Document:

Filed by Bowne Pure Compliance

 

Exhibit 4.3

FIXED/FLOATING RATE JUNIOR SUBORDINATED DEFERRABLE INTEREST DEBENTURE

[FACE OF SECURITY]

THIS SECURITY HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE
“SECURITIES ACT”), ANY STATE SECURITIES LAWS OR ANY OTHER APPLICABLE SECURITIES LAW. NEITHER THIS
SECURITY NOR ANY INTEREST OR PARTICIPATION HEREIN MAY BE REOFFERED, SOLD, ASSIGNED, TRANSFERRED,
PLEDGED, ENCUMBERED OR OTHERWISE DISPOSED OF IN THE ABSENCE OF SUCH REGISTRATION OR UNLESS SUCH
TRANSACTION IS EXEMPT FROM, OR NOT SUBJECT TO, THE REGISTRATION REQUIREMENTS OF THE SECURITIES ACT
AND ANY APPLICABLE STATE SECURITIES LAWS. THE HOLDER OF THIS SECURITY BY ITS ACCEPTANCE HEREOF
AGREES TO OFFER, SELL OR OTHERWISE TRANSFER THIS SECURITY ONLY (A) TO FIRST MERCURY FINANCIAL
CORPORATION (THE “COMPANY”), (B) PURSUANT TO A REGISTRATION STATEMENT THAT HAS BEEN DECLARED
EFFECTIVE UNDER THE SECURITIES ACT, (C) TO A PERSON WHOM THE SELLER REASONABLY BELIEVES IS A
QUALIFIED INSTITUTIONAL BUYER IN A TRANSACTION MEETING THE REQUIREMENTS OF RULE 144A SO LONG AS
THIS SECURITY IS ELIGIBLE FOR RESALE PURSUANT TO RULE 144A IN ACCORDANCE WITH RULE 144A, (D) TO A
NON-U.S. PERSON IN AN OFFSHORE TRANSACTION IN ACCORDANCE WITH RULE 903 OR RULE 904 (AS APPLICABLE)
OF REGULATION S UNDER THE SECURITIES ACT, (E) TO AN INSTITUTIONAL “ACCREDITED INVESTOR” WITHIN THE
MEANING OF SUBPARAGRAPH (A) OF RULE 501 UNDER THE SECURITIES ACT THAT IS ACQUIRING THIS SECURITY
FOR ITS OWN ACCOUNT, OR FOR THE ACCOUNT OF SUCH AN INSTITUTIONAL ACCREDITED INVESTOR, FOR
INVESTMENT PURPOSES AND NOT WITH A VIEW TO, OR FOR OFFER OR SALE IN CONNECTION WITH, ANY
DISTRIBUTION IN VIOLATION OF THE SECURITIES ACT, OR (F) PURSUANT TO ANY OTHER AVAILABLE EXEMPTION
FROM THE REGISTRATION REQUIREMENTS OF THE SECURITIES ACT, SUBJECT TO THE COMPANY’S RIGHT PRIOR TO
ANY SUCH OFFER, SALE OR TRANSFER TO REQUIRE THE DELIVERY OF AN OPINION OF COUNSEL, CERTIFICATION
AND/OR OTHER INFORMATION SATISFACTORY TO IT IN ACCORDANCE WITH THE INDENTURE, A COPY OF WHICH MAY
BE OBTAINED FROM THE COMPANY. HEDGING TRANSACTIONS INVOLVING THIS SECURITY MAY NOT BE CONDUCTED
UNLESS IN COMPLIANCE WITH THE SECURITIES ACT.

 

A-1-1

 

THE HOLDER OF THIS SECURITY BY ITS ACCEPTANCE HEREOF ALSO AGREES, REPRESENTS AND WARRANTS THAT
IT IS NOT AN EMPLOYEE BENEFIT, INDIVIDUAL RETIREMENT ACCOUNT OR OTHER PLAN OR ARRANGEMENT SUBJECT
TO TITLE I OF THE EMPLOYEE RETIREMENT INCOME SECURITY ACT OF 1974, AS AMENDED (“ERISA”), OR
SECTION 4975 OF THE INTERNAL REVENUE CODE OF 1986, AS AMENDED (THE “CODE”) (EACH A “PLAN”), OR AN
ENTITY WHOSE UNDERLYING ASSETS INCLUDE “PLAN ASSETS” BY REASON OF ANY PLAN’S INVESTMENT IN THE ENTITY, AND NO PERSON INVESTING “PLAN ASSETS” OF ANY PLAN MAY ACQUIRE
OR HOLD THIS SECURITY OR ANY INTEREST THEREIN, UNLESS SUCH PURCHASER OR HOLDER IS ELIGIBLE FOR
EXEMPTIVE RELIEF AVAILABLE UNDER U.S. DEPARTMENT OF LABOR PROHIBITED TRANSACTION CLASS EXEMPTION
96-23, 95-60, 91-38, 90-1 OR 84-14 OR ANOTHER APPLICABLE EXEMPTION OR ITS PURCHASE AND HOLDING OF
THIS SECURITY IS NOT PROHIBITED BY SECTION 406 OF ERISA OR SECTION 4975 OF THE CODE WITH RESPECT TO
SUCH PURCHASE OR HOLDING. ANY PURCHASER OR HOLDER OF THIS SECURITY OR ANY INTEREST THEREIN WILL BE
DEEMED TO HAVE REPRESENTED BY ITS PURCHASE AND HOLDING THEREOF THAT EITHER (i) IT IS NOT AN
EMPLOYEE BENEFIT PLAN WITHIN THE MEANING OF SECTION 3(3) OF ERISA, OR A PLAN TO WHICH SECTION 4975
OF THE CODE IS APPLICABLE, A TRUSTEE OR OTHER PERSON ACTING ON BEHALF OF AN EMPLOYEE BENEFIT PLAN
OR PLAN, OR ANY OTHER PERSON OR ENTITY USING THE ASSETS OF ANY EMPLOYEE BENEFIT PLAN OR PLAN TO
FINANCE SUCH PURCHASE, OR (ii) SUCH PURCHASE WILL NOT RESULT IN A PROHIBITED TRANSACTION UNDER
SECTION 406 OF ERISA OR SECTION 4975 OF THE CODE FOR WHICH THERE IS NO APPLICABLE STATUTORY OR
ADMINISTRATIVE EXEMPTION.

THIS SECURITY WILL BE ISSUED AND MAY BE TRANSFERRED ONLY IN BLOCKS HAVING AN AGGREGATE
PRINCIPAL AMOUNT OF NOT LESS THAN $100,000.00 AND MULTIPLES OF $1,000.00 IN EXCESS THEREOF. ANY
ATTEMPTED TRANSFER OF THIS SECURITY IN A BLOCK HAVING AN AGGREGATE PRINCIPAL AMOUNT OF LESS THAN
$100,000.00 SHALL BE DEEMED TO BE VOID AND OF NO LEGAL EFFECT WHATSOEVER.

THE HOLDER OF THIS SECURITY AGREES THAT IT WILL COMPLY WITH THE FOREGOING RESTRICTIONS.

THIS SECURITY IS IN REGISTERED FORM WITHIN THE MEANING OF TREASURY REGULATIONS SECTION
1.871-14(c)(1)(i) FOR U.S. FEDERAL INCOME AND WITHHOLDING TAX PURPOSES.

IN CONNECTION WITH ANY TRANSFER, THE HOLDER WILL DELIVER TO THE REGISTRAR AND TRANSFER AGENT
SUCH CERTIFICATES AND OTHER INFORMATION AS MAY BE REQUIRED BY THE INDENTURE TO CONFIRM THAT THE
TRANSFER COMPLIES WITH THE FOREGOING RESTRICTIONS.

 

 

 

Fixed/Floating Rate Junior Subordinated Deferrable Interest Debenture

of

First Mercury Financial Corporation

September 26, 2007

First Mercury Financial Corporation, a corporation duly organized and existing under the laws
of Delaware (the “Company,” which term includes any successor Person under the Indenture
hereinafter referred to), for value received promises to pay to Wilmington Trust Company, not in
its individual capacity but solely as Institutional Trustee for First Mercury Capital Trust IV (the
“Holder”) or registered assigns, the principal sum of twenty million six hundred and nineteen
thousand dollars ($20,619,000) on September 26, 2037, and to pay interest on said principal sum
from September 26, 2007, or from the most recent Interest Payment Date (defined herein) to which
interest has been paid or duly provided for, quarterly (subject to deferral as set forth herein) in
arrears on March 15, June 15, September 15 and December 15 of each year or if such day is not a
Business Day, then the next succeeding Business Day (each such date, an “Interest Payment Date”)
commencing on the Interest Payment Date in March 2008, at an annual rate equal to 8.25% beginning
on (and including) the date of original issuance and ending on (but excluding) the Interest Payment
Date in December 2012, and at an annual rate for each successive period beginning on (and
including) the Interest Payment Date in December 2012, and each succeeding Interest Payment Date,
and ending on (but excluding) the next succeeding Interest Payment Date (each a “Distribution
Period”), equal to 3-Month LIBOR, determined as described below, plus 3.30% (the “Coupon Rate”),
applied to the principal amount hereof, until the principal hereof is paid or duly provided for or
made available for payment, and on any overdue principal and (without duplication and to the extent
that payment of such interest is enforceable under applicable law) on any overdue installment of
interest (including Additional Interest) at the Interest Rate in effect for each applicable period,
compounded quarterly, from the dates such amounts are due until they are paid or made available for
payment. The amount of interest payable for any period will be computed on the basis of the actual
number of days in the Distribution Period concerned divided by 360. The interest installment so
payable, and punctually paid or duly provided for, on any Interest Payment Date will, as provided
in the Indenture, be paid to the Person in whose name this Debenture (or one or more Predecessor
Securities) is registered at the close of business on the regular record date for such interest
installment, which shall be fifteen days prior to the day on which the relevant Interest Payment
Date occurs. Any such interest installment not so punctually paid or duly provided for shall
forthwith cease to be payable to the Holder on such regular record date and may be paid to the
Person in whose name this Debenture (or one or more Predecessor Securities) is registered at the
close of business on a special record date.

Capitalized terms used and not defined in this Debenture shall have the meanings assigned in
the Indenture dated as of the date of original issuance of this Debenture between the Trustee and
the Company.

 

 

 

“3-Month LIBOR” as used herein, means the London interbank offered interest rate for
three-month U.S. dollar deposits determined by the Trustee in the following order of priority: (i)
the rate (expressed as a percentage per annum) for U.S. dollar deposits having a three-month
maturity that appears on Reuters Screen LIBOR01 Page as of 11:00 a.m. (London time) on the
related Determination Date (“Reuters Screen LIBOR01 Page” means the display designated as “Reuters
Screen LIBOR01 Page” or such other page as may replace Reuters Screen LIBOR01 Page on that service
or such other service or services as may be nominated by the British Bankers’ Association as the
information vendor for the purpose of displaying London interbank offered rates for U.S. dollar
deposits. If at least two rates appear on the Reuters Screen LIBOR01 Page, the rate on the
Determination Date will be the arithmetic mean of such rates); (ii) if such rate cannot be
identified on the related Determination Date, the Trustee will request the principal London offices
of four leading banks in the London interbank market to provide such banks’ offered quotations
(expressed as percentages per annum) to prime banks in the London interbank market for U.S. dollar
deposits having a three-month maturity as of 11:00 a.m. (London time) on such Determination Date.
If at least two quotations are provided, 3-Month LIBOR will be the arithmetic mean of such
quotations; (iii) if fewer than two such quotations are provided as requested in clause (ii) above,
the Trustee will request four major New York City banks to provide such banks’ offered quotations
(expressed as percentages per annum) to leading European banks for loans in U.S. dollars as of
11:00 a.m. (London time) on such Determination Date. If at least two such quotations are provided,
3-Month LIBOR will be the arithmetic mean of such quotations; and (iv) if fewer than two such
quotations are provided as requested in clause (iii) above, 3-Month LIBOR will be a 3-Month LIBOR
determined with respect to the Distribution Period immediately preceding such current Distribution
Period. If the rate for U.S. dollar deposits having a three-month maturity that initially appears
on Reuters Screen LIBOR01 Page as of 11:00 a.m. (London time) on the related Determination Date is
superseded on the Reuters Screen LIBOR01 Page by a corrected rate by 12:00 noon (London time) on
such Determination Date, then the corrected rate as so substituted on the applicable page will be
the applicable 3-Month LIBOR for such Determination Date. As used herein, “Determination Date”
means the date that is two London Banking Days (i.e., a business day in which dealings in deposits
in U.S. dollars are transacted in the London interbank market) preceding the commencement of the
relevant Distribution Period.

“Interest Rate” means for the period beginning on (and including) the date of original
issuance and ending on (but excluding) the Interest Payment Date in December 2012 the rate per
annum of 8.25% and for each Distribution Period thereafter, the Coupon Rate.

The Interest Rate for any Distribution Period will at no time be higher than the maximum rate
then permitted by New York law as the same may be modified by United States law.

All percentages resulting from any calculations on the Debentures will be rounded, if
necessary, to the nearest one hundred-thousandth of a percentage point, with five one-millionths of
a percentage point rounded upward (e.g., 9.876545% (or .09876545) being rounded to 9.87655% (or .0987655), and all dollar amounts used in or resulting from such calculation will be rounded to the
nearest cent (with one-half cent being rounded upward)).

The principal of and interest on this Debenture shall be payable at the office or agency of
the Trustee (or other paying agent appointed by the Company) maintained for that purpose in any
coin or currency of the United States of America that at the time of payment is legal tender for
payment of public and private debts; provided, however, that payment of interest
may be made by check mailed to the registered holder at such address as shall appear in the
Debenture Register if a request for a wire transfer by such holder has not been received by the Company or by
wire transfer to an account appropriately designated by the holder hereof. Notwithstanding the
foregoing, so long as the holder of this Debenture is the Institutional Trustee, the payment of the
principal of and interest on this Debenture will be made in immediately available funds at such
place and to such account as may be designated by the Trustee.

 

 

 

So long as no Event of Default has occurred and is continuing, the Company shall have the
right, from time to time, and without causing an Event of Default, to defer payments of interest on
the Debentures by extending the interest payment period on the Debentures at any time and from time
to time during the term of the Debentures, for up to 20 consecutive quarterly periods (each such
extended interest payment period, an “Extension Period”), during which Extension Period no interest
(including Additional Interest) shall be due and payable (except any Additional Sums that may be
due and payable). No Extension Period may end on a date other than an Interest Payment Date.
During an Extension Period, interest will continue to accrue on the Debentures, and interest on
such accrued interest will accrue at an annual rate equal to the Interest Rate in effect for such
Extension Period, compounded quarterly from the date such interest would have been payable were it
not for the Extension Period, to the extent permitted by law (such interest referred to herein as
“Additional Interest”). At the end of any such Extension Period the Company shall pay all interest
then accrued and unpaid on the Debentures (together with Additional Interest thereon);
provided, however, that no Extension Period may extend beyond the Maturity Date;
provided further, however, that during any such Extension Period, the
Company shall not and shall not permit any Affiliate of the Company controlled by the Company to
engage in any of the activities or transactions described on the reverse side hereof and in the
Indenture. Prior to the termination of any Extension Period, the Company may further extend such
period, provided that such period together with all such previous and further consecutive
extensions thereof shall not exceed 20 consecutive quarterly periods, or extend beyond the Maturity
Date. Upon the termination of any Extension Period and upon the payment of all accrued and unpaid
interest and Additional Interest, the Company may commence a new Extension Period, subject to the
foregoing requirements. No interest or Additional Interest shall be due and payable during an
Extension Period, except at the end thereof, but each installment of interest that would otherwise
have been due and payable during an Extension Period shall bear Additional Interest to the extent
permitted by applicable law. The Company must give the Trustee notice of its election to begin or
extend an Extension Period at least 5 Business Days prior to the regular record date (as such term
is used in Section 2.8 of the Indenture) immediately preceding the Interest Payment Date with
respect to which interest on the Debentures would have been payable except for the election to
begin or extend an Extension Period. The Trustee shall give notice of the Company’s election to
begin a new Extension Period to the holders of the Debentures.

The indebtedness evidenced by this Debenture is, to the extent provided in the Indenture,
subordinate and junior in right of payment to the prior payment in full of all Senior Indebtedness,
and this Debenture is issued subject to the provisions of the Indenture with respect thereto. Each
holder of this Debenture, by accepting the same, (a) agrees to and shall be bound by such
provisions, (b) authorizes and directs the Trustee on his or her behalf to take such action as may
be necessary or appropriate to acknowledge or effectuate the subordination so provided and
(c) appoints the Trustee his or her attorney-in-fact for any and all such purposes. Each holder
hereof, by his or her acceptance hereof, hereby waives all notice of the acceptance of the
subordination provisions contained herein and in the Indenture by each holder of Senior
Indebtedness, whether now outstanding or hereafter incurred, and waives reliance by each such
holder upon said provisions.

 

 

 

This Debenture shall not be entitled to any benefit under the Indenture hereinafter referred
to, be valid or become obligatory for any purpose until the certificate of authentication hereon
shall have been signed by or on behalf of the Trustee.

The provisions of this Debenture are continued on the reverse side hereof and such provisions
shall for all purposes have the same effect as though fully set forth at this place.

 

 

 

IN WITNESS WHEREOF, the Company has duly executed this certificate.

	 	 	 	 	 
	 	FIRST MERCURY FINANCIAL CORPORATION

 	 
	 	By:  	/s/
Jeffrey R. Wawok	 
	 	 	Name:  	Jeffrey R. Wawok 	 
	 	 	Title:  	Executive Vice President 	 
	 

CERTIFICATE OF AUTHENTICATION

This is one of the Debentures referred to in the within-mentioned Indenture.

	 	 	 	 	 
	 	WILMINGTON TRUST COMPANY, as Trustee

 	 
	 	By:  	/s/
Christopher J. Slaybaugh	 
	 	 	Authorized Officer 	 
	 	 	 	 
	 

 

 

 

[REVERSE OF DEBENTURE]

This Debenture is one of the fixed/floating rate junior subordinated deferrable interest
debentures of the Company, all issued or to be issued under and pursuant to the Indenture dated as
of September 26, 2007 (the “Indenture”), duly executed and delivered between the Company and the
Trustee, to which Indenture reference is hereby made for a description of the rights, limitations
of rights, obligations, duties and immunities thereunder of the Trustee, the Company and the
holders of the Debentures. The Debentures are limited in aggregate principal amount as specified
in the Indenture.

Upon the occurrence and continuation of a Special Event prior to the Interest Payment Date in
December 15, 2012, the Company shall have the right to redeem the Debentures in whole, but not in
part, at any Interest Payment Date, within 120 days following the occurrence of such Special Event,
at the Special Redemption Price.

In addition, the Company shall have the right to redeem the Debentures, in whole or in part,
but in all cases in a principal amount with integral multiples of $1,000.00, on any Interest
Payment Date on or after the Interest Payment Date in December 15, 2012 at the Optional Redemption
Price.

Prior to 10:00 a.m. New York City time on the Optional Redemption Date or Special Redemption
Date, as applicable, the Company will deposit with the Trustee or with one or more paying agents an
amount of money sufficient to redeem on the Optional Redemption Date or the Special Redemption
Date, as applicable, all the Debentures so called for redemption at the appropriate Optional
Redemption Price or Special Redemption Price.

If all, or less than all, the Debentures are to be redeemed, the Company will give the Trustee
notice not less than 45 nor more than 60 days prior to the Optional Redemption Date or Special
Redemption Date, as applicable, as to the aggregate principal amount of Debentures to be redeemed
and the Trustee shall select, in such manner as in its sole discretion it shall deem appropriate
and fair, the Debentures or portions thereof (in integral multiples of $1,000.00) to be redeemed.

Notwithstanding the foregoing, any redemption of Debentures by the Company shall be subject to
the receipt of any and all required regulatory approvals.

In case an Event of Default shall have occurred and be continuing, upon demand of the Trustee,
the principal of all of the Debentures shall become due and payable in the manner, with the effect
and subject to the conditions provided in the Indenture.

The Indenture contains provisions permitting the Company and the Trustee, with the consent of
the holders of not less than a majority in aggregate principal amount of the Debentures at the time
outstanding, to execute supplemental indentures for the purpose of adding any provisions to or
changing in any manner or eliminating any of the provisions of this Indenture or of any
supplemental indenture or of modifying in any manner the rights of the holders of the Debentures;
provided, however, that no such supplemental indenture shall without the consent of
the holders of each Debenture then outstanding and affected thereby (i) change the fixed maturity
of any Debenture, or reduce the principal amount thereof or any premium thereon, or reduce the rate or extend the time of payment of interest thereon, or reduce any amount
payable on redemption thereof or make the principal thereof or any interest or premium thereon
payable in any coin or currency other than that provided in the Debentures, or impair or affect the
right of any Securityholder to institute suit for payment thereof or impair the right of repayment,
if any, at the option of the holder, or (ii) reduce the aforesaid percentage of Debentures the
holders of which are required to consent to any such supplemental indenture.

 

 

 

The Indenture also contains provisions permitting the holders of a majority in aggregate
principal amount of the Debentures at the time outstanding on behalf of the holders of all of the
Debentures to waive (or modify any previously granted waiver of) any past default or Event of
Default, and its consequences, except an Event of Default (a) specified in Sections 5.1(a) and (b),
(b) in respect of covenants or provisions hereof or of the Indenture which cannot be modified or
amended without the consent of the holder of each Debenture affected, or (c) in respect of the
covenants contained in Section 3.9 of the Indenture; provided, however, that if the
Debentures are held by the Trust or a trustee of the Trust, such waiver or modification to such
waiver shall not be effective until the holders of a majority in Liquidation Amount of the Trust
Securities shall have consented to such waiver or modification to such waiver, provided,
further, that if the consent of the holder of each outstanding Debenture is required, such
waiver shall not be effective until each holder of the Trust Securities shall have consented to
such waiver. Upon any such waiver, the default covered thereby shall be deemed to be cured for all
purposes of the Indenture and the Company, the Trustee and the holders of the Debentures shall be
restored to their former positions and rights hereunder, respectively; but no such waiver shall
extend to any subsequent or other default or Event of Default or impair any right consequent
thereon. Whenever any default or Event of Default hereunder shall have been waived as permitted by
the Indenture, said default or Event of Default shall for all purposes of the Debentures and the
Indenture be deemed to have been cured and to be not continuing.

No reference herein to the Indenture and no provision of this Debenture or of the Indenture
shall alter or impair the obligation of the Company, which is absolute and unconditional, to pay
the principal of and premium, if any, and interest, including Additional Interest, on this
Debenture at the time and place and at the rate and in the money herein prescribed.

The Company has agreed that if Debentures are initially issued to the Trust or a trustee of
such Trust in connection with the issuance of Trust Securities by the Trust (regardless of whether
Debentures continue to be held by such Trust) and (i) there shall have occurred and be continuing
an Event of Default, (ii) the Company shall be in default with respect to its payment of any
obligations under the Capital Securities Guarantee, or (iii) the Company shall have given notice of
its election to defer payments of interest on the Debentures by extending the interest payment
period as provided herein and such Extension Period, or any extension thereof, shall be continuing,
then the Company shall not, and shall not permit any Affiliate of the Company controlled by the
Company to, (x) declare or pay any dividends or distributions on, or redeem, purchase, acquire, or
make a liquidation payment with respect to, any of the Company’s or such Affiliates’ Capital Stock
(other than payments of dividends or distributions to the Company or a Subsidiary of the Company)
or make any guarantee payments with respect to the foregoing, (y) make any payment of principal of
or interest or premium, if any, on or repay, repurchase or redeem any debt securities of the
Company or any Affiliate of the Company controlled by the

 

 

 

Company that rank pari passu in all respects with or junior in interest to the Debentures or
(z) enter into, amend or modify any contracts with shareholders holding more than 10% of the
outstanding shares of common stock of the Company (other than, with respect to clauses (x) and (y)
above, (1) repurchases, redemptions or other acquisitions of shares of Capital Stock of the Company
or any Subsidiary of the Company in connection with any employment contract, benefit plan or other
similar arrangement with or for the benefit of one or more employees, officers, directors or
consultants, in connection with a dividend reinvestment or stockholder stock purchase plan or in
connection with the issuance of Capital Stock of the Company or of such Subsidiary (or securities
convertible into or exercisable for such Capital Stock) as consideration in an acquisition
transaction entered into prior to the applicable Extension Period, (2) as a result of any exchange
or conversion of any class or series of the Company’s Capital Stock (or any Capital Stock of a
Subsidiary of the Company) for any class or series of the Company’s Capital Stock (or in the case
of a Subsidiary of the Company, any class or series of such Subsidiary’s Capital Stock) or of any
class or series of the Company’s indebtedness for any class or series of the Company’s Capital
Stock (or in the case of indebtedness of a Subsidiary of the Company, of any class or series of
such Subsidiary’s indebtedness or any class or series of such Subsidiary’s Capital Stock), (3) the
purchase of fractional interests in shares of the Company’s Capital Stock (or the Capital Stock of
a Subsidiary of the Company) pursuant to the conversion or exchange provisions of such Capital
Stock or the security being converted or exchanged, (4) any declaration of a dividend in connection
with any stockholders’ rights plan, or the issuance of rights, stock or other property under any
stockholders’ rights plan, or the redemption or repurchase of rights pursuant thereto, (5) any
dividend in the form of stock, warrants, options or other rights where the dividend stock or the
stock issuable upon exercise of such warrants, options or other rights is the same stock as that on
which the dividend is being paid or ranks pari passu with or junior to such stock and any cash
payments in lieu of fractional shares issued in connection therewith, or (6) payments under the
Capital Securities Guarantee).

The Debentures are issuable only in registered, certificated form without coupons and in
minimum denominations of $100,000.00 and any multiple of $1,000.00 in excess thereof. As provided
in the Indenture and subject to the transfer restrictions and limitations as may be contained
herein and therein from time to time, this Debenture is transferable by the holder hereof on the
Debenture Register of the Company. Upon due presentment for registration of transfer of any
Debenture at the Principal Office of the Trustee or at any office or agency of the Company
maintained for such purpose as provided in Section 3.2 of the Indenture, the Company shall execute,
the Company or the Trustee shall register and the Trustee or the Authenticating Agent shall
authenticate and make available for delivery in the name of the transferee or transferees a new
Debenture for a like aggregate principal amount. All Debentures presented for registration of
transfer or for exchange or payment shall (if so required by the Company or the Trustee or the
Authenticating Agent) be duly endorsed by, or be accompanied by a written instrument or instruments
of transfer in form satisfactory to, the Company and the Trustee or the Authenticating Agent duly
executed by the holder or his attorney duly authorized in writing. No service charge shall be made
for any exchange or registration of transfer of Debentures, but the Company or the Trustee may
require payment of a sum sufficient to cover any tax, fee or other governmental charge that may be
imposed in connection therewith.

 

 

 

Prior to due presentment for registration of transfer of any Debenture, the Company, the
Trustee, any Authenticating Agent, any paying agent, any transfer agent and any Debenture
registrar may deem the Person in whose name such Debenture shall be registered upon the
Debenture Register to be, and may treat him as, the absolute owner of such Debenture (whether or
not such Debenture shall be overdue) for the purpose of receiving payment of or on account of the
principal of, premium, if any, and interest on such Debenture and for all other purposes; and
neither the Company nor the Trustee nor any Authenticating Agent nor any paying agent nor any
transfer agent nor any Debenture registrar shall be affected by any notice to the contrary. All
such payments so made to any holder for the time being or upon his order shall be valid, and, to
the extent of the sum or sums so paid, effectual to satisfy and discharge the liability for moneys
payable upon any such Debenture.

The Debentures are in registered form within the meaning of Treasury Regulations Section
1.871-14(c)(1)(i) for U.S. federal income and withholding tax purposes.

No recourse for the payment of the principal of or premium, if any, or interest on any
Debenture, or for any claim based thereon or otherwise in respect thereof, and no recourse under or
upon any obligation, covenant or agreement of the Company in the Indenture or in any supplemental
indenture, or in any such Debenture, or because of the creation of any indebtedness represented
thereby, shall be had against any incorporator, stockholder, employee, officer or director, as
such, past, present or future, of the Company or of any successor Person of the Company, either
directly or through the Company or any successor Person of the Company, whether by virtue of any
constitution, statute or rule of law, or by the enforcement of any assessment or penalty or
otherwise, it being expressly understood that all such liability is hereby expressly waived and
released as a condition of, and as a consideration for, the execution of the Indenture and the
issue of the Debentures.

PURSUANT TO SECTION 5-1401 OF THE GENERAL OBLIGATIONS LAW OF THE STATE OF NEW YORK, THE
INDENTURE AND THIS DEBENTURE SHALL BE GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH THE LAWS OF THE
STATE OF NEW YORK.Filed by Bowne Pure Compliance

 

Exhibit 4.4

 

GUARANTEE AGREEMENT

by and between

FIRST MERCURY FINANCIAL CORPORATION

and

WILMINGTON TRUST COMPANY

Dated as of September 26, 2007

 

 

 

 

TABLE OF CONTENTS

	 	 	 	 	 
	 	 	Page	 
	 
	ARTICLE I DEFINITIONS AND INTERPRETATION
	 	 	1	 
	 
	 	 	 	 
	Section 1.1 Definitions and Interpretation
	 	 	1	 
	 
	 	 	 	 
	ARTICLE II POWERS, DUTIES AND RIGHTS OF THE GUARANTEE TRUSTEE
	 	 	5	 
	 
	 	 	 	 
	Section 2.1 Powers and Duties of the Guarantee Trustee
	 	 	5	 
	Section 2.2 Certain Rights of the Guarantee Trustee
	 	 	6	 
	Section 2.3 Not Responsible for Recitals or Issuance of Guarantee
	 	 	8	 
	Section 2.4 Events of Default; Waiver
	 	 	8	 
	Section 2.5 Events of Default; Notice
	 	 	8	 
	 
	 	 	 	 
	ARTICLE III GUARANTEE TRUSTEE
	 	 	9	 
	 
	 	 	 	 
	Section 3.1 Guarantee Trustee; Eligibility
	 	 	9	 
	Section 3.2 Appointment, Removal and Resignation of the Guarantee Trustee
	 	 	9	 
	 
	 	 	 	 
	ARTICLE IV GUARANTEE
	 	 	10	 
	 
	 	 	 	 
	Section 4.1 Guarantee
	 	 	10	 
	Section 4.2 Waiver of Notice and Demand
	 	 	10	 
	Section 4.3 Obligations Not Affected
	 	 	10	 
	Section 4.4 Rights of Holders
	 	 	11	 
	Section 4.5 Guarantee of Payment
	 	 	12	 
	Section 4.6 Subrogation
	 	 	12	 
	Section 4.7 Independent Obligations
	 	 	12	 
	Section 4.8 Enforcement by a Beneficiary
	 	 	12	 
	 
	 	 	 	 
	ARTICLE V LIMITATION OF TRANSACTIONS; SUBORDINATION
	 	 	13	 
	 
	 	 	 	 
	Section 5.1 Limitation of Transactions
	 	 	13	 
	Section 5.2 Ranking
	 	 	14	 
	 
	 	 	 	 
	ARTICLE VI TERMINATION
	 	 	14	 
	 
	 	 	 	 
	Section 6.1 Termination
	 	 	14	 
	 
	 	 	 	 
	ARTICLE VII INDEMNIFICATION
	 	 	14	 
	 
	 	 	 	 
	Section 7.1 Exculpation
	 	 	14	 
	Section 7.2 Indemnification
	 	 	15	 
	Section 7.3 Compensation; Reimbursement of Expenses
	 	 	16	 

 

i 

 

	 	 	 	 	 
	 	 	Page	 
	 
	ARTICLE VIII MISCELLANEOUS
	 	 	16	 
	 
	 	 	 	 
	Section 8.1 Successors and Assigns
	 	 	16	 
	Section 8.2 Amendments
	 	 	17	 
	Section 8.3 Notices
	 	 	17	 
	Section 8.4 Benefit
	 	 	17	 
	Section 8.5 Governing Law
	 	 	18	 
	Section 8.6 Counterparts
	 	 	18	 
	Section 8.7 Separability
	 	 	18	 

 

ii 

 

GUARANTEE AGREEMENT

This GUARANTEE AGREEMENT (this “Guarantee”), dated as of September 26, 2007, is executed and
delivered by First Mercury Financial Corporation, a Delaware corporation (the “Guarantor”), and
Wilmington Trust Company, a Delaware banking corporation, as trustee (the “Guarantee Trustee”), for
the benefit of the Holders (as defined herein) from time to time of the Capital Securities (as
defined herein) of First Mercury Capital Trust IV, a Delaware statutory trust (the “Issuer”).

WHEREAS, pursuant to an Amended and Restated Declaration of Trust (the “Declaration”), dated
as of the date hereof among Wilmington Trust Company, not in its individual capacity but solely as
institutional trustee, the administrators of the Issuer named therein, the Guarantor, as sponsor,
and the holders from time to time of undivided beneficial interests in the assets of the Issuer,
the Issuer is issuing on the date hereof those undivided beneficial interests, having an aggregate
liquidation amount of $20,000,000 (the “Capital Securities”); and

WHEREAS, as incentive for the Holders to purchase the Capital Securities, the Guarantor
desires irrevocably and unconditionally to agree, to the extent set forth in this Guarantee, to pay
to the Holders of Capital Securities the Guarantee Payments (as defined herein) and to make certain
other payments on the terms and conditions set forth herein;

NOW, THEREFORE, in consideration of the purchase by each Holder of the Capital Securities,
which purchase the Guarantor hereby agrees shall benefit the Guarantor, the Guarantor executes and
delivers this Guarantee for the benefit of the Holders.

ARTICLE I

DEFINITIONS AND INTERPRETATION

Section 1.1 Definitions and Interpretation.

In this Guarantee, unless the context otherwise requires:

(a) capitalized terms used in this Guarantee but not defined in the preamble above have the
respective meanings assigned to them in this Section 1.1;

(b) a term defined anywhere in this Guarantee has the same meaning throughout;

(c) all references to “the Guarantee” or “this Guarantee” are to this Guarantee as modified,
supplemented or amended from time to time;

(d) all references in this Guarantee to “Articles” or “Sections” are to Articles or Sections
of this Guarantee, unless otherwise specified;

(e) terms defined in the Declaration as at the date of execution of this Guarantee have the
same meanings when used in this Guarantee, unless otherwise defined in this Guarantee or unless the
context otherwise requires; and

 (f) a reference to the singular includes the plural and vice versa.

 

 

 

“Affiliate” has the same meaning as given to that term in Rule 405 of the Securities
Act of 1933, as amended, or any successor rule thereunder.

“Beneficiaries” means any Person to whom the Issuer is or hereafter becomes indebted
or liable.

“Capital Securities” has the meaning set forth in the recitals to this Guarantee.

“Common Securities” means the common securities issued by the Issuer to the Guarantor
pursuant to the Declaration.

“Corporate Trust Office” means the office of the Guarantee Trustee at which the
corporate trust business of the Guarantee Trustee shall, at any particular time, be principally
administered, which office at the date of execution of this Guarantee is located at 1100 North
Market Street, Wilmington, Delaware 19890-1600, Attention: Corporate Trust Administration.

“Covered Person” means any Holder of Capital Securities.

“Debentures” means the debt securities of the Guarantor designated the Fixed/Floating
Rate Junior Subordinated Deferrable Interest Debentures due 2037 held by the Institutional Trustee
(as defined in the Declaration) of the Issuer.

“Declaration” has the meaning set forth in the recitals to this Guarantee.

“Declaration Event of Default” means an “Event of Default” as defined in the
Declaration.

“Event of Default” has the meaning set forth in Section 2.4(a).

“Guarantee Payments” means the following payments or distributions, without
duplication, with respect to the Capital Securities, to the extent not paid or made by the Issuer:
(i) any accrued and unpaid Distributions (as defined in the Declaration) which are required to be
paid on such Capital Securities to the extent the Issuer shall have funds available therefor,
(ii) the Optional Redemption Price to the extent the Issuer has funds available therefor, with
respect to any Capital Securities called for redemption by the Issuer, (iii) the Special Redemption
Price to the extent the Issuer has funds available therefor, with respect to Capital Securities
redeemed upon the occurrence of a Special Event, and (iv) upon a voluntary or involuntary
liquidation, dissolution, winding-up or termination of the Issuer (other than in connection with
the distribution of Debentures to the Holders of the Capital Securities in exchange therefor as
provided in the Declaration), the lesser of (a) the aggregate of the liquidation amount and all
accrued and unpaid Distributions on the Capital Securities to the date of payment, to the extent
the Issuer shall have funds available therefor, and (b) the amount of assets of the Issuer
remaining available for distribution to Holders in liquidation of the Issuer (in either case, the
“Liquidation Distribution”).

 

 

 

“Guarantee Trustee” means Wilmington Trust Company, until a Successor Guarantee
Trustee has been appointed and has accepted such appointment pursuant to the terms of this
Guarantee and thereafter means each such Successor Guarantee Trustee.

“Guarantor” means First Mercury Financial Corporation and each of its successors and
assigns.

“Holder” means any holder, as registered on the books and records of the Issuer, of
any Capital Securities; provided, however, that, in determining whether the Holders
of the requisite percentage of Capital Securities have given any request, notice, consent or waiver
hereunder, “Holder” shall not include the Guarantor or any Affiliate of the Guarantor.

“Indemnified Person” means the Guarantee Trustee, any Affiliate of the Guarantee
Trustee, or any officers, directors, shareholders, members, partners, employees, representatives,
nominees, custodians or agents of the Guarantee Trustee.

“Indenture” means the Indenture dated as of the date hereof between the Guarantor and
Wilmington Trust Company, not in its individual capacity but solely as trustee, and any indenture
supplemental thereto pursuant to which the Debentures are to be issued to the institutional trustee
of the Issuer.

“Issuer” has the meaning set forth in the opening paragraph to this Guarantee.

“Liquidation Distribution” has the meaning set forth in the definition of “Guarantee
Payments” herein.

“Majority in liquidation amount of the Capital Securities” means Holder(s) of
outstanding Capital Securities, voting together as a class, but separately from the holders of
Common Securities, of more than 50% of the aggregate liquidation amount (including the stated
amount that would be paid on redemption, liquidation or otherwise, plus accrued and unpaid
Distributions to the date upon which the voting percentages are determined) of all Capital
Securities then outstanding.

“Obligations” means any costs, expenses or liabilities (but not including liabilities
related to taxes) of the Issuer other than obligations of the Issuer to pay to holders of any Trust
Securities the amounts due such holders pursuant to the terms of the Trust Securities.

“Officer’s Certificate” means, with respect to any Person, a certificate signed by one
Authorized Officer of such Person. Any Officer’s Certificate delivered with respect to compliance
with a condition or covenant provided for in this Guarantee shall include:

(a) a statement that the officer signing the Officer’s Certificate has read the
covenant or condition and the definitions relating thereto;

(b) a brief statement of the nature and scope of the examination or investigation
undertaken by the officer in rendering the Officer’s Certificate;

 

 

 

(c) a statement that the officer has made such examination or investigation as, in such
officer’s opinion, is necessary to enable such officer to express an informed opinion as to
whether or not such covenant or condition has been complied with; and

(d) a statement as to whether, in the opinion of the officer, such condition or
covenant has been complied with.

“Optional Redemption Price” has the meaning set forth in the Indenture.

“Person” means a legal person, including any individual, corporation, estate,
partnership, joint venture, association, joint stock company, limited liability company, trust,
unincorporated association, or government or any agency or political subdivision thereof, or any
other entity of whatever nature.

“Responsible Officer” means, with respect to the Guarantee Trustee, any officer within
the Corporate Trust Office of the Guarantee Trustee including any Vice President, Assistant Vice
President, Secretary, Assistant Secretary or any other officer of the Guarantee Trustee customarily
performing functions similar to those performed by any of the above designated officers and also,
with respect to a particular corporate trust matter, any other officer to whom such matter is
referred because of that officer’s knowledge of and familiarity with the particular subject.

“Special Event” has the meaning set forth in the Indenture.

“Special Redemption Price” has the meaning set forth in the Indenture.

“Subsidiary” means with respect to any Person, (i) any corporation at least a
majority of the outstanding voting stock of which is owned, directly or indirectly, by such Person
or by one or more of its Subsidiaries, or by such Person and one or more of its Subsidiaries, (ii)
any general partnership, joint venture or similar entity, at least a majority of the outstanding
partnership or similar interests of which shall at the time be owned by such Person, or by one or
more of its Subsidiaries, or by such Person and one or more of its Subsidiaries and (iii) any
limited partnership of which such Person or any of its Subsidiaries is a general partner. For the
purposes of this definition, “voting stock” means shares, interests, participations or other
equivalents in the equity interest (however designated) in such Person having ordinary voting power
for the election of a majority of the directors (or the equivalent) of such Person, other than
shares, interests, participations or other equivalents having such power only by reason of the
occurrence of a contingency.

“Successor Guarantee Trustee” means a successor Guarantee Trustee possessing the
qualifications to act as Guarantee Trustee under Section 3.1.

“Trust Securities” means the Common Securities and the Capital Securities.

 

 

 

ARTICLE II

POWERS, DUTIES AND RIGHTS OF THE

GUARANTEE TRUSTEE

Section 2.1 Powers and Duties of the Guarantee Trustee.

(a) This Guarantee shall be held by the Guarantee Trustee for the benefit of the Holders of
the Capital Securities, and the Guarantee Trustee shall not transfer this Guarantee to any Person
except a Holder of Capital Securities exercising his or her rights pursuant to Section 4.4(b) or to
a Successor Guarantee Trustee on acceptance by such Successor Guarantee Trustee of its appointment
to act as Successor Guarantee Trustee. The right, title and interest of the Guarantee Trustee
shall automatically vest in any Successor Guarantee Trustee, and such vesting and cessation of
title shall be effective whether or not conveyancing documents have been executed and delivered
pursuant to the appointment of such Successor Guarantee Trustee.

(b) If an Event of Default actually known to a Responsible Officer of the Guarantee Trustee
has occurred and is continuing, the Guarantee Trustee shall enforce this Guarantee for the benefit
of the Holders of the Capital Securities.

(c) The Guarantee Trustee, before the occurrence of any Event of Default and after the curing
or waiving of all Events of Default that may have occurred, shall undertake to perform only such
duties as are specifically set forth in this Guarantee, and no implied covenants shall be read into
this Guarantee against the Guarantee Trustee. In case an Event of Default has occurred (that has
not been cured or waived pursuant to Section 2.4) and is actually known to a Responsible Officer of
the Guarantee Trustee, the Guarantee Trustee shall exercise such of the rights and powers vested in
it by this Guarantee, and use the same degree of care and skill in its exercise thereof, as a
prudent person would exercise or use under the circumstances in the conduct of his or her own
affairs.

(d) No provision of this Guarantee shall be construed to relieve the Guarantee Trustee from
liability for its own negligent action, its own negligent failure to act, or its own willful
misconduct, except that:

(i) prior to the occurrence of any Event of Default and after the curing or waiving of
all such Events of Default that may have occurred:

(A) the duties and obligations of the Guarantee Trustee shall be determined
solely by the express provisions of this Guarantee, and the Guarantee Trustee shall
not be liable except for the performance of such duties and obligations as are
specifically set forth in this Guarantee, and no implied covenants or obligations
shall be read into this Guarantee against the Guarantee Trustee; and

(B) in the absence of bad faith on the part of the Guarantee Trustee, the
Guarantee Trustee may conclusively rely, as to the truth of the statements and the
correctness of the opinions expressed therein, upon any certificates or opinions
furnished to the Guarantee Trustee and conforming to the requirements of this Guarantee; but in the case of any such certificates or opinions that by any
provision hereof are specifically required to be furnished to the Guarantee Trustee,
the Guarantee Trustee shall be under a duty to examine the same to determine whether
or not they conform to the requirements of this Guarantee;

 

 

 

(ii) the Guarantee Trustee shall not be liable for any error of judgment made in good
faith by a Responsible Officer of the Guarantee Trustee, unless it shall be proved that such
Responsible Officer of the Guarantee Trustee or the Guarantee Trustee was negligent in
ascertaining the pertinent facts upon which such judgment was made;

(iii) the Guarantee Trustee shall not be liable with respect to any action taken or
omitted to be taken by it in good faith in accordance with the written direction of the
Holders of not less than a Majority in liquidation amount of the Capital Securities relating
to the time, method and place of conducting any proceeding for any remedy available to the
Guarantee Trustee, or relating to the exercise of any trust or power conferred upon the
Guarantee Trustee under this Guarantee; and

(iv) no provision of this Guarantee shall require the Guarantee Trustee to expend or
risk its own funds or otherwise incur personal financial liability in the performance of any
of its duties or in the exercise of any of its rights or powers, if the Guarantee Trustee
shall have reasonable grounds for believing that the repayment of such funds is not
reasonably assured to it under the terms of this Guarantee or security and indemnity,
reasonably satisfactory to the Guarantee Trustee, against such risk or liability is not
reasonably assured to it.

Section 2.2 Certain Rights of the Guarantee Trustee.

(a) Subject to the provisions of Section 2.1:

(i) The Guarantee Trustee may conclusively rely, and shall be fully protected in acting
or refraining from acting upon, any resolution, certificate, statement, instrument, opinion,
report, notice, request, direction, consent, order, bond, debenture, note, other evidence of
indebtedness or other paper or document believed by it to be genuine and to have been
signed, sent or presented by the proper party or parties.

(ii) Any direction or act of the Guarantor contemplated by this Guarantee shall be
sufficiently evidenced by an Officer’s Certificate.

(iii) Whenever, in the administration of this Guarantee, the Guarantee Trustee shall
deem it desirable that a matter be proved or established before taking, suffering or
omitting any action hereunder, the Guarantee Trustee (unless other evidence is herein
specifically prescribed) may, in the absence of bad faith on its part, request and
conclusively rely upon an Officer’s Certificate of the Guarantor which, upon receipt of such
request, shall be promptly delivered by the Guarantor.

(iv) The Guarantee Trustee shall have no duty to see to any recording, filing or
registration of any instrument (or any re-recording, refiling or re-registration thereof).

 

 

 

(v) The Guarantee Trustee may consult with counsel of its selection, and the advice or
opinion of such counsel with respect to legal matters shall be full and complete
authorization and protection in respect of any action taken, suffered or omitted by it
hereunder in good faith and in accordance with such advice or opinion. Such counsel may be
counsel to the Guarantor or any of its Affiliates and may include any of its employees. The
Guarantee Trustee shall have the right at any time to seek instructions concerning the
administration of this Guarantee from any court of competent jurisdiction.

(vi) The Guarantee Trustee shall be under no obligation to exercise any of the rights
or powers vested in it by this Guarantee at the request or direction of any Holder, unless
such Holder shall have provided to the Guarantee Trustee such security and indemnity,
reasonably satisfactory to the Guarantee Trustee, against the costs, expenses (including
attorneys’ fees and expenses and the expenses of the Guarantee Trustee’s agents, nominees or
custodians) and liabilities that might be incurred by it in complying with such request or
direction, including such reasonable advances as may be requested by the Guarantee Trustee;
provided, however, that nothing contained in this Section 2.2(a)(vi) shall
relieve the Guarantee Trustee, upon the occurrence of an Event of Default, of its obligation
to exercise the rights and powers vested in it by this Guarantee.

(vii) The Guarantee Trustee shall not be bound to make any investigation into the facts
or matters stated in any resolution, certificate, statement, instrument, opinion, report,
notice, request, direction, consent, order, bond, debenture, note, other evidence of
indebtedness or other paper or document, but the Guarantee Trustee, in its discretion, may
make such further inquiry or investigation into such facts or matters as it may see fit.

(viii) The Guarantee Trustee may execute any of the trusts or powers hereunder or
perform any duties hereunder either directly or by or through agents, nominees, custodians
or attorneys, and the Guarantee Trustee shall not be responsible for any misconduct or
negligence on the part of any agent or attorney appointed with due care by it hereunder.

(ix) Any action taken by the Guarantee Trustee or its agents hereunder shall bind the
Holders of the Capital Securities, and the signature of the Guarantee Trustee or its agents
alone shall be sufficient and effective to perform any such action. No third party shall be
required to inquire as to the authority of the Guarantee Trustee to so act or as to its
compliance with any of the terms and provisions of this Guarantee, both of which shall be
conclusively evidenced by the Guarantee Trustee’s or its agent’s taking such action.

(x) Whenever in the administration of this Guarantee the Guarantee Trustee shall deem
it desirable to receive instructions with respect to enforcing any remedy or right or taking
any other action hereunder, the Guarantee Trustee (i) may request instructions from the
Holders of a Majority in liquidation amount of the Capital Securities, (ii) may refrain from
enforcing such remedy or right or taking such other action until such instructions are
received, and (iii) shall be protected in conclusively relying on or acting in accordance
with such instructions.

 

 

 

(xi) The Guarantee Trustee shall not be liable for any action taken, suffered, or
omitted to be taken by it in good faith, without negligence, and reasonably believed by it
to be authorized or within the discretion or rights or powers conferred upon it by this
Guarantee.

(b) No provision of this Guarantee shall be deemed to impose any duty or obligation on the
Guarantee Trustee to perform any act or acts or exercise any right, power, duty or obligation
conferred or imposed on it, in any jurisdiction in which it shall be illegal or in which the
Guarantee Trustee shall be unqualified or incompetent in accordance with applicable law to perform
any such act or acts or to exercise any such right, power, duty or obligation. No permissive power
or authority available to the Guarantee Trustee shall be construed to be a duty.

Section 2.3 Not Responsible for Recitals or Issuance of Guarantee.

The recitals contained in this Guarantee shall be taken as the statements of the Guarantor,
and the Guarantee Trustee does not assume any responsibility for their correctness. The Guarantee
Trustee makes no representation as to the validity or sufficiency of this Guarantee.

Section 2.4 Events of Default; Waiver.

(a) An Event of Default under this Guarantee will occur upon the failure of the Guarantor to
perform any of its payment or other obligations hereunder.

(b) The Holders of a Majority in liquidation amount of the Capital Securities may, voting or
consenting as a class, on behalf of the Holders of all of the Capital Securities, waive any past
Event of Default and its consequences. Upon such waiver, any such Event of Default shall cease to
exist, and shall be deemed to have been cured, for every purpose of this Guarantee, but no such
waiver shall extend to any subsequent or other default or Event of Default or impair any right
consequent thereon.

Section 2.5 Events of Default; Notice.

(a) The Guarantee Trustee shall, within 90 days after the occurrence of an Event of Default,
transmit by mail, first class postage prepaid, to the Holders of the Capital Securities and the
Guarantor, notices of all Events of Default actually known to a Responsible Officer of the
Guarantee Trustee, unless such defaults have been cured before the giving of such notice,
provided, however, that the Guarantee Trustee shall be protected in withholding
such notice if and so long as a Responsible Officer of the Guarantee Trustee in good faith
determines that the withholding of such notice is in the interests of the Holders of the Capital
Securities.

(b) The Guarantee Trustee shall not be deemed to have knowledge of any Event of Default unless
the Guarantee Trustee shall have received written notice from the Guarantor or a Holder of the
Capital Securities (except in the case of a payment default), or a Responsible Officer of the
Guarantee Trustee charged with the administration of this Guarantee shall have obtained actual
knowledge thereof.

 

 

 

ARTICLE III

GUARANTEE TRUSTEE

Section 3.1 Guarantee Trustee; Eligibility.

(a) There shall at all times be a Guarantee Trustee which shall:

(i) not be an Affiliate of the Guarantor, and

(ii) be a banking corporation or national association organized and doing business
under the laws of the United States of America or any State or Territory thereof or of the
District of Columbia, or Person authorized under such laws to exercise corporate trust
powers, having a combined capital and surplus of at least fifty million U.S. dollars
($50,000,000), and subject to supervision or examination by Federal, State, Territorial or
District of Columbia authority. If such corporation or national association publishes
reports of condition at least annually, pursuant to law or to the requirements of the
supervising or examining authority referred to above, then, for the purposes of this Section
3.1(a)(ii), the combined capital and surplus of such corporation or national association
shall be deemed to be its combined capital and surplus as set forth in its most recent
report of condition so published.

(b) If at any time the Guarantee Trustee shall cease to be eligible to so act under
Section 3.1(a), the Guarantee Trustee shall immediately resign in the manner and with the effect
set forth in Section 3.2(c).

(c) If the Guarantee Trustee has or shall acquire any “conflicting interest” within the
meaning of Section 310(b) of the Trust Indenture Act, the Guarantee Trustee shall either eliminate
such interest or resign to the extent and in the manner provided by, and subject to this Guarantee.

Section 3.2 Appointment, Removal and Resignation of the Guarantee Trustee.

(a) Subject to Section 3.2(b), the Guarantee Trustee may be appointed or removed without cause
at any time by the Guarantor except during an Event of Default.

(b) The Guarantee Trustee shall not be removed in accordance with Section 3.2(a) until a
Successor Guarantee Trustee has been appointed and has accepted such appointment by written
instrument executed by such Successor Guarantee Trustee and delivered to the Guarantor.

(c) The Guarantee Trustee appointed to office shall hold office until a Successor Guarantee
Trustee shall have been appointed or until its removal or resignation. The Guarantee Trustee may
resign from office (without need for prior or subsequent accounting) by an instrument in writing
executed by the Guarantee Trustee and delivered to the Guarantor, which resignation shall not take
effect until a Successor Guarantee Trustee has been appointed and has accepted such appointment by
an instrument in writing executed by such Successor Guarantee Trustee and delivered to the
Guarantor and the resigning Guarantee Trustee.

 

 

 

(d) If no Successor Guarantee Trustee shall have been appointed and accepted appointment as
provided in this Section 3.2 within 60 days after delivery of an instrument of removal or
resignation, the Guarantee Trustee resigning or being removed may petition any court of competent
jurisdiction for appointment of a Successor Guarantee Trustee. Such court may thereupon, after
prescribing such notice, if any, as it may deem proper, appoint a Successor Guarantee Trustee.

(e) No Guarantee Trustee shall be liable for the acts or omissions to act of any Successor
Guarantee Trustee.

(f) Upon termination of this Guarantee or removal or resignation of the Guarantee Trustee
pursuant to this Section 3.2, the Guarantor shall pay to the Guarantee Trustee all amounts owing to
the Guarantee Trustee under Sections 7.2 and 7.3 accrued to the date of such termination, removal
or resignation.

ARTICLE IV

GUARANTEE

Section 4.1 Guarantee.

(a) The Guarantor irrevocably and unconditionally agrees to pay in full to the Holders the
Guarantee Payments (without duplication of amounts theretofore paid by the Issuer), as and when
due, regardless of any defense (except the defense of payment by the Issuer), right of set-off or
counterclaim that the Issuer may have or assert. The Guarantor’s obligation to make a Guarantee
Payment may be satisfied by direct payment of the required amounts by the Guarantor to the Holders
or by causing the Issuer to pay such amounts to the Holders.

(b) The Guarantor hereby also agrees to assume any and all Obligations of the Issuer and in
the event any such Obligation is not so assumed, subject to the terms and conditions hereof, the
Guarantor hereby irrevocably and unconditionally guarantees to each Beneficiary the full payment,
when and as due, of any and all Obligations to such Beneficiaries. This Guarantee is intended to
be for the benefit of, and to be enforceable by, all such Beneficiaries, whether or not such
Beneficiaries have received notice hereof.

Section 4.2 Waiver of Notice and Demand.

The Guarantor hereby waives notice of acceptance of this Guarantee and of any liability to
which it applies or may apply, presentment, demand for payment, any right to require a proceeding
first against the Issuer or any other Person before proceeding against the Guarantor, protest,
notice of nonpayment, notice of dishonor, notice of redemption and all other notices and demands.

Section 4.3 Obligations Not Affected.

The obligations, covenants, agreements and duties of the Guarantor under this Guarantee shall
in no way be affected or impaired by reason of the happening from time to time of any of the
following:

 

 

 

(a) the release or waiver, by operation of law or otherwise, of the performance or observance
by the Issuer of any express or implied agreement, covenant, term or condition relating to the
Capital Securities to be performed or observed by the Issuer;

(b) the extension of time for the payment by the Issuer of all or any portion of the
Distributions, Optional Redemption Price, Special Redemption Price, Liquidation Distribution or any
other sums payable under the terms of the Capital Securities or the extension of time for the
performance of any other obligation under, arising out of or in connection with, the Capital
Securities (other than an extension of time for payment of Distributions, Optional Redemption
Price, Special Redemption Price, Liquidation Distribution or other sum payable that results from
the extension of any interest payment period on the Debentures or any extension of the maturity
date of the Debentures permitted by the Indenture);

(c) any failure, omission, delay or lack of diligence on the part of the Holders to enforce,
assert or exercise any right, privilege, power or remedy conferred on the Holders pursuant to the
terms of the Capital Securities, or any action on the part of the Issuer granting indulgence or
extension of any kind;

(d) the voluntary or involuntary liquidation, dissolution, sale of any collateral,
receivership, insolvency, bankruptcy, assignment for the benefit of creditors, reorganization,
arrangement, composition or readjustment of debt of, or other similar proceedings affecting, the
Issuer or any of the assets of the Issuer;

(e) any invalidity of, or defect or deficiency in, the Capital Securities;

(f) the settlement or compromise of any obligation guaranteed hereby or hereby incurred; or

(g) any other circumstance whatsoever that might otherwise constitute a legal or equitable
discharge or defense of a guarantor, it being the intent of this Section 4.3 that the obligations
of the Guarantor hereunder shall be absolute and unconditional under any and all circumstances.

There shall be no obligation of the Holders to give notice to, or obtain consent of, the
Guarantor with respect to the happening of any of the foregoing.

Section 4.4 Rights of Holders.

(a) The Holders of a Majority in liquidation amount of the Capital Securities have the right
to direct the time, method and place of conducting any proceeding for any remedy available to the
Guarantee Trustee in respect of this Guarantee or to direct the exercise of any trust or power
conferred upon the Guarantee Trustee under this Guarantee; provided, however, that
(subject to Section 2.1) the Guarantee Trustee shall have the right to decline to follow any such
direction if the Guarantee Trustee being advised by counsel determines that the action or
proceeding so directed may not lawfully be taken or if the Guarantee Trustee in good faith by its
board of directors or trustees, executive committees or a trust committee of directors or trustees
and/or Responsible Officers shall determine that the action or proceedings so directed would
involve the Guarantee Trustee in personal liability.

 

 

 

(b) Any Holder of Capital Securities may institute a legal proceeding directly against the
Guarantor to enforce the Guarantee Trustee’s rights under this Guarantee, without first instituting
a legal proceeding against the Issuer, the Guarantee Trustee or any other Person. The Guarantor
waives any right or remedy to require that any such action be brought first against the Issuer, the
Guarantee Trustee or any other Person before so proceeding directly against the Guarantor.

Section 4.5 Guarantee of Payment.

This Guarantee creates a guarantee of payment and not of collection.

Section 4.6 Subrogation.

The Guarantor shall be subrogated to all (if any) rights of the Holders of Capital Securities
against the Issuer in respect of any amounts paid to such Holders by the Guarantor under this
Guarantee; provided, however, that the Guarantor shall not (except to the extent
required by applicable provisions of law) be entitled to enforce or exercise any right that it may
acquire by way of subrogation or any indemnity, reimbursement or other agreement, in all cases as a
result of payment under this Guarantee, if, after giving effect to any such payment, any amounts
are due and unpaid under this Guarantee. If any amount shall be paid to the Guarantor in violation
of the preceding sentence, the Guarantor agrees to hold such amount in trust for the Holders and to
pay over such amount to the Holders.

Section 4.7 Independent Obligations.

The Guarantor acknowledges that its obligations hereunder are independent of the obligations
of the Issuer with respect to the Capital Securities and that the Guarantor shall be liable as
principal and as debtor hereunder to make Guarantee Payments pursuant to the terms of this
Guarantee notwithstanding the occurrence of any event referred to in subsections (a) through (g),
inclusive, of Section 4.3 hereof.

Section 4.8 Enforcement by a Beneficiary.

A Beneficiary may enforce the obligations of the Guarantor contained in Section 4.1(b)
directly against the Guarantor and the Guarantor waives any right or remedy to require that any
action be brought against the Issuer or any other person or entity before proceeding against the
Guarantor. The Guarantor shall be subrogated to all rights (if any) of any Beneficiary against the
Issuer in respect of any amounts paid to the Beneficiaries by the Guarantor under this Guarantee;
provided, however, that the Guarantor shall not (except to the extent required by
mandatory provisions of law) be entitled to enforce or exercise any rights that it may acquire by
way of subrogation or any indemnity, reimbursement or other agreement, in all cases as a result of
payment under this Guarantee, if at the time of any such payment, and after giving effect to such
payment, any amounts are due and unpaid under this Guarantee.

 

 

 

ARTICLE V

LIMITATION OF TRANSACTIONS; SUBORDINATION

Section 5.1 Limitation of Transactions.

So long as any Capital Securities remain outstanding, if (a) there shall have occurred and be
continuing an Event of Default or a Declaration Event of Default or (b) the Guarantor shall have
selected an Extension Period as provided in the Declaration and such period, or any extension
thereof, shall have commenced and be continuing, then the Guarantor shall not and shall not permit
any Affiliate of the Guarantor controlled by the Guarantor to (x) declare or pay any dividends or
distributions on, or redeem, purchase, acquire, or make a liquidation payment with respect to, any
of the Guarantor’s or such Affiliate’s capital stock (other than payments of dividends or
distributions to the Guarantor or a Subsidiary of the Guarantor) or make any guarantee payments
with respect to the foregoing; (y) make any payment of principal of or interest or premium, if any,
on or repay, repurchase or redeem any debt securities of the Guarantor or any Affiliate of the
Guarantor controlled by the Guarantor that rank pari passu in all respects with or junior in
interest to the Debentures; or (z) enter into, amend or modify any contract with a shareholder that
directly or indirectly beneficially owns (as determined under Rule 13d-3 of the Exchange Act and
which shall include securities beneficially owned by (i) all controlled Affiliates of such
shareholder and (ii) all other Persons with whom such shareholder would constitute a “group” within
the meaning of Section 13(d) of the Exchange Act and the rules promulgated thereunder) more than
10% of the outstanding shares of common stock of the Guarantor (other than, with respect to clauses
(x) and (y) above, (i) repurchases, redemptions or other acquisitions of shares of capital stock of
the Guarantor or any Subsidiary of the Guarantor in connection with any employment contract,
benefit plan or other similar arrangement with or for the benefit of one or more employees,
officers, directors or consultants, in connection with a dividend reinvestment or stockholder stock
purchase plan or in connection with the issuance of capital stock of the Guarantor or of such
Subsidiary (or securities convertible into or exercisable for such capital stock) as consideration
in an acquisition transaction entered into prior to the occurrence of the Event of Default,
Declaration Event of Default or Extension Period, as applicable, (ii) as a result of any exchange
or conversion of any class or series of the Guarantor’s capital stock (or any capital stock of a
Subsidiary of the Guarantor) for any class or series of the Guarantor’s capital stock (or in the
case of a Subsidiary of the Guarantor, any class or series of such Subsidiary’s capital stock) or
of any class or series of the Guarantor’s indebtedness for any class or series of the Guarantor’s
capital stock (or in the case of indebtedness of a Subsidiary of the Guarantor, of any class or
series of such Subsidiary’s indebtedness for any class or series of such Subsidiary’s capital
stock), (iii) the purchase of fractional interests in shares of the Guarantor’s capital stock (or
the capital stock of a Subsidiary of the Guarantor) pursuant to the conversion or exchange
provisions of such capital stock or the security being converted or exchanged, (iv) any declaration
of a dividend in connection with any stockholders’ rights plan, or the issuance of rights, stock or
other property under any stockholders’ rights plan, or the redemption or repurchase of rights
pursuant thereto, (v) any dividend in the form of stock, warrants, options or other rights where
the dividend stock or the stock issuable upon exercise of such warrants, options or other rights is
the same stock as that on which the dividend is being paid or ranks pari passu with or junior to
such stock and any cash payments in lieu of fractional shares issued in connection therewith, or
(vi) payments under this Guarantee).

 

 

 

Section 5.2 Ranking.

This Guarantee will constitute an unsecured obligation of the Guarantor and will rank
subordinate and junior in right of payment to all present and future Senior Indebtedness (as
defined in the Indenture) of the Guarantor. The Guarantor’s obligations in respect of this
Guarantee shall rank pari passu with the Guarantor’s obligations under the Guarantee Agreement by
and between the Guarantor and Wilmington Trust Company, as Guarantee Trustee, dated as of April 29,
2004, the Guarantor’s obligations under the Guarantee Agreement by and between the Guarantor and
Wilmington Trust Company, as Guarantee Trustee, dated as of May 26, 2004, and the Guarantor’s
obligations under the Guarantee Agreement by and between the Guarantor and Wilmington Trust
Company, as Guarantee Trustee, dated as of December 14, 2006. By their acceptance thereof, each
Holder of Capital Securities agrees to the foregoing provisions of this Guarantee and the other
terms set forth herein.

The right of the Guarantor to participate in any distribution of assets of any of its
Subsidiaries upon any such Subsidiary’s liquidation or reorganization or otherwise is subject to
the prior claims of creditors of that Subsidiary, except to the extent the Guarantor may itself be
recognized as a creditor of that Subsidiary. Accordingly, the Guarantor’s obligations under this
Guarantee will be effectively subordinated to all existing and future liabilities of the
Guarantor’s Subsidiaries, and claimants should look only to the assets of the Guarantor for
payments hereunder. This Guarantee does not limit the incurrence or issuance of other secured or
unsecured debt of the Guarantor, including Senior Indebtedness of the Guarantor, under any
indenture that the Guarantor may enter into in the future or otherwise.

ARTICLE VI

TERMINATION

Section 6.1 Termination.

This Guarantee shall terminate as to the Capital Securities (i) upon full payment of the
Optional Redemption Price or Special Redemption Price of all Capital Securities then outstanding,
(ii) upon the distribution of all of the Debentures to the Holders of all of the Capital Securities
or (iii) upon full payment of the amounts payable in accordance with the Declaration upon
dissolution of the Issuer. This Guarantee will continue to be effective or will be reinstated, as
the case may be, if at any time any Holder of Capital Securities must restore payment of any sums
paid under the Capital Securities or under this Guarantee.

ARTICLE VII

INDEMNIFICATION

Section 7.1 Exculpation.

(a) No Indemnified Person shall be liable, responsible or accountable in damages or otherwise
to the Guarantor or any Covered Person for any loss, damage or claim incurred by reason of any act
or omission performed or omitted by such Indemnified Person in good faith in accordance with this
Guarantee and in a manner that such Indemnified Person reasonably
believed to be within the scope of the authority conferred on such Indemnified Person by this
Guarantee or by law, except that an Indemnified Person shall be liable for any such loss, damage or
claim incurred by reason of such Indemnified Person’s negligence or willful misconduct with respect
to such acts or omissions.

 

 

 

(b) An Indemnified Person shall be fully protected in relying in good faith upon the records
of the Issuer or the Guarantor and upon such information, opinions, reports or statements presented
to the Issuer or the Guarantor by any Person as to matters the Indemnified Person reasonably
believes are within such other Person’s professional or expert competence and who, if selected by
such Indemnified Person, has been selected with reasonable care by such Indemnified Person,
including information, opinions, reports or statements as to the value and amount of the assets,
liabilities, profits, losses, or any other facts pertinent to the existence and amount of assets
from which Distributions to Holders of Capital Securities might properly be paid.

Section 7.2 Indemnification.

(a) The Guarantor agrees to indemnify each Indemnified Person for, and to hold each
Indemnified Person harmless against, any and all loss, liability, damage, claim or expense incurred
without negligence or willful misconduct on the part of the Indemnified Person, arising out of or
in connection with the acceptance or administration of the trust or trusts hereunder, including,
but not limited to, the costs and expenses (including reasonable legal fees and expenses) of the
Indemnified Person defending itself against, or investigating, any claim or liability in connection
with the exercise or performance of any of the Indemnified Person’s powers or duties hereunder.
The obligation to indemnify as set forth in this Section 7.2 shall survive the resignation or
removal of the Guarantee Trustee and the termination of this Guarantee.

(b) Promptly after receipt by an Indemnified Person under this Section 7.2 of notice of the
commencement of any action, such Indemnified Person will, if a claim in respect thereof is to be
made against the Guarantor under this Section 7.2, notify the Guarantor in writing of the
commencement thereof; but the failure so to notify the Guarantor (i) will not relieve the Guarantor
from liability under paragraph (a) above unless and to the extent that the Guarantor did not
otherwise learn of such action and such failure results in the forfeiture by the Guarantor of
substantial rights and defenses and (ii) will not, in any event, relieve the Guarantor from any
obligations to any Indemnified Person other than the indemnification obligation provided in
paragraph (a) above. The Guarantor shall be entitled to appoint counsel of the Guarantor’s choice
at the Guarantor’s expense to represent the Indemnified Person in any action for which
indemnification is sought (in which case the Guarantor shall not thereafter be responsible for the
fees and expenses of any separate counsel retained by the Indemnified Person or Persons except as
set forth below); provided, however, that such counsel shall be reasonably
satisfactory to the Indemnified Person. Notwithstanding the Guarantor’s election to appoint
counsel to represent the Guarantor in an action, the Indemnified Person shall have the right to
employ separate counsel (including local counsel), and the Guarantor shall bear the reasonable
fees, costs and expenses of such separate counsel if (i) the use of counsel chosen by the Guarantor
to represent the Indemnified Person would present such counsel with a conflict of interest,
(ii) the actual or potential defendants in, or targets of, any such action include both the
Indemnified Person and

 

 

 

the Guarantor and the Indemnified Person shall have reasonably concluded that there may be
legal defenses available to it and/or other Indemnified Person(s) which are different from or
additional to those available to the Guarantor, (iii) the Guarantor shall not have employed counsel
satisfactory to the Indemnified Person to represent the Indemnified Person within a reasonable time
after notice of the institution of such action or (iv) the Guarantor shall authorize the
Indemnified Person to employ separate counsel at the expense of the Guarantor. The Guarantor will
not, without the prior written consent of the Indemnified Persons, settle or compromise or consent
to the entry of any judgment with respect to any pending or threatened claim, action, suit or
proceeding in respect of which indemnification or contribution may be sought hereunder (whether or
not the Indemnified Persons are actual or potential parties to such claim or action) unless such
settlement, compromise or consent includes an unconditional release of each Indemnified Person from
all liability arising out of such claim, action, suit or proceeding.

Section 7.3 Compensation; Reimbursement of Expenses.

The Guarantor agrees:

(a) to pay to the Guarantee Trustee from time to time such compensation for all services
rendered by it hereunder as the parties shall agree to from time to time (which compensation shall
not be limited by any provision of law in regard to the compensation of a trustee of an express
trust); and

(b) except as otherwise expressly provided herein, to reimburse the Guarantee Trustee upon
request for all reasonable expenses, disbursements and advances incurred or made by it in
accordance with any provision of this Guarantee (including the reasonable compensation and the
expenses and disbursements of its agents and counsel), except any such expense, disbursement or
advance as may be attributable to its negligence or willful misconduct.

The provisions of this Section 7.3 shall survive the resignation or removal of the Guarantee
Trustee and the termination of this Guarantee.

ARTICLE VIII

MISCELLANEOUS

Section 8.1 Successors and Assigns.

All guarantees and agreements contained in this Guarantee shall bind the successors, assigns,
receivers, trustees and representatives of the Guarantor and shall inure to the benefit of the
Holders of the Capital Securities then outstanding. Except in connection with any merger or
consolidation of the Guarantor with or into another entity or any sale, transfer or lease of the
Guarantor’s assets to another entity, in each case, to the extent permitted under the Indenture,
the Guarantor may not assign its rights or delegate its obligations under this Guarantee without
the prior approval of the Holders of at least a Majority in liquidation amount of the Capital
Securities.

 

 

 

Section 8.2 Amendments.

Except with respect to any changes that do not adversely affect the rights of Holders of the
Capital Securities in any material respect (in which case no consent of Holders will be required),
this Guarantee may be amended only with the prior approval of the Holders of not less than a
Majority in liquidation amount of the Capital Securities and the Guarantor. The provisions of the
Declaration with respect to amendments thereof apply to the giving of such approval.

Section 8.3 Notices.

All notices provided for in this Guarantee shall be in writing, duly signed by the party
giving such notice, and shall be delivered, telecopied or mailed by first class mail, as follows:

(a) If given to the Guarantee Trustee, at the Guarantee Trustee’s mailing address set forth
below (or such other address as the Guarantee Trustee may give notice of to the Holders of the
Capital Securities and the Guarantor):

Wilmington Trust Company

1100 North Market Street

Wilmington, Delaware 19890-1600

Attention: Corporate Trust Administration

Telecopy: 302-636-4140

(b) If given to the Guarantor, at the Guarantor’s mailing address set forth below (or such
other address as the Guarantor may give notice of to the Holders of the Capital Securities and to
the Guarantee Trustee):

First Mercury Financial Corporation

29110 Inkster Road

Southfield, Michigan 48034

Attention: Jeffery R. Wawok

Telecopy: 248-353-5879

(c) If given to any Holder of the Capital Securities, at the address set forth on the books
and records of the Issuer.

All such notices shall be deemed to have been given when received in person, telecopied with
receipt confirmed, or mailed by first class mail, postage prepaid, except that if a notice or other
document is refused delivery or cannot be delivered because of a changed address of which no notice
was given, such notice or other document shall be deemed to have been delivered on the date of such
refusal or inability to deliver.

Section 8.4 Benefit.

This Guarantee is solely for the benefit of the Beneficiaries and, subject to Section 2.1(a),
is not separately transferable from the Capital Securities.

 

 

 

Section 8.5 Governing Law.

PURSUANT TO SECTION 5-1401 OF THE GENERAL OBLIGATIONS LAW OF THE STATE OF NEW YORK, THIS
GUARANTEE SHALL BE GOVERNED BY, AND CONSTRUED AND INTERPRETED IN ACCORDANCE WITH, THE LAW OF THE
STATE OF NEW YORK.

Section 8.6 Counterparts.

This Guarantee may be executed in one or more counterparts, each of which shall be an
original, but all of which taken together shall constitute one and the same instrument.

Section 8.7 Separability.

In case one or more of the provisions contained in this Guarantee shall for any reason be held
to be invalid, illegal or unenforceable in any respect, such invalidity, illegality or
unenforceability shall not affect any other provisions of this Guarantee, but this Guarantee shall
be construed as if such invalid or illegal or unenforceable provision had never been contained
herein.

Signatures appear on the following page

 

 

 

THIS GUARANTEE is executed as of the day and year first above written.

	 	 	 	 	 
	 	FIRST MERCURY FINANCIAL CORPORATION, as Guarantor

 	 
	 	By:  	/s/
Jeffrey R. Wawok	 
	 	 	Name:  	Jeffery R. Wawok 	 
	 	 	Title:  	Executive Vice President 	 
	 

	 	 	 	 	 
	 	WILMINGTON TRUST COMPANY, as Guarantee Trustee

 	 
	 	By:  	/s/
Christopher J. Slaybaugh	 
	 	 	Name:  	Christopher J. Slaybaugh	 
	 	 	Title:  	Senior Financial Services Officer

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