Document:

EX-10.1

 Exhibit 10.1 

PREFERRED INTEREST PURCHASE AGREEMENT 

PREFERRED INTEREST PURCHASE AGREEMENT (this “Agreement”), dated as of August 27, 2020 (the “Purchase
Agreement Effective Time”), by and between GLOBAL INDEMNITY GROUP, LLC, a Delaware limited liability company (the “Company”), and WYNCOTE LLC, a Nevada limited liability company (the
“Purchaser” and, together with the Company, each, a “Party” and collectively the “Parties”). 

RECITALS 
 WHEREAS,
on June 26, 2020, Global Indemnity Limited, a Cayman Islands exempted company limited by shares (“GI Cayman”), filed a petition with the Grand Court of the Cayman Islands (the “Cayman Court”),
seeking the Cayman Court’s sanction of a proposed scheme of arrangement and amalgamation, pursuant to which, at the effective time thereof, GI Cayman will merge with and into New CayCo, a Cayman Islands exempted company with limited liability
(“New CayCo”) and a wholly owned subsidiary of the Company, with New CayCo continuing as the surviving entity of the merger, and, in consideration therefor, the existing shares of GI Cayman will be cancelled and the Company
will issue common shares of the Company to the holders of GI Cayman ordinary shares immediately prior to the merger as set forth therein, and pursuant to the scheme of arrangement and amalgamation, GI Cayman will be dissolved (collectively, the
“Scheme of Arrangement”), such that, upon the Scheme of Arrangement becoming effective, the existing shareholders of GI Cayman will become shareholders of the Company; 

WHEREAS, as of the date hereof, GI Cayman is the sole member of the Company and GI Cayman, as sole member of the Company, is party to
that certain Amended and Restated Limited Liability Company Agreement of the Company, dated as of July 16, 2020 (the “First A&R LLC Agreement”); 

WHEREAS, each of the Board of Directors of GI Cayman (the “Board”) and the Audit Committee of the Board has
determined that it would be in the best interests of the shareholders of the Company following the effective time of the Scheme of Arrangement (the “Scheme Effective Time”) for the Company to be treated as a partnership for
U.S. federal income tax purposes prior to the Scheme Effective Time, and GI Cayman, in its capacity as the sole member of the Company, has adopted that certain Interest Designation in connection therewith (the “Interest
Designation”), pursuant to which the Company authorized the issuance, prior to the Scheme Effective Time, for fair value of approximately one percent (1%) of the value of the issued and outstanding limited liability company interests of
the Company (calculated assuming the effectiveness of the Scheme of Arrangement and the transactions contemplated thereby) as Series A Cumulative Fixed Rate Perpetual Preferred Interests; 

 WHEREAS, pursuant to the Scheme of Arrangement, at the Scheme Effective Time
(i) the First A&R LLC Agreement shall be amended and restated in the form of the Second Amended and Restated Limited Liability Company Agreement of the Company to govern the affairs of the Company and the conduct of its business from and
after the Scheme Effective Time (the “Second A&R LLC Agreement”), and (ii) the Interest Designation shall be amended and restated in the form of that certain Share Designation that sets forth the designation, rights,
preferences, powers, duties, restrictions, limitations and obligations of the Series A Cumulative Fixed Rate Perpetual Preferred Interests from and after the Scheme Effective Time (the “Share Designation”); 

WHEREAS, following the Scheme Effective Time, all of the issued and outstanding Series A Cumulative Fixed Rate Perpetual Preferred
Interests shall remain outstanding, unaffected by the Scheme of Arrangement, except as set forth in the Second A&R LLC Agreement and the Share Designation; and 

WHEREAS, the Purchaser desires to subscribe for and acquire from the Company, and the Company desires to issue and sell to the
Purchaser, 4,000 Series A Cumulative Fixed Rate Perpetual Preferred Interests, on the terms and subject to the conditions set forth herein. 

NOW, THEREFORE, in order to implement the foregoing, and in consideration of the mutual agreements contained herein, the Parties
hereto agree as follows: 
 1. Subscription for and Purchase of the Series A Preferred Interests. 

1.1 Purchase of the Series A Preferred Interests. Upon the terms and subject to the conditions of this Agreement, the Purchaser
hereby subscribes for and purchases from the Company, and the Company hereby issues and sells to the Purchaser, 4,000 Series A Cumulative Fixed Rate Perpetual Preferred Interests (the “Series A Preferred Interests”), at a
price of U.S. $1,000.00 per Series A Preferred Interest, for the aggregate amount of U.S. $4,000,000 (the “Purchase Price”), effective as of the Purchase Agreement Effective Time. 

1.2 Payment of Purchase Price. The entire Purchase Price shall be paid by the Purchaser to the Company on the date hereof in cash in
immediately available funds to an account designated by the Company. 
 1.3 Terms of the Series A Preferred Interests. The Series A
Preferred Interests are limited liability company interests of the Company pursuant to the Delaware Limited Liability Company Act (together with any successor statute, and as amended from time to time, the “Act”), and are
subject, as of the Purchase Agreement Effective Time, to the terms and conditions set forth in the Interest Designation and the First A&R LLC Agreement and, from and after the Scheme Effective Time, the Share Designation and the Second A&R
LLC Agreement. The Purchaser hereby acknowledges receipt of (i) the First A&R LLC Agreement, (ii) the Interest Designation, (iii) the Scheme of Arrangement, (iv) the form of Second A&R LLC Agreement and (v) the form
of Share Designation, and in the case of the form of Second A&R LLC Agreement and the form of 

  
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Share Designation, the Purchaser acknowledges and agrees that each is contemplated to take effect at the effective time as set forth therein. The Purchaser agrees to be bound by (i) the
First A&R LLC Agreement (including, without limitation, all of the terms, restrictions, requirements and limitations set forth therein) as a “Member” thereunder and the Interest Designation as a holder of Series A Preferred Interests
and, (ii) if and to the extent effective, the Second A&R LLC Agreement (including, without limitation, all of the terms restrictions, requirements and limitations set forth therein) as a “Shareholder” thereunder and the Share
Designation as a holder of Series A Preferred Shares (as defined therein). The Purchaser hereby consents to the adoption of the Second A&R LLC Agreement and the Share Designation for all purposes of the Act, the First A&R LLC Agreement and
the Interest Designation. 
 1.4 Use of Proceeds. The Company shall use the proceeds from the sale of the Series A Preferred
Interests pursuant to this Agreement for general corporate purposes, including investment in securities or investment in the operations and growth of the Company’s and its subsidiaries’ current and future businesses. 

1.5 Registration Rights. The Series A Preferred Interests will not initially be registered or listed securities. If the Series A
Preferred Interests have not been redeemed pursuant to the terms of the Share Designation on the date that is five years after the date hereof and the Company is then subject to the reporting requirements of the Securities Exchange Act of 1934, as
amended, then the Company and the holders of the Series A Preferred Interests will negotiate in good faith and enter into a registration rights agreement that includes customary demand and piggyback rights in respect of the Series A Preferred
Interests. 
 2. Investment Representations and Warranties. 

2.1 The Purchaser is a limited liability company duly formed, validly existing and in good standing under the laws of the State of Nevada. 

2.2 The Purchaser has all requisite limited liability company power and authority to execute and deliver this Agreement, to perform its
obligations hereunder and to consummate the transactions contemplated hereby, including the purchase of the Series A Preferred Interests from the Company in accordance with the terms hereof. The execution and delivery by the Purchaser of this
Agreement, and the performance by the Purchaser of its obligations hereunder, and the consummation of the transactions contemplated hereby, including the purchase of the Series A Preferred Interests from the Company in accordance with the terms
hereof have been duly authorized by all necessary limited liability company action on behalf of the Purchaser. This Agreement has been duly executed and delivered by the Purchaser and constitutes the valid and binding obligation of the Purchaser
enforceable against the Purchaser in accordance with its terms, except as the same may be limited by bankruptcy, insolvency, reorganization, fraudulent conveyance, arrangement, moratorium or other similar laws relating to or affecting the rights of
creditors generally, or by general equitable principles. 

  
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 2.3 Neither the execution, delivery and performance of this Agreement nor the consummation
of the transactions contemplated hereby will (with or without notice or lapse of time or both) (i) conflict with or breach any provision of the Purchaser’s organizational documents, (ii) violate, in any material respect, any law, rule
or regulation by which the Purchaser or any of its assets may be bound or affected or (iii) conflict with, in any material respect, or result in a material default under any contract or other agreement to which the Purchaser is a party or by
which it or any of its assets may be bound or affected. 
 2.4 The Purchaser is acquiring the Series A Preferred Interests pursuant to this
Agreement for its own account, for investment and not with a view to, or for offer or sale in connection with, any distribution thereof. 

2.5 The Purchaser understands that the Series A Preferred Interests have not been registered under the Securities Act of 1933, as amended (the
“Securities Act”), by reason of its issuance in a transaction exempt from the registration requirements of the Securities Act, and that they must be held indefinitely unless a subsequent disposition thereof is registered
under the Securities Act or is exempt from registration thereunder. 
 2.6 The Purchaser understands that the exemption from registration
afforded by Rule 144 (the provisions of which are known to the Purchaser) promulgated under the Securities Act depends on the satisfaction of various conditions and may not ever be available, and that, if applicable, Rule 144 may afford a basis for
sales only under certain circumstances and only in limited amounts. 
 2.7 The Purchaser is an “accredited investor” as such term
is defined in Regulation D under the Securities Act. 
 2.8 The Purchaser and its counsel have had a reasonable time prior to the date
hereof to review the Scheme of Arrangement, the First A&R LLC Agreement, the Interest Designation, the Second A&R LLC Agreement, the Share Designation, that certain Definitive Proxy Statement of GI Cayman filed on July 23, 2020 pursuant
to Section 14(a) of the Securities Exchange Act of 1934 for the Special Scheme Meeting and the Extraordinary General Meeting of the Holders of GI Cayman A Ordinary Shares and B Ordinary Shares to be held on August 25, 2020 (the
“Proxy Statement”) and other relevant information provided by the Company, to ask questions and receive answers concerning the terms and conditions of the issuance, purchase and sale of the Series A Preferred Interests
pursuant to this Agreement, to discuss the terms and conditions under which its investment in the Company is made, and to obtain any additional information that the Company possessed or could acquire without unreasonable effort or expense. The
Purchaser has such knowledge and experience in business and financial matters and with respect to investments in securities as to enable the Purchaser to understand and evaluate the risks of such investment and form an investment decision with
respect thereto. The Purchaser has relied only on its own tax advisor, and not the Company or any of its advisors, with respect to the federal, state, local, foreign and other tax consequences arising from the Purchaser’s purchase, ownership
and disposition of the Series A Preferred Interests. 

  
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 2.9 The Purchaser (a) has been advised and understands that no public market now exists
for the Series A Preferred Interests and that a public market may never exist for the Series A Preferred Interests, (b) has no need for liquidity in its investment in the Company, (c) is able to bear the economic risk of such investment
for an indefinite period and to afford a complete loss thereof, and (d) understands all of the risks associated with the acquisition of Series A Preferred Interests. 

2.10 The Purchaser acknowledges and agrees that the Series A Preferred Interests purchased by it pursuant to this Agreement are subject to
restrictions on transfer under the provisions of the First A&R LLC Agreement (as the same may be amended, restated or otherwise modified from time to time, including by the Interest Designation, the Second A&R LLC Agreement and the Share
Designation), the Securities Act and applicable state securities laws and may not be resold in violation thereof. The Company shall make a notation regarding the restrictions on transfer of the Series A Preferred Interests pursuant to this Agreement
in its books, and such Series A Preferred Interests shall be transferred on the books of the Company only pursuant to and in compliance with the provisions of the First A&R LLC Agreement (as the same may be amended, restated or otherwise
modified from time to time, including by the Interest Designation, the Second A&R LLC Agreement and the Share Designation), the Securities Act and applicable state securities laws. 

3. Company Representations and Warranties. 

3.1 The Company is a limited liability company duly formed, validly existing and in good standing under the laws of the State of Delaware. 

3.2 The Company has all requisite limited liability company power and authority to execute and deliver this Agreement, to perform its
obligations hereunder and to consummate the transactions contemplated hereby, including the issuance and sale of the Series A Preferred Interests to the Purchaser in accordance with the terms hereof. The execution and delivery by the Company of this
Agreement, and the performance by the Company of its obligations hereunder, and the consummation of the transactions contemplated hereby, including the sale of the Series A Preferred Interests to the Purchaser in accordance with the terms hereof
have been duly authorized by all necessary limited liability company action on behalf of the Company. This Agreement has been duly executed and delivered by the Company and constitutes the valid and binding obligation of the Company enforceable
against the Company in accordance with its terms, except as the same may be limited by bankruptcy, insolvency, reorganization, fraudulent conveyance, arrangement, moratorium or other similar laws relating to or affecting the rights of creditors
generally, or by general equitable principles. 

  
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 3.3 Neither the execution, delivery and performance of this Agreement nor the consummation
of the transactions contemplated hereby will (with or without notice or lapse of time or both) (i) conflict with or breach any provision of the Company’s organizational documents, (ii) violate, in any material respect, any law, rule
or regulation by which the Company or any of its assets may be bound or affected or (iii) conflict with, in any material respect, or result in a material default under any contract or other agreement to which the Company is a party or by which
it or any of its assets may be bound or affected. 
 3.4 The Series A Preferred Interests, when issued and delivered to the Purchaser
pursuant to this Agreement, (i) will have been validly issued and will be fully paid and nonassessable and (ii) will not have been issued in violation of any preemptive or other similar rights of any person. Assuming the accuracy of the
representations and warranties of the Purchaser contained in Section 2 of this Agreement, the issuance and sale of the Series A Preferred Interests to the Purchaser pursuant to this Agreement is exempt from registration
requirements under the Securities Act. 
 4. Non-Reliance; Independent Investigation. Each of the Purchaser
and the Company hereby acknowledges and agrees, and represents and warrants to the other Party, that it is a sophisticated Purchaser or, with respect to the Company, issuer and seller, as applicable, with respect to the transactions contemplated by
this Agreement, and has such information as it deems appropriate under the circumstances concerning the business and financial condition of the Company, GI Cayman, New CayCo, the Scheme of Arrangement, the other transactions contemplated by the
Proxy Statement, and the Series A Preferred Interests to make an informed decision regarding the issuance and sale or purchase, as applicable, of the Series A Preferred Interests. Each of the Purchaser and the Company further hereby agrees that it
has independently made its own analysis and decision to enter into the transactions contemplated by this Agreement based on such information as it has deemed appropriate under the circumstances and without reliance on the other Party, except as
expressly set forth herein. Without limiting the generality of the foregoing, the Purchaser and the Company acknowledge and agree that the other Party makes no representations or warranties as to the Company, the Series A Preferred Interests or the
transactions contemplated hereby, other than as expressly set forth in this Agreement, and that such Party is not relying on any representation or warranty other than those expressly set forth in this Agreement 

5. Miscellaneous. 
 5.1 Binding
Effect. The provisions of this Agreement shall be binding upon and inure to the benefit of the Parties hereto and their respective heirs, legal representatives, successors and permitted assigns. 

5.2 Amendment. This Agreement may be amended only by a written instrument signed by the Company and the Purchaser. 

5.3 Applicable Law. The laws of the State of Delaware shall govern the interpretation, validity and performance of the terms of this
Agreement, regardless of the law that might be applied under principles of conflicts of law. 

  
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 5.4 Waiver of Jury Trial. Each of the Parties hereto hereby waives, and agrees to
cause its Affiliates to waive, to the fullest extent permitted by law, any right to trial by jury of any claim, demand, action or cause of action (i) arising under this Agreement or (ii) in any way connected with or related or incidental
to the dealings of the Parties hereto in respect of this Agreement or any of the transactions contemplated hereby, in each case whether now existing or hereafter arising, and whether in contract, tort, equity or otherwise. Each of the Parties hereto
hereby agrees and consents that any such claim, demand, action or cause of action shall be decided by court trial without a jury and that the Parties hereto may file an original counterpart of a copy of this Agreement with any court as written
evidence of the consent of the Parties hereto to the waiver of their right to trial by jury. 
 5.5 Integration. This Agreement and
the documents referred to herein or delivered pursuant hereto that form a part hereof contain the entire understanding of the Parties with respect to the subject matter hereof. This Agreement supersedes all prior agreements and understandings
between the Parties with respect to its subject matter. 
 5.6 Counterparts. This Agreement may be executed in counterparts, each of
which shall be deemed an original, but all of which shall constitute one and the same instrument. 
 5.7 Specific Performance. Each
Party hereto acknowledges that money damages would be both incalculable and an insufficient remedy for any breach of this Agreement by such Party and that any such breach would cause the other Party hereto irreparable harm. Accordingly, each Party
hereto also agrees that, in the event of any breach or threatened breach of the provisions of this Agreement by such Party, the other Party hereto shall be entitled to equitable relief without the requirement of posting a bond or other security,
including in the form of injunctions and orders for specific performance, in addition to all other remedies available to such other Parties at law or in equity. 

5.8 Further Assurances. Each Party hereto agrees to execute and deliver, or cause to be executed and delivered, such further
instruments or documents or take such other action as may be reasonably necessary or convenient to carry out the transactions contemplated hereby. 

5.9 Descriptive Headings; Definitions. The headings in this Agreement are for convenience of reference only and shall not limit or
otherwise affect the meaning of terms contained herein. As used in this Agreement, (a) “$” means the lawful currency of the United States of America and (b) the term “Affiliate” shall have the meaning set forth in Rule 12b-2 under the Securities Exchange Act of 1934, as amended. 
 [SIGNATURE PAGE FOLLOWS] 

  
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 IN WITNESS WHEREOF, the Parties have executed and delivered this Agreement as of the
date first above written. 
  

			
	THE COMPANY:
	
	GLOBAL INDEMNITY GROUP, LLC
		
	By:	 	 /s/ Thomas M. McGeehan

		 	Name: Thomas M. McGeehan
		 	Title: Chief Financial Officer
	
	THE PURCHASER:
	
	WYNCOTE LLC
		
	By:	 	 /s/ Saul Fox

		 	Name: Saul Fox
		 	Title: PresidentEX-10.2

 Exhibit 10.2 

FOX PAINE & COMPANY, LLC 

2105 Woodside Rd., Suite D 

Woodside, California 94062 

August 28, 2020 
 Global Indemnity Group,
LLC 
 Three Bala Plaza East 
 Suite 300 

Bala Cynwyd, PA 19004 
  

	 	Re:	 Third Amended and Restated Management Agreement 

Dear Ladies and Gentlemen: 
 We refer to
(i) the Management Agreement, dated September 5, 2003, by and among United America Indemnity, Ltd., formerly Vigilant International, Ltd., an exempted company formed with limited liability under the laws of the Cayman Island
(“UAIL”), Fox Paine & Company, LLC, a Delaware limited liability company (“Fox Paine”) and Wind River Holding, L.P., formerly The AMC Group, L.P., a Pennsylvania limited partnership
(“Wind River”), whereby UAIL contracted for certain services from each of Fox Paine and Wind River (the “Original Agreement”), (ii) the Second Amended and Restated Management Agreement, dated as of
May 6, 2020 (the “Second Amended and Restated Management Agreement”), by and between Fox Paine and Global Indemnity Limited, a Cayman Islands exempted company (“GI Cayman”), which replaced and
superseded in its entirety the Original Agreement (as previously amended prior to the date thereof), whereby GI Cayman contracted for certain services from Fox Paine, and (iii) the indemnification letter, dated as of September 5, 2003 (as
amended, restated or otherwise modified from time to time, the “Indemnification Letter”), by and among Fox Paine & Company, LLC, The AMC Group, L.P., and Vigilant International, Ltd. For the avoidance of doubt, all
references in this Third Amended and Restated Management Agreement to an entity include the successor(s) to such entity. 
 By way of a
scheme of arrangement and amalgamation under Cayman Islands law (the “Scheme of Arrangement”), on the date hereof, (i) GI Cayman merged with and into a newly formed exempted company incorporated under Cayman Islands law
(“New CayCo”), with New CayCo surviving, and (ii) following such initial merger, New CayCo merged with and into Global Indemnity Group, LLC, a Delaware limited liability company (the “Company”),
with the Company surviving as the ultimate parent company of the Global Indemnity group of companies. By operation of the Scheme of Arrangement, the Company assumed all rights and obligations of GI Cayman under the Second Amended and Restated
Management Agreement and the Indemnification Letter. 
 Simultaneously with the effectiveness of the merger of New CayCo with and into the
Company pursuant to the Scheme of Arrangement, the Company and Fox Paine hereby amend and restate in its entirety the Second Amended and Restated Management Agreement. This Third Amended and Restated Management Agreement, together with the
Indemnification Letter, reflects the entire agreement of the parties and replaces and supersedes the Second Amended and Restated Management Agreement in its entirety. 

 Global Indemnity Group, LLC 

August 28, 2020 
 Page 2 

 

 In connection with the ongoing operations of the Company and its affiliates, the Company
agrees to pay, or to cause one of its affiliates to pay, an annual service fee equal to $2,634,707 for the twelve-month period beginning on September 5, 2019 and ending September 4, 2020 and for each subsequent twelve-month period, as
compensation for Fox Paine’s ongoing provision of certain financial and strategic consulting, advisory and other services to the Company and its affiliates (collectively, the “Services”); provided that such annual
service fee shall be increased in each subsequent twelve-month period to reflect the aggregate increase in the Consumer Price Index as published by the U.S. Department of Labor Bureau of Labor Statistics (the “CPI-U”) during the twelve-month period ended August 31 immediately prior to the commencement of such subsequent twelve-month period (the annual service fee as so increased annually, the
“Annual Service Fee”). In addition, should the Company and Fox Paine agree that the Annual Service Fee will be deferred, the Annual Service Fee will be subject to an adjustment amount (the “Adjustment
Amount”) equal to, on each September 5 (the “Annual Accrual Date”), the percentage rate of return the Company earned on its investment portfolio over the same twelve month period multiplied by the aggregate
Annual Service Fees and Adjustment Amounts accumulated and unpaid through such date. 
 For the avoidance of doubt, as an example of how the
Annual Service Fee will be adjusted annually, if the CPI-U increases 2% from August 31, 2019 to August 31, 2020, then the Annual Service Fee for the twelve-month period beginning on September 5,
2020 and ending on September 4, 2021 will be increased by 2% from $2,634,707 to $2,687,401. 
 Should the Company and Fox Paine agree
that the Annual Service Fee will be deferred, an example of how the Annual Service Fee will be adjusted is as follows: if the CPI-U increases by 2% from August 31, 2020 to August 31, 2021 and the
Company earns 3% on its investment portfolio over the same period, then the Annual Service Fee for September 5, 2021 will be increased from $2,687,401 to $2,741,149, and the Adjustment Amount for September 5, 2021 will be $80,622 which is
3% of the Annual Service Fee of $2,687,401 accrued on September 5, 2020. The Company shall provide quarterly statements of account to Fox Paine indicating as of the last day of each such calendar quarter, the aggregate Annual Service Fees and
Adjustment Amounts accrued and unpaid as of such date as well as the amount of any outstanding unpaid expense reimbursements invoiced by Fox Paine as of such date. 

The Annual Service Fee with respect to each twelve-month period beginning on September 5 of each year will be billed to the Company by
Fox Paine and paid by the Company or one of its affiliates to Fox Paine on or before November 1 of such twelve month period (the “Payment Date”), unless the Company and Fox Paine agree that the Annual Service Fee will be
deferred. The parties hereto acknowledge that, as of the date hereof, the Company has previously paid to Fox Paine the Annual Service Fee for the twelve-month period beginning on September 5, 2019 and ending on September 4, 2020. 

The parties hereto acknowledge that the Services contemplated hereby, and the Annual Service Fee payable therefor, shall not include
investment banking or other similar services that may be provided to the Company and its affiliates from time to time by Fox Paine and its affiliates, or any transaction fees that may be payable in connection with any such services. 

 Global Indemnity Group, LLC 

August 28, 2020 
 Page 3 

 

 Subject to the following sentence, the Annual Service Fees and Adjustment Amounts shall
continue as obligations of the Company and be payable in accordance with the terms hereof until the earlier of (1) such time as Fox Paine, Fox Paine Capital Fund II International L.P., a Cayman Islands exempted limited partnership, and their
respective affiliates (collectively, the “Fox Paine Entities”) no longer hold or beneficially own a direct or indirect equity investment in the Company or any successor thereto and (2) such time as Fox Paine and the
Company agree in writing to modify or terminate the arrangements contemplated hereby. In addition, upon the consummation of a Change of Control (as defined herein), the Company will immediately pay Fox Paine a lump sum payment in an amount to be
agreed between the Company and Fox Paine (the “Termination Fee”), and, upon receipt of the Termination Fee, the Transaction Fee (as defined herein) and all other amounts payable or reimbursable pursuant to this Third Amended
and Restated Management Agreement incurred at or prior to the consummation of such Change of Control, the Company and Fox Paine agree that Fox Paine’s obligation to provide the Services and the Advisory Services and the Company’s
obligation to pay the Annual Service Fee, Adjustment Amount and any other amounts payable pursuant to this Third Amended and Restated Management Agreement shall thereupon immediately terminate; provided, however, that, notwithstanding
anything to the contrary herein or otherwise, in the event that Fox Paine and the Company fail to agree on the amount of the Termination Fee and the Transaction Fee, the Company’s obligation to pay the Annual Service Fee and Adjustment Amount
shall not terminate and Fox Paine’s right to perform all consulting, financing, investment banking and similar services for the Company and its affiliates shall continue regardless of whether any Fox Paine Entities continue to hold a direct or
indirect equity investment in the Company or any successor thereto without prejudice to Fox Paine’s entitlement to the Termination Fee and the Transaction Fee. 

As used herein, the term “Change of Control” shall mean, whether effected directly or indirectly or in one or a series
of transactions: (i) the sale or exchange of all or substantially all the operating assets of the Company and its subsidiaries, taken as a whole, or (ii) the sale or exchange of (A) at least the majority of the outstanding shares of
the capital stock of the Company and representing at least a majority of the voting power of the Company or (B) all outstanding shares of capital stock of the Company that are not held directly or indirectly by a Fox Paine Entity (exclusive, in
the case of each of clauses (A) and (B), of any shares of capital stock of the Company owned by officers or employees of the Company or any of its subsidiaries that a buyer requires be retained), including, in the case of each of clauses
(i) and (ii), without limitation, by means of a merger, amalgamation, scheme of arrangement, consolidation or other business combination, a tender or exchange offer, a leveraged buy-out, reinsurance
transaction, lease or license, the formation of a partnership, joint or collaborative venture or similar arrangement; provided, however, that a direct or indirect sale or exchange of only capital stock owned by Fox Paine Entities shall not
constitute a Change of Control. For purposes of interpreting the definition of “Change of Control,” the phrase “series of transactions” shall mean and refer to a plan of disposition adopted and approved by the Board of Directors
of the Company or the applicable company. 

 Global Indemnity Group, LLC 

August 28, 2020 
  Page
 4
 
  

 In addition, the Company and Fox Paine agree that Fox Paine will provide to the Company and
its affiliates financial advice and assistance in the event of a possible Change of Control transaction, including, as appropriate, advice and assistance with respect to arranging the transaction or acting as a finder, defining objectives,
performing valuation analyses and structuring, planning and negotiating any such transaction (together with any other consulting, financing, investment banking and similar services provided by Fox Paine to the Company and its affiliates, the
“Advisory Services”). The Company understands that Fox Paine would not be providing (nor would the Company and its affiliates be relying on it for) tax, regulatory, legal or accounting advice in connection with a Change of
Control and that Fox Paine is not rendering any formal opinions to the Company with respect to the Advisory Services. If a Change of Control is consummated, the Company agrees to pay, or to cause one of its affiliates to pay, to Fox Paine, upon the
consummation of the Change of Control, an amount in cash to be agreed between the Company and Fox Paine (the “Transaction Fee”). The Company also agrees to engage Fox Paine to perform any consulting, financing, investment
banking and similar services for the Company and its affiliates in connection with any transaction that does not constitute a “Change of Control”, and agrees to pay, or to cause one of its affiliates to pay, to Fox Paine a mutually agreed
advisory or arrangement/finders’ fee in connection with the provision of such Advisory Services. 
 In addition, the Company agrees, as
and when such are invoiced to the Company by Fox Paine, to promptly reimburse the Fox Paine Entities for all direct and indirect expenses paid or incurred in connection with the Services and/or Advisory Services, including, for the avoidance of
doubt, in connection with efforts to arrange or consummate a Change of Control as well as for reasonable, estimated foreseeable post-closing expenses, which shall be invoiced (including a description of the basis thereof) to the Company prior to the
consummation of the Change of Control. Notwithstanding the foregoing, the Company shall not reimburse the Fox Paine Entities for travel expenses (airfare, hotel, transportation, meals and other miscellaneous travel costs including telephone, travel
insurance, fax and print charges and executive risk bond) incurred in the ordinary course relating to attendance at regularly scheduled meetings of the Board of Directors (or any committee of the Board of Directors) of the Company or its
subsidiaries (the “Excluded Expenses”). For the avoidance of doubt, Excluded Expenses do not include any other expenses of the Fox Paine Entities that may be incurred in connection with the provision of the Services or
Advisory Services, and the Company shall continue to reimburse the Fox Paine Entities for all direct or indirect expenses (other than Excluded Expenses) paid or incurred in connection with the Services and/or Advisory Services. 

Fox Paine may assign its rights and delegate its obligations hereunder, in whole or in part, to any of its present or future affiliates, and
shall provide written notice to the Company of any such assignment. 
 Fox Paine and the Company agree that the Indemnification Letter,
shall continue to survive this amendment and restatement of the Second Amended and Restated Management Agreement and shall survive any termination, expiration or assignment of this Third Amended and Restated Management Agreement. The Indemnification
Letter applies to both Services and Advisory Services. 

 Global Indemnity Group, LLC 

August 28, 2020 
  Page
 5
 
  

 Except as may be required by applicable law or regulation or in connection with any
proceeding, inquiry or request by or before, or a filing with or submission to, a court, governmental or judicial authority, regulatory or administrative body or securities exchange, neither the Company, nor any of its subsidiaries will disclose to
any third party, or publicly refer to, any written or oral advice provided by Fox Paine pursuant to this Third Amended and Restated Management Agreement, without the prior written consent of Fox Paine. The Advisory Services provided by Fox Paine
hereunder are intended solely for the benefit and use of the senior management and the Board of Directors of the Company and its subsidiaries, are not on behalf of, and are not intended to confer rights or remedies upon, any shareholder of the
Company, any employee or creditor of the Company, or any of their respective subsidiaries or any other person, and may not be used or relied upon for any other purpose. 

All amounts payable to Fox Paine hereunder shall be paid free and clear of all deductions or withholdings unless the deduction or withholding
is required by applicable law, in which event the Company shall pay such additional amounts as shall be necessary to ensure that the net amount received by Fox Paine will equal the full amount that would otherwise have been received by Fox Paine had
no such deduction or withholding been made. Payments made by the Company pursuant to this Third Amended and Restated Management Agreement shall be made by wire transfer of immediately available funds to such account as Fox Paine shall designate to
the Company in writing from time to time. 
 This Third Amended and Restated Management Agreement shall be governed by and construed and
enforced in accordance with the laws of the State of New York without regard to choice of law or conflicts of law principles that would result in the application of the laws of any other jurisdiction. Any suit, action or proceeding seeking to
enforce any provision of, or based on any matter arising out of or in connection with, this Third Amended and Restated Management Agreement or the transactions contemplated hereby shall be brought in any federal court located in the State of New
York or any New York state court, and each of the parties hereto hereby (1) consents and submits itself and its property to the exclusive jurisdiction of such courts (and of the appropriate appellate courts therefrom) in any such suit, action
or proceeding, (2) consents to and submits itself and its property to the personal jurisdiction of such courts (and of the appropriate appellate courts therefrom) in any such suit, action or proceeding, and (3) irrevocably waives, to the
fullest extent permitted by law, any objection that it may now or hereafter have to the laying of the venue of any such suit, action or proceeding in any such court or that any such suit, action or proceeding brought in any such court has been
brought in an inconvenient forum. Process in any such suit, action or proceeding may be served on any party anywhere in the world, whether within or without the jurisdiction of any such court. We and you (on your behalf and, to the extent permitted
by applicable law, on behalf of your stockholders and creditors) waive all right to trial by jury in any action, proceeding or counterclaim (whether based upon contract, tort or otherwise) related to or arising out of or in connection with this
letter agreement or our engagement. 
 [SIGNATURE PAGE FOLLOWS] 

 Please confirm that the foregoing is in accordance with your understanding and agreement
with Fox Paine by signing a copy of this Third Amended and Restated Management Agreement in the space provided below. 
  

			
	Very truly yours,
	
	FOX PAINE & COMPANY, LLC
		
	By:	 	 /s/ Saul Fox

	Name: Saul Fox
	Title: Chief Executive

			
	ACCEPTED AND AGREED AS OF THE DATE FIRST ABOVE WRITTEN:
	
	GLOBAL INDEMNITY GROUP, LLC
		
	By:	 	 /s/ Thomas M. McGeehan

	Name: Thomas M. McGeehan
	Title: CFO

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