Document:

Exhibit 10.5

 

CONTINUING GUARANTY OF PAYMENT

 

WHEREAS, James River
Group Holdings, Ltd., a Bermuda company (the “Parent”), directly owns all of the issued and outstanding capital stock
of the undersigned JAMES RIVER GROUP HOLDINGS UK LIMITED, a private limited company incorporated under the Laws of England and
Wales (the “Guarantor”);

 

WHEREAS, the Guarantor
directly or indirectly owns 100% of the issued and outstanding capital stock of James River Group, Inc. (“James River”);

 

WHEREAS, the Parent
and JRG Reinsurance Company Ltd., as “Borrowers”; KeyBank National Association, as Administrative Agent (in such capacity,
the “Administrative Agent”) and as “Letter of Credit Issuer”; and certain “Lender” parties;
and certain other parties are the parties to that certain Credit Agreement of dated June 5, 2013 (as the same heretofore has been
and hereafter may from time to time be amended, supplemented or replaced, the “Credit Agreement”);

 

WHEREAS, pursuant
to the Credit Agreement, inter alia, the Lenders have agreed to advance Loans (as this and other capitalized terms
used herein and not otherwise defined herein are defined in the Credit Agreement) to the Borrowers and issue Letters of Credit;

 

WHEREAS, the Guarantor
and its subsidiaries, including James River, will receive substantial benefit from the proceeds of the Loans; and

 

WHEREAS, the Lenders
and the Administrative Agent have required that the Guarantor execute this guaranty of payment (this “Guaranty”) as
a condition to the effectiveness of the Second Amendment;

 

NOW, THEREFORE,
in order to induce the Lenders and the Administrative Agent to enter into the Second Amendment, and in consideration of the benefits
to accrue to the Guarantor by reason thereof, and for other good and valuable consideration, receipt and sufficiency of which are
hereby acknowledged, the Guarantor hereby represents and warrants to, and covenants and agrees with each of each Lender, the Letter
of Credit Issuer and the Administrative Agent (each a “Guaranteed Creditor” and, collectively, the “Guaranteed
Creditors”) as follows:

 

1.  Guaranty;
Guaranteed Obligations.

 

(a)     The
Guarantor does hereby irrevocably and unconditionally guarantee to the Guaranteed Creditors, and each of them, the punctual (i)
payment of the full amount, when due (whether by demand, acceleration or otherwise), of the principal and interest on each of the
notes issued by the Borrowers pursuant to the Credit Agreement (the “Notes”) and any amendment or supplement thereto
whether now outstanding or hereafter issued (including interest accruing thereon after the commencement of any case or proceeding
under any federal or state

 

    	 	 	 

     

    

 

bankruptcy, insolvency or similar law (a “Proceeding”)
whether or not a claim for such interest is allowable in such Proceeding (“Post-Petition Interest”)) and (ii) payment
and performance of all other Indebtedness and other obligations of each Borrower under the Credit Agreement and each of the other
Loan Documents, whether now or hereafter existing, due or to become due, direct or contingent, joint, several or independent, secured
or unsecured and whether matured or unmatured (including Post-Petition Interest ) (all of the liabilities included in clauses (i)
and (ii) of this Paragraph are hereinafter collectively referred to as the “Guaranteed Obligations”).

 

(b)     This
is a guaranty of payment and performance and not of collection and is the primary obligation of the Guarantor; and the Guaranteed
Creditors, and each of them, may enforce this Guaranty against the Guarantor without any prior pursuit or enforcement of the Guaranteed
Obligations against the Borrowers, any collateral, any right of set-off or similar right, any other guarantor or other obligor
or any other recourse or remedy in the power of the Guaranteed Creditors or any of them.

 

(c)     All
payments made by the Guarantor under or by virtue of this Guaranty shall be paid to the Administrative Agent, for the benefit of
the Guaranteed Creditors, at the Payment Office or such other place as the Administrative Agent may hereafter designate in writing.  The
Guarantor hereby agrees to make all payments under or by virtue of this Guaranty to the Administrative Agent as aforesaid on demand;
provided that all of the Guaranteed Obligations shall automatically be due and payable in full upon the occurrence of an
Event of Default of the type described in clause (h) or clause (i) of Article 7 of the Credit Agreement.

 

2.  Waivers.  The
Guarantor hereby waives (i) notice of acceptance of this Guaranty, notice of the creation, renewal or accrual of any of the Guaranteed
Obligations and notice of any other liability to which it may apply, and notice of or proof of reliance by the Guaranteed Creditors
upon this Guaranty, (ii) diligence, protest, notice of protest, presentment, demand of payment, notice of dishonor or nonpayment
of any of the Guaranteed Obligations, suit or taking other action or making any demand against, and any other notice to the Borrowers
or any other party liable thereon, (iii) any defense based upon any statute or rule of law to the effect that the obligation of
a surety must be neither larger in amount nor in other respects more burdensome than that of the principal, (iv) any defense based
upon any Guaranteed Creditor’s administration or handling of the Guaranteed Obligations, except behavior which amounts to
bad faith and (v) to the fullest extent permitted by law, any defenses or benefits which may be derived from or afforded by law
which limit the liability of or exonerate guarantors or sureties, or which may conflict with terms of this Guaranty.

 

3.  Certain
Rights of the Guaranteed Creditors.

 

(a)     So
far as the Guarantor is concerned, the Guaranteed Creditors may, at any time and from time to time, without the consent of, or
notice to, the Guarantor, and without impairing or releasing any of the Guaranteed Obligations hereunder, upon or without any terms
or conditions and in whole or in part:

 

    	 	Page 2 of 11	 

     

    

 

1.     modify
or change the manner, place or terms of, and/or change or extend or accelerate the time of payment of, renew or alter any of the
Guaranteed Obligations, any security therefor or any liability incurred directly or indirectly in respect thereof (including, without
limitation, (A) increase or decrease in the Guaranteed Obligations or the rate of interest on the Guaranteed Obligations and (B)
any amendment of the Guaranteed Obligations to permit any Guaranteed Creditors to extend further or additional accommodations to
the Borrowers in any form, including credit by way of loan, lease, sale or purchase of assets, guarantee, or otherwise, which shall
thereupon be Guaranteed Obligations), and this Guaranty shall apply to the Guaranteed Obligations as so modified, changed, extended,
renewed or altered;

 

2.     request,
accept, sell, exchange, release, subordinate, surrender, realize upon or otherwise deal with, in any manner and in any order, (a)
any other guaranty by whomsoever at any time made of the Guaranteed Obligations or any liabilities (including any of those hereunder)
incurred directly or indirectly in respect thereof or hereof, and/or any offset or right with respect thereto and (b) any property
by whomsoever at any time pledged, mortgaged or otherwise encumbered to secure, or howsoever securing, the Guaranteed Obligations
or any liabilities (including any of those hereunder) incurred directly or indirectly in respect thereof or hereof, and/or any
offset or right with respect thereto;

 

3.     exercise
or refrain from exercising any rights against the Borrowers or against any collateral or others (including, without limitation,
any other guarantor) or otherwise act or refrain from acting;

 

4.     settle
or compromise any of the Guaranteed Obligations, and security therefor or any liability (including any of those hereunder) incurred
directly or indirectly in respect thereof or hereof, and subordinate the payment of all or any part thereof to the payment of any
liability (whether due or not) of the Borrowers to creditors of the Borrowers other than the Guaranteed Creditors when, in the
Required Lenders’ sole judgment, it considers such subordination necessary or helpful in the protection of its interest or
the exercise of its remedies, including, without limitation, the sale or other realization upon collateral;

 

5.     apply
in the manner determined by the Required Lenders any sums by whomsoever paid or howsoever realized to any of the Guaranteed Obligations,
regardless of what liability or liabilities of the Borrowers remain unpaid; and

 

6.     amend
or otherwise modify, consent to or waive any breach of, or any act, omission or default or Event of Default under the Credit Agreement,
the Notes, any other Loan Document or any agreements, instruments or documents referred to therein or executed and delivered pursuant
thereto or in connection therewith.

 

    	 	Page 3 of 11	 

     

    

 

(b)     Without
limiting the generality of paragraph (a), above, the Guarantor consents that the Guaranteed Creditors may, and authorizes the Guaranteed
Creditors at any time in their discretion without notice demand and without affecting the indebtedness and liabilities of the Guarantor
hereunder, to: (i) accept new or additional documents, instruments, or agreements relative to the Guaranteed Obligations, (ii)
consent to the change, restructure or termination of the individual, partnership, or company structure or existence of a Borrower,
the Guarantor, any other guarantor obligor or any Affiliate of a Borrower or the Guarantor and correspondingly restructure the
Guaranteed Obligations, (iii) accept partial payments on the Guaranteed Obligations, (iv) amend, alter, exchange, substitute, transfer,
enforce, perfect or fail to perfect, waive, subordinate, terminate, or release any collateral or other guaranties and (iv) assign
the Guaranteed Obligations or any rights related thereto in whole or in part.

 

3.  Obligations
Absolute.  This Guaranty and the obligations of the Guarantor hereunder shall be valid and enforceable and shall
not be subject to limitation, impairment or discharge for any reason (other than the payment in full of the Guaranteed Obligations),
including, without limitation, the occurrence of any of the following, whether or not the Guarantor shall have had notice or knowledge
of any of them: (i) any failure to assert or enforce or agreement not to assert or enforce, or the stay or enjoining by order of
court, by operation of law or otherwise, of the exercise or enforcement of, any claim or demand of any right, power or remedy with
respect to the Guaranteed Obligations or any agreement relating thereto or with respect to any other guaranty thereof or security
therefor, (ii) any waiver, amendment or modification of, or any consent to departure from, any of the terms or provisions (including,
without limitation, provisions relating to Events of Default) of the Credit Agreement, the Notes, any other Loan Document or any
other agreement at any time executed in connection therewith, (iii) the Guaranteed Obligations or any portion thereof at any time
being found to be illegal, invalid or unenforceable in any respect, (iv) the application of payments received from any source to
the payment of indebtedness other than the Guaranteed Obligations, even though the Guaranteed Creditors might have elected to apply
such payment to the payment of all or any part of the Guaranteed Obligations, (v) any failure to perfect or continue perfection
of a security interest in any collateral which secures any of the Guaranteed Obligations, (vi) any defenses, set-offs or counterclaims
which the Borrowers may allege or assert against the Guaranteed Creditors or any of them in respect of the Guaranteed Obligations,
(vii) the avoidance or voidability of the Guaranteed Obligations under the Bankruptcy Code or other applicable laws and (viii)
any other act or thing or omission which may or might in any manner or to any extent vary the risk of the Guarantor as an obligor
in respect of the Guaranteed Obligations.

 

4.  Representations
and Warranties.  The Guarantor hereby represents and warrants to the Guaranteed Creditors that the Guarantor has,
independently and without reliance upon the Guaranteed Creditors and based on such documents and information as it has deemed appropriate,
made its own credit analysis and decision to enter into this Guaranty, and the Guarantor has established adequate means of obtaining
from any other obligors on a continuing basis information pertaining to, and is now and on a continuing basis will be completely
familiar with, the financial condition, operations, properties and prospects of such other obligors.

 

    	 	Page 4 of 11	 

     

    

 

5.  Subrogation.

 

(a)    Any
and all rights and claims of the Guarantor against a Borrower or any of its property arising by reason of any payment by the Guarantor
to the Guaranteed Creditors or any of them pursuant to the provisions of this Guaranty, shall be subordinate and subject in right
of payment to the prior and indefeasible payment in full of all Guaranteed Obligations to the Guaranteed Creditors, and until such
time the Guarantor shall have no right of subrogation, contribution, reimbursement or similar right and hereby waives any right
to enforce any remedy the Guaranteed Creditors or the Guarantor may now or hereafter have against such Borrower, any endorser of
any other guarantor of all or any part of the Guaranteed Obligations of such Borrower and any right to participate in, or benefit
from, any security given to the Guaranteed Creditors to secure any Guaranteed Obligations.  Any promissory note evidencing
such liability of such Borrower to the Guarantor shall be non-negotiable and shall expressly state that it is subordinated pursuant
to this Guaranty.

 

(b)    All
Liens of the Guarantor, if any, whether now or hereafter arising and however existing, in any assets of a Borrower or any assets
securing Guaranteed Obligations shall be and hereby are subordinated to the rights and interests of the Guaranteed Creditors in
those assets until the prior and indefeasible payment in full of all Guaranteed Obligations to the Guaranteed Creditors and termination
of all commitments and other financing arrangements between the Borrowers and the Guaranteed Creditors; provided that the
provisions of this sentence shall not be construed as a waiver or modification of the provisions of the Credit Agreement restricting
the Borrowers’ right to grant or permit Liens on their respective property.

 

6.  Borrower
and Other Guarantor Information.  The Guarantor acknowledges that the Guarantor is relying upon the Guarantor’s
own knowledge and is fully informed with respect to each Borrower’s financial condition.  The Guarantor assumes
full responsibility for keeping fully informed of the financial condition of the Borrowers and all other circumstances affecting
the Borrowers’ ability to perform their obligations to the Guaranteed Creditors, and agrees that the Guaranteed Creditors
will have no duty to report to the Guarantor any information that the Guaranteed Creditors or any of them receive about the Borrowers’
financial condition or any circumstances bearing on the Borrowers’ ability to perform all or any portion of the Guaranteed
Obligations, regardless of whether any Guaranteed Creditor has reason to believe that any such facts materially increase the risk
beyond that which the Guarantor intends to assume or has reason to believe that such facts are unknown to the Guarantor or has
a reasonable opportunity to communicate such facts to the Guarantor.

 

7.  Losses
and Expenses.  The Guarantor hereby agrees to defend, indemnify and hold harmless each Guaranteed Creditor from and
against any losses, costs or expenses (including, without limitation, reasonable attorneys’ fees and litigation costs) incurred
by such Guaranteed Creditor in connection with any Guaranteed Creditor’s collection of any sum due hereunder or its enforcement
of its and the other Guaranteed Creditors’ rights hereunder.

 

8.  Payments
Net.  All payments made by the Guarantor hereunder will be made without setoff, counterclaim or other defense.  All
such payments will be made free and clear of, and

 

    	 	Page 5 of 11	 

     

    

 

without deduction or withholding for, any present
or future taxes, levies, imposts, duties, fees, assessments or other charges of whatever nature now or hereafter imposed by any
jurisdiction or by any political subdivision or taxing authority thereof or therein with respect to such payments (but excluding,
except as provided in the second succeeding sentence, tax imposed on or measured by the net income or net profits of any Guaranteed
Creditor pursuant to the laws of the jurisdiction in which such Guaranteed Creditor is organized or the jurisdiction in which the
principal office or applicable lending office of such Guaranteed Creditor is located or any subdivision thereof or therein) and
all interest, penalties or similar liabilities with respect thereto (all such non-excluded taxes, levies, imposts, duties, fees,
assessments or other charges being referred to collectively as “Taxes”).  If any Taxes are so levied or imposed,
the Guarantor agrees to pay the full amount of such Taxes, and such additional amounts as may be necessary so that every payment
of all amounts due under this Guaranty, after withholding or deduction for or on account of any Taxes, will not be less than the
amount provided for herein.  If any amounts are payable in respect of Taxes pursuant to the preceding sentence, the Guarantor
agrees to reimburse each Guaranteed Creditor, upon the written request of such Guaranteed Creditor, for Taxes imposed on or measured
by the net income or net profits of such Guaranteed Creditor pursuant to the laws of the jurisdiction in which the principal office
or applicable lending office of such Guaranteed Creditor is located and for any withholding of Taxes as such Guaranteed Creditor
shall determine are payable by, or withheld from, such Guaranteed Creditor in respect of such amounts so paid to or on behalf of
such Guaranteed Creditor pursuant to the preceding sentence and in respect of any amounts paid to or on behalf of such Guaranteed
Creditor pursuant to this sentence.  The Guarantor will furnish to the Administrative Agent, within 30 days after the
date the payment of any Taxes is due pursuant to applicable law, certified copies of tax receipts evidencing such payment by the
Guarantor.  The Guarantor agrees to indemnify and hold harmless each Guaranteed Creditor, and reimburse such Guaranteed
Creditor upon its written request, for the amount of any Taxes so levied or imposed and paid by such Guaranteed Creditor.  Without
prejudice to the survival of any other agreement of the Guarantor hereunder or under any other Loan Document, the agreements and
obligations of the Guarantor contained in this paragraph shall survive the payment in full of the Guaranteed Obligations and all
other amounts payable under this Guaranty.

 

9.  Notices.  All
notices, requests, demands or other communications hereunder shall be in writing delivered by hand or overnight courier service,
mailed by certified or registered mail or sent by telecopy, as follows:

 

If to the Guarantor:

 

44 Church Street

P.O. Box 1502

Hamilton HM FX

Bermuda

Attention of Gregg Davis, Chief Financial Officer

(Facsimile No. (441) 278-4588)

 

    	 	Page 6 of 11	 

     

    

 

If to a Guaranteed Creditor:

 

c/o KeyBank National Association,
as Administrative Agent

127 Public Square

Cleveland, Ohio 44114

Attention of James Cribbet,
Senior Vice President

(Facsimile No. (216) 689-4981)

 

Any notice, request, demand or other communication
hereunder shall be deemed to have been duly given when deposited in the mails, postage prepaid, or in the case of telecopy notice,
when sent, addressed as aforesaid.  The Administrative Agent and the Guarantor may change the person or address to whom
or which notices are to be given hereunder, by notice duly given hereunder.

 

10.  No Waiver
by the Guaranteed Creditors.  No delay on the part of the Guaranteed Creditors in exercising any of their options,
powers or rights, and no partial or single exercise thereof, whether arising hereunder, under the Credit Agreement, the Notes,
the other Loan Documents or otherwise, shall constitute a waiver thereof or affect any right hereunder.  No waiver of
any such rights and no modification, amendment or discharge of this Guaranty shall be deemed to be made by any Guaranteed Creditor
or shall be effective unless the same shall be in writing signed by such Guaranteed Creditor, and then such waiver shall apply
only with respect to the specific instance involved and shall in no way impair the rights of any other Guaranteed Creditor or of
such Guaranteed Creditor or the obligations of the Guarantor to such Guaranteed Creditor in any other respect at any other time.

 

11.  Authorization
to Debit Account.  If and to the extent payment owed to the Guaranteed Creditors is not made when due hereunder or
within three (3) days thereafter, the Guarantor hereby authorizes each Guaranteed Creditor to debit from time to time against any
or all of the Guarantor’s general deposit accounts with such Guaranteed Creditor any amount so due.

 

12.  Payments
Final.  Whenever the Guaranteed Creditors shall credit any payment to the Guaranteed Obligations or any part thereof,
whatever the source or form of payment, the credit shall be conditional as to the Guarantor unless and until the payment shall
be final and valid and indefeasible as to all the world.  Without limiting the generality of the foregoing, the Guarantor
agrees that if any check or other instrument so applied shall be dishonored by the drawer or any party thereto, or if any payment
by the Guarantor or any proceeds of collateral so applied shall thereafter be recovered by any trustee in bankruptcy or anyone
else, each Guaranteed Creditor in each case may reverse any entry relating thereto in its books, and the Guarantor shall remain
liable therefor even if such Guaranteed Creditor may no longer have in its possession any evidence of the Guaranteed Obligations
to which the payment in question was applied.

 

13.  Governing
Law; Service; No Set-off.  This Guaranty and the respective rights and obligations of the Guaranteed Creditors and
the Guarantor hereunder shall be construed and enforced in accordance with the laws of the State of New York applicable to contracts
made and

 

    	 	Page 7 of 11	 

     

    

 

to be performed wholly within such state.  The
Guarantor irrevocably consents that service of notice, summons or other process in any action or suit in any court of record to
enforce this Guaranty may be made upon the Guarantor by mailing a copy of the summons to the Guarantor by certified or registered
mail, at the address specified above.  The Guarantor hereby waives the right to interpose counterclaims or set-offs of
any kind and description in any such action or suit arising hereunder or in connection herewith.

 

14.  Successors
and Assigns.  This Guaranty shall be binding upon the Guarantor and its successors and assigns, and shall inure to
the benefit of the Guaranteed Creditors and their respective successors and assigns.  Without limiting the generality
of the foregoing, each Guaranteed Creditor may assign its rights under this Guaranty in whole or in part and upon any such assignment,
all the terms and provisions of this Guaranty shall inure to the benefit of such assignee to the extent so assigned.  The
terms used to designate any of the parties herein shall be deemed to include the successors and assigns of such parties and the
term “Lender” shall include, in addition to such Lender, any lawful owner, holder or pledgee of a Note or other Obligations
or any of them.

 

15.  Final
Agreement.  This Guaranty, the Credit Agreement and the other Loan Documents represent the final agreement among
the parties and may not be contradicted by evidence of prior, contemporaneous or subsequent oral agreements.  There are
no unwritten oral agreements between the parties.  All prior or contemporaneous agreements, understandings, representations
and statements, oral or written, are merged into this Guaranty, the Credit Agreement and the other Loan Documents.  Guarantor
acknowledges that it has received copies of the Notes and all other Loan Documents.

 

16.  Severability;
Limitations.

 

(a)    If
this Guaranty by the Guarantor is held or determined to be void, invalid or unenforceable, in whole or in part, such holding or
determination shall not impair or affect the validity and enforceability of any clause or provision not so held to be void, invalid
or unenforceable.  If this Guaranty as to the Guarantor would be held or determined by a court or tribunal having competent
jurisdiction to be void, invalid or unenforceable on account of the amount of its aggregate liability under this Guaranty, then,
notwithstanding any other provision of this Guaranty to the contrary, the aggregate amount of the liability of the Guarantor under
this Guaranty shall, without any further action by the Guarantor, the Guaranteed Creditors or any other person, be automatically
limited and reduced to an amount which is valid and enforceable.

 

(b)    Without
limiting the generality of paragraph (a), above, the Guarantor, and by acceptance hereof, the Guaranteed Creditors, hereby confirm
that it is the intention of all such parties that this Guaranty not constitute a fraudulent transfer or conveyance under the federal
Bankruptcy Code, the Uniform Fraudulent Conveyances Act, the Uniform Fraudulent Transfer Act or similar state statute applicable
to this Guaranty.  Therefore, such parties agree that the Guaranteed Obligations shall be limited to maximum amount as
will, after giving effect to such maximum amount and other contingent and fixed liabilities of the Guarantor that are relevant
under such laws, and after giving effect to any collections from, rights to receive contribution

 

    	 	Page 8 of 11	 

     

    

 

from or payments made by or on behalf of any
other obligor, result in the Guaranteed Obligations not constituting a fraudulent transfer or conveyance.

 

17.  Jurisdiction.  This
Guaranty is delivered in Cleveland, Ohio, and the Guarantor (a) hereby irrevocably submits to the jurisdiction of the state courts
of the State of Ohio and to the jurisdiction of the United States District Court for the Northern District of Ohio, for the purpose
of any suit, action or other proceeding arising out of or based upon this Guaranty or the subject matter hereof brought by the
Guaranteed Creditors or their successors or assigns, (b) hereby waives, and agrees not to assert, by way of motion, as a defense,
or otherwise, in any such suit, action or proceeding, any claim that it is not subject personally to the jurisdiction of the above-named
courts, that its property is exempt or immune from attachment or execution, that the suit, action or proceeding is brought in an
inconvenient forum, that the venue of the suit, action or proceeding is improper or that this Guaranty or the subject matter hereof
may not be enforced in or by such court and (c) hereby waives and agrees not to seek any review by any court of any other jurisdiction
which may be called upon to grant an enforcement of the judgment of any such Ohio state or federal court.  The Guarantor
agrees that its submission to jurisdiction and its consent to service of process by mail is made for the express benefit of the
Guaranteed Creditors.  Final judgment against the Guarantor in any such action, suit or proceeding may be enforced in
other jurisdictions (a) by suit, action or proceeding on the judgment or (b) in any other manner provided by or pursuant to the
laws of such other jurisdiction; provided, however, that the Guaranteed Creditors may at their option bring suit,
or institute other judicial proceedings, against the Guarantor in any state or federal court of the United States or of any country
or place where the Guarantor or its property may be found.

 

18.  Separate
Indemnity.  As a separate, additional and continuing obligation, the Guarantor unconditionally and irrevocably undertakes
and agrees, for the benefit of the Guaranteed Creditors, that, should any amounts not be recoverable from the Guarantor under the
above provisions of this Guaranty for any reason whatsoever (including, without limitation, by reason of any provision of the Credit
Agreement or any other Loan Documents being or becoming void, unenforceable, or otherwise invalid under any applicable law) then,
notwithstanding any notice or knowledge thereof by the Guaranteed Creditors, any of their Affiliates, or any other person, at any
time, the Guarantor as sole, original and independent obligor, upon demand by the Administrative Agent or any other the Guaranteed
Creditors, will make payment to the Guaranteed Creditors of all such obligations not so recoverable by way of full indemnity, in
such currency and otherwise in such manner as is provided in the Credit Agreement or any other Loan Document.

 

19.  Service.

 

(a)    The
Guarantor irrevocably consents to service of process in the manner provided for notices in Section 9, above.  Nothing
in any Loan Document will affect the right of any Guaranteed Creditor to serve process in any other manner permitted by law.

 

(b)    The
Guarantor hereby irrevocably designates, appoints and empowers Corporation Service Company, with offices on the Effective Date
at 80 State Street, Albany, New York

 

    	 	Page 9 of 11	 

     

    

 

12207-2543, as its designee, appointee and
agent to receive, accept and acknowledge for and on its behalf, and in respect of its property, service of any and all legal process,
summon, notices and documents which may be served in any such action or proceeding.  If for any reason such designee,
appointee and agent shall cease to be available to act as such, the Guarantor agrees to designate a new designee, appoint and agent
in New York City on the terms and for the purposes of this provision reasonably satisfactory to the Administrative Agent.

 

20.  WAIVER
OF JURY TRIAL.  THE GUARANTOR AND, BY THEIR ACCEPTANCE OF THIS GUARANTY, THE GUARANTEED CREDITORS HEREBY IRREVOCABLY
AGREE TO WAIVE THEIR RESPECTIVE RIGHTS TO A JURY TRIAL OF ANY CLAIM OR CAUSE OF ACTION BASED UPON OR ARISING OUT OF THE CREDIT
AGREEMENT, THE NOTES, THE OTHER LOAN DOCUMENTS OR THIS GUARANTY OR ANY DEALINGS AMONG THEM RELATING TO THE SUBJECT MATTER OF THE
CREDIT AGREEMENT, THE NOTES, THE OTHER LOAN DOCUMENTS OR THIS GUARANTY AND THE RELATIONSHIPS THEREBY ESTABLISHED.  The
scope of this waiver is intended to be all-encompassing of any and all disputes that may be filed in any court and that relate
to the subject matter of this transaction, including, without limitation, contract claims, tort claims, breach of duty claims,
and all other statutory and common law claims.  THIS WAIVER SHALL APPLY TO ANY SUBSEQUENT AMENDMENTS, RENEWALS, SUPPLEMENTS
OR MODIFICATIONS OF THIS GUARANTY.  In the event of litigation, this provision may be filed as a written consent to a
trial by the court.

 

[No additional provisions are on this page;
the page next following is the signature page.]

 

    	 	Page 10 of 11	 

     

    

 

IN WITNESS WHEREOF,
the Guarantor has caused this Guaranty to be duly executed as fully written above as of this 15TH day of December, 2015.

 

	Executed by	Signature: 	/s/ Gregg Davis 
	JAMES RIVER GROUP	Print name: 	Gregg Davis 
	HOLDINGS UK LIMITED	 	 
	acting by a director in the presence of:	 
	 	 
	Witness’ signature:	/s/ Kevin Copeland 
	Witness’ name:	Kevin Copeland 
	Witness’ address:	18 North Shore Rd 
	 	Bermuda 
	Witness’ occupation:	CFO JRG RE 

 

    	 	Page 11 of 11Exhibit 10.6

 

THIRD AMENDMENT TO CREDIT AGREEMENT

 

THIS THIRD AMENDMENT
TO CREDIT AGREEMENT (this “Third Amendment”) is made and entered into as of the 30th day of December, 2015,
by and among:

 

(i)          JAMES
RIVER GROUP HOLDINGS, LTD., a Bermuda company (the former company name of which is Franklin Holdings (Bermuda), Ltd.), and JRG
REINSURANCE COMPANY LTD., a regulated insurance company domiciled in Bermuda (each a “Borrower” and, collectively,
the “Borrowers”);

 

(ii)         THE
FINANCIAL INSTITUTIONS as signatory lender parties hereto and their successors and assigns (each a “Lender” and, collectively,
the “Lenders”); and

 

(iii)        KEYBANK
NATIONAL ASSOCIATION, a national banking association, in its capacity as “Administrative Agent” under the Credit Agreement
(defined below).

 

Recitals:

 

A.           The
Borrowers, the Lenders and the Administrative Agent and certain other parties are the parties to that certain Credit Agreement
dated as of June 5, 2013, as amended by a First Amendment dated September 24, 2014, a Waiver Letter dated February 6, 2015, a Commitment
Acceptance Agreement dated May 20, 2015 and a Second Amendment dated December 15, 2015 (collectively, the “Credit Agreement”),
pursuant to which, inter alia, the Lenders agreed, subject to the terms and conditions thereof, to advance Loans
(as this and other capitalized terms used herein and not otherwise defined herein are defined in the Credit Agreement) to the Borrowers;
and the Letter of Credit Issuer agreed, subject to the terms and conditions thereof, to issue Letters of Credit.

 

B.           The
Borrowers have requested the Lenders to agree to an amendment to Section 6.13 of the Credit Agreement.

 

     

     

    

 

Agreements:

 

NOW, THEREFORE, in
consideration of the foregoing Recitals and the mutual agreements hereinafter set forth, the Borrowers, the Lenders and the Administrative
Agent, intending to be legally bound, hereby agree as follows:

 

1.          Amendment
to Credit Agreement. Subject to the terms and conditions of this Third Amendment, including, without limitation, Paragraph
2, below, paragraph (a) of Section 6.13 (Risk-Based Capital Ratio; Other Minimum Capital Requirements) of the Credit Agreement
is hereby amended and restated in its entirety to provide as follows:

 

(a)      (i) The Borrowers shall not,
as of the end of any Fiscal Year ending December 31, 2012 and thereafter through and including December 31, 2014, permit the Risk-Based
Capital Ratio of any Domestic Insurance Subsidiary to be less than 2.50 to 1, and (ii) the Borrowers shall not, as of the end of
any Fiscal Year ending December 31, 2015 and thereafter, permit the Risk-Based Capital Ratio (A) of James River Insurance to be
less than 2.00 to 1 or (B) of any other Domestic Insurance Subsidiary to be less than 2.50 to 1.

 

2.          Amendment
Effective Date; Conditions Precedent. The amendment set forth in Paragraph 1, above, shall not be effective unless and until
the date on which all of the following conditions precedent have been satisfied (such date of effectiveness being the “Third
Amendment Effective Date”); provided, however, that upon the effectiveness of this Third Amendment as provided
in this Paragraph 2, the amendment provided for in Paragraph 1, above, shall be deemed to be effective, nunc pro tunc, as
of the 30th day of December, 2015:

 

(a)          Officer’s
Certificate. On the Third Amendment Effective Date, after giving effect to the amendment set forth in Paragraph 1, above, (i)
there shall exist no Default, and a Financial Officer or other executive officer of each Borrower, on behalf of such Borrower,
shall have delivered to the Administrative Agent written confirmation thereof dated as of the Third Amendment Effective Date, (ii)
the representations and warranties of the Borrowers under Article 3 of the Credit Agreement shall have been reaffirmed in writing
by each Borrower as being true and correct in all material respects as of the Third Amendment Effective Date (unless

 

    	 	2	 

     

    

 

and to the extent that any such representation
and warranty is stated to relate solely to an earlier date, in which case such representation and warranty shall have been true
and correct in all material respects as of such earlier date), (iii) each Borrower shall have represented in writing that its execution,
delivery and performance of this Third Amendment have been authorized by all necessary corporate or company action, and (iv) each
Borrower shall have reaffirmed in writing that the Regulatory Condition Satisfaction remains effective.

 

(b)          Third
Amendment. The Administrative Agent or the Special Counsel (defined below) shall have received from each Borrower and the Required
Lenders either (i) a counterpart of this Third Amendment signed on behalf of such party or (ii) written evidence satisfactory to
the Administrative Agent (which may include telecopy or email transmission of a signed signature page of this Third Amendment)
that such party has signed and delivered a counterpart of this Third Amendment.

 

(c)          Guarantor
Confirmations. Each of James River and James River UK shall have executed and delivered to the Administrative Agent a confirmation
of its Payment Guaranty in form and substance reasonably satisfactory to the Administrative Agent, accompanied by such certifications
regarding good standing and authorization as the Administrative Agent may reasonably request.

 

(d)          Agent
Expenses. The Borrowers shall have paid or caused to be paid to the Administrative Agent all fees and other amounts due and
payable on or prior to the Third Amendment Effective Date, including, to the extent invoiced, reimbursement or payment of all reasonable
out-of-pocket expenses (including fees, charges and disbursements of the Special Counsel) required to be reimbursed or paid by
the Borrowers hereunder, under any other Loan Document or under said fee letter agreement.

 

    	 	3	 

     

    

 

(e)          Legal
Matters. All legal matters incident to this Third Amendment and the consummation of the transactions contemplated hereby shall
be reasonably satisfactory to Squire Patton Boggs (US) LLP, Cleveland, Ohio, special counsel to the Administrative Agent (the
“Special Counsel”). Notwithstanding the foregoing, if the Third Amendment Effective Date has not occurred on or before
March 31, 2016, this Third Amendment shall not become effective and shall be deemed of no further force and effect.

 

3.          No
Other Modifications. Except as expressly provided in this Third Amendment, all of the terms and conditions of the Credit Agreement
and the other Loan Documents remain unchanged and in full force and effect.

 

4.          Confirmation
of Obligations; Release. Each Borrower hereby affirms as of the date hereof all of its respective Debt and other obligations
to each of the Lender Parties under and pursuant to the Credit Agreement and each of the other Loan Documents and that such Debt
and other obligations are owed to each of the Lender Parties according to their respective terms. Each Borrower hereby affirms
as of the date hereof that there are no claims or defenses to the enforcement by the Lender Parties of the Debt and other obligations
of such Borrower to each of them under and pursuant to the Credit Agreement or any of the other Loan Documents.

 

5.          Administrative
Agent’s Expense. The Borrowers agree to reimburse the Administrative Agent promptly for its reasonable invoiced out-of-pocket
costs and expenses incurred in connection with this Third Amendment and the transactions contemplated hereby, including, without
limitation, the reasonable fees and expenses of the Special Counsel.

 

6.          Governing
Law; Binding Effect. THIS THIRD AMENDMENT SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH THE LAWS OF THE

 

    	 	4	 

     

    

 

STATE OF NEW YORK AND SHALL BE BINDING
UPON AND INURE TO THE BENEFIT OF THE BORROWERS, THE LENDERS AND THE ADMINISTRATIVE AGENT AND THEIR RESPECTIVE SUCCESSORS AND ASSIGNS.

 

7.          Counterparts.
This Third Amendment may be executed in any number of counterparts, each of which when so executed shall be deemed to be an original,
but all such counterparts shall constitute one and the same instrument, and all signatures need not appear on any one counterpart.
Any party hereto may execute and deliver a counterpart of this Third Amendment by delivering by facsimile or email transmission
a signature page of this Third Amendment signed by such party, and any such facsimile or email signature shall be treated in all
respects as having the same effect as an original signature. Any party delivering by facsimile or email transmission a counterpart
executed by it shall promptly thereafter also deliver a manually signed counterpart of this Third Amendment.

 

8.          Miscellaneous.

 

(a)          Upon
the effectiveness of this Third Amendment, this Third Amendment shall be a Loan Document.

 

(b)          The
invalidity, illegality, or unenforceability of any provision in or Obligation under this Third Amendment in any jurisdiction shall
not affect or impair the validity, legality, or enforceability of the remaining provisions or obligations under this Third Amendment
or of such provision or obligation in any other jurisdiction.

 

(c)          This
Third Amendment and all other agreements and documents executed in connection herewith have been prepared through the joint efforts
of all of the parties. Neither the provisions of this Third Amendment or any such other agreements and documents nor any alleged
ambiguity shall be interpreted or resolved against any party on the ground that such

 

    	 	5	 

     

    

 

party’s counsel drafted this Third
Amendment or such other agreements and documents, or based on any other rule of strict construction. Each of the parties hereto
represents and declares that such party has carefully read this Third Amendment and all other agreements and documents executed
in connection herewith and therewith, and that such party knows the contents thereof and signs the same freely and voluntarily.
The parties hereby acknowledge that they have been represented by legal counsel of their own choosing in negotiations for and preparation
of this Third Amendment and all other agreements and documents executed in connection therewith and that each of them has read
the same and had their contents fully explained by such counsel and is fully aware of their contents and legal effect.

 

(d)          The
Obligations of the Borrowers hereunder are joint and several, all as more fully set forth in Article 10 of the Credit Agreement.

 

9.          Waiver
of Jury Trial. Each of the parties to this Third Amendment hereby irrevocably waives
all right to a trial by jury in any action, proceeding or counterclaim (WHETHER SOUNDING IN CONTRACT, TORT OR OTHERWISE) arising
out of or relating to this Third Amendment, the other LOAN Documents or the transactions contemplated hereby or thereby. Each party
hereto hereby (a) certifies that no representative, agent or attorney oF any other party has represented, expressly or otherwise,
that such other party would not, in the event of litigation, seek to enforce the foregoing waiver, and (b) acknowledges that it
and the other parties hereto have been induced to enter into this Third 

 

    	 	6	 

     

    

 

Amendment
by, among other things, the mutual waivers and certificatION in this section.

 

[No
additional provisions are on this page; the page next following is the signature page.]

 

    	 	7	 

     

    

 

IN WITNESS WHEREOF, the Borrowers, the Lenders
and the Administrative Agent have hereunto set their hands as of the date first above written.

 

	 	BORROWERS
	 	 
	 	JAMES RIVER GROUP HOLDINGS, LTD.
	 	 	 
	 	By:	 /s/ Gregg Davis
	 	 	Gregg Davis, Chief Financial Officer
	 	 	 
	 	JRG REINSURANCE COMPANY LTD.
	 	 	 
	 	By:	 /s/ Kevin Copeland
	 	 	Kevin Copeland, Chief Financial Officer

 

    	 	8	 

     

    

 

	 	ADMINISTRATIVE AGENT
	 	 
	 	KEYBANK NATIONAL ASSOCIATION, as Administrative Agent as Lender
	 	 	 
	 	By: 	 /s/ James Cribbet
	 	 	James Cribbet, Senior Vice President
	 	 	 
	 	LENDERS
	 	 
	 	KEYBANK NATIONAL ASSOCIATION, 

as Lender
	 	 	 
	 	By:	 /s/ James Cribbet
	 	 	James Cribbet, Senior Vice President

 

    	 	9	 

     

    

 

[Lender Signatures Continued]

 

	 	SUNTRUST BANK,
	 	as Lender
	 	 	 
	 	By:	 /s/ Paula Mueller
	 	 	Name: Paula Mueller
	 	 	Title: Director

 

    	 	10	 

     

    

 

[Lender Signatures Continued]

 

	 	BANK OF MONTREAL, CHICAGO BRANCH,
	 	as Lender
	 	 	 
	 	By:	 /s/ Joan Murphy
	 	 	Name: Joan Murphy
	 	 	Title: Director

 

    	 	11	 

     

    

 

[Lender Signatures Continued]

 

	 	THE BANK OF NOVA SCOTIA,
	 	as Lender
	 	 	 
	 	By:	 /s/ Kevin Chan
	 	 	Name: Kevin Chan
	 	 	Title: Director

 

    	 	12	 

     

    

 

[Lender Signatures Continued]

 

	 	FIRST TENNESSEE BANK, N.A.,
	 	as Lender
	 	 	 
	 	By:	 /s/ Keith Sherman
	 	 	Name: Keith Sherman
	 	 	Title: Senior Vice President

 

    	 	13	 

     

    

 

[Lender Signatures Continued]

 

	 	YADKIN BANK, as Lender
	 	 	 
	 	By:	 /s/ Jeff Hendrick
	 	 	Name: Jeff Hendrick
	 	 	Title: Vice President

 

    	 	14

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