[SCHEDULE 13D/A] Enstar Group SEC Filing

Rhea-AI Filing Summary

Lemonade, Inc. (symbol LMND) has filed a Form 144 notice covering a proposed sale of 11,000 common shares. The shares are intended to be sold on 07 July 2025 through Fidelity Brokerage Services LLC on the NYSE at an aggregate market value of $466,400. The notice states that 73,266,170 shares of the class are outstanding, so the planned sale represents roughly 0.015 % of that total.

The filing is submitted on behalf of Timothy E. Bixby, the “person for whose account the securities are to be sold.” Acquisition information shows the shares derive from an option granted 01 Dec 2019, exercised for cash on 07 July 2025.

Prior insider activity: Over the past three months, the same seller has executed seven separate transactions totaling 45,916 shares for gross proceeds of approximately $1.86 million, with individual sale dates ranging from 03 June 2025 to 30 June 2025.

The signatory affirms awareness of Rule 10b5-1 obligations and declares no undisclosed material adverse information. No additional financial or operational data about Lemonade is included in this Form 144.

Positive

• Sale represents only 0.015 % of outstanding shares, implying negligible dilution or liquidity impact.
• Full Rule 144 disclosure including prior 90-day transactions and broker details, indicating regulatory compliance and transparency.

Negative

• Continued insider selling trend: 45,916 shares already sold over past three months plus an additional planned 11,000 shares.
• Gross proceeds of ~$1.86 M in recent sales may be interpreted by some investors as reduced insider confidence.

Insights

Financial Analyst

TL;DR: Modest–scale insider sale adds to recent $1.9 M disposals; unlikely to affect float but continues selling trend.

This Form 144 indicates another 11 k-share sale by Timothy E. Bixby, bringing his three-month total to roughly 46 k shares worth $1.86 M. The planned sale equals only 0.015 % of shares outstanding, so share-supply impact is minimal. Nevertheless, the continued liquidation pattern may be viewed cautiously by investors who monitor insider sentiment, especially because the sales are clustered within a single quarter. Absent any accompanying business update, the filing is information-only; valuation impact should therefore be limited unless the market extrapolates a negative signal from the selling cadence.

Corporate Governance Specialist

TL;DR: Routine Rule 144 filing; demonstrates compliance but flags sustained insider selling streak.

From a governance standpoint, the issuer is meeting disclosure requirements: the form details broker, dates, share counts, prior 90-day sales, and asserts no undisclosed MNPI. The proposed transaction appears to follow a structured plan (possible 10b5-1 usage noted), supporting transparency. However, consecutive sales totalling nearly $2 M within three months can raise perception risk among shareholders tracking leadership alignment. Because the stake sold is minute relative to float, I classify the market impact as low but directionally negative.

SECURITIES AND EXCHANGE COMMISSION
Washington, D.C. 20549

SCHEDULE 13D

Under the Securities Exchange Act of 1934

(Amendment No. 7)

Enstar Group Limited

(Name of Issuer)

Ordinary Shares, par value $1.00 per share

(Title of Class of Securities)

G3075P101

(CUSIP Number)

Jacqueline Giammarco
20 Horseneck Lane,
Greenwich, CT, 06830
(203) 862-2900

(Name, Address and Telephone Number of Person Authorized to Receive Notices and Communications)

07/02/2025

(Date of Event Which Requires Filing of This Statement)

If the filing person has previously filed a statement on Schedule 13G to report the acquisition that is the subject of this Schedule 13D, and is filing this schedule because of §§ 240.13d-1(e), 240.13d-1(f) or 240.13d-1(g), check the following box.

The information required on the remainder of this cover page shall not be deemed to be "filed" for the purpose of Section 18 of the Securities Exchange Act of 1934 ("Act") or otherwise subject to the liabilities of that section of the Act but shall be subject to all other provisions of the Act (however, see the Notes).

SCHEDULE 13D

CUSIP No. G3075P101

1

Name of reporting person

Trident V, L.P.

2

Check the appropriate box if a member of a Group (See Instructions)

(a)
(b)

3

SEC use only

4

Source of funds (See Instructions)

OO

5

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

6

Citizenship or place of organization

CAYMAN ISLANDS

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 0.00
8	Shared Voting Power 0.00
9	Sole Dispositive Power 0.00
10	Shared Dispositive Power 0.00

11

Aggregate amount beneficially owned by each reporting person

0.00

12

Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)

13

Percent of class represented by amount in Row (11)

0 %

14

Type of Reporting Person (See Instructions)

PN

SCHEDULE 13D

CUSIP No. G3075P101

1

Name of reporting person

Trident Capital V, L.P.

2

Check the appropriate box if a member of a Group (See Instructions)

(a)
(b)

3

SEC use only

4

Source of funds (See Instructions)

OO

5

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

6

Citizenship or place of organization

CAYMAN ISLANDS

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 0.00
8	Shared Voting Power 0.00
9	Sole Dispositive Power 0.00
10	Shared Dispositive Power 0.00

11

Aggregate amount beneficially owned by each reporting person

0.00

12

Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)

13

Percent of class represented by amount in Row (11)

0 %

14

Type of Reporting Person (See Instructions)

PN

SCHEDULE 13D

CUSIP No. G3075P101

1

Name of reporting person

Trident V Parallel Fund, L.P.

2

Check the appropriate box if a member of a Group (See Instructions)

(a)
(b)

3

SEC use only

4

Source of funds (See Instructions)

OO

5

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

6

Citizenship or place of organization

CAYMAN ISLANDS

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 0.00
8	Shared Voting Power 0.00
9	Sole Dispositive Power 0.00
10	Shared Dispositive Power 0.00

11

Aggregate amount beneficially owned by each reporting person

0.00

12

Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)

13

Percent of class represented by amount in Row (11)

0 %

14

Type of Reporting Person (See Instructions)

PN

SCHEDULE 13D

CUSIP No. G3075P101

1

Name of reporting person

Trident Capital V-PF, L.P.

2

Check the appropriate box if a member of a Group (See Instructions)

(a)
(b)

3

SEC use only

4

Source of funds (See Instructions)

OO

5

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

6

Citizenship or place of organization

CAYMAN ISLANDS

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 0.00
8	Shared Voting Power 0.00
9	Sole Dispositive Power 0.00
10	Shared Dispositive Power 0.00

11

Aggregate amount beneficially owned by each reporting person

0.00

12

Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)

13

Percent of class represented by amount in Row (11)

0 %

14

Type of Reporting Person (See Instructions)

PN

SCHEDULE 13D

CUSIP No. G3075P101

1

Name of reporting person

Trident V Professionals Fund, L.P.

2

Check the appropriate box if a member of a Group (See Instructions)

(a)
(b)

3

SEC use only

4

Source of funds (See Instructions)

OO

5

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

6

Citizenship or place of organization

CAYMAN ISLANDS

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 0.00
8	Shared Voting Power 0.00
9	Sole Dispositive Power 0.00
10	Shared Dispositive Power 0.00

11

Aggregate amount beneficially owned by each reporting person

0.00

12

Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)

13

Percent of class represented by amount in Row (11)

0 %

14

Type of Reporting Person (See Instructions)

PN

SCHEDULE 13D

CUSIP No. G3075P101

1

Name of reporting person

Stone Point GP Ltd.

2

Check the appropriate box if a member of a Group (See Instructions)

(a)
(b)

3

SEC use only

4

Source of funds (See Instructions)

OO

5

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

6

Citizenship or place of organization

CAYMAN ISLANDS

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 0.00
8	Shared Voting Power 0.00
9	Sole Dispositive Power 0.00
10	Shared Dispositive Power 0.00

11

Aggregate amount beneficially owned by each reporting person

0.00

12

Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)

13

Percent of class represented by amount in Row (11)

0 %

14

Type of Reporting Person (See Instructions)

OO

SCHEDULE 13D

CUSIP No. G3075P101

1

Name of reporting person

Stone Point Capital LLC

2

Check the appropriate box if a member of a Group (See Instructions)

(a)
(b)

3

SEC use only

4

Source of funds (See Instructions)

OO

5

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

6

Citizenship or place of organization

DELAWARE

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 0.00
8	Shared Voting Power 0.00
9	Sole Dispositive Power 0.00
10	Shared Dispositive Power 0.00

11

Aggregate amount beneficially owned by each reporting person

0.00

12

Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)

13

Percent of class represented by amount in Row (11)

0 %

14

Type of Reporting Person (See Instructions)

OO

SCHEDULE 13D

CUSIP No. G3075P101

1

Name of reporting person

Trident Public Equity LP

2

Check the appropriate box if a member of a Group (See Instructions)

(a)
(b)

3

SEC use only

4

Source of funds (See Instructions)

OO

5

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

6

Citizenship or place of organization

DELAWARE

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 0.00
8	Shared Voting Power 0.00
9	Sole Dispositive Power 0.00
10	Shared Dispositive Power 0.00

11

Aggregate amount beneficially owned by each reporting person

0.00

12

Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)

13

Percent of class represented by amount in Row (11)

0 %

14

Type of Reporting Person (See Instructions)

PN

SCHEDULE 13D

CUSIP No. G3075P101

1

Name of reporting person

Trident Public Equity GP LLC

2

Check the appropriate box if a member of a Group (See Instructions)

(a)
(b)

3

SEC use only

4

Source of funds (See Instructions)

OO

5

Check if disclosure of legal proceedings is required pursuant to Items 2(d) or 2(e)

6

Citizenship or place of organization

DELAWARE

Number of Shares Beneficially Owned by Each Reporting Person With:

7	Sole Voting Power 0.00
8	Shared Voting Power 0.00
9	Sole Dispositive Power 0.00
10	Shared Dispositive Power 0.00

11

Aggregate amount beneficially owned by each reporting person

0.00

12

Check if the aggregate amount in Row (11) excludes certain shares (See Instructions)

13

Percent of class represented by amount in Row (11)

0 %

14

Type of Reporting Person (See Instructions)

OO

SCHEDULE 13D

Item 1.	Security and Issuer
(a)	Title of Class of Securities: Ordinary Shares, par value $1.00 per share
(b)	Name of Issuer: Enstar Group Limited
(c)	Address of Issuer's Principal Executive Offices: A.S. Cooper Building, 4th Floor, 26 Reid Street, Hamilton, BERMUDA , HM 11.
Item 1 Comment: This filing is made jointly on behalf of Trident V, L.P. ("Trident V"), Trident Capital V, L.P. ("Trident V GP"), Trident V Parallel Fund, L.P. ("Trident V Parallel"), Trident Capital V-PF, L.P. ("Trident V Parallel GP"), Trident V Professionals Fund, L.P. ("Trident V Professionals" and, together with Trident V and Trident V Parallel, the "Trident V Funds"), Stone Point GP Ltd. ("Trident V Professionals GP" and, together with Trident V GP and Trident V Parallel GP, the "Trident V GPs") (collectively, the "Stone Point Partnerships"), Stone Point Capital LLC ("Stone Point"), Trident Public Equity LP ("TPE LP") and Trident Public Equity GP LLC ("TPE GP" and, together with the Stone Point Partnerships, Stone Point and TPE LP, the "Reporting Persons") with respect to the voting ordinary shares, par value $1.00 per share ("Ordinary Shares"), of Enstar Group Limited, a Bermuda company (the "Issuer" or the "Company"), having its principal executive offices at A.S. Cooper Building, 4th Floor, 26 Reid Street, Hamilton, HM 11 Bermuda. This filing modifies that certain Schedule 13D filed by the Trident V Funds, Trident V GP, and Stone Point on November 15, 2013 (the "Initial Schedule 13D"), as amended by Amendment No. 1 filed (together with TPE LP and TPE GP) on November 25, 2016 ("Schedule 13D/A No. 1"), Amendment No. 2 filed (together with Trident V Parallel GP and Trident V Professionals GP) on May 15, 2018 ("Schedule 13D/A No. 2"), Amendment No. 3 filed on June 22, 2020 ("Schedule 13D/A No. 3"), Amendment No. 4 filed on May 12, 2022 ("Schedule 13D/A No. 4"), Amendment No. 5 filed on July 31, 2024 ("Schedule 13D/A No. 5") and Amendment No. 6 filed on August 19, 2024 ("Schedule 13D/A No. 6"). This filing constitutes: (i) Amendment No. 7, in respect of Trident V Funds, Trident V GP, and Stone Point; (ii) Amendment No. 6 to the initial Schedule 13D of Schedule 13D/A No. 1, as amended by Schedule 13D/A No. 2, Schedule 13D/A No. 3, Schedule 13D/A No. 4, Schedule 13D/A No. 5 and Schedule 13D/A No. 6, in respect of TPE LP and TPE GP; and (iii) Amendment No. 5 to the initial Schedule 13D/A of Schedule 13D filed as Schedule 13D/A No. 2, as amended by Schedule 13D/A No. 3, Schedule 13D/A No. 4, Schedule 13D/A No. 5 and Schedule 13D/A No. 6, in respect of Trident V Parallel GP and Trident V Professionals GP. The Initial Schedule 13D, as amended by Schedule 13D/A Nos. 1, 2, 3, 4, 5 and 6 and modified by this filing, is referenced herein as the "Schedule 13D/A," which remains unchanged, except as specifically amended by this filing in respect of the respective filers described in the foregoing paragraph. Capitalized terms used but not defined herein shall have the respective meanings defined in the Schedule 13D/A as previously amended.
Item 3.	Source and Amount of Funds or Other Consideration
	Item 3 of the Schedule 13D is hereby supplemented to incorporate by reference the information set forth in Item 4 below.
Item 4.	Purpose of Transaction
	Item 4 is hereby amended and supplemented by adding the following information: On July 2, 2025, the Issuer completed the transactions contemplated by that certain Agreement and Plan of Merger, dated as of July 29, 2024 (the "Merger Agreement") by and among Deer Ltd., an exempted company limited by shares existing under the laws of Bermuda and a direct wholly owned Subsidiary of the Issuer ("New Company Holdco"), 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"), Elk Bidco Limited, an exempted company limited by shares existing under the laws of Bermuda ("Parent"), and 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"). Parent and Merger Sub were backed by equity commitments from investment vehicles managed or advised by affiliates of Sixth Street Partners, LLC. Pursuant to the Merger Agreement, the Issuer, New Company Holdco, Company Merger Sub, Parent and Parent Merger Sub effected a series of mergers (collectively, the "Mergers"), with the Issuer surviving such mergers as a wholly owned subsidiary of Parent. Capitalized terms used in this Item 4 but not otherwise defined have the meaning set forth in the Merger Agreement. As a result of the Mergers, and upon the terms and subject to the conditions set forth in the Merger Agreement, among other things, each Ordinary Share issued and outstanding as of immediately prior to the First Effective Time (other than (w) Ordinary Shares owned by Parent, Parent Merger Sub, the Company or their respective wholly owned Subsidiaries, (x) all Reinvesting Shares, (y) all Ordinary Shares subject to the Company's equity awards (other than Company Restricted Shares) and (z) all Ordinary Shares that were Dissenting Shares) was converted into the right to receive a total of $338 in cash, without interest. Following consummation of the Mergers, holders of Ordinary Shares no longer directly own any shares of the Company, which is the Third Surviving Company following the Mergers. In connection with the Closing, the Issuer notified representatives of the NASDAQ Stock Market LLC ("NASDAQ") that the Mergers had been completed and requested that NASDAQ suspend trading of the Ordinary Shares. In addition, the Issuer requested that NASDAQ file with the SEC a Notification of Removal from Listing and/or Registration under Section 12(b) of the Act on Form 25 (the "Ordinary Shares Form 25") to effect the delisting of the Ordinary Shares and the deregistration of such shares under Section 12(b) of the Act. Following the effectiveness of the Form 25, the Issuer intends to file with the SEC a certification on Form 15 requesting the termination of registration of Ordinary Shares under Section 12(g) of the Act and the suspension of reporting obligations under Sections 13 and 15(d) of the Act. Such deregistration of the Ordinary Shares will become effective 90 days after the filing of the Form 25 or such shorter period as may be determined by the SEC. The Issuer's reporting obligations under the Act will be suspended immediately upon the filing of Form 15. In connection with the Mergers, affiliates and managed funds of Stone Point Credit Adviser LLC, an affiliate of Stone Point, together with certain third party co-investors, purchased, pursuant to the preferred equity commitment letter dated July 29, 2024 (the "Preferred Equity Commitment Letter"), preferred equity interests in a parent entity of Parent with an aggregate liquidation preference of $175,000,000, on the terms and subject to the conditions set forth in the Preferred Equity Commitment Letter. The preferred equity interests were issued pursuant to a Certificate of Designation, dated as of July 2, 2025, and were purchased pursuant to an Investment Agreement, dated as of July 2, 2025.
Item 5.	Interest in Securities of the Issuer
(a)	As of the date hereof, following the Mergers, the Reporting Persons did not beneficially own any Ordinary Shares.
(b)	Item 5(b) of the Schedule 13D is hereby supplemented to incorporate by reference the information set forth in Item 5(a) above.
(c)	Other than as set forth in Item 4 of the Schedule 13D, no transactions in the Issuer's securities have been effected by the Reporting Persons during the past 60 days.
(e)	On July 2, 2025 each of the Reporting Persons ceased to be the beneficial owners of more than 5% of the outstanding Ordinary Shares.
Item 6.	Contracts, Arrangements, Understandings or Relationships With Respect to Securities of the Issuer
	Item 6 of the Schedule 13D is hereby supplemented to incorporate by reference the information set forth in Item 4 above.

SIGNATURE

After reasonable inquiry and to the best of my knowledge and belief, I certify that the information set forth in this statement is true, complete and correct.

Trident V, L.P.

Signature:	/s/ Jacqueline Giammarco
Name/Title:	By: Trident Capital V, L.P., its sole general partner; DW Trident V, LLC, a general partner; its Vice President/Jacqueline Giammarco
Date:	07/07/2025

Trident Capital V, L.P.

Signature:	/s/ Jacqueline Giammarco
Name/Title:	By: DW Trident V, LLC, a general partner; its Vice President/Jacqueline Giammarco
Date:	07/07/2025

Trident V Parallel Fund, L.P.

Signature:	/s/ Jacqueline Giammarco
Name/Title:	By: Trident Capital V-PF, L.P., its sole general partner; DW Trident V, LLC, a general partner; its Vice President/Jacqueline Giammarco
Date:	07/07/2025

Trident Capital V-PF, L.P.

Signature:	/s/ Jacqueline Giammarco
Name/Title:	By: DW Trident V, LLC, a general partner; its Vice President/Jacqueline Giammarco
Date:	07/07/2025

Trident V Professionals Fund, L.P.

Signature:	/s/ Jacqueline Giammarco
Name/Title:	By: Stone Point GP Ltd., its sole general partner; its Vice President/Jacqueline Giammarco
Date:	07/07/2025

Stone Point GP Ltd.

Signature:	/s/ Jacqueline Giammarco
Name/Title:	Vice President/Jacqueline Giammarco
Date:	07/07/2025

Stone Point Capital LLC

Signature:	/s/ Jacqueline Giammarco
Name/Title:	Chief Compliance Officer/Jacqueline Giammarco
Date:	07/07/2025

Trident Public Equity LP

Signature:	/s/ Sally DeVino
Name/Title:	By: Trident Public Equity GP LLC, its general partner; its Vice President/Sally DeVino
Date:	07/07/2025

Trident Public Equity GP LLC

Signature:	/s/ Sally DeVino
Name/Title:	Vice President/Sally DeVino
Date:	07/07/2025

FAQ

How many Lemonade (LMND) shares are being proposed for sale in the latest Form 144?

The filing covers 11,000 common shares with an estimated market value of $466,400.

What percentage of LMND’s outstanding shares does the 11,000-share sale represent?

Approximately 0.015 % of the 73,266,170 shares outstanding.

Who is the selling shareholder listed in the Form 144 for Lemonade?

The notice is filed for Timothy E. Bixby, as the person for whose account the shares will be sold.

How many LMND shares has Timothy E. Bixby sold in the last three months?

He has already sold 45,916 shares across seven transactions, generating roughly $1.86 million in gross proceeds.

When is the proposed sale date for the 11,000 LMND shares?

The approximate sale date disclosed is 07 July 2025.