Document:

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GUARANTEE

     FOR VALUE RECEIVED, the sufficiency of which is hereby acknowledged, and in connection with
that certain funding agreement (the “Funding Agreement”), entered into by and between Principal
Life Insurance Company, an Iowa insurance company (“Principal Life”), and Principal Life Income
Fundings Trust 2007-89, a New York common law trust (the “Trust”), relating to the notes (the
“Notes”) issued by the Trust, Principal Financial Group, Inc., a Delaware corporation and the
indirect parent company of Principal Life (the “Guarantor”), hereby furnishes to the Trust its full
and unconditional guarantee of the Guaranteed Amounts (as hereinafter defined) as follows:

     1. Guarantee.

          (a) The Guarantor hereby fully, irrevocably, absolutely and unconditionally guarantees, as a
guarantee of payment and not merely as a guarantee of collection, immediate payment when due to the
Trust any payments required to be made by Principal Life to the Trust under the Funding Agreement
which shall become due and payable regardless of whether such payment is due at maturity, on an
interest payment date or as a result of redemption or otherwise (the “Scheduled Payments”) but
shall be unpaid by Principal Life (the “Guaranteed Amounts”). Notwithstanding anything to the
contrary contained herein, in no event shall the Guaranteed Amounts exceed the Deposit (as defined
in the Funding Agreement) of the Funding Agreement, plus accrued but unpaid interest and any other
amounts due and owing under the Funding Agreement, less any amounts paid by Principal Life to the
Trust.

          (b) In the event that Principal Life fails to make a Scheduled Payment in full when due (the
“Payment Notice Date”), then the Trust or Citibank, N.A., as indenture trustee for the benefit of
the holders of the Notes (the “Indenture Trustee”), pursuant to the indenture (the “Indenture”)
between the Trust and the Indenture Trustee, may present the Guarantor with notice (each, a
“Payment Notice”) of such failure in writing on or after the Payment Notice Date. The Payment
Notice shall identify (1) the Funding Agreement, (2) the Trust, (3) the Payment Notice Date and (4)
the amount of the Scheduled Payments not paid by Principal Life to the Trust as of the Payment
Notice Date. Upon receipt of such Payment Notice, the Guarantor will immediately pay the
Guaranteed Amounts pursuant to Section 7.

          (c) In the event that, after receipt of a Payment Notice from the Trust, the Guarantor fails
to make immediate payment to the Trust or the Indenture Trustee of the Guaranteed Amounts, then
the Trust and the Indenture Trustee may enforce the obligations of the Guarantor under this
Guarantee, including by immediately bringing suit directly against the Guarantor (without first
bringing suit against Principal Life) for the Guaranteed Amounts not paid to the Trust as of the
Payment Notice Date.

          (d) This Guarantee is an unsecured, unsubordinated and contingent obligation of the Guarantor
and ranks equally with all other unsecured and unsubordinated obligations of the Guarantor.

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     2. Termination. This Guarantee is a continuing and irrevocable guarantee of the
Guaranteed Amounts now or hereafter existing and shall terminate and be of no further force and
effect with respect to the Funding Agreement and the Notes upon the full payment of the Scheduled
Payments or upon the earlier extinguishment of the obligations of Principal Life under the Funding
Agreement.

     3. Amendments. Subject to the trust agreement relating to the Trust and the Indenture, no
provision of this Guarantee may be waived, amended, supplemented or modified, except by a written
instrument executed by the Trust and the Guarantor.

     4. Assignment; Governing Law. This Guarantee shall inure to the benefit of the Trust and its
successors, assigns and pledgees. This Guarantee shall be governed by, and construed in accordance
with, the laws of the State of New York without regard to conflict of law principles.

     5. Notices. All notices given pursuant to this Guarantee shall be in writing, and shall
either be delivered, mailed or telecopied to the locations listed below or at such other address or
to the attention of such other persons as such party shall have designated for such purpose in a
written notice complying as to delivery with the terms of this Section 5. Each such notice shall
be effective (i) if given by telecopy, when transmitted to the applicable number so specified in
this Section 5 (such notice shall also be sent by mail, with first class postage prepaid), (ii) if
given by mail, three days after deposit in the mails with first class postage prepaid, or (iii) if
given by any other means, when actually delivered at such address.

If to the Guarantor:

Principal Financial Group, Inc.

711 High Street

Des Moines, Iowa 50392

Attention: General Counsel

Telephone: (515) 247-5111

Facsimile: (515) 248-3011

With a copy to:

Principal Life Insurance Company

711 High Street

Des Moines, Iowa 50392

Attention: Jim Fifield

Telephone: (515) 248-9196

Facsimile: (866) 496-6527

If to the Trust:

Principal Life Income Fundings Trust (followed by the number of the Trust specified in this Guarantee)

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c/o U.S. Bank Trust National Association

100 Wall Street, 16th Floor

New York, New York 10005

Attention: Thomas E. Tabor

Telephone: (212) 361-6184

Facsimile: (212) 809-5459

With a copy to:

Citibank, N.A.

Citibank Agency and Trust

388 Greenwich Street, 14th Floor

New York, New York 10013

Attention: Nancy Forte

Telephone: (212) 816-5685

Facsimile: (212) 816-5527

     6. Representations and Warranties. The Guarantor represents and warrants that: (i) it is duly
organized and in good standing under the laws of the jurisdiction of its organization and has full
capacity and right to make and perform this Guarantee, and all necessary authority has been
obtained; (ii) this Guarantee constitutes a legal, valid and binding obligation of the Guarantor
enforceable in accordance with its terms, subject to applicable bankruptcy, insolvency and similar
laws affecting creditors’ rights and general principles of equity, regardless of whether
enforcement is sought in a proceeding in equity or at law; (iii) the making and performance of this
Guarantee does not and will not violate the provisions of any applicable law, regulation or order,
and does not and will not result in the breach of, or constitute a default under, any material
agreement, instrument or document to which it is a party or by which it or any of its property may
be bound or affected, except to the extent disclosed in the registration statement registering the
issuance of this Guarantee and the Funding Agreement, as amended, supplemented or modified from
time to time (the “Registration Statement”), and to the extent that any such violation, breach or
default does not result in a material adverse effect on the Guarantor; and (iv) all consents,
approvals, licenses and authorizations of, and filings and registrations with, any governmental
authority required under applicable law and regulations for the making and performance of this
Guarantee have been obtained or made and are in full force and effect, except to the extent
disclosed in the Registration Statement and to the extent that the failure to acquire any such
consent, approval, license, authorization, filing or registration does not result in a material
adverse effect on the Guarantor.

     7. Notice of, and Consent to, Security Interest. The Trust hereby notifies the Guarantor that
it has granted to the Indenture Trustee, on behalf of the holders of the Notes, a security interest
in the Collateral (as defined in the Indenture), including, but not limited to, any and all payment
to be made by the Guarantor to the Trust under this Guarantee. The Trust hereby notifies the
Guarantor that it has collaterally assigned to the Indenture Trustee, for the benefit of the
holders of the Notes, this Guarantee. The Guarantor, by executing this Guarantee, hereby (i)
affirms that it has made or simultaneously will make changes to its books and records to reflect
such security interest and collateral assignment, (ii) consents to the security interest

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granted, and collateral assignment made, by the Trust to the Indenture Trustee of this
Guarantee, (iii) agrees to make all payments due under this Guarantee to the Collection Account (as
defined in the Indenture) or any other account designated in writing to the Guarantor by the
Indenture Trustee and (iv) agrees to comply with all orders of the Indenture Trustee with respect
to this Guarantee without any further consent from the Trust.

     8. WAIVER OF JURY TRIAL; FINAL AGREEMENT. TO THE EXTENT ALLOWED BY APPLICABLE LAW, THE
GUARANTOR WAIVES TRIAL BY JURY WITH RESPECT TO ANY ACTION, CLAIM, SUIT OR PROCEEDING ON OR ARISING
OUT OF THIS GUARANTEE. THIS GUARANTEE REPRESENTS THE FINAL AGREEMENT BETWEEN THE GUARANTOR AND THE
TRUST AND MAY NOT BE CONTRADICTED BY EVIDENCE OF PRIOR, CONTEMPORANEOUS OR SUBSEQUENT ORAL
AGREEMENTS AMONG SUCH PARTIES. THERE ARE NO UNWRITTEN ORAL AGREEMENTS AMONG SUCH PARTIES.

	 	 	 	 	 
	 	 	PRINCIPAL FINANCIAL GROUP, INC.
	 
	 	 	 	 
	 

	 	By:
	 	/s/ Elizabeth D. Swanson
	 

	 	 	 	 
	 
	 	 	 	 
	 

	 	Name:
	 	Elizabeth D. Swanson
	 
	 	 	 	 
	 

	 	Title:
	 	Counsel
	 
	 	 	 	 
	 

	 	Date:
	 	The Effective Date (as defined in the Funding Agreement)

Acknowledged and Agreed:

THE PRINCIPAL LIFE INCOME FUNDINGS

TRUST DESIGNATED IN THIS GUARANTEE

	 	 	 	 	 
	By:	 	U.S. Bank Trust National Association,
	 	 	not in its individual capacity, but solely in its
	 	 	capacity as trustee
	 
	 	 	 	 
	By:	 	Bankers Trust Company, N.A.,
	 	 	under Limited Power of Attorney, dated March 2, 2007
	 
	 	 	 	 
	By:

	 	/s/ Diana L. Cook
	 	 
	 

	 	 	 	 
	 
	 	 	 	 
	Name:

	 	Diana L. Cook	 	 
	 
	 	 	 	 
	Title:

	 	Vice President	 	 
	 
	 	 	 	 
	Date:

	 	The Effective Date (as defined in the Funding Agreement)
	 	

4exv10w1

 

THIRD AMENDMENT TO THIRD AMENDED AND RESTATED LOAN AGREEMENT

     THIS THIRD AMENDMENT TO THIRD AMENDED AND RESTATED LOAN AGREEMENT (this
“Amendment”) dated as of September 7, 2007, by and between: MERCANTILE BANCORP,
INC., a Delaware corporation (“Borrower”): and U.S. BANK NATIONAL ASSOCIATION, formerly
known as Firstar Bank, N.A., a national banking association, the successor by merger to Mercantile
Bank National Association (“Lender”): has reference to the following facts and
circumstances (the “Recitals”):

     A. Borrower and Lender executed the Third Amended and Restated Loan Agreement dated
as of November 10, 2006 (as amended, the “Agreement”: all capitalized terms herein not
otherwise
defined shall have the same meanings as ascribed to them in the Agreement).

     B. The Agreement was previously amended as described in the First Amendment to Third
Amended and Restated Loan Agreement dated as of March 20, 2007 and the Second Amendment to
Third Amended and Restated Loan Agreement dated as of June 30, 2007; Borrower and Guarantors
desire to further amend the terms of the Agreement and the Notes in the manner set forth
herein; and
Lender is willing to agree to said amendments on the terms and conditions set forth herein.

     NOW, THEREFORE, in consideration of the premises, and other good and valuable consideration,
the receipt and sufficiency of which are hereby acknowledged, Borrower and Lender hereby agree as
follows:

     1. Recitals. The Recitals are true and correct, and, with the defined terms set forth
herein,
are incorporated by this reference.

     2. Amendment to Agreement. The Agreement is amended as follows:

(a) Recital C on page 1 of the Agreement is deleted and replaced with the following:

     “C. Borrower and Lender desire to amend and restate the Original Loan
Agreement to, among other things, provide for a revolving credit facility to the
aggregate amount of up to $8,000,000, Term Loan A in the original principal amount
of $15,000,000, Term Loan B in the original principal amount of $5,000,000, and
Term Loan C in the original principal amount of $5,000,000 upon, and subject to,
the terms, provisions and conditions hereinafter set forth.”

(b) The following definitions of “Initial Money Market Rate”, “Loan”, “Loans”, “Money Market
Rate At Prepayment”, “Net Present Value”, ‘Note”, “Notes”, “Subsidiary Bank”, “Subsidiary
Banks”, “Term Loan”, and “Term Note” are deleted from Section 1.01 of the Agreement and
replaced with the following in the correct alphabetical order:

     “Initial Money Market Rate shall mean the annual rate, determined
solely by Lender, on the first day of the term of Term Loan A, Term Loan B or Term
Loan C (whichever is applicable) or the most recent repricing date or as mutually
agreed upon by Borrower and Lender, as the rate at which Lender would be able to
borrow funds in the Money Markets for the amount of Term Loan A, Term Loan B or
Term Loan C (whichever is applicable) and with an interest payment frequency and
principal repayment schedule equal to Term Loan A, Term Loan B or Term Loan C
(whichever is applicable), and for a term as may be arranged and agreed upon by
Borrower and Lender, adjusted for any reserve requirement and any subsequent costs
arising from a change in government regulation; provided, that Borrower
acknowledges that Lender is

 

 

under no obligation to actually purchase and/or match funds for the Initial Money Market Rate of
Term Loan A, Term Loan B or Term Loan C (whichever is applicable).”

     “Loan shall mean each Revolving Credit Loan and each Term Loan; and
Loans shall mean any or all of the foregoing.”

     “Money Market Rate At Prepayment shall mean that zero-coupon rate,
calculated on each Prepayment Date, and determined solely by Lender, as the rate at
which Lender would be able to borrow funds in Money Markets for the prepayment
amount matching the maturity of a specific prospective Term Loan A, Term Loan B or
Term Loan C (whichever is applicable) payment or repricing date, adjusted for any
reserve requirement and any subsequent costs arising from a change in government
regulation; provided, that a separate Money Market Rate at Prepayment will be
calculated for each prospective interest and/or principal payment date.”

     “Net Present Value shall mean the amount which is derived by summing
the present values of each prospective payment of principal and interest which,
without such full or partial prepayment, could otherwise have been received by
Lender over the shorter of the remaining contractual life of Term Loan A, Term Loan
B or Term Loan C (whichever is applicable) or next repricing date if Lender had
instead initially invested Term Loan A, Term Loan B or Term Loan C (whichever is
applicable) proceeds at the Initial Money Market Rate; provided, that the
individual discount rate used to present value each prospective payment of interest
and/or principal shall be the Money Market Rate at Prepayment for the maturity
matching that of each specific payment of principal and/or interest.”

     “Note shall mean each of the Revolving Note and each Term Note; and
Notes shall mean either or both of the foregoing.”

     “Subsidiary Bank shall mean, each of: Heartland Bank, a Kansas banking
corporation; Farmers State Bank of Northern Missouri, a Missouri banking
corporation; New Frontier Bank, a Missouri banking corporation; Brown County State
Bank, an Illinois banking corporation; Perry State Bank, a Missouri banking
corporation; Marine Bank & Trust, an Illinois banking corporation; Mercantile Trust
& Savings Bank, an Illinois banking corporation; and The Royal Palm Bank of
Florida, a Florida banking corporation; and further upon consummation of the HNB
Merger Transaction, HNB National Bank, a national banking association;
and Subsidiary Banks shall mean some or all of the foregoing.”

     “Term Loan shall mean each of Term Loan A, Term Loan B, and Term Loan
C; and Term Loans shall mean any or all of the foregoing.”

     “Term Note shall mean each of Term Note A, Term Note B, and Term Note
C; and Term Notes shall mean any or all of the foregoing.”

(c) The following new definitions are added to Section 1.01 of the Agreement in the correct
alphabetical order:

     “Acquisition shall mean any transaction or series of related
transactions, consummated on or after the date of this Agreement, by which Borrower
or any Subsidiary directly or indirectly (a) acquires all or substantially all of
the assets comprising one or more business units of any other Person, whether
through purchase

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of assets, merger or otherwise or (b) acquires (in one transaction or as the
most recent transaction in a series of transactions) at least (i) a majority (in
number of votes) of the stock and/or other securities of a corporation having
ordinary voting power for the election of directors (other than stock and/or other
securities having such power only by reason of the happening of a contingency),
(ii) a majority (by percentage of voting power) of the outstanding partnership
interests of a partnership, (iii) a majority (by percentage of voting power) of the
outstanding membership interests of a limited liability company or (iv) a majority
of the ownership interests in any organization or entity other than a corporation,
partnership or limited liability company.

     “HNB shall mean HNB Financial Services, Inc., a Missouri corporation.”

     “HNB Merger Agreement shall mean the Agreement and Plan of Merger dated as of February
8, 2007, executed by Borrower, HNB, HNB National Bank, and Mercantile Merger Corp.”

     “HNB Merger Transaction shall mean collectively the transactions contemplated by and
described in the HNB Merger Agreement.”

     “Term Loan A shall have the meaning ascribed thereto in Section 2.02(a).”

     “Term Loan B shall have the meaning ascribed thereto in Section 2.02(b).”

     “Term Loan C shall have the meaning ascribed thereto in Section 2.02(c).”

     “Term Note A shall have the meaning ascribed thereto in Section 2.03(b).”

     “Term Note B shall have the meaning ascribed thereto in Section 2.03(b).”

     “Term Note C shall have the meaning ascribed thereto in Section 2.03(b).”

(d) Section 2.02 of the Agreement is deleted and replaced with the following:

     “Term Loan Commitments.

     (a) Subject to the terms and conditions set forth in this Agreement and so long as no Default
or Event of Default under this Agreement has occurred and is continuing, Lender agrees to make to
Borrower a term loan of Fifteen Million Dollars ($15,000,000.00) (“Term Loan A”). Term Loan
A shall be advanced in one disbursement on the effective date of this Agreement. Term Loan A is not
revolving in nature and any principal repaid on Term Loan A may not be reborrowed. The principal
amount of Term Loan A shall be due and payable in three (3) equal consecutive quarterly
installments in
the amount of $375,000.00 each, due and payable on December 31, 2008, March 31, 2009, and June
30, 2009, and a final installment in the amount of the then outstanding and unpaid principal
balance of Term Loan A due and payable on November 10, 2009.

     (b) Subject to the terms and conditions set forth in this Agreement and so long as no Default
or Event of Default under this Agreement has occurred and is continuing, Lender agrees to make to
Borrower a term loan of Five Million Dollars ($5,000,000.00) (“Term Loan B”). Term Loan B
shall be advanced in one disbursement on September 7, 2007. Term Loan B is not revolving in nature
and any principal repaid on Term Loan B may not be reborrowed. The principal amount of Term Loan B
shall be

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due and payable in three (3) equal consecutive quarterly
installments in the amount of $125,000.00 each, due and
payable on December 31, 2009, March 31, 2010, and June 30,
2010, and a final installment in the amount of the then
outstanding and unpaid principal balance of Term Loan B due
and payable on August 31, 2010.

     (c) Subject to the terms and conditions set forth in this Agreement and so
long as no Default or Event of Default under this Agreement has occurred and is
continuing, Lender agrees to make to Borrower a term loan of Five Million Dollars
($5,000,000.00) (“Term Loan C”). Term Loan C shall be advanced in one
disbursement on September 7, 2007. Term Loan C is not revolving in nature and any
principal repaid on Term Loan C may not be reborrowed. The principal amount of
Term Loan C shall be due and payable in three (3) equal consecutive quarterly
installments in the amount of $125,000.00 each, due and payable on December 31,
2009, March 31, 2010, and June 30, 2010, and a final installment in the amount of
the then outstanding and unpaid principal balance of Term Loan C due and payable
on August 31, 2010.”

(e) Section 2.03(b) of the Agreement is deleted and replaced with the following:

     ”(b) Term Loan A shall be evidenced by the Term Loan Promissory Note of
Borrower dated November 10, 2006, and payable to the order of Lender in the
original principal amount of $15,000,000.00, which Term Loan Promissory Note shall
be in substantially the form of Exhibit B attached hereto and incorporated
herein by reference (as the same may from time to time be amended, modified
extended, renewed or restated, “Term Note A”). Term Loan B shall be
evidenced by the Term Loan B Promissory Note of Borrower dated September 7, 2007,
and payable to the order of Lender in the original principal amount of
$5,000,000.00, which Term Loan B Promissory Note shall be in substantially the form
of Exhibit B1 attached hereto and incorporated herein by reference (as the
same may from time to time be amended, modified extended, renewed or restated,
“Term Note B”). Term Loan C shall be evidenced by the Term Loan C
Promissory Note of Borrower dated September 7, 2007, and payable to the order of
Lender in the original principal amount of $5,000,000.00, which Term Loan C
Promissory Note shall be in substantially the form of Exhibit B2 attached
hereto and incorporated herein by reference (as the same may from time to time be
amended, modified extended, renewed or restated, “Term Note C”).”

(f) Sections 2.04(d) and 2.04(g) of the Agreement are deleted and replaced with the
following:

     ”(d) Effective March 5, 2007 and thereafter, interest on Term Loan A shall
accrue at a fixed annual rate of Six and 9/100 Percent (6.09%). Interest on Term
Loan B shall accrue at a fixed annual rate of Six and 13/100 Percent (6.13%).
Interest on Term Loan C shall accrue at a fixed annual rate of Six and 27/100
Percent (6.27%). Interest on each Term Loan shall be paid in consecutive quarterly
installments due and payable on each February 10, May 10, August 10, and November
10, and on the maturity dates of the Term Notes.”

     ”(g) Borrower shall have the right to prepay Term Loan C in whole or in part
at any time, provided: (i) all billed/due and unpaid interest shall accompany such
prepayment; (ii) there is no Default or Event of Default at the time of prepayment;
and (iii) all prepayments shall be credited and applied to the installments of
principal in inverse order of their stated maturity. Borrower shall not have the
right to prepay Term Loan A or Term Loan B, provided that Lender may consider
requests for its consent with

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respect to prepayment of Term Loan A or Term Loan B, without incurring an
obligation to do so, and Borrower acknowledges that in the event that such consent
is granted, Borrower shall be required to pay Lender, upon prepayment of all or
part of the principal amount of Term Loan A or Term Loan B before final maturity, a
prepayment indemnity (the “Prepayment Fee”) equal to the greater of zero
(0), or that amount, calculated on any date of prepayment (“Prepayment
Date”), which is derived by subtracting: (i) the outstanding principal amount
of Term Loan A or Term Loan B or portion of Term Loan A or Term Loan B to be
prepaid from (ii) the Net Present Value of Term Loan A or Term Loan B or portion of
Term Loan A or Term Loan B to be prepaid on such Prepayment Date; provided,
however, that the Prepayment Fee shall not in any event exceed the maximum
prepayment fee permitted by applicable law. In calculating the amount of the
Prepayment Fee, Lender is hereby authorized by Borrower to make such assumptions
regarding the source of funding, redeployment of funds and other related matters,
as Lender may deem appropriate. If Borrower fails to pay the Prepayment Fee when
due, the amount of such Prepayment Fee shall thereafter bear interest until paid at
the default rate specified in Section 2.04(e) above (computed on the basis of a
360-day year, actual days elapsed). Each prepayment of the principal amount of Term
Loan A or Term Loan B shall be accompanied by a payment of interest accrued to date
thereon; applied to the principal installments in the inverse order of their
maturities, and in an amount of at least $100,000 or, if less, the remaining entire
principal balance of Term Loan A or Term Loan B.”

(g) Section 6.02 of the Agreement is deleted and replaced with the following:

     “6.02 Merger or Consolidation, etc. (a) Merge into or consolidate with
any other entity provided that (i) Royal Palm may merge into Borrower, (ii) HNB may
merge into Borrower, (iii) the non-trust related assets of HNB National Bank may be
transferred to Perry State Bank, and (iv) the trust related assets of the other
Subsidiary Banks may be transferred to HNB National Bank; or (b) cause or permit
any material change in the ownership of Borrower, Royal Palm, HNB, any Subsidiary
Bank, or any Subsidiary, or in the identity of Borrower’s executive officers or
directors (except for changes necessitated by death, incapacity, natural retirement
or similar causes). In addition, Borrower shall not, and it shall not cause or
permit any Subsidiary to, directly or indirectly, make any Acquisitions or acquire
any minority ownership interests in any other Person without Lender’s prior written
consent.”

(h) Section 6.12 of the Agreement is deleted and replaced with the following:

     “6.12 Non-Performing Assets. Permit the aggregate amount of
Non-Performing Assets of all Subsidiary Banks on a combined basis to equal or
exceed Eighteen Percent (18%) of the then Primary Capital of all Subsidiary Banks
at anytime during the term of this Agreement, as determined according to GAAP.”

(i) Schedule 4.08 (Subsidiaries), Schedule 4.10 (Other Loans and Guaranties), and
Schedule 4.14 (Stock of Subsidiary Banks) are deleted and replaced with Schedule
4.08, Schedule 4.10, and Schedule 4.14 attached hereto and incorporated by
reference.

(j) Exhibit B1 (Form of Term Note B) and Exhibit B2 (Form of Term Note C) attached
hereto and incorporated by reference into the Agreement.

     3. Waiver. Lender waives any Default or Event of Default under the Agreement
caused solely by Borrower’s noncompliance with Section 6.12 (Non-Performing Assets) of the
Agreement for

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the reporting period ending June 30, 2007. The waiver described in the preceding sentence shall not
be deemed to apply to any other or future terms, provisions, conditions or covenants of the
Agreement, as amended by this Amendment, or to any other Default or Event of Default, if any,
existing under the Agreement, and shall not create any expectation on the part of Borrower of any
other or similar waiver(s) of any provision of the Agreement in the future.

     4. Continuing Security. The Agreement, as hereby amended, and the Notes, are and shall
continue to be, guarantied and/or secured by the Borrower Pledge and the Subsidiary Pledge, and any
reference to the Agreement in the Borrower Pledge and the Subsidiary Pledge shall hereafter be
deemed to include the Agreement as hereby amended.

     5. Binding Obligations. The Agreement, Notes, and the other Transaction Documents,
are, and shall remain, the binding obligations of Borrower and/or Royal Palm, and all of the
provisions, terms, stipulations, conditions, covenants and powers contained therein shall stand and
remain in full force and effect, except only as the same are herein and hereby expressly and
specifically varied or amended, and the same are hereby ratified and confirmed, and Lender reserves
unto itself all rights and privileges granted thereunder.

     6. Reaffirmation: Authority. Borrower hereby reaffirms all representations,
warranties, covenants and agreements recited in the Agreement, Notes, and the other Transaction
Documents, as of the date hereof, and the same are hereby adopted as representations, warranties,
covenants and agreements of Borrower herein. Borrower further represents and warrants that it is
not in default under any of its obligations under the Agreement, Notes, and the other Transaction
Documents, and that Borrower has the full power and authority to execute and deliver this
Amendment, and that the execution and delivery hereof has been duly authorized, and that all
necessary and proper acts have been performed or taken.

     7. Expenses. Borrower agrees to pay all expenses incurred by Lender in connection with
this Amendment, including, but not limited to, Lender’s legal fees. Said sums are payable on demand
and are secured by the Borrower Pledge and the Subsidiary Pledge.

     8. Release. Borrower hereby releases Lender and its successors, assigns, directors,
officers, agents, employees, representatives and attorneys from any and all claims, demands, causes
of action, liabilities or damages, whether now existing or hereafter arising or contingent or
noncontingent, or actions in law or equity of any type or matter, relating to or in connection with
any statements, agreements, action or inaction on the part of Lender occurring at any time prior to
the execution of this
Amendment, with respect to Borrower, the Agreement, Notes, and all other Transaction
Documents.

     9. Applicable Law. This Amendment shall be governed by and construed in accordance
with the internal laws of the State of Missouri.

     10. Notice Required by Section 432.047 R.S. Mo. ORAL AGREEMENTS OR COMMITMENTS TO LOAN
MONEY, EXTEND CREDIT OR TO FORBEAR FROM ENFORCING REPAYMENT OF A DEBT INCLUDING PROMISES TO EXTEND
OR RENEW SUCH DEBT ARE NOT ENFORCEABLE, REGARDLESS OF THE LEGAL THEORY UPON WHICH IT IS BASED THAT
IS IN ANY WAY RELATED TO THE CREDIT AGREEMENT. TO PROTECT YOU (BORROWER(S)) AND US (CREDITOR) FROM
MISUNDERSTANDING OR DISAPPOINTMENT, ANY AGREEMENTS WE REACH COVERING SUCH MATTERS ARE CONTAINED IN
THIS WRITING, WHICH IS THE COMPLETE AND EXCLUSIVE STATEMENT OF THE AGREEMENT BETWEEN US, EXCEPT AS
WE MAY LATER AGREE IN WRITING TO MODIFY IT.

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     11. Closing Conditions. Notwithstanding any provision contained in this Amendment to the
contrary, this Amendment shall not be effective unless and until Lender shall have received the
following, all in form and substance acceptable to Lender:

(a) this Amendment, Term Note B, and Term Note C, duly executed by Borrower;

(b) the Stock Pledge Agreement (Subsidiary), duly executed by HNB, and any collateral schedule(s),
stock power(s), UCC financing statement(s), and such other documents as Lender may require in
connection with the Stock Pledge Agreement (Subsidiary);

(c) 64,000 shares of the common stock of HNB National Bank, representing all of the issued and
outstanding common stock of HNB National Bank;

(d) the Certificate of Secretary of Borrower (with the accompanying Resolutions), duly executed by
the Secretary of Borrower;

(e) the Certificate of Secretary of HNB National Bank, duly executed by the Secretary of HNB
National Bank;

(f) the Certificate of Secretary, duly executed by the Secretary of HNB (with the accompanying
Resolutions) and a copy of the Articles of Incorporation of HNB (including any amendments thereto,
certified by the Secretary of State of the Missouri) and;

(g) a copy of the Articles of Association of HNB National Bank, certified by the Office of the
Comptroller of the Currency;

(h) copies of the By-Laws of HNB and HNB National Bank, including any amendments thereto, certified
by the Secretary of HNB, and the Secretary of HNB National Bank, respectively;

(i) Certificates of Good Standing for Borrower, issued by the Secretary of State of the State of
Delaware and by the Secretary of State of the State of Illinois, and a Certificate of Good Standing
for HNB issued by the Secretary of State of the State of Missouri (or other evidence of good
standing acceptable to Lender);

(j) an opinion of counsel from Schmiedeskamp, Robertson, Neu & Mitchell, the counsel representing
Borrower, in the form acceptable to Lender;

(k) evidence that no change in the financial condition of Borrower, any Subsidiary Bank,
or any Subsidiary shall have occurred since June 30, 2007 that could have a Material Adverse
Effect;

(l) copies of all documents executed in connection with the HNB Merger Transaction including, but
not limited to the HNB Merger Agreement, and evidence satisfactory to Lender that the HNB Merger
Transaction has been approved by all applicable Regulatory Agencies;

(m) copies of all documents executed in connection with the issuance by Borrower of Pooled Trust
Preferred Securities on or about August 30, 2007; and

(n) such other documents and information as Lender may reasonably require.

- 7 -

 

     IN WITNESS WHEREOF, the parties hereto have executed this Amendment as of the day and year first
above written.

(SIGNATURES ON FOLLOWING PAGE)

- 8 -

 

SIGNATURE PAGE-

THIRD AMENDMENT TO THIRD AMENDED AND RESTATED LOAN AGREEMENT

	 	 	 	 	 
	 	Borrower: 

MERCANTILE BANCORP, INC

 	 
	 	By:  	/s/ Ted T. Awerkamp
 	 
	 	 	Ted T. Awerkamp, President & CEO 	 
	 	 	 	 
	 
	 	Lender: 

U.S. BANK NATIONAL ASSOCIATION

 	 
	 	By:  	/s/ Gary D. Taylor
 	 
	 	 	Gary D. Taylor, Vice President      	 
	 	 	 	 

- 9 -

 

	 	 	 	 	 

SCHEDULE 4.08 

(Subsidiaries)

Mid-America Bancorp, Inc.

Heartland Bank

Farmers State Bank of Northern Missouri

New Frontier Bancshares, Inc.

NFBI Capital Trust I

New Frontier Bank

New Frontier Personal Investment Centers, Inc.

Mercantile Bancorp Capital Trust I

Mercantile Bancorp Capital Trust II

Mercantile Bancorp Capital Trust III

Mercantile Bancorp Capital Trust IV

Brown County State Bank

Perry State Bank

Marine Bank & Trust

Mercantile Merger Corp.

Mercantile Trust & Savings Bank

Mercantile Investments Inc.

Royal Palm Bancorp, Inc.

The Royal Palm Bank of Florida

HNB Financial Services, Inc.

HNB National Bank

 

 

SCHEDULE 4.10

(Other Loans and Guarantees)

Trust Preferred Securities:

Mercantile Bancorp Capital Trust I

Mercantile Bancorp Capital Trust II

Mercantile Bancorp Capital Trust III

Mercantile Bancorp Capital Trust IV

NFBI Capital Trust I

 

 

SCHEDULE 4.14

(Stock of Subsidiary Banks)

	 	 	 	 	 	 	 	 	 
	Subsidiary Bank
	 	Owner
	 	Authorized Capital
	 	Par Value

	 
	Heartland Bank

	 	Mid-America Bancorp, Inc.
	 	3,000 shares
	 	$	100.00	 
	 
	Farmers State Bank of Northern Missouri

	 	Mercantile Bancorp, Inc.
	 	2,700 shares
	 	$	100.00	 
	 
	New Frontier Bank

	 	New Frontier Bancshares, Inc.
	 	30,000 shares
	 	$	100.00	 
	 
	Brown County State Bank

	 	Mercantile Bancorp, Inc.
	 	3,000 shares
	 	$	100.00	 
	 
	Perry State Bank

	 	Mercantile Bancorp, Inc.
	 	2,700 shares
	 	$	100.00	 
	 
	Marine Bank & Trust

	 	Mercantile Bancorp, Inc.
	 	13,010 shares
	 	$	100.00	 
	 
	Mercantile Trust & Savings Bank

	 	Mercantile Bancorp, Inc.
	 	360,000 shares
	 	$	6.25	 
	 
	The Royal Palm Bank of Florida

	 	Royal Palm Bancorp, Inc.
	 	3,000,000 shares
	 	$	5.00	 
	 
	HNB National Bank

	 	HNB Financial Services, Inc.
	 	64,000 shares
	 	$	6.25	 

	 	 	 	 	 	 	 
	Shares Owned by Owner
	 	 	 	 	 	 
	 
	Heartland Bank

	 	3,000 shares	 	 	 	 
	 
	Farmers State Bank of Northern Missouri

	 	2,700 shares	 	 	 	 
	 
	New Frontier Bank

	 	30,000 shares	 	 	 	 
	 
	Brown County State Bank

	 	3,000 shares	 	 	 	 
	 
	Perry State Bank

	 	2,700 shares	 	 	 	 
	 
	Marine Bank & Trust

	 	13,010 shares	 	 	 	 
	 
	Mercantile Trust & Savings Bank

	 	360,000 shares	 	 	 	 
	 
	The Royal Palm Bank of Florida

	 	1,038,294 shares	 	 	 	 
	 
	HNB National Bank

	 	64,000 shares	 	 	 	 

 

 

EXHIBIT B1

(Form of Term Note B)

TERM LOAN B PROMISSORY NOTE

			
	$5,000,000.00
	 	St. Louis, Missouri

September 7, 2007

     FOR VALUE RECEIVED, the undersigned, MERCANTILE BANCORP, INC., a Delaware corporation
(“Borrower”), promises to pay to the order of U.S. BANK NATIONAL ASSOCIATION, a
national banking association (“Lender”), the principal sum of Five Million Dollars
($5,000,000.00) or, if less, the aggregate unpaid principal amount of all advances made by Lender
to Borrower and evidenced by this Term Loan B Promissory Note (this “Note”). The principal
amount of this Note shall be due and payable in the amounts and on the dates set forth in the Loan
Agreement (defined below). Borrower further promises to pay to the order of Lender interest on the
unpaid principal balance from time to time outstanding under this Note at the rate(s) and on the
dates set forth in the Loan Agreement.

     All payments received by Lender under this Note shall be allocated among the principal,
interest, collection costs and expenses and other amounts due under this Note in such order and
manner as Lender shall elect. The amount of interest accruing under this Note shall be computed on
an actual day, 360-day year basis.

     All payments of principal and interest under this Note shall be made in lawful currency of the
United States in Federal or other immediately available funds at the office of Lender situated at
One US Bank Plaza, 7th Streets Washington Avenue, St. Louis, Missouri 63101, or at such
other place as Lender may from time to time designate in writing.

     Lender shall record in its books and records the date and amount of each Loan advance made by
it to Borrower under this Note and the date and amount of each payment of principal and/or interest
made by Borrower with respect thereto; provided, however, that the obligation of Borrower to repay
each Loan advance made to Borrower under this Note shall be absolute and unconditional,
notwithstanding any failure of Lender to make any such recordation or any mistake by Lender in
connection with any such recordation. The books and records of Lender showing the account between
Lender and Borrower shall be admissible in evidence in any action or proceeding and shall
constitute prima facie proof of the items therein set forth.

     This Note is Term Note B referred to in the Third Amended and Restated Loan Agreement dated as
of November 10, 2006 by and between Borrower and Lender, as the same may from time to time be
amended, modified, extended, renewed or restated (the “Loan Agreement”; all capitalized
terms used and not otherwise defined in this Note shall have the respective meanings ascribed to
them in the Loan Agreement). The Loan Agreement, among other things, contains provisions for
acceleration of the maturity of this Note upon the occurrence of certain stated events and also for
prepayments on account of the principal of this Note and interest on this Note prior to the
maturity of this Note upon the terms and conditions specified therein.

     If Borrower shall fail to make any payment of any principal of or interest on this Note as and
when the same shall become due and payable whether by reason of demand, maturity, acceleration or
otherwise, and any such failure shall remain unremedied for five (5) days, or if any other Event of
Default shall occur under or within the meaning of the Loan Agreement, then Lender’s obligation to
make additional Loan advances under this Note may be terminated in the manner and with the effect
as

 

 

provided in the Loan Agreement and the entire outstanding principal balance of this Note and all
accrued and unpaid interest thereon may be declared to be immediately due and payable in the manner
and with the effect as provided in the Loan Agreement.

     In the event that any payment of any principal of or interest on this Note is not paid when
due, whether by reason of maturity, acceleration or otherwise, and this Note is placed in the hands
of an attorney or attorneys for collection, or if this Note is placed in the hands of an attorney
or attorneys for representation of Lender in connection with bankruptcy or insolvency proceedings
relating to or affecting this Note, Borrower hereby promises to pay to the order of Lender, in
addition to all other amounts otherwise due on, under or in respect of this Note, the costs and
expenses of such collection, foreclosure and representation, including, without limitation,
reasonable attorneys’ fees and expenses (whether or not litigation shall be commenced in aid
thereof). All parties hereto severally waive presentment for payment, demand for payment, protest,
notice of protest and notice of dishonor. This Note shall be governed by and construed in
accordance with the substantive laws of the State of Missouri (without reference to conflict of law
principles).

	 	 	 	 	 
	 	Borrower:

MERCANTILE BANCORP, INC.

 	 
	 	By:  	 	 
	 	 	Ted T. Awerkamp, President & CEO 	 
	 	 	 	 

- 2 -

 

	 	 	 	 	 

EXHIBIT B2

(Form of Term Note C)

TERM LOAN C PROMISSORY NOTE

			
	$5,000,000.00
	 	St. Louis, Missouri

September 7, 2007

     FOR VALUE RECEIVED, the undersigned, MERCANTILE BANCORP, INC., a Delaware corporation
(“Borrower”), promises to pay to the order of U.S. BANK NATIONAL ASSOCIATION, a national
banking association (“Lender”), the principal sum of Five Million Dollars ($5,000,000.00)
or, if less, the aggregate unpaid principal amount of all advances made by Lender to Borrower and
evidenced by this Term Loan C Promissory Note (this “Note”). The principal amount of this
Note shall be due and payable in the amounts and on the dates set forth in the Loan Agreement
(defined below). Borrower further promises to pay to the order of Lender interest on the unpaid
principal balance from time to time outstanding under this Note at the rate(s) and on the dates set
forth in the Loan Agreement.

     All payments received by Lender under this Note shall be allocated among the principal,
interest, collection costs and expenses and other amounts due under this Note in such order and
manner as Lender shall elect. The amount of interest accruing under this Note shall be computed on
an actual day, 360-day year basis.

     All payments of principal and interest under this Note shall be made in lawful currency of the
United States in Federal or other immediately available funds at the office of Lender situated at
One US Bank Plaza, 7th Streets Washington Avenue, St. Louis, Missouri 63101, or at such
other place as Lender may from time to time designate in writing.

     Lender shall record in its books and records the date and amount of each Loan advance made by
it to Borrower under this Note and the date and amount of each payment of principal and/or interest
made by Borrower with respect thereto; provided, however, that the obligation of Borrower to repay
each Loan advance made to Borrower under this Note shall be absolute and unconditional,
notwithstanding any failure of Lender to make any such recordation or any mistake by Lender in
connection with any such recordation. The books and records of Lender showing the account between
Lender and Borrower shall be admissible in evidence in any action or proceeding and shall
constitute prima facie proof of the items therein set forth.

     This Note is Term Note C referred to in the Third Amended and Restated Loan Agreement dated as
of November 10, 2006 by and between Borrower and Lender, as the same may from time to time be
amended, modified, extended, renewed or restated (the “Loan Agreement”; all capitalized
terms used and not otherwise defined in this Note shall have the respective meanings ascribed to
them in the Loan Agreement). The Loan Agreement, among other things, contains provisions for
acceleration of the maturity of this Note upon the occurrence of certain stated events and also for
prepayments on account of the principal of this Note and interest on this Note prior to the
maturity of this Note upon the terms and conditions specified therein.

     If Borrower shall fail to make any payment of any principal of or interest on this Note as and
when the same shall become due and payable whether by reason of demand, maturity, acceleration or
otherwise, and any such failure shall remain unremedied for five (5) days, or if any other Event of
Default shall occur under or within the meaning of the Loan Agreement, then Lender’s obligation to
make additional Loan advances under this Note may be terminated in the manner and with the effect
as

 

 

provided in the Loan Agreement and the entire outstanding principal balance of this Note and all
accrued and unpaid interest thereon may be declared to be immediately due and payable in the manner
and with the effect as provided in the Loan Agreement.

     In the event that any payment of any principal of or interest on this Note is not paid when
due, whether by reason of maturity, acceleration or otherwise, and this Note is placed in the hands
of an attorney or attorneys for collection, or if this Note is placed in the hands of an attorney
or attorneys for representation of Lender in connection with bankruptcy or insolvency proceedings
relating to or affecting this Note, Borrower hereby promises to pay to the order of Lender, in
addition to all other amounts otherwise due on, under or in respect of this Note, the costs and
expenses of such collection, foreclosure and representation, including, without limitation,
reasonable attorneys’ fees and expenses (whether or not litigation shall be commenced in aid
thereof). All parties hereto severally waive presentment for payment, demand for payment, protest,
notice of protest and notice of dishonor. This Note shall be governed by and construed in
accordance with the substantive laws of the State of Missouri (without reference to conflict of law
principles).

	 	 	 	 	 
	 	Borrower:

MERCANTILE BANCORP, INC.

 	 
	 	By:  	 	 
	 	 	Ted T. Awerkamp, President & CEO 	 
	 	 	 	 
	 

- 2 -

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