[Form 4] Enstar Group Insider Trading Activity

Filing Impact

(Low)

Filing Sentiment

(Neutral)

Form Type

07/07/2025 - 05:00 PM

SEC Form 4

FORM 4

UNITED STATES SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP

Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934
or Section 30(h) of the Investment Company Act of 1940

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Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

Check this box to indicate that a transaction was made pursuant to a contract, instruction or written plan for the purchase or sale of equity securities of the issuer that is intended to satisfy the affirmative defense conditions of Rule 10b5-1(c). See Instruction 10.

1. Name and Address of Reporting Person^*

Schlesinger Stuart

(Last)

(First)

(Middle)

C/O J.C. FLOWERS & CO. LLC

1301 AVENUE OF THE AMERICAS, 16TH FLOOR

(Street)

NEW YORK

10019

(City)

(State)

(Zip)

2. Issuer Name and Ticker or Trading Symbol
Enstar Group LTD [ ESGR ]

5. Relationship of Reporting Person(s) to Issuer
(Check all applicable)

Director		10% Owner
Officer (give title below)	X	Other (specify below)
		See Remarks

3. Date of Earliest Transaction (Month/Day/Year)
07/02/2025

4. If Amendment, Date of Original Filed (Month/Day/Year)

6. Individual or Joint/Group Filing (Check Applicable Line)

	Form filed by One Reporting Person
X	Form filed by More than One Reporting Person

Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	3. Transaction Code (Instr. 8)		4. Securities Acquired (A) or Disposed Of (D) (Instr. 3, 4 and 5)			5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4)	6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
1. Title of Security (Instr. 3)	2. Transaction Date (Month/Day/Year)	2A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	Amount	(A) or (D)	Price		6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	7. Nature of Indirect Beneficial Ownership (Instr. 4)
Ordinary Shares	07/02/2025		J⁽¹⁾		10,750	D	⁽¹⁾	0	I	See footnote⁽²⁾⁽³⁾

Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned (e.g., puts, calls, warrants, options, convertible securities)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	4. Transaction Code (Instr. 8)		5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5)		6. Date Exercisable and Expiration Date (Month/Day/Year)		7. Title and Amount of Securities Underlying Derivative Security (Instr. 3 and 4)		8. Price of Derivative Security (Instr. 5)	9. Number of derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)	10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)
1. Title of Derivative Security (Instr. 3)	2. Conversion or Exercise Price of Derivative Security	3. Transaction Date (Month/Day/Year)	3A. Deemed Execution Date, if any (Month/Day/Year)	Code	V	(A)	(D)	Date Exercisable	Expiration Date	Title	Amount or Number of Shares	8. Price of Derivative Security (Instr. 5)		10. Ownership Form: Direct (D) or Indirect (I) (Instr. 4)	11. Nature of Indirect Beneficial Ownership (Instr. 4)

1. Name and Address of Reporting Person^*

Schlesinger Stuart

(Last)

(First)

(Middle)

C/O J.C. FLOWERS & CO. LLC

1301 AVENUE OF THE AMERICAS, 16TH FLOOR

(Street)

NEW YORK

10019

(City)

(State)

(Zip)

Relationship of Reporting Person(s) to Issuer

Director		10% Owner
Officer (give title below)	X	Other (specify below)
		See Remarks

1. Name and Address of Reporting Person^*

Hyman 2018 Family Trust

(Last)

(First)

(Middle)

C/O J.C. FLOWERS & CO. LLC

1301 AVENUE OF THE AMERICAS, 16TH FLOOR

(Street)

NEW YORK

10019

(City)

(State)

(Zip)

Relationship of Reporting Person(s) to Issuer

Director		10% Owner
Officer (give title below)	X	Other (specify below)
		See Remarks

Explanation of Responses:

1. On July 2, 2025, pursuant to a rollover and support agreement by and among Elk Topco, LLC ("Topco"), the Hyman 2018 Family Trust (the "Hyman Trust") and J.C. Flowers & Co. LLC, and that certain Agreement and Plan of Merger by and among, the Issuer, Deer Ltd., Deer Merger Sub Ltd., Elk Bidco Limited and Elk Merger Sub Limited, the Reporting Persons transferred, contributed and delivered (or caused to be transferred, contributed and delivered) to Topco all Ordinary Shares beneficially owned by the Reporting Persons in exchange for equity interests therein.

2. The reported securities were directly held by the Hyman Trust.

3. Stuart Schlesinger, in his capacity as trustee of the Hyman Trust, may have been deemed to beneficially own the reported securities. Stuart Schlesinger disclaims beneficial ownership of the securities directly held by the Hyman Trust except to the extent of his pecuniary interest therein this report shall not be deemed an admission that Stuart Schlesinger was the beneficial owner of such securities for purposes of Section 16 or for any other purpose.

Remarks:

The Reporting Persons were members of a "group" for purposes of Section 13(d) of the Securities Exchange Act of 1934 (the "Group") that beneficially owned more than 10% of the Issuer's outstanding Ordinary Shares. The other members of the Group include Elk Evergreen Investments, LLC, Elk Cypress Investments, LLC, TSS Sub-Fund Holdco, LLC, Alan Waxman, J. Christopher Flowers, Paula Mims (not in her individual capacity but solely as executor of the Estate of Nimrod T. Frazer), Frazer Holdings LLC, the Estate of Nimrod T. Frazer, Anne Oros, the John J. Oros 1998 Family Trust, Steven D. Arnold, the Arnold 1997 Limited Partnership, SAS GP, L.L.C. and David G. Walsh (collectively, the "Other Group Members"). The Reporting Persons disclaim beneficial ownership of the Ordinary Shares of the Issuer beneficially owned by the Other Group Members except to the extent of the Reporting Persons' pecuniary interest therein.

	/s/ Stuart Schlesinger	07/07/2025
	/s/ Stuart Schlesinger, as trustee of the Hyman 2018 Family Trust	07/07/2025
	** Signature of Reporting Person	Date
Reminder: Report on a separate line for each class of securities beneficially owned directly or indirectly.
* If the form is filed by more than one reporting person, see Instruction 4 (b)(v).
** Intentional misstatements or omissions of facts constitute Federal Criminal Violations See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
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