has added additional disclosure on page 58 to address the
      Staff's comment regarding the $5,076,000 payment.

      Enstar's commitment to invest $25 million in J.C. Flowers II L.P. in June
      of 2006 was not related to the transactions between Castlewood and Enstar.
      The Company has, 

<PAGE>

      however, notes on page 179 that Enstar will pay no fees in connection
      with this commitment, which is a benefit to Enstar.

35.   WE HAVE CONSIDERED YOUR RESPONSE TO COMMENT 36, BUT WE DISAGREE WITH YOUR
      CONCLUSION. PLEASE INCLUDE APPROPRIATE RISK FACTOR DISCLOSURE REGARDING
      THE TRANSFER OF CASH FROM ENSTAR TO THE MEMBERS OF CASTLEWOOD'S
      MANAGEMENT.

      As discussed with Ms. Hayes and Ms. Fraser during the Conference Call, the
      Company does not believe there is a risk associated with this payment and
      no risk factor has been added.

MATERIAL U.S. FEDERAL INCOME TAX CONSEQUENCES OF THE MERGER -- PAGE 46

36.   WE NOTE THAT THE TAX OPINION YOU HAVE FILED AS EXHIBIT 8.1 TO THE
      REGISTRATION STATEMENT IS A "FORM OF OPINION" RATHER THAN AN ACTUAL
      OPINION. PLEASE NOTE THAT THE ACTUAL SIGNED OPINION MUST BE FILED PRIOR TO
      REQUESTING EFFECTIVENESS. ALSO, THE EXHIBIT DOES NOT IDENTIFY THE COUNSEL
      GIVING THE OPINION. PLEASE REVISE IT TO INCLUDE THIS INFORMATION.

      Enstar's counsel, Debevoise & Plimpton LLP, will provide a signed legal
      opinion on the date on which the Registration Statement becomes effective.
      Such opinion will be on Debevoise & Plimpton LLP letterhead and signed by
      Debevoise & Plimpton LLP, thus indicating the source of the opinion.
      Exhibit 8.1 has been revised to indicate that the opinion will be on
      Debevoise & Plimpton LLP letterhead.

37.   THE OPINION, AND THE DISCLOSURE IN THE PROSPECTUS, SHOULD ALSO BE REVISED
      TO INCLUDE THE BASIS FOR COUNSEL'S OPINION AND SHOULD CITE THE RELEVANT
      AUTHORITIES.

      The Company has added additional disclosure on pages 54 and 55 to address
      the Staff's comment. The opinion has also been revised to address the
      Staff's comment.

38.   THE FORM OF OPINION STATES THAT "THE MERGER SHOULD QUALIFY AS A
      REORGANIZATION WITHIN THE MEANING OF SECTION 368(A) OF THE U.S. INTERNAL
      REVENUE CODE OF 1986, AS AMENDED." THE USE OF THE WORD "SHOULD" SUGGESTS
      THAT THE OPINION IS SUBJECT TO A DEGREE OF UNCERTAINTY. PLEASE EXPLAIN WHY
      COUNSEL CANNOT GIVE A "WILL" OPINION, DESCRIBE THE DEGREE OF UNCERTAINTY
      IN THE OPINION AND PROVIDE RISK FACTOR AND/OR OTHER APPROPRIATE DISCLOSURE
      SETTING FORTH THE RISKS TO INVESTORS. WE MAY HAVE FURTHER COMMENT.

      Debevoise & Plimpton LLP is providing a "should" opinion, rather than
      "will" opinion, because there is no controlling interpretation directly on
      point. The uncertainty is not based upon the presence of contrary
      authority, but rather the lack of direct authority. The risk factor on
      page 21 under the heading "If the merger does not constitute a
      reorganization under section 368(a) of the Code, then Enstar shareholders
      may be responsible for payment of U.S. federal income taxes" appropriately
      describes the risk to investors if the opinion is incorrect.


<PAGE>


39.   THE DISCUSSION OF UNITED STATES TAXATION OF SHAREHOLDERS BEGINNING ON PAGE
      206 IS NOT INCLUDED IN THE TAX OPINION. PLEASE TELL US WHY IT IS NOT. ALSO
      TELL US WHOSE OPINION IS BEING PRESENTED IN THIS DISCUSSION. WE MAY HAVE
      FURTHER COMMENT.

      The discussion of United States Taxation of shareholders beginning on page
      206 of Amendment No. 1 to the Registration Statement represents, insofar
      as it involves matters of law, the opinion of Drinker Biddle & Reath LLP.
      The Company has revised the disclosure on page 214 to make that point
      clearer.

40.   WE NOTE FURTHER THAT THE TAX DISCUSSION BEGINNING ON PAGE 206 CONTAINS
      NUMEROUS REFERENCES INDICATING THAT THE IRS "SHOULD" OR "SHOULD NOT" TREAT
      VARIOUS THINGS IN CERTAIN WAYS. PLEASE TELL US WHY THE DISCLOSURE DOES NOT
      SAY THAT THE IRS "WILL" OR "WILL NOT" TREAT THE ITEMS IN THE SPECIFIED
      WAYS AND REVISE THE DISCLOSURE ACCORDINGLY. WE MAY HAVE ADDITIONAL
      COMMENTS.

      The Company has added additional disclosure beginning on page 214 to
      address the Staff's comment. The Company has changed most of the
      references indicating what the Company believes "should" be the tax
      consequences to what the Company believes "will" be the tax consequences.
      In one instance, however, on page 222, the Company is leaving the relevant
      word as "should." In that case, the reason why the result is not certain
      enough to warrant the word "will" is explained in the immediately prior
      sentence -i.e., the absence of any proposed or final regulations that
      address the issue.

INTERESTS OF CERTAIN PERSONS IN THE MERGER -- PAGE 52

41.   PLEASE DISCLOSE WHETHER ADDITIONAL OR NEW OPTIONS WILL BE GRANTED TO THE
      MEMBERS OF EITHER ENSTAR'S OR CASTLEWOOD'S MANAGEMENT AS PART OF THE
      TRANSACTIONS CONTEMPLATED HERE.

      Other than options issued by New Enstar in replacement of currently
      outstanding options to acquire Enstar common stock, no additional or new
      options will be granted to the members of either Enstar's or Castlewood's
      management as part of the transactions. The Company has added additional
      disclosure on page 58 to address the Staff's comment.

42.   PLEASE PROVIDE QUANTIFIED DISCLOSURE, AND IDENTIFY, THE PERSONS WHO ARE,
      OR WILL BECOME, PARTIES TO THE REGISTRATION RIGHTS AGREEMENT.

      The Company has added additional disclosure on page 59 to address the
      Staff's comment.

43.   PLEASE QUANTIFY THE AGGREGATE VALUE OF THE AGREEMENTS WITH MSSRS.
      ARMSTRONG AND DAVIS AS OF THE MOST RECENT PRACTICABLE DATE.

      The Company has added additional disclosure on page 59 to address the
      Staff's comment.

44.   PLEASE QUANTIFY THE VALUE OF MR. FLOWERS' TAX INDEMNIFICATION AGREEMENT.
      PLEASE PROVIDE DISCLOSURE EXPLAINING WHY THE BOARD ENTERED INTO THE
      AGREEMENT AND WHY IT 

<PAGE>

      BELIEVES THE PROVISIONS OF THE AGREEMENT ARE FAIR AND IN THE BEST INTEREST
      OF THE UNAFFILIATED PUBLIC SHAREHOLDERS.

      The Company has added additional disclosure on page 60 to address the
      Staff's comment.

INFORMATION ABOUT CASTLEWOOD -- PAGE 72

COMPANY OVERVIEW -- PAGE 72

45.   WE NOTE YOUR RESPONSE TO COMMENT 41. PLEASE INCLUDE A MORE DETAILED
      DISCUSSION OF THE MARKET THAT IS AVAILABLE FOR THESE COMMUTATIONS AND
      POLICY BUY-BACKS. EXPLAIN WHAT ALLOWS YOU TO APPARENTLY IMMEDIATELY
      COMMUTE OR REINSURE THESE POLICIES THAT YOU RECENTLY ACQUIRED, OR CLARIFY
      WHETHER THIS STRATEGY IS USED MORE WHEN MANAGING ANOTHER RUN-OFF
      PORTFOLIO.

      The Company has added additional disclosure on page 80 to address the
      Staff's comment.

      Please also note that the Company does not reinsure policies that it
      acquires but retains existing reinsurance protections already in place
      prior to acquisition.

RESERVES FOR UNPAID LOSSES AND LOSS ADJUSTMENT EXPENSE -- PAGE 77

46.   REFER TO YOUR RESPONSE TO COMMENT 42. PLEASE EXPLAIN TO US WHY THE AMOUNTS
      INCLUDED AS THE "CUMULATIVE REDUNDANCY" FOR THE 2004 PERIOD IN THE TABLE
      AT THE BOTTOM OF PAGE 79 DOES NOT AGREE WITH THE AMOUNT SHOWN AS "INCURRED
      RELATED TO PRIOR YEARS" FOR THE 2005 PERIOD IN THE TABLE ON PAGE 80.
      FURTHER EXPLAIN WHY THE FIRST RE-ESTIMATION INCLUDED IN THE 2003 PERIOD
      FOR THE "CUMULATIVE REDUNDANCY" DOES NOT AGREE WITH THE AMOUNT RECORDED AS
      YOUR "INCURRED RELATED TO PRIOR YEARS" FOR THE 2004 PERIOD.

      The Company has revised its disclosure on pages 87 and 88 to address the
      Staff's comment by disclosing, on page 88, the items that are not
      reflected in the first re-estimation of loss reserves each year in the
      table on page 87, but are included in the amount recorded as "Incurred
      related to prior years" in the table on page 88.

47.   WE NOTE YOUR RESPONSE TO COMMENT 43. PLEASE DISCLOSE THE EXPLANATION FOR
      THE PAID LOSS RECOVERIES EXCEEDING THE GROSS PAID LOSSES AS REQUIRED BY
      GUIDE 6. EXPLAIN TO US WHAT CONSIDERATION YOU GAVE TO THE FACT THAT
      CASTLEWOOD WILL OWN 100% OF B.H. ACQUISITION AFTER THE MERGER IN
      DETERMINING THE MOST APPROPRIATE PRESENTATION OF THIS INFORMATION.

      The previous presentation reflected the Company's current 45% ownership
      interest in B.H. Acquisition. The Company has revised its presentation on
      page 88 to reflect its pro forma 100% ownership in B.H. Acquisition, which
      will occur upon consummation of the merger.


<PAGE>


MANAGEMENT'S DISCUSSION AND ANALYSIS OF FINANCIAL CONDITION AND RESULTS OF
OPERATIONS -- PAGE 106

CRITICAL ACCOUNTING POLICIES -- PAGE 111

LOSS AND LOSS ADJUSTMENT EXPENSES -- PAGE 111

48.   WE NOTE YOUR RESPONSE TO COMMENT 45. HOWEVER, IT IS STILL NOT CLEAR TO US
      WHICH OF THE FIVE METHODS DESCRIBED WAS USED TO RECORD YOUR RESERVES.
      PLEASE EXPLAIN WHICH METHODOLOGY WAS SELECTED AND WHETHER THE SAME
      METHODOLOGY WAS USED FOR ALL PERIODS PRESENTED. FOR CHANGES THAT HAVE
      OCCURRED TO THE PROVISION FOR LOSSES ATTRIBUTABLE TO INSURED EVENTS OF
      PRIOR YEARS, WE NOTE THAT YOU CANNOT QUANTIFY THE ISOLATED IMPACT.
      HOWEVER, WE BELIEVE IT IS IMPORTANT FOR INVESTORS TO UNDERSTAND THE
      INFORMATION AVAILABLE THAT LED TO THE CHANGE IN ESTIMATE. PLEASE PROVIDE
      US WITH AN EXPANDED DISCUSSION OF THE NATURE OF THE EVENTS THAT LED TO THE
      REVISIONS. FOR INSTANCE IT IS UNCLEAR HOW THE "LOWER THAN EXPECTED
      INCURRED ADVERSE LOSS DEVELOPMENT" DESCRIBED ON PAGE 80 RESULTED FROM THE
      METHODOLOGIES DISCUSSED.

      The Company has revised its disclosure on pages 89 through 93 to address
      the Staff's comment.

49.   REFER TO YOUR RESPONSE TO COMMENT 46. PLEASE INCLUDE A MORE DETAILED
      DISCUSSION OF THE FACTORS AT THE "(RE)INSURED LEVEL" THAT CAUSE THE
      VARIATIONS IN YOUR RESERVES. FOR EXAMPLE WHEN YOU DISCUSS THE 68
      COMMUTATIONS ON PAGE 80 THAT AFFECTED YOUR CURRENT YEAR RESERVES, INCLUDE
      HOW MANY ADDITIONAL EXPOSURES EXIST ALONG WITH OTHER PERTINENT INFORMATION
      SUCH AS THE AVERAGE RESERVE AMOUNTS FOR THE EXPOSURES IF RELEVANT.
      DISCLOSE SPECIFICALLY WHETHER THE CHANGES IN THE RESERVES WERE RELATED TO
      THE ESTABLISHED CASE RESERVES, OR THE IBNR.

      The Company has revised its disclosure on pages 88, 89 and 124 to address
      the Staff's comment.

COMPARISON OF THE YEAR ENDED DECEMBER 31, 2005 AND 2004

NET REDUCTION IN LOSS AND LOSS ADJUSTMENT EXPENSE LIABILITIES -- PAGE 131

50.   PLEASE EXPLAIN TO US HOW THE AMOUNTS INCLUDED IN THE NEW TABLES ON PAGE
      132 RELATE TO EACH OTHER. IT SEEMS THAT THE AMOUNTS IN THE "NET CHANGE IN
      CASE AND LAE RESERVES" AND "NET CHANGE IN IBNR" INCLUDED IN THE FIRST
      TABLE SHOULD CORRELATE TO THE AMOUNTS IN THE "INCURRED RELATED TO PRIOR
      YEARS" INCLUDED IN THE SECOND TABLE. PLEASE CLARIFY THIS RELATIONSHIP FOR
      US AS WELL, AS WHY THE "NET LOSSES PAID" AMOUNTS APPEAR TO BE AFFECTING
      THE AMOUNT REPORTED IN THE INCOME STATEMENT.

      The first table on page 134 is an analysis of the income statement effect
      of the components of the Net Reduction in Loss and Loss Adjustment Expense
      Liabilities. For the year ended December 31, 2005, the Net Change, or
      reduction, in Case and LAE Reserves of $95,156 plus the Net Change, or
      reduction, in IBNR of $69,858 provides for 

<PAGE>

      a total reduction in Net Reserves for Losses and Loss Adjustment Expenses
      of $165,014. The total reduction in Net Reserves for Losses and Loss
      Adjustment Expenses of $165,014 less the Net Losses Paid of $69,007
      results in an income statement gain, or Net Reduction in Loss and Loss
      Adjustment Expense Liabilities, of $96,007 for the year ended December 31,
      2005.

      The second table is an analysis reconciling opening and closing balance
      sheet net loss reserves. For the year ended December 31, 2005, the
      Incurred Losses Related to Prior Years of $96,007, which equals the income
      statement impact of the Net Reduction in Loss and Loss Adjustment Expense
      Liabilities in the first table, plus the Paid losses Related to Prior
      Years of $69,007 equals the total reduction in Net Reserves for Losses and
      Loss Adjustment Expenses of $165,014 (comprising a Net Change in Case and
      LAE Reserves of $95,156 plus a Net Change in IBNR of $69,858).

UNAUDITED PRO FORMA CONDENSED COMBINED FINANCIAL INFORMATION -- PAGE 152

1.  ADJUSTMENTS TO THE PRO FORMA CONDENSED COMBINED BALANCE SHEET, PAGE 156

NOTE M, PAGE 158

51.   WE NOTE YOUR RESPONSE TO COMMENT 51. WE NOTE ON PAGE 47 THAT YOU INTEND TO
      ACCOUNT FOR THIS TRANSACTION AS A PURCHASE. PLEASE PROVIDE TO US AND
      INCLUDE IN YOUR DISCLOSURE A PURCHASE PRICE ALLOCATION THAT CONSOLIDATES
      ALL OF THE ADJUSTMENTS FOR THIS TRANSACTION IN ONE TABLE. INCLUDE A
      DISCUSSION OF HOW THIS INCREASE TO ADDITIONAL PAID IN CAPITAL RESULTS FROM
      THIS ALLOCATION.

      The Company has revised its disclosure on pages 169 and 170 to address the
      Staff's comment.

      The purchase price allocation does not directly result in any increase to
      additional paid-in capital. The reason for the increase in additional
      paid-in capital is discussed in Note l, on page 169, in the notes to the
      pro forma balance sheet.

SECURITY OWNERSHIP OF CERTAIN BENEFICIAL OWNERS AND MANAGEMENT OF NEW ENSTAR --
PAGE 172

52.   PLEASE PRESENT THIS INFORMATION AS OF THE MOST RECENT PRACTICABLE DATE.
      PLEASE CONFIRM THAT THE INFORMATION INCLUDES OPTIONS THAT HAVE VESTED,
      OPTIONS THAT WILL VEST AS A RESULT OF THE ACCELERATED VESTING PROVISIONS
      IN THE MERGER AGREEMENT, AND ANY SECURITIES THAT WILL BE RECEIVED IN
      CONNECTION WITH THE MERGER AND RECAPITALIZATION TRANSACTIONS.

      The Company has revised its disclosure on pages 181 and 182 to reflect the
      information presented as of September 28, 2006.

      The Company confirms that the information provided includes all options
      that have vested, all options that will vest as a result of the
      accelerated vesting provisions in the 

<PAGE>

      merger agreement, and any securities that will be received in connection
      with the merger and recapitalization transactions.

FINANCIAL STATEMENTS -- DECEMBER 31, 2005

CONSOLIDATED STATEMENTS OF CASH FLOWS, PAGE F-7

53.   WE NOTE YOUR RESPONSE TO COMMENT 58. YOUR DISCLOSURE HERE AND IN NOTE 3
      INDICATES THAT YOU PAID $46 MILLION FOR YOUR INTEREST AND THAT SHINSEI
      PAID $23 MILLION FOR ITS INTEREST. PLEASE EXPLAIN TO US WHY YOU APPARENTLY
      PAID AN AMOUNT THAT IS ROUGHLY TWICE THE AMOUNT THAT YOUR EQUITY PARTNER
      PAID IN THIS ACQUISITION WHEN YOUR RELATIVE OWNERSHIPS DO NOT APPEAR TO
      REPRESENT SUCH A DIFFERENCE. CLARIFY FOR US WHETHER THE NET ASSETS
      DISCLOSED IN NOTE 3 INCLUDES BOTH YOUR AND SHINSEI'S CONTRIBUTIONS OR ONLY
      THE AMOUNTS THAT YOU PAID. 

      Hillcot Holdings Ltd., which is owned 50.1% by Castlewood and 49.9% by
      Shinsei, was incorporated specially for the purpose of acquiring 100% of
      Hillcot Reinsurance Company Limited ("Hillcot Re").

      Shinsei paid $23 million to Hillcot Holdings Ltd. for its 49.9% ownership
      interest in Hillcot Holdings Ltd., which amount represented its share of
      the $46 million purchase price of Hillcot Re. Castlewood also contributed
      $23 million to Hillcot Holdings Ltd. representing its 50.1% share of the
      $46 million purchase price paid by Hillcot Holdings Ltd. for Hillcot Re.

      As Castlewood owns 50.1% of Hillcot Holdings Ltd., it consolidates Hillcot
      Holdings Ltd.'s operating results and balance sheet. As such, the net
      assets acquired of Hillcot Re disclosed in Note 3 includes both
      Castlewood's and Shinsei's contributions.

      The $46 million purchase price paid by Hillcot Holdings Ltd. to acquire
      Hillcot Re is recorded as an investing activity on the statement of cash
      flows. The $23 million contributed by Shinsei to Hillcot Holdings Ltd. is
      recorded as a financing activity on the statement of cash flows.

NOTES TO THE CONSOLIDATED FINANCIAL STATEMENTS, PAGE F-8

2. SIGNIFICANT ACCOUNTING POLICIES, PAGE F-8

LOSSES AND LOSS ADJUSTMENT EXPENSES, PAGE F-9

54.   WE NOTE YOUR RESPONSE TO COMMENT 59. PLEASE EXPLAIN TO US AND DISCLOSE THE
      METHODOLOGY THAT YOU USE TO DETERMINE THE AMOUNT OF THESE EXPENSES TO BE
      "RELEASED" IN EACH PERIOD PRESENTED.

      The Company's insurance and reinsurance subsidiaries establish provisions
      for loss adjustment expense for the estimated duration of the run-off.
      These provisions are assessed at each reporting date and provisions
      relating to future periods are adjusted to reflect any changes in
      estimates of the periodic costs for the duration of the run-off.
      Provisions relating to the current period together with any adjustments to
      future run-off cost provisions are included in loss and loss adjustment
      expenses in the statement of income.


<PAGE>


      The Company has revised its disclosure on page F-9 to address the Staff's
      comment.

5. INVESTMENTS, PAGE F-12

TRADING, PAGE F-14

55.   WE NOTE YOUR RESPONSE TO COMMENT 61. PLEASE REVISE YOUR DISCUSSION HERE
      AND IN THE LIQUIDITY SECTION OF THE DOCUMENT TO INCLUDE A DISCUSSION
      SIMILAR TO THAT WHICH YOU PROVIDED TO US TO HELP BETTER UNDERSTAND THE
      DECISION PROCESS AND IMPACT RELATED TO THESE SECURITIES.

      The Company has revised its disclosure on pages 151 and F-14 to address
      the Staff's comment.

14. EARNINGS PER SHARE, PAGE F-19

56.   WE NOTE YOUR RESPONSE TO COMMENT 65 AND YOUR STATEMENT THAT THE CLASS E
      SHARES DO NOT MEET THE DEFINITION OF A PARTICIPATING SECURITY. PLEASE TELL
      US YOUR CONSIDERATION OF EITF 03-6 WHICH STATES THAT ANY FORM OF
      UNDISTRIBUTED EARNINGS WOULD CONSTITUTE PARTICIPATION BY THAT SECURITY.
      YOUR RESPONSE ONLY ADDRESSES THE FACT THAT CLASS E SHARES ARE NOT ENTITLED
      TO ANY DIVIDENDS OR RIGHTS TO PARTICIPATE IN ANY DISTRIBUTIONS OF ASSETS
      UPON LIQUIDATION.

      We have considered EITF 03-6 and have updated our disclosure on pages F-19
      and F-20 to reflect the fact that the Class E shares have no entitlement
      to undistributed earnings. We have also expanded our disclosure of the
      nature of the Class E shares on pages F-19 and 20.

FINANCIAL STATEMENTS -- JUNE 30, 2006

UNAUDITED CONDENSED CONSOLIDATED STATEMENTS OF CASH FLOWS, PAGE F-34

57.   PLEASE EXPLAIN TO US WHAT THE "DISTRIBUTION OF CAPITAL TO MINORITY
      SHAREHOLDERS" REPRESENTS. ALSO CLARIFY FOR US AND IN YOUR DISCLOSURE
      WHETHER THE $23 MILLION DISCUSSED IN NOTE 3 AS BEING RETURNED TO HILLCOT
      HOLDINGS SHAREHOLDERS IS INCLUDED IN THE "DIVIDEND PAID."

      The $23 million discussed in Note 3 was paid by Hillcot Holdings Ltd. to
      its two shareholders. The distribution of capital to minority shareholders
      represents Shinsei's 49.9% share of the $23 million dividend paid by
      Hillcot Holdings Ltd. to its shareholders. The Company also received its
      50.1% share of the dividend from Hillcot Holdings Ltd., Shinsei and the
      Company. Shinsei's portion of the dividend paid was accounted for on the
      balance sheet as a reduction in minority interest and shown on page F-35
      as "Distribution of capital to minority shareholders." The Company's
      portion of the dividend received from Hillcot Holdings Ltd. was eliminated
      on consolidation and, 

<PAGE>

      therefore, is not reflected as part the unaudited condensed consolidated
      statements of cash flows.

      The $23 million does not form part of the balance shown as 'Dividend
      Paid.' The Dividend Paid amount of $27.95 million represents the dividend
      paid by the Company to its shareholders.

3. ACQUISITION, PAGE F-37

58.   WE NOTE YOUR RESPONSE TO COMMENT 69. PLEASE INCLUDE THE ADDITIONAL
      INFORMATION YOU PROVIDED TO US IN YOUR DISCLOSURE SO THAT AN INVESTOR CAN
      UNDERSTAND THAT THIS REPURCHASE WAS CONTEMPLATED BY THE PURCHASE
      TRANSACTION. INCLUDE SPECIFICALLY THE FOLLOWING POINTS:

      -     DISCLOSE THE TOTAL NUMBER OF SHARES ACQUIRED IN THE PURCHASE AND THE
            RELATIVE PERCENTAGES OF OWNERSHIP THAT RESULTED FROM THE
            TRANSACTION.

      -     CLARIFY WHAT IS MEANT BY THE STATEMENT IN YOUR RESPONSE THAT "THE
            VENDOR DID NOT WANT TO GO THROUGH THE PROCESS ITSELF" IN ORDER TO
            HELP CLARIFY THE ACTUAL REASONS FOR THIS STRUCTURE TO THE
            TRANSACTION.

      -     INCLUDE A DISCUSSION OF HOW THE REPURCHASE PRICE OF THE SHARES BY
            AIOI WAS DETERMINED.

      The Company has revised its disclosure on page F-38 to address the Staff's
      comment.

7. DIVIDEND PAID AND SHARE REDEMPTION, PAGE F-39

59.   PLEASE INCLUDE A DISCUSSION OF THE REDEMPTION PRICE PAID RELATED TO THE
      SERIES E SHARES AS WELL AS HOW THIS PRICE WAS DETERMINED.

      The Company has revised its disclosure on page F-40 to address the Staff's
      comment.

FORM 10-K/A (AMENDMENT NO. 1) -- DECEMBER 31, 2005 -- THE ENSTAR GROUP, INC.

ITEM 8.  FINANCIAL STATEMENTS AND SUPPLEMENTARY DATA, PAGE 28

CONSOLIDATED STATEMENTS OF CASH FLOWS, PAGE 37

60.   WE NOTE YOUR RESPONSE TO COMMENT 73. WE ARE UNABLE TO UNDERSTAND WHY IT IS
      APPROPRIATE TO INCLUDE THIS LINE ITEM AS CASH FLOWS FROM OPERATIONS.
      PLEASE PROVIDE US WITH THE ACCOUNTING LITERATURE THAT SUPPORTS YOUR
      CONCLUSION.

      Statement 95 distinguishes between returns of investment, which should be
      classified as inflows from investing activities (see paragraph 16b), and
      returns on investment, which should be classified as inflows from
      operating activities (see paragraph 22b). AICPA Technical Practice Aid
      (TIS Section 1300.18), "Presentation on the Statement of Cash

<PAGE>

      Flows of Distributions From Investees With Operating Losses," also
      highlights the distinction made in Statement 95. Accordingly, Enstar
      determined whether the distributions received from its equity method
      investee represent a "return on" or a "return of" the related investment.
      Since Enstar has life to date equity in earnings for each of the relevant
      equity method investees that are in excess of distributions from those
      investees, it has included the dividends and distributions from
      partially-owned equity affiliates as an operating item in the statement of
      cash flows.

                                    * * * * *

      The Company believes that Amendment No. 2 and the responses provided above
fully address the matters contained in the Comment Letter. Please forward copies
of any further comments that you may have to undersigned at (215) 988-2757. If
you have questions, please do not hesitate to contact the undersigned at (215)
988-2759 or Joseph Guerriero at (609) 716-6587.

                                           Sincerely,



                                           Robert C. Juelke

cc:   Richard J. Harris
      John J. Oros
      Robert F. Quaintance, Jr.
      Mark Smith