Exhibit 4.9.2
Floating Rate Junior Subordinated Deferrable Interest Debenture
FLOATING RATE JUNIOR SUBORDINATED
DEFERRABLE INTEREST DEBENTURE
OF ENTERPRISE FINANCIAL SERVICES CORP.
THIS DEBENTURE HAS NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS
AMENDED (THE "SECURITIES ACT"), ANY STATE SECURITIES LAWS OR ANY OTHER
APPLICABLE SECURITIES LAWS. NEITHER THIS DEBENTURE 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 THE TRANSACTION IS EXEMPT FROM, OR NOT SUBJECT TO, SUCH REGISTRATION.
PRIOR TO (X) THE DATE WHICH IS TWO YEARS (OR SUCH SHORTER PERIOD OF TIME AS
PERMITTED BY RULE 144(k) UNDER THE SECURITIES ACT) AFTER THE LATER OF (i) THE
ORIGINAL ISSUE DATE HEREOF OR (ii) THE LAST DATE ON WHICH THE COMPANY OR ANY
AFFILIATE OF THE COMPANY WAS THE OWNER OF THIS DEBENTURE (OR ANY PREDECESSOR OF
THIS DEBENTURE) AND (Y) SUCH LATER DATE, IF ANY, AS MAY BE REQUIRED BY
APPLICABLE LAWS (THE "RESALE RESTRICTION TERMINATION DATE"), THE HOLDER OF THIS
DEBENTURE BY ITS ACCEPTANCE HEREOF AGREES FOR THE BENEFIT OF THE COMPANY TO
OFFER, SELL OR OTHERWISE TRANSFER THIS DEBENTURE ONLY (A) TO THE COMPANY OR AN
AFFILIATE OF THE COMPANY, (B) PURSUANT TO A REGISTRATION STATEMENT WHICH HAS
BEEN DECLARED EFFECTIVE UNDER THE SECURITIES ACT, (C) FOR SO LONG AS THIS
DEBENTURE IS ELIGIBLE FOR RESALE PURSUANT TO RULE 144A ("RULE 144A") PROMULGATED
UNDER THE SECURITIES ACT, TO A PERSON IT REASONABLY BELIEVES IS A "QUALIFIED
INSTITUTIONAL BUYER" AS DEFINED IN RULE 144A THAT PURCHASES FOR ITS OWN ACCOUNT
OR FOR THE ACCOUNT OF A QUALIFIED INSTITUTIONAL BUYER IN COMPLIANCE WITH RULE
144A, (D) TO AN INSTITUTIONAL "ACCREDITED INVESTOR" WITHIN THE MEANING OF
SUBPARAGRAPH (A)(1), (2), (3) OR (7) OF RULE 501 UNDER THE SECURITIES ACT THAT
IS ACQUIRING THIS DEBENTURE 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 (E) PURSUANT TO ANOTHER AVAILABLE EXEMPTION FROM THE
REGISTRATION REQUIREMENTS OF THE SECURITIES ACT, SUBJECT TO THE COMPANY'S AND
THE TRUSTEE'S RIGHT PRIOR TO ANY SUCH OFFER, SALE, TRANSFER OR OTHER DISPOSITION
(i) PURSUANT TO CLAUSES (D) OR (E) TO REQUIRE THE DELIVERY BY THE HOLDER OF AN
OPINION OF COUNSEL, CERTIFICATIONS AND/OR OTHER INFORMATION SATISFACTORY TO THE
COMPANY TO CONFIRM THAT SUCH TRANSFER IS BEING MADE PURSUANT TO
AN EXEMPTION FROM, OR IN A TRANSACTION NOT SUBJECT TO THE REGISTRATION
REQUIREMENTS OF THE SECURITIES ACT AND (ii) IN EACH OF THE FOREGOING CASES, TO
REQUIRE THAT A CERTIFICATE OF TRANSFER IN THE FORM APPEARING ON THE OTHER SIDE
OF THIS DEBENTURE IS COMPLETED AND DELIVERED BY THE TRANSFEROR TO THE TRUSTEE
AND THE DEBENTURE REGISTRAR IN CONNECTION WITH ANY TRANSFER OF THIS DEBENTURE
PRIOR TO THE RESALE RESTRICTION TERMINATION DATE. THE HOLDER MUST CHECK THE
APPROPRIATE BOX SET FORTH ON THE CERTIFICATE OF TRANSFER RELATING TO THE MANNER
OF SUCH TRANSFER AND SUBMIT THE CERTIFICATE OF TRANSFER TO THE TRUSTEE AND THE
DEBENTURE REGISTRAR. THIS LEGEND WILL BE REMOVED UPON REQUEST OF THE HOLDER
AFTER THE EARLIER OF (i) THE TRANSFER OF THE DEBENTURE EVIDENCED HEREBY PURSUANT
TO CLAUSE (B) ABOVE OR (ii) THE RESALE RESTRICTION TERMINATION DATE. THE HOLDER
WILL, AND EACH SUBSEQUENT HOLDER IS REQUIRED TO, NOTIFY ANY PURCHASER OF THIS
DEBENTURE OF THE RESALE RESTRICTIONS REFERRED TO HEREIN.
PRIOR TO THE RESALE RESTRICTION TERMINATION DATE, THIS DEBENTURE MAY BE
TRANSFERRED OR EXCHANGED ONLY IN A MINIMUM AGGREGATE PRINCIPAL AMOUNT OF NOT
LESS THAN $100,000. ANY ATTEMPTED TRANSFER OF THIS DEBENTURE IN AN AGGREGATE
PRINCIPAL AMOUNT OF LESS THAN $100,000 PRIOR TO THE RESALE RESTRICTION
TERMINATION DATE SHALL BE DEEMED TO BE VOID AND OF NO LEGAL EFFECT WHATSOEVER.
AFTER SUCH RESALE RESTRICTION TERMINATION DATE, ANY ATTEMPTED TRANSFER OF THIS
DEBENTURE IN AN AGGREGATE PRINCIPAL AMOUNT OF LESS THAN $100,000 SHALL BE DEEMED
TO BE VOID AND OF NO LEGAL EFFECT WHATSOEVER. ANY SUCH PURPORTED TRANSFEREE
SHALL BE DEEMED NOT TO BE THE HOLDER OF THIS DEBENTURE FOR ANY PURPOSE,
INCLUDING, BUT NOT LIMITED TO, THE RIGHT TO RECEIVE INTEREST PAYMENTS ON THIS
DEBENTURE, AND SUCH PURPORTED TRANSFEREE SHALL BE DEEMED TO HAVE NO INTEREST
WHATSOEVER IN THIS DEBENTURE.
IN CONNECTION WITH ANY TRANSFER, THE HOLDER WILL DELIVER TO THE REGISTRAR
SUCH CERTIFICATES AND OTHER INFORMATION AS MAY BE REQUIRED BY THE INDENTURE TO
CONFIRM THAT THE TRANSFER COMPLIES WITH THE FOREGOING RESTRICTIONS.
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ENTERPRISE FINANCIAL SERVICES CORP.
FLOATING RATE JUNIOR SUBORDINATED DEFERRABLE INTEREST
DEBENTURE
DUE JUNE 30, 2032
No. Four Million One Hundred Twenty Four Thousand Dollars ($4,124,000)
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Enterprise Financial Services Corp., a Delaware corporation (the "Company,"
which term includes any successor corporation under the Indenture hereinafter
referred to), for value received, hereby promises to pay to, Wells Fargo Bank,
National Association or any successor thereto, as property trustee of EFSC
Capital Trust I or registered assigns, the principal sum of Four Million One
Hundred Twenty Four Thousand Dollars ($4,124,000) on June 30, 2032 (the "Stated
Maturity"), and to pay interest on said principal sum from June 28, 2002, or
from the most recent interest payment date to which interest has been paid or
duly provided for, quarterly (subject to deferral as set forth herein) in
arrears on March 30, June 30, September 30 and December 30 of each year (each
such date, an "Interest Payment Date") commencing September 30, 2002, at the
rate of 3.65% per annum over the Three-Month LIBOR Rate (the "Floating Interest
Rate"), applied to the aggregate principal amount of the Debentures Outstanding
as of such Interest Payment Date, until the principal hereof shall have become
due and payable, 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 at the same rate per annum compounded
quarterly. In no event shall the Floating Interest Rate exceed 12% prior to June
30, 2007.
The "Three-Month LIBOR Rate" shall mean the rate determined in accordance
with the following provisions:
(i) On the second LIBOR BUSINESS DAY (provided that on such day
commercial banks are open for business (including dealings in foreign
currency deposits) in London (a "LIBOR Banking Day") preceding each January
15, April 15, July 15 and October 15 (except with respect to the Interest
Payment Period commencing June 28, 2002) (each such date, an "Interest
Reset Date"), Wells Fargo Bank, National Association (the "Calculation
Agent"), will determine the Three-Month LIBOR Rate which shall be the rate
for deposits in the London interbank market in U.S. dollars having a
three-month maturity which appears on the Telerate Page 3750 as of 11:00
a.m., London time, on such Interest Reset Date. "Telerate Page 3750" means
the display on Page 3750 of the Bloomberg Financial Markets Commodities
News (or such other page as may replace that page on that service for the
purpose of displaying London interbank offered rates of major banks for
U.S. dollar deposits). If the Three-Month LIBOR Rate on such Interest Reset
Date does not appear on the Telerate Page 3750, such Three-Month LIBOR Rate
will be determined as described in (ii) below. "LIBOR Business Day" means
any day that is not a Saturday, Sunday or other day on which commercial
banking institutions in New York, New York or Wilmington, Delaware are
authorized or obligated by law or executive order to be closed. If such
rate is superseded on Telerate Page 3750 by a
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corrected rate before 12:00 noon (London time) on the same Interest Reset
Date, the corrected rate as so substituted will be the applicable LIBOR for
that Interest Reset Date.
(ii) If, on any Interest Reset Date, such rate does not appear on
Telerate Page 3750 as reported by Bloomberg Financial Markets Commodities
News or such other page as may replace such Telerate Page 3750, the
Calculation Agent shall determine the arithmetic mean of quotations of the
Reference Banks (defined below) to leading banks in the London interbank
market for three-month U.S. Dollar deposits in Europe (in an amount
determined by the Calculation Agent by reference to requests for quotations
as of approximately 11:00 a.m. (London time) on the Interest Reset Date
made by the Calculation Agent to the Reference Banks. If, on any Interest
Reset Date, at least two of the Reference Banks provide such quotations,
LIBOR shall equal the arithmetic mean of such quotations. If, on any
Interest Reset Date, only one or none of the Reference Banks provide such a
quotation, LIBOR shall be deemed to be the arithmetic mean of the offered
quotations that at least two leading banks in the City of New York (as
selected by the Calculation Agent) are quoting on the relevant Interest
Reset Date for three-month U.S. Dollar deposits in Europe at approximately
11:00 a.m. (London time) (in an amount determined by the Calculation
Agent). As used herein, "Reference Banks" means four major banks in the
London interbank market selected by the Calculation Agent.
(iii) If the Calculation Agent is required but is unable to determine
a rate in accordance with at least one of the procedures provided above,
LIBOR shall be LIBOR in effect on the previous Interest Reset Date (whether
or not LIBOR for such period was in fact determined on such Interest Reset
Date).
The amount of interest payable for any full Interest Payment Period shall
be computed on the basis of a 360-day year and the actual number of days in such
Interest Payment Period. In the event that any date on which interest is payable
on this Debenture is not a Business Day, then payment of interest payable on
such date shall be made on the next succeeding day that is a Business Day except
that, if such Business Day is in the next succeeding calendar year, payment of
such interest will be made on the immediately preceding Business Day. The
interest installment so payable, and punctually paid or duly provided for, on
any Interest Payment Date shall, be paid to the Person in whose name this
Debenture (or one or more Predecessor Debentures, as defined in said Indenture)
is registered as provided in the Indenture.
The Floating Interest Rate will in no event be higher than the maximum rate
permitted by the law of the State of Delaware, or, if higher, the law of the
United States of America.
The principal of and the interest on this Debenture shall be payable at or
through the office or agency of the Trustee 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 at the option of the Company by check mailed to
the registered holder at such address as shall appear in the Debenture Register.
Notwithstanding the foregoing, so long as the holder of this Debenture is the
Property Trustee, the payment of the principal of and interest on this Debenture
shall be made at such place and to such account as may be designated by the
Property Trustee.
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The Floating Interest Rate and amount of interest to be paid on the
Debentures for each Interest Payment Period will be determined by the
Calculation Agent. All calculations made by the Calculation Agent shall, in the
absence of manifest error, be conclusive for all purposes and binding on the
Company and the holders of this Debenture. In the event that any then acting
Calculation Agent shall be unable or unwilling to act, or that such Calculation
Agent shall fail duly to establish the Floating Interest Rate for any Interest
Payment Period, or that the Company proposes to remove such Calculation Agent,
or that the Calculation Agent proposes to terminate its service as Calculation
Agent, the Company shall appoint another Person, which is a bank, trust company,
investment banking firm or other financial institution, to act as the
Calculation Agent. The Calculation Agent shall certify the Floating Interest
Rate on each Interest Reset Date and shall provide a copy of such certification
to the Trustee under the Indenture and to the Property Trustee as soon as
practicable following each Interest Reset Date. The Trustee will provide written
notice of the Floating Interest Rate as certified by the Calculation Agent to
the holder of this Debenture within five Business Days following each Interest
Reset Date.
Subject to the Company having received prior approval of the Federal
Reserve if then required under applicable capital guidelines, policies or
regulations of the Federal Reserve, the Company may redeem this Debenture prior
to the Stated Maturity in the manner and at the times set forth in the
Indenture.
The payment by the Company of the principal and interest on the
indebtedness evidenced by this Debenture is, to the extent and in the manner
provided in the Indenture, subordinate and junior in right of payment to the
prior payment in full of all Senior Indebtedness. 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 the Company advises the Trustee in writing is 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.
Capitalized terms used and not defined in this Debenture shall have the
meanings assigned in the Indenture.
The provisions of this Debenture are continued on the reverse side hereof
and such continued provisions shall for all purposes have the same effect as
though fully set forth at this place.
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IN WITNESS WHEREOF, the Company has caused this instrument to be effective
June 28, 2002.
Enterprise Financial Services Corp.
By:
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Name:
--------------------------------
Title:
-------------------------------
Attest:
By:
-------------------------
Name:
------------------------
Title: Secretary
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CERTIFICATE OF AUTHENTICATION
This is one of the Debentures described in the within-mentioned Indenture.
Wells Fargo Bank, National Association,
as Trustee or Authenticating Agent
By:
---------------------------------
Authorized Signatory
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FLOATING RATE JUNIOR SUBORDINATED
DEFERRABLE INTEREST DEBENTURE
(CONTINUED)
This Debenture is one of the subordinated debentures of the Company (herein
sometimes referred to as the "Debentures"), specified in the Indenture, all
issued or to be issued under and pursuant to an Indenture effective as of June
28, 2002 (the "Indenture") duly executed and delivered between the Company and
Wells Fargo Bank, National Association, as Trustee (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 and of the terms upon which the
Debentures are, and are to be, authenticated and delivered. The Debentures are
limited in aggregate principal amount as specified in the Indenture.
Because of the occurrence and continuation of a Special Event, in certain
circumstances, this Debenture may become due and payable at the principal amount
together with any interest accrued thereon (the "Redemption Price"). The
Redemption Price shall be paid prior to 12:00 noon, Eastern Standard Time, on
the date of such redemption or at such earlier time as the Company determines.
The Company shall have the right as set forth in the Indenture to redeem this
Debenture at the option of the Company, without premium or penalty, (i) in whole
or in part, at any time on or after June 30, 2007 (an "Optional Redemption"), or
(ii) in whole, but not in part, at any time in certain circumstances upon the
occurrence of a Special Event, at a Redemption Price equal to 103% of the
principal amount plus any accrued but unpaid interest hereon, to the date of
such redemption. Any redemption pursuant to this paragraph shall be made upon
not less than 30 days' nor more than 60 days' notice, at the Redemption Price.
The Redemption Price shall be paid at the time and in the name provided therefor
in the Indenture. If the Debentures are only partially redeemed by the Company
pursuant to an Optional Redemption, the Debentures shall be redeemed pro rata or
by lot or by any other method utilized by the Trustee as described in the
Indenture.
In the event of redemption of this Debenture in part only, a new Debenture
or Debentures for the unredeemed portion hereof shall be issued in the name of
the holder hereof upon the cancellation hereof. In case an Event of Default, as
defined in the Indenture, shall have occurred and be continuing, the principal
of all of the Debentures may be declared, and upon such declaration 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, as defined in the
Indenture, to execute supplemental indentures for the purpose of adding any
provisions to or changing in any manner or eliminating any of the provisions of
the 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, except as provided in the Indenture (i) extend the
fixed maturity of
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the Debentures, reduce the principal amount thereof, or reduce the rate or
extend the time of payment of interest thereon, without the consent of the
holder of each Debenture so affected thereby; or (ii) reduce the aforesaid
percentage of Debentures, the holders of which are required to consent to any
such supplemental indenture, without the consent of the holders of each
Debenture then Outstanding and so affected thereby. 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 all of the holders of the
Debentures, to waive any past default in the performance of any of the covenants
contained in the Indenture, or established pursuant to the Indenture, and its
consequences, except a default in the payment of the principal of or interest on
any of the Debentures. Any such consent or waiver by the registered holder of
this Debenture (unless revoked as provided in the Indenture) shall be conclusive
and binding upon such holder and upon all future holders and owners of this
Debenture and of any Debenture issued in exchange herefor or in place hereof
(whether by registration of transfer or otherwise), irrespective of whether or
not any notation of such consent or waiver is made upon this Debenture.
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 and interest on this Debenture
at the time (subject to the Company's right to defer payment of interest during
an Extended Interest Payment Period as described herein) and place and at the
rate and in the money herein prescribed.
As further described in the Indenture, the Company shall have the right at
any time during the term of the Debentures and from time to time to defer
payments of interest by extending the interest payment period of such Debentures
for up to 20 consecutive quarters (each, an "Extended Interest Payment Period"),
at the end of which period the Company shall pay all interest then accrued and
unpaid (together with interest thereon at the rate specified for the Debentures
to the extent that payment of such interest is enforceable under applicable
law). Before the termination of any such Extended Interest Payment Period, so
long as no Event of Default shall have occurred and be continuing, the Company
may further extend such Extended Interest Payment Period, provided that such
Extended Interest Payment Period together with all such further extensions
thereof shall not exceed 20 consecutive quarters, extend beyond the Stated
Maturity or end on a date other than an Interest Payment Date. At the
termination of any such Extended Interest Payment Period and upon the payment of
all accrued and unpaid interest and any additional amounts then due and subject
to the foregoing conditions, the Company may commence a new Extended Interest
Payment Period.
As provided in the Indenture and subject to certain limitations therein set
forth, this Debenture is transferable by the registered holder hereof on the
Debenture Register at the office or agency of the Company designated for such
purpose upon surrender of this Debenture for registration of transfer
accompanied by a written instrument or instruments of transfer in form
satisfactory to the Company duly executed by the registered holder hereof or his
attorney duly authorized in writing, and thereupon one or more new Debentures of
authorized denominations and for the same aggregate principal amount shall be
issued to the designated transferee or transferees. No service charge shall be
made for any such transfer, but the Company may require payment of a sum
sufficient to cover any tax or other governmental charge payable in relation
thereto.
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Prior to due presentment for registration of transfer of this Debenture,
the Company, the Trustee, any Paying Agent and the Debenture Registrar may deem
and treat the registered holder hereof as the absolute owner hereof (whether or
not this Debenture shall be overdue and notwithstanding any notice of ownership
or writing hereon made by anyone other than the Debenture Registrar) for the
purpose of receiving payment of or on account of the principal hereof and
interest due hereon and for all other purposes, and neither the Company nor the
Trustee nor any Paying Agent nor any Debenture Registrar shall be affected by
any notice to the contrary (by anyone other than the Debenture Registrar).
No recourse shall be had for the payment of the principal of or the
interest on this Debenture, or for any claim based hereon, or otherwise in
respect hereof, or based on or in respect of the Indenture, against any
incorporator, stockholder, officer or director, past, present or future, as
such, of the Company or of any predecessor or successor corporation, whether by
virtue of any constitution, statute or rule of law, or by the enforcement of any
assessment or penalty or otherwise, all such liability being, by the acceptance
hereof and as part of the consideration for the issuance hereof, expressly
waived and released.
Subject to Section 2.3 of the Indenture, the Debentures are issuable only
in registered form without coupons in denominations of $1,000 and any integral
multiple thereof.
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