Exhibit 4.2

    

    

    

    ENTERPRISE FINANCIAL SERVICES CORP

    

    

    Issuer

    

    

    And

    

    

    U.S. BANK NATIONAL ASSOCIATION

    

    

    Trustee

    

    

    FIRST SUPPLEMENTAL INDENTURE

    

    

    Dated as of May 21, 2020

    

    

    to

    

    

    the Indenture

    

    

    Dated as of May 21, 2020

    

    

    5.75% Fixed-to-Floating Rate

    Subordinated Notes due 2030

    
      
        


    

    
    

    

    

    

    

    

    FIRST SUPPLEMENTAL INDENTURE (this “Supplemental Indenture”), dated as of May 21, 2020, between ENTERPRISE FINANCIAL SERVICES CORP, a Delaware corporation (the “Company”),



      and U.S. BANK NATIONAL ASSOCIATION, a national banking association organized and existing under the laws of the United States of America, as trustee (“Trustee”).

    

    

    RECITALS OF THE COMPANY

    

    

    The Company and the Trustee will have executed and delivered a Subordinated Debt Securities Indenture dated as of the date hereof (the “Base Indenture” and, as the same
      may from time to time be amended, supplemented or otherwise modified in accordance therewith, including by this Supplemental Indenture, the “Indenture”), to provide for the issuance from time to time by the Company of its unsecured
      subordinated indebtedness to be issued in one or more series as provided in the Indenture.

    

    

    The Company desires to issue and sell on the date hereof Sixty-Three Million Two Hundred and Fifty Thousand Dollars ($63,250,000) aggregate principal amount of a new series of
      Securities of the Company designated as its 5.75% Fixed-to-Floating Rate Subordinated Notes due 2030 (the “Notes”), and such issuance and sale have been authorized by resolutions duly adopted by the Board of Directors of the Company and by the
      Executive Committee of the Board of Directors of the Company.

    

    

    The Company desires to establish the terms of the Notes.

    

    

    The Company acknowledges that all things necessary to make this Supplemental Indenture a legal, binding and enforceable instrument, and to make the Notes, when executed by the
      Company and authenticated and delivered by the Trustee, the legal, binding and enforceable obligations of the Company in accordance with their terms and the terms of the Base Indenture, have been done.

    

    

    The Company has complied with all conditions precedent provided for in the Base Indenture relating to this Supplemental Indenture.

    

    

    The Company has requested that the Trustee execute and deliver this Supplemental Indenture.

    

    

    NOW, THEREFORE, THIS SUPPLEMENTAL INDENTURE WITNESSETH:

    

    

    For and in consideration of the premises and the purchase of the Notes by the Holders thereof, it is mutually agreed, for the equal and proportionate benefit of all Holders of
      the Notes, as follows:

    
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    ARTICLE I.

    

    

    SCOPE OF SUPPLEMENTAL INDENTURE

    

    

    Section 1.01                          Scope.

    

    

    This Supplemental Indenture constitutes an indenture supplemental to the Base Indenture and an integral part of the Indenture and shall be read together with the Base Indenture
      as though all the provisions hereof and thereof are contained in one instrument. All provisions included in this Supplemental Indenture supersede any conflicting provisions included in the Base Indenture unless not permitted by law. Except as
      expressly amended by the Supplemental Indenture, the terms and provisions of the Base Indenture shall remain in full force and effect. Notwithstanding the foregoing, this Supplemental Indenture shall only apply to the Notes.

    

    

    ARTICLE II.

    

    

    DEFINITIONS

    

    

    Section 2.01                          Definitions and Other Provisions of General Application.

    

    

    For all purposes of this Supplemental Indenture, except as otherwise expressly provided or unless the context otherwise requires:

    

    

    	

          	(1)	
            all terms used in this Supplemental Indenture which are not otherwise defined herein shall have the meanings assigned to them in the Base Indenture and include the plural as well as the singular; and

          


    

    

    	

          	(2)	
            Section 101 of the Base Indenture is amended and supplemented by inserting the following additional defined terms in their appropriate alphabetical positions (and, in the case of any defined term which is duplicated in Section 101 of the
              Base Indenture, by deleting the duplicate definition set forth in such Section 101 in its entirety):

          


    

    

    “Additional Notes” has the meaning specified in Section 3.02(b).

    

    

    “Administrative or Judicial Action” has the meaning specified in the definition of “Tax Event.”

    

    

    “Benchmark” means, initially, Three-Month Term SOFR; provided that if the Calculation Agent determines on or prior to the Reference Time for any Interest Period that a
      Benchmark Transition Event and its related Benchmark Replacement Date have occurred with respect to Three-Month Term SOFR or the then-current Benchmark, then “Benchmark” means the applicable Benchmark Replacement for such Interest Period and any
      subsequent Interest Periods.

    

    

    “Benchmark Replacement” means the Interpolated Benchmark with respect to the then-current Benchmark, plus the Benchmark Replacement Adjustment for such Benchmark; provided
      that if (a) the Calculation Agent cannot determine the Interpolated Benchmark as of the Benchmark Replacement Date or (b) the then-current Benchmark is Three-Month Term SOFR and a Benchmark Transition Event and its related Benchmark Replacement Date
      have occurred with respect to Three-Month Term SOFR (in which event no Interpolated Benchmark with respect to Three-Month Term SOFR shall be determined), then “Benchmark Replacement” means the first alternative set forth in the order below that can
      be determined by the Calculation Agent as of the Benchmark Replacement Date:

    

    

    	

          	(1)	
            Compounded SOFR;

          


    

    

    	

          	(2)	
            the sum of (a) the alternate rate that has been selected or recommended by the Relevant Governmental Body as the replacement for the then-current Benchmark for the applicable Corresponding Tenor and (b) the Benchmark Replacement
              Adjustment;

          


    
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          	(3)	
            the sum of (a) the ISDA Fallback Rate and (b) the Benchmark Replacement Adjustment; and

          


    

    

    	

          	(4)	
            the sum of (a) the alternate rate that has been selected by the Calculation Agent as the replacement for the then-current Benchmark for the applicable Corresponding Tenor, giving due consideration to any industry-accepted rate as a
              replacement for the then-current Benchmark for U.S. dollar-denominated floating rate securities at such time, and (b) the Benchmark Replacement Adjustment.

          


    

    

    “Benchmark Replacement Adjustment” means the first alternative set forth in the order below that can be determined by the Calculation Agent as of the Benchmark Replacement Date:

    

    

    	

          	(1)	
            the spread adjustment, or method for calculating or determining such spread adjustment (which may be a positive or negative value or zero), that has been selected or recommended by the Relevant Governmental Body for the applicable
              Unadjusted Benchmark Replacement;

          


    

    

    	

          	(2)	
            if the applicable Unadjusted Benchmark Replacement is equivalent to the ISDA Fallback Rate, then the ISDA Fallback Adjustment; and

          


    

    

    	

          	(3)	
            the spread adjustment (which may be a positive or negative value or zero) that has been selected by the Calculation Agent, giving due consideration to any industry-accepted spread adjustment or method for calculating or determining such
              spread adjustment, for the replacement of the then-current Benchmark with the applicable Unadjusted Benchmark Replacement for U.S. dollar-denominated floating rate securities at such time.

          


    

    

    “Benchmark Replacement Conforming Changes” means, with respect to any Benchmark Replacement, any technical, administrative or operational changes (including changes to the
      definition of “Interest Period”, timing and frequency of determining rates with respect to each Interest Period and making payments of interest, rounding of amounts or tenors, and other administrative matters) that the Calculation Agent determines
      may be appropriate to reflect the adoption of such Benchmark Replacement in a manner substantially consistent with market practice (or, if the Calculation Agent determines that adoption of any portion of such market practice is not administratively
      feasible or if the Calculation Agent determines that no market practice for use of the Benchmark Replacement exists, in such other manner as the Calculation Agent determines is reasonably necessary).

    
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    “Benchmark Replacement Date” means the earliest to occur of the following events with respect to the then-current Benchmark:

    

    

    	

          	(1)	
            in the case of clause (1) of the definition of “Benchmark Transition Event,” the relevant Reference Time in respect of any determination;

          


    

    

    	

          	(2)	
            in the case of clause (2) or (3) of the definition of “Benchmark Transition Event,” the later of (a) the date of the public statement or publication of information referenced therein and (b) the date on which the administrator of the
              Benchmark permanently or indefinitely ceases to provide the Benchmark; or

          


    

    

    	

          	(3)	
            in the case of clause (4) of the definition of “Benchmark Transition Event,” the date of the public statement or publication of information referenced therein.

          


    

    

    For the avoidance of doubt, if the event giving rise to the Benchmark Replacement Date occurs on the same day as, but earlier than, the Reference Time in respect of any determination, the Benchmark
      Replacement Date will be deemed to have occurred prior to the Reference Time for such determination.

    

    

    “Benchmark Transition Event” means the occurrence of one or more of the following events with respect to the then-current Benchmark:

    

    

    	

          	(1)	
            if the Benchmark is Three-Month Term SOFR, (a) the Relevant Governmental Body has not selected or recommended a forward-looking term rate for a tenor of three months based on SOFR, (b) the development of a forward-looking term rate for a
              tenor of three months based on SOFR that has been recommended or selected by the Relevant Governmental Body is not complete or (c) the Company determines that the use of a forward-looking rate for a tenor of three months based on SOFR is not
              administratively feasible;

          


    

    

    	

          	(2)	
            a public statement or publication of information by or on behalf of the administrator of the Benchmark announcing that such administrator has ceased or will cease to provide the Benchmark, permanently or indefinitely, provided that, at the
              time of such statement or publication, there is no successor administrator that will continue to provide the Benchmark;

          


    

    

    	

          	(3)	
            a public statement or publication of information by the regulatory supervisor for the administrator of the Benchmark, the central bank for the currency of the Benchmark, an insolvency official with jurisdiction over the administrator for
              the Benchmark, a resolution authority with jurisdiction over the administrator for the Benchmark or a court or an entity with similar insolvency or resolution authority over the administrator for the Benchmark, which states that the
              administrator of the Benchmark has ceased or will cease to provide the Benchmark permanently or indefinitely, provided that, at the time of such statement or publication, there is no successor administrator that will continue to provide the
              Benchmark; or

          


    
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          	(4)	
            a public statement or publication of information by the regulatory supervisor for the administrator of the Benchmark announcing that the Benchmark is no longer representative.

          


    

    

    “Business Day” means (i) each Monday, Tuesday, Wednesday, Thursday and Friday which is not a day on which banking institutions in New York are authorized or obligated by
      law or executive order to close or (ii) a day on which the corporate trust office of the trustee is not closed for business.

    

    

    “Calculation Agent” means the agent appointed by the Company prior to the commencement of the Floating Rate Period (which may be the Company or any of its Affiliates) to
      act in accordance with Section 3.02(e)(iv).

    

    

    “Compounded SOFR” means the compounded average of SOFRs for the applicable Corresponding Tenor, with the rate, or methodology for this rate, and conventions for this rate
      being established by the Calculation Agent in accordance with:

    

    

    	

          	(1)	
            the rate, or methodology for this rate, and conventions for this rate selected or recommended by the Relevant Governmental Body for determining compounded SOFR; provided that:

          


    

    

    	

          	(2)	
            if, and to the extent that, the Calculation Agent determines that Compounded SOFR cannot be determined in accordance with clause (1) above, then the rate, or methodology for this rate, and conventions for this rate that have been selected
              by the Calculation Agent giving due consideration to any industry-accepted market practice for U.S. dollar-denominated floating rate securities at such time.

          


    

    

    For the avoidance of doubt, the calculation of Compounded SOFR shall exclude the Benchmark Replacement Adjustment and the spread specified in Section 3.02(e)(ii).

    

    

    “Corresponding Tenor” means (i) with respect to Term SOFR, three months, and (ii) with respect to a Benchmark Replacement, a tenor (including overnight) having
      approximately the same length (disregarding business day adjustment) as the applicable tenor for the then-current Benchmark.

    

    

    “Designated Senior Indebtedness” means any Senior Indebtedness that expressly provides that it is “designated senior indebtedness” for purposes of the Indenture, provided
      that the instrument, agreement or other document creating or evidencing such Senior Indebtedness may place limitations and conditions on the right of such Senior Indebtedness to exercise the rights of Designated Senior Indebtedness.

    
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    “Federal Reserve” means the Board of Governors of the Federal Reserve System or any successor federal banking agency.

    

    

    “Fixed Rate Interest Payment Date” has the meaning specified in Section 3.02(e)(i), and shall constitute an “Interest Payment Date.”

    

    

    “Fixed Rate Period” has the meaning specified in Section 3.02(e)(i).

    

    

    “Floating Rate Interest Payment Date” has the meaning specified in Section 3.02(e)(ii) and shall constitute an “Interest Payment Date.”

    

    

    “Floating Rate Period” has the meaning specified in Section 3.02(e)(ii).

    

    

    “FRBNY” means the Federal Reserve Bank of New York.

    

    

    “FRBNY’s Website” means the website of the FRBNY at http://www.newyorkfed.org, or any successor source.

    

    

    “Interest Period” means the period from and including the immediately preceding Interest Payment Date in respect of which interest has been paid or duly provided for or,
      if no interest has been paid or duly provided for, from and including the Issue Date to, but excluding, the applicable Interest Payment Date for such period (or the Maturity Date or earlier Redemption Date, if applicable).

    

    

    “Interpolated Benchmark” with respect to the Benchmark means the rate determined by the Calculation Agent for the Corresponding Tenor by interpolating on a linear basis
      between: (1) the Benchmark for the longest period (for which the Benchmark is available) that is shorter than the Corresponding Tenor and (2) the Benchmark for the shortest period (for which the Benchmark is available) that is longer than the
      Corresponding Tenor.

    

    

    “ISDA Definitions” means the 2006 ISDA Definitions published by the International Swaps and Derivatives Association, Inc. or any successor thereto, as amended or
      supplemented from time to time, or any successor definitional booklet for interest rate derivatives published from time to time.

    

    

    “ISDA Fallback Adjustment” means the spread adjustment (which may be a positive or negative value or zero) that would apply for derivatives transactions referencing the ISDA Definitions to be
      determined upon the occurrence of an index cessation event with respect to the Benchmark for the applicable tenor.

    

    

    “ISDA Fallback Rate” means the rate that would apply for derivatives transactions referencing the ISDA Definitions to be effective upon the occurrence of an index cessation date with respect
      to the Benchmark for the applicable tenor excluding the applicable ISDA Fallback Adjustment.

    

    

    “Issue Date” means May 21, 2020.

    
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    “Material Subsidiary” means Enterprise Bank & Trust or any successor thereof or any of the Company’s Subsidiaries that is a depository institution and that has
      consolidated assets equal to 80% or more of the Company’s consolidated assets.

    

    

    “Maturity Date,” with respect to the principal of the Notes, has the meaning specified in Section 3.02(d), which date shall constitute the “Stated Maturity”
      thereof.

    

    

    “Payment Blockage Notice” has the meaning provided in Section 5.02(b).

    

    

    “Reference Time” with respect to any determination of the Benchmark means (1) if the Benchmark is Three-Month Term SOFR, the time determined by the Calculation Agent after
      giving effect to the Three-Month Term SOFR Conventions, or (2) if the Benchmark is not Three-Month Term SOFR, the time determined by the Calculation Agent after giving effect to the Benchmark Replacement Conforming Changes.

    

    

    “Relevant Governmental Body” means the Federal Reserve and/or the FRBNY, or a committee officially endorsed or convened by the Federal Reserve and/or the FRBNY or any
      successor thereto.

    

    

    “Representative” means the (a) indenture trustee or other trustee, agent or representative for any Senior Indebtedness or (b) with respect to any Senior Indebtedness that
      does not have any such trustee, agent or other representative, (i) in the case of such Senior Indebtedness issued pursuant to an agreement providing for voting arrangements as among the holders or owners of such Senior Indebtedness, any holder or
      owner of such Senior Indebtedness acting with the consent of the required Persons necessary to bind such holders or owners of such Senior Indebtedness and (ii) in the case of all other such Senior Indebtedness, the holder or owner of such Senior
      Indebtedness.

    

    

    “Senior Indebtedness” means, without duplication, the principal, premium, if any, unpaid interest (including interest accruing on or after the filing of any petition in
      bankruptcy or for reorganization relating to the Company, whether or not a claim for post-filing interest is allowed in such proceeding), fees, charges, expenses, reimbursement and indemnification obligations, and all other amounts payable under or
      in respect of the following indebtedness of the Company, whether any such indebtedness exists as of the date of the Indenture or is created, incurred or assumed after such date: (i) all obligations for borrowed money; (ii) all obligations evidenced
      by debentures, notes, debt securities or other similar instruments; (iii) all obligations in respect of letters of credit, security purchase facilities or bankers acceptances or similar instruments (or reimbursement obligations with respect thereto);
      (iv) all obligations to pay the deferred purchase price of property or services, except trade accounts payable arising in the ordinary course of business; (v) indebtedness secured by any mortgage, pledge, lien, charge, encumbrance or any security
      interest existing on property owned by the Company; (vi) obligations associated with derivative products including, but not limited to, interest rate and currency future or exchange contracts, foreign exchange contracts, swap agreements (including
      interest rate and foreign exchange rate swap agreements), cap agreements, floor agreements, collar agreements, options, interest rate future or option contracts, commodity contracts, and similar arrangements; (vii) purchase money debt and similar
      obligations; (viii) obligations to general creditors of the Company; (ix) a deferred obligation of, or any such obligation, directly or indirectly guaranteed by, the Company which obligation is incurred in connection with the acquisition of any
      business, properties or assets not evidenced by a note or similar instrument given in connection therewith; (x) all obligations of the type referred to in the foregoing subclauses above of other Persons for the payment of which the Company is
      responsible or liable as obligor, guarantor or otherwise, whether or not classified as a liability on a balance sheet prepared in accordance with GAAP; and (xi) any renewals, amendments, deferrals, supplements, extensions, refundings or replacements
      of any of the foregoing. Senior Indebtedness excludes: (v) any such indebtedness, obligation or liability referred to above as to which, in the instrument creating or evidencing the same or pursuant to which the same is outstanding, it is provided
      that such indebtedness, obligation or liability is not superior in right of payment to the Notes, or ranks pari passu with the Notes; (w) any such indebtedness, obligation or liability which is subordinated to indebtedness of the Company to
      substantially the same extent as, or to a greater extent than, the Notes are subordinated; (x) any indebtedness to a Subsidiary; (y) any trade account payables in the ordinary course of business; and (z) the Notes. Notwithstanding the foregoing, and
      for the avoidance of doubt, if the Federal Reserve (or other applicable regulatory agency or authority) promulgates any rule or issues any interpretation that defines general creditor(s), the main purpose of which is to establish criteria for
      determining whether the subordinated debt of a financial or bank holding company is to be included in its capital, then the term “general creditors” as used in this definition of “Senior Indebtedness” will have the meaning as described in that rule
      or interpretation.

    
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    “SOFR” means the secured overnight financing rate published by the FRBNY, as the administrator of the Benchmark (or any successor administrator), on the FRBNY’s Website.

    

    

    “Tax Event” means the receipt by the Company of an opinion of independent tax counsel to the effect that as a result of (1) an amendment to or change (including any
      announced prospective amendment or change) in any law or treaty, or any regulation thereunder, of the United States or any of its political subdivisions or taxing authorities; (2) a judicial decision, administrative action, official administrative
      pronouncement, ruling, regulatory procedure, regulation, notice or announcement, including any notice or announcement of intent to adopt or promulgate any ruling, regulatory procedure or regulation (any of the foregoing, an “Administrative or
        Judicial Action”); or (3) an amendment to or change in any official position with respect to, or any interpretation of, an Administrative or Judicial Action or a law or regulation of the United States that differs from the previously generally
      accepted position or interpretation, in each case, which change or amendment or challenge becomes effective or which pronouncement, decision or challenge is announced on or after the Issue Date, there is more than an insubstantial risk that interest
      payable by the Company on the Notes is not, or, within 90 days of the date of such opinion, will not be, deductible by the Company, in whole or in part, for United States federal income tax purposes.

    

    

    “Term SOFR” means the forward-looking term rate for the applicable Corresponding Tenor based on SOFR that has been selected or recommended by the Relevant Governmental
      Body.

    
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    “Term SOFR Administrator” means any entity designated by the Relevant Governmental Body as the administrator of Term SOFR (or any successor administrator).

    

    

    “Three-Month Term SOFR” means Term SOFR for a tenor of three months that is published by the Term SOFR Administrator at the Reference Time for any Interest Period, as
      determined by the Calculation Agent after giving effect to the Three-Month Term SOFR Conventions. All percentages used in or resulting from any calculation of Three-Month Term SOFR shall be rounded, if necessary, to the nearest one-hundred-thousandth
      of a percentage point, with 0.000005% rounded up to 0.00001%.

    

    

    “Three-Month Term SOFR Conventions” means any determination, decision or election with respect to any technical, administrative or operational matter (including with
      respect to the manner and timing of the publication of Three-Month Term SOFR, or changes to the definition of “Interest Period”, timing and frequency of determining Three-Month Term SOFR with respect to each Interest Period and making payments of
      interest, rounding of amounts or tenors, and other administrative matters) that the Calculation Agent determines may be appropriate to reflect the use of Three-Month Term SOFR as the Benchmark in a manner substantially consistent with market practice
      (or, if the Calculation Agent determines that adoption of any portion of such market practice is not administratively feasible or if the Calculation Agent determines that no market practice for the use of Three-Month Term SOFR exists, in such other
      manner as the Calculation Agent determines is reasonably necessary).

    

    

    “Tier 2 Capital Event” means the Company’s good faith determination that, as a result of (1) any amendment to, or change in, the laws, rules or regulations of the United
      States (including, for the avoidance of doubt, any agency or instrumentality of the United States, including the Federal Reserve and other federal bank regulatory agencies) or any political subdivision of or in the United States that is enacted or
      becomes effective after the Issue Date, (2) any proposed change in those laws, rules or regulations that is announced or becomes effective after the Issue Date, or (3) any official administrative decision or judicial decision or administrative action
      or other official pronouncement interpreting or applying those laws, rules, regulations, policies or guidelines with respect thereto that is announced after the Issue Date, there is more than an insubstantial risk that the Company will not be
      entitled to treat the Notes then outstanding as “Tier 2 Capital” (or its equivalent), for purposes of the capital adequacy rules or regulations of the Federal Reserve as then in effect and applicable to the Company, for so long as any Notes are
      outstanding.

    

    

    “Unadjusted Benchmark Replacement” means the Benchmark Replacement excluding the Benchmark Replacement Adjustment.

    

    

    ARTICLE III.

    

    

    FORM AND TERMS OF THE NOTES

    

    

    Section 3.01                          Form and Dating.

    

    

    (a)            The Notes shall be substantially in the form of Exhibit A attached hereto.
      The Notes shall be executed on behalf of the Company by its Chairman of the Board, its Vice Chairman of the Board, its Chief Executive Officer, its President, its Chief Financial Officer or one of its Executive Vice Presidents.

    
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    (b)            The terms contained in the Notes shall constitute, and are hereby expressly made, a
      part of the Base Indenture as supplemented by this Supplemental Indenture, and the Company and the Trustee, by their execution and delivery of this Supplemental Indenture, expressly agree to such terms and provisions and to be bound thereby.

    

    

    Section 3.02                          Terms.

    

    

    The following terms relating to the Notes are hereby established:

    

    

    (a)            Title. The Notes shall constitute a series
      of Securities having the title “5.75% Fixed-to-Floating Rate Subordinated Notes due 2030” and the CUSIP number 293712 AB1.

    

    

    (b)            Principal Amount. The aggregate principal
      amount of the Notes that may be authenticated and delivered under the Indenture on the Issue Date shall be SIXTY-THREE MILLION TWO HUNDRED AND FIFTY THOUSAND DOLLARS ($63,250,000). If no Event of Default has occurred and is continuing with respect to
      the Notes, the Company may, from time to time, without notice to or the consent of the Holders, create and issue additional notes (“Additional Notes”) pursuant to the Indenture ranking equally with the Notes and with identical terms in all
      respects (or in all respects except for the offering price, the payment of interest accruing prior to the issue date of such Additional Notes and the first payment of interest following the issue date of such Additional Notes); provided, however,
      that a separate CUSIP number will be issued for any such Additional Notes unless such Additional Notes are fungible with the Notes for U.S. federal income tax purposes, subject to the procedures of DTC. The Notes and any Additional Notes shall
      constitute a single series under the Indenture. All references to the Notes shall include any Additional Notes, unless the context otherwise requires.

    

    

    (c)            Person to Whom Interest Is Payable.
      Defaulted Interest may be paid as provided in Section 307 of the Base Indenture.  However, interest that is paid on the Maturity Date will be paid to the Person to whom the principal is payable.

    

    

    (d)            Maturity Date. The entire outstanding Principal of the Notes
      shall be payable on June 1, 2030 (the “Maturity Date”).

    

    

    (e)            Interest.

    

    

    (i)            The Notes will bear interest at a fixed rate of 5.75% per annum
      from and including May 21, 2020, to but excluding June 1, 2025, or earlier Redemption Date (the “Fixed Rate Period”).  Interest accrued on the Notes during the Fixed Rate Period will be payable semi-annually in arrears on June 1 and December 1
      of each year, commencing on December 1, 2020 (each such date, a “Fixed Rate Interest Payment Date”). The last Fixed Rate Interest Payment Date shall be June 1, 2025, unless the Notes are earlier redeemed. The interest payable during the Fixed
      Rate Period will be paid to each Holder in whose name a Note is registered at the close of business on the fifteenth day (whether or not a Business Day) immediately preceding the applicable Fixed Rate Interest Payment Date.

    
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    (ii)            The Notes will bear a floating interest rate from and including
      June 1, 2025, to but excluding the Maturity Date or earlier Redemption Date (the “Floating Rate Period”). The floating interest rate will be reset for each Interest Period in the Floating Rate Period, and the interest rate for each such
      Interest Period shall be equal to the then-current Three-Month Term SOFR for such Interest Period plus 566.0 basis points, provided that if Three-Month Term SOFR (or other applicable Benchmark) is less than zero for any Interest Period during the
      Floating Rate Period, then Three-Month Term SOFR (or other such Benchmark) shall be deemed to be zero for such Interest Period. During the Floating Rate Period, interest on the Notes will be payable quarterly in arrears on March 1, June 1, September
      1 and December 1 of each year, commencing on September 1, 2025 (each such date, a “Floating Rate Interest Payment Date” and, together with each Fixed Rate Interest Payment Date, each an “Interest Payment Date”). The last Floating Rate
      Interest Payment Date shall be June 1, 2030, unless the Notes are earlier redeemed.  The interest payable during the Floating Rate Period will be paid to each Holder in whose name a Note is registered at the close of business on the fifteenth day
      (whether or not a Business Day) immediately preceding the applicable Floating Rate Interest Payment Date. The Calculation Agent will provide the Company and the Trustee with the interest rate in effect for each Interest Period during the Floating
      Rate Period promptly after the Reference Time therefor (or other date of determination for the applicable Benchmark).

    

    

    (iii)            The amount of interest payable on any Fixed Rate Interest
      Payment Date during the Fixed Rate Period will be computed on the basis of a 360-day year consisting of twelve 30-day months, and the amount of interest payable on any Floating Rate Interest Payment Date during the Floating Rate Period will be
      computed on the basis of a 360-day year and the actual number of days elapsed. In the event that any scheduled Interest Payment Date or the Maturity Date for the Notes falls on a day that is not a Business Day, then payment shall be made as provided
      in Section 113 of the Base Indenture; provided, that if any scheduled Floating Rate Interest Payment Date falls on a day that is not a Business Day and the next succeeding Business Day falls in the next succeeding calendar month, such Floating Rate
      Interest Payment Date will be accelerated to the immediately preceding Business Day, and, in each such case, the amounts payable on such Business Day will include interest accrued to, but excluding such Business Day. Dollar amounts resulting from
      interest calculations will be rounded to the nearest cent, with one-half cent being rounded upward.

    

    

    (iv)            The Company shall take such actions as are necessary to ensure
      that from the commencement of the Floating Rate Period for so long as any of the Notes remain outstanding there will at all times be a Calculation Agent appointed to calculate Three-Month Term SOFR in respect of each Floating Rate Period. The
      calculation of Three-Month Term SOFR for each applicable Floating Rate Period by the Calculation Agent will (in the absence of manifest error) be final and binding. The Calculation Agent shall have all the rights, protections and indemnities afforded
      to the Trustee under the Base Indenture and hereunder. The Calculation Agent may be removed by the Company at any time. If the Calculation Agent is unable or unwilling to act as Calculation Agent or is removed by the Company, the Company will
      promptly appoint a replacement Calculation Agent, which shall not be the Trustee without the Trustee’s express written consent. The Calculation Agent may not resign its duties without a successor having been duly appointed; provided, that if a
      successor Calculation Agent has not been appointed by the Company and such successor accepted such position within 30 days after the giving of notice of resignation by the Calculation Agent, then the resigning Calculation Agent may petition, at the
      expense of the Company, any court of competent jurisdiction for the appointment of a successor Calculation Agent with respect to such series. For the avoidance of doubt, if at any time there is no Calculation Agent appointed by the Company, then the
      Company shall be the Calculation Agent. The Company may appoint itself or any of its Affiliates to be the Calculation Agent.

    
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    (v)            Effect of Benchmark Transition Event and Benchmark Replacement Date.

    

    

    (1)            If the Calculation Agent determines that a Benchmark Transition
      Event and its related Benchmark Replacement Date have occurred on or prior to the Reference Time in respect of any Interest Period during the Floating Rate Period, then the Benchmark Replacement will replace the then-current Benchmark for all
      purposes relating to the Notes during such Interest Period and all subsequent Interest Periods.

    

    

    (2)            Notwithstanding anything set forth in clause (ii) above, if the
      Calculation Agent determines that a Benchmark Transition Event and its related Benchmark Replacement Date have occurred on or prior to the relevant Reference Time with respect to Three-Month Term SOFR, then the provisions set forth in this clause (v)
      will thereafter apply to all determinations of the rate or interest payable on the Notes during the Floating Rate Period. After a Benchmark Transition Event and its related Benchmark Replacement Date have occurred, the interest rate on the Notes for
      each Interest Period during the Floating Rate Period will be an annual rate equal to the Benchmark Replacement plus the spread specified in clause (ii) above.

    

    

    (3)            The Company and the Calculation Agent are expressly authorized
      to make determinations, decisions and elections under the terms of the Notes, including with respect to the use of any Benchmark Replacement for the Floating Rate Period and under this clause (v). Any determination, decision or election that may be
      made by the Company or by the Calculation Agent under the terms of the Notes, including any determination with respect to a tenor, rate or adjustment or of the occurrence or non-occurrence of an event, circumstance or date and any decision to take or
      refrain from taking any action or selection (A) will be conclusive and binding on the Holders and the Trustee absent manifest error, (B) if made by the Company, will be made in the Company’s sole discretion, (C) if made by the Calculation Agent, will
      be made after consultation with the Company, and the Calculation Agent will not make any such determination, decision or election to which the Company reasonably objects, and (D) notwithstanding anything to the contrary herein or in the Base
      Indenture, shall become effective without consent from the Holders or the Trustee. If the Calculation Agent fails to make any determination, decision or election that it is required to make under the terms of the Notes, then the Company will make
      such determination, decision or election on the same basis as described above.

    
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    (vi)            The Company (or its Calculation Agent) shall notify the Trustee
      in writing (1) upon the occurrence of the Benchmark Transition Event or the Benchmark Replacement Date, and (2) of any Benchmark Replacements, Benchmark Replacement Conforming Changes and other items affecting the interest rate on the Notes after a
      Benchmark Transition Event.

    

    

    (vii)            The Trustee (including in its capacity as Paying Agent),
      unless acting as the Calculation Agent, shall have no (1) responsibility or liability for (A) Three-Month Term SOFR Conventions, (B) selection of an alternative reference rate to Three-Month Term SOFR (including whether the conditions for the
      designation of such rate have been satisfied or whether such rate is a Benchmark Replacement or an Unadjusted Benchmark Replacement), (C) determination or calculation of a Benchmark Replacement, or (D) determination of whether a Benchmark Transition
      Event or Benchmark Replacement Date has occurred, and in each such case under clauses (A) through (D) above shall be entitled to conclusively rely upon the selection, determination, and/or calculation thereof as provided by the Company or its
      Calculation Agent, as applicable, or (2) liability for any failure or delay in performing its duties hereunder as a result of the unavailability of a Benchmark as described in the definition thereof, including as a result of the Company’s or
      Calculation Agent’s failure to select a Benchmark Replacement or the Calculation Agent’s failure to calculate a Benchmark. The Trustee shall be entitled to rely conclusively on all notices from the Company or its Calculation Agent regarding any
      Benchmark or Benchmark Replacement, including in regards to Three-Month Term SOFR Conventions, a Benchmark Transition Event, Benchmark Replacement Date, and Benchmark Replacement Conforming Changes.

    

    

    (viii)            If the then-current Benchmark is Three-Month Term SOFR and any of the foregoing
      provisions concerning the calculation of the interest rate and the payment of interest during the Floating Rate Period are inconsistent with any of the Three-Month Term SOFR Conventions determined by the Calculation Agent, then the relevant
      Three-Month Term SOFR Conventions will apply.

    

    

    (f)            Place of Payment of Principal and Interest.
      So long as the Notes are issued in the form of one or more Global Securities, the Company shall make, or cause the Paying Agent to make, all payments of principal and interest on the Notes by wire transfer in immediately available funds to DTC or its
      nominee, in accordance with applicable procedures of DTC. If the Notes are not so issued, the Company may, at its option, make, or cause the Paying Agent to make, payments of principal and interest on the Notes by check mailed to the address of the
      Holder specified in accordance with Sections 3.02(e)(i) or (e)(ii).

    
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    (g)            Redemption. The Notes are not subject to
      redemption or prepayment at the option of the Holders.

    

    

    The Notes shall be redeemable at the option of the Company, in whole or in part from time to time, beginning with the Interest Payment Date on June 1, 2025, and on any Interest
      Payment Date thereafter, subject to obtaining the prior approval of the Federal Reserve to the extent such approval is then required under the rules of the Federal Reserve.

    

    

    In addition, the Company may, at its option, redeem the Notes at any time before the Maturity Date, in whole but not in part, subject to obtaining the prior approval of the
      Federal Reserve to the extent such approval is then required under the rules of the Federal Reserve, upon the occurrence of a Tier 2 Capital Event or a Tax Event, or if the Company is required to register as an investment company pursuant to the
      Investment Company Act of 1940, as amended (15 U.S.C. 80a-1 et seq.).

    

    

    The Notes may not otherwise be redeemed prior to the Maturity Date.

    

    

    The Redemption Price shall equal 100% of the principal amount of the Notes to be redeemed plus accrued and unpaid interest to, but excluding, the Redemption Date fixed by the
      Company. The provisions of Article XI of the Base Indenture shall apply to any redemption of the Notes. Any partial redemption will be made in accordance with DTC’s applicable procedures among all Holders. If any Note is to be redeemed in part only,
      the notice of redemption relating to such Note shall state, in addition to the information specified in Section 1104 of the Base Indenture, that such redemption is a partial redemption, the portion of the principal amount thereof to be redeemed, and
      that a replacement Note in principal amount equal to the unredeemed portion thereof will be issued in the name of the Holder thereof upon cancellation of the original Note.

    

    

    Any notice of redemption may be conditional in the Company’s discretion on one or more conditions precedent, and the Redemption Date may be delayed until such time as any or all
      of such conditions have been satisfied or revoked by the Company if it determines that such conditions will not be satisfied; provided that the Company must deliver a certificate to the Trustee instructing the Trustee to delay or revoke the notice of
      redemption prior to the Redemption Date.  In addition, the Company is solely responsible for determining if the conditions precedent in any notice of redemption have been satisfied.

    

    

    (h)            Sinking Fund. There shall be no sinking
      fund for the Notes.

    

    

    (i)            Conversion and Exchange. The Notes are not
      convertible into, or exchangeable for, equity securities, other securities or assets of the Company or its Subsidiaries.

    

    

    (j)            Denomination. The Notes and any beneficial
      interest in the Notes shall be in minimum denominations of $1,000 and integral multiples of $1,000 in excess thereof.

    

    

    (k)            Currency of the Notes. The Notes shall be
      denominated, and the principal thereof and interest thereon shall be payable, in Dollars.

    

    

    (l)            Registered Form. The Notes shall be
      issuable as Global Securities, and DTC (or any successor thereto or successor depositary appointed by the Company within 90 days of the termination of services of DTC) shall be the depositary for the Notes. Sections 304 and 307 of the Base Indenture
      shall apply to the Notes.

    
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    (m)            Events of Default. The Events of Default
      provided for in Section 501 of the Base Indenture shall apply to the Notes, provided that clause (6) thereof shall be deleted in its entirety and the following shall be inserted in lieu thereof (and shall constitute “Events of Default”):

    

    

    “(6) appointment of a Custodian for the Material Subsidiary; or

    

    

    (7) the Company pursuant to or within the meaning of any Bankruptcy Law generally is unable to pay its debts as the same become due.”

    

    

    (n )            Acceleration of Maturity. Section 502 of
      the Base Indenture shall apply to the Notes, except that the first paragraph thereof shall be deleted in its entirety and the following text inserted in lieu thereof:

    

    

    “If an Event of Default under clause (4), (5), (6) or (7) of Section 501 occurs and is continuing, then the principal amount of all the Notes, together with accrued and unpaid
      interest, if any, thereon, shall automatically, and without any declaration or other action on the part of the Trustee or any Holder, become immediately due and payable. The Maturity of the Notes shall not otherwise be accelerated as a result of an
      Event of Default.”

    

    

    In addition, the second paragraph of Section 502 of the Base Indenture shall be amended by (i) deleting all occurrences of the text “declaration of” appearing in such paragraph
      and (ii) deleting the text “declaration and” appearing in such paragraph and inserting the text “acceleration and” in lieu thereof.

    

    

    (o)            Statement by Officers as to Default.
      Section 1004 of the Base Indenture shall apply to the Notes, except the reference in that Section to “150 days” shall be replaced with “120 days.”

    

    

    (p)            No Collateral. The Notes shall not be
      entitled to the benefit of any security interest in, or collateralization by, any rights, property or interest of the Company.

    

    

    (q)            Satisfaction and Discharge; Defeasance.
      Articles IV and XIII of the Base Indenture shall apply to the Notes.

    

    

    (r)            No Additional Amounts. In the event that
      any payment on the Notes is subject to withholding of any U.S. federal income tax or other tax or assessment (whether as a result of a change in law or otherwise), the Company will not pay additional amounts with respect to such tax or assessment.

    

    

    (s)            Notices to Holders. Any notices required
      to be given to Holders shall be given to the Trustee. Notwithstanding any other provision of the Indenture or any Note, where the Indenture or any Note provides for notice of any event or any other communication (including any notice of redemption)
      to a Holder (whether by mail or otherwise), such notice shall be sufficiently given if given to DTC (or its designee) pursuant to the applicable procedures from DTC or its designee, including by electronic mail in accordance with accepted practices
      at DTC.

    

    

    (t)            Additional Terms. Other terms applicable to the Notes are as
      otherwise provided for in the Base Indenture, as supplemented by this Supplemental Indenture, including Articles IV and V hereof.

    
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    ARTICLE IV.

    

    

    ADDITIONAL PROVISIONS

    

    

    Section 4.01                          Additional Provision.

    

    

    Section 901 of the Base Indenture shall apply to the Notes, provided that the following text shall be inserted at the end of such Section:

    

    

    “Without limitation of the foregoing, the Company and the Trustee may amend or supplement the Indenture or the Notes without the consent of any Holder to implement any
      Three-Month Term SOFR Conventions or any benchmark transition provisions after a Benchmark Transition Event and its related Benchmark Replacement Date have occurred (or in anticipation thereof).  The Trustee may conclusively rely on a Company Request
      (in addition to any other orders, certificates and opinions) as to whether a Benchmark Transition Event and Benchmark Replacement Date have occurred.”

    

    

    ARTICLE V.

    

    

    SUBORDINATION OF SECURITIES

    

    

    Section 5.01                          Agreement of Subordination.

    

    

    The Company covenants and agrees, and each Holder by accepting a Note likewise covenants and agrees, that all Notes shall be issued subject to the provisions of this Article; and
      each Person holding any Note, whether upon original issue or upon transfer, assignment or exchange thereof, accepts and agrees to be bound by such provisions.

    

    

    The payment of the principal of, interest on and any Redemption Price for the Notes shall, to the extent and in the manner hereinafter set forth, be subordinated and subject in
      right of payment to the prior payment in full of all Senior Indebtedness, whether outstanding at the date of the Indenture or thereafter incurred.

    

    

    No provision of this Article shall prevent the occurrence of any Default or Event of Default hereunder.

    

    

    Section 5.02                          Payments to Holders.

    

    

    No payment or distribution shall be made with respect to the principal of, interest on or any Redemption Price for the Notes, except for payments and distributions made by the Trustee as permitted by
      the first or second paragraph of Section 5.05, if:

    

    

    (a)            (i) a default in the payment of principal, premium, interest or other obligations
      constituting Senior Indebtedness occurs and is continuing (or, in the case of Senior Indebtedness for which there is a period of grace, such a default occurs and continues beyond the period of grace specified in the instrument or lease evidencing
      such Senior Indebtedness), unless and until such default shall have been cured or waived or shall have ceased to exist, and (ii) the Trustee receives a notice of such default from a Representative or the Company; or

    
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    (b)            (i) a default under any Designated Senior Indebtedness (other than a default
      described in clause (a) above) occurs and is continuing, if the effect of such default is to permit holders of such Designated Senior Indebtedness to accelerate its maturity, and (ii) the Trustee receives a notice of such default from a
      Representative or the Company (a “Payment Blockage Notice”).

    

    

    Upon the Trustee’s receipt of a Payment Blockage Notice, no subsequent Payment Blockage Notice shall be effective for purposes of this Section unless and until (A) at least 365
      days shall have elapsed since the initial effectiveness of the immediately prior Payment Blockage Notice and (B) all scheduled payments of principal of, interest on and any Redemption Price for the Notes that have come due have been paid in full in
      cash. No default described in clause (b) above that existed or was continuing on the date of delivery of any Payment Blockage Notice shall be, or be made, the basis for a subsequent Payment Blockage Notice.

    

    

    The Company may and shall resume payments on and distributions in respect of the Notes upon the earlier of:

    

    

    (1)            the date upon which the default is cured or waived or ceases to
      exist, or

    

    

    (2)            in the case of a default described in clause (b) above, the
      180th day after receipt of the corresponding Payment Blockage Notice, unless the maturity of such Designated Senior Indebtedness has been accelerated or this Article otherwise prohibits such payment or distribution at the time thereof.

    

    

    Upon any payment by the Company, or distribution of assets of the Company of any kind or character, whether in cash, property or Notes, to creditors upon any dissolution or
      winding-up or liquidation or reorganization of the Company, whether voluntary or involuntary or in bankruptcy, insolvency, receivership or other proceedings, all amounts due or to become due upon all Senior Indebtedness shall first be paid in full in
      cash or other payment satisfactory to the holders of such Senior Indebtedness, or payment thereof in accordance with its terms provided for in cash or other payment satisfactory to the holders of such Senior Indebtedness, before any payment is made
      on account of the principal of or interest on the Notes (except payments made pursuant to Article V of the Base Indenture from monies deposited with the Trustee pursuant thereto prior to commencement of proceedings for such dissolution, winding-up,
      liquidation or reorganization); and upon any such dissolution or winding-up or liquidation or reorganization of the Company or bankruptcy, insolvency, receivership or other proceeding, any payment by the Company, or distribution of assets of the
      Company of any kind or character, whether in cash, property or Notes, to which the Holders or the Trustee would be entitled, except for the provision of this Article, shall (except as aforesaid) be paid by the Company or by any receiver, trustee in
      bankruptcy, liquidating trustee, agent or other Person making such payment or distribution, or by the Holders or by the Trustee under the Indenture if received by them or it, directly to the holders of Senior Indebtedness (pro rata to such holders on
      the basis of the respective amounts of Senior Indebtedness held by such holders, or as otherwise required by law or a court order) or to their Representative, as their respective interests may appear, to the extent necessary to pay all Senior
      Indebtedness in full, in cash or other payment satisfactory to the holders of such Senior Indebtedness, after giving effect to any concurrent payment or distribution to or for the holders of Senior Indebtedness, before any payment or distribution or
      provision therefor is made to the Holders or to the Trustee.  Whenever a distribution is to be made or a notice given to the holders of Senior Indebtedness, the distribution may be made and the notice given to their Representative.

    
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    For purposes of this Article, the words, “cash, property or Notes” shall not be deemed to include shares of stock of the Company as reorganized or readjusted, or Notes of the
      Company or any other Person provided for by a plan of reorganization or readjustment, the payment of which is subordinated at least to the extent provided in this Article with respect to the Notes to the payment of all Senior Indebtedness which may
      at the time be outstanding; provided that (i) the Senior Indebtedness is assumed by the new Person, if any, resulting from any reorganization or readjustment, and (ii) the rights of the holders of Senior Indebtedness (other than leases which are not
      assumed by the Company or the new Person, as the case may be) are not, without the consent of such holders, altered by such reorganization or readjustment.

    

    

    The consolidation of the Company with, or the merger of the Company into, another Person, or the liquidation or dissolution of the Company following the conveyance or transfer of
      its property as an entirety, or substantially as an entirety, to another Person upon the terms and conditions provided for in Article VIII of the Base Indenture shall not be deemed a dissolution, winding-up, liquidation or reorganization for the
      purposes of this Section if such other Person shall, as a part of such consolidation, merger, conveyance or transfer, comply with the conditions stated in Article VIII of the Base Indenture.

    

    

    In the event of the acceleration of the Notes because of an Event of Default, no payment or distribution shall be made to the Trustee or any Holder in respect of the principal of
      or interest on the Notes (including, but not limited to, the Redemption Price with respect to the Notes called for redemption in accordance with Section 3.02(g)), except payments and distributions made by the Trustee as permitted by the first
      or second paragraph of Section 5.05, until all Senior Indebtedness has been paid in full in cash or other payment satisfactory to the holders of Senior Indebtedness or such acceleration is rescinded in accordance with the terms of the
      Indenture. If payment of the Notes is accelerated because of an Event of Default, the Company shall promptly notify holders of Senior Indebtedness of the acceleration at the address set forth in the notice from the Representative to the Trustee as
      being the address to which the Trustee should send its notice pursuant to this Section, unless there are no payment obligations of the Company thereunder and all obligations thereunder to extend credit have been terminated or expired.

    
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    In the event that, notwithstanding the foregoing provisions, any payment or distribution of assets of the Company of any kind or character, whether in cash, property or Notes
      (including by way of setoff or otherwise), prohibited by the foregoing, shall be received by the Trustee or the Holders before all Senior Indebtedness is paid in full in cash or other payment satisfactory to the holders of such Senior Indebtedness,
      or provision is made for such payment thereof in accordance with its terms in cash or other payment satisfactory to the holders of such Senior Indebtedness, such payment or distribution shall be held in trust for the benefit of and shall be paid over
      or delivered to the holders of Senior Indebtedness or their Representative, as their respective interests may appear, as calculated by the Company and directed by the Company pursuant to a Company Order, for application to the payment of all Senior
      Indebtedness remaining unpaid to the extent necessary to pay all Senior Indebtedness in full in cash or other payment satisfactory to the holders of such Senior Indebtedness, after giving effect to any concurrent payment or distribution to or for the
      holders of such Senior Indebtedness.

    

    

    Nothing in this Article shall apply to claims of, or payments to, the Trustee under or pursuant to Section 607 of the Base Indenture. This Section shall be subject to the further
      provisions of Section 5.05.  For the avoidance of doubt, such payments are not subordinated to the Company’s Senior Indebtedness.

    

    

    Section 5.03                          Subrogation of Notes.

    

    

    Subject to the payment in full of all Senior Indebtedness, the rights of the Holders shall be subrogated to the extent of the payments or distributions made to the holders of
      such Senior Indebtedness pursuant to the provisions of this Article (equally and ratably with the holders of all indebtedness of the Company which by its express terms is subordinated to other indebtedness of the Company to substantially the same
      extent as the Notes are subordinated and is entitled to like rights of subrogation) to the rights of the holders of Senior Indebtedness to receive payments or distributions of cash, property or Notes of the Company applicable to the Senior
      Indebtedness until the principal and interest on the Notes shall be paid in full; and, for the purposes of such subrogation, no payments or distributions to the holders of the Senior Indebtedness of any cash, property or Notes to which the Holders or
      the Trustee would be entitled except for the provisions of this Article, and no payment over pursuant to the provisions of this Article, to or for the benefit of the holders of Senior Indebtedness by Holders or the Trustee, shall, as between the
      Company, its creditors other than holders of Senior Indebtedness, and the Holders, be deemed to be a payment by the Company to or on account of the Senior Indebtedness; and no payments or distributions of cash, property or Notes to or for the benefit
      of the Holders pursuant to the subrogation provisions of this Article, which would otherwise have been paid to the holders of Senior Indebtedness shall be deemed to be a payment by the Company to or for the account of the Notes. It is understood that
      the provisions of this Article are and are intended solely for the purposes of defining the relative rights of the Holders, on the one hand, and the holders of the Senior Indebtedness, on the other hand.

    
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    Nothing contained in this Article or elsewhere in the Indenture or in the Notes is intended to or shall impair, as among the Company, its creditors other than the holders of
      Senior Indebtedness, and the Holders, the obligation of the Company, which is absolute and unconditional, to pay to the Holders the principal of and interest on the Notes as and when the same shall become due and payable in accordance with their
      terms, or is intended to or shall affect the relative rights of the Holders and creditors of the Company other than the holders of the Senior Indebtedness, nor shall anything herein or therein prevent the Trustee or the Holder of any Note from
      exercising all remedies otherwise permitted by applicable law upon default under the Indenture, subject to the rights, if any, under this Article of the holders of Senior Indebtedness in respect of cash, property or Notes of the Company received upon
      the exercise of any such remedy.

    

    

    Upon any payment or distribution of assets of the Company referred to in this Article, the Trustee, subject to the provisions of Section 601 of the Base Indenture, and the
      Holders shall be entitled to conclusively rely upon any order or decree made by any court of competent jurisdiction in which such bankruptcy, dissolution, winding-up, liquidation or reorganization proceedings are pending, or a certificate of the
      receiver, trustee in bankruptcy, liquidating trustee, agent or other Person making such payment or distribution, delivered to the Trustee or to the Holders, for the purpose of ascertaining the Persons entitled to participate in such distribution, the
      holders of the Senior Indebtedness and other indebtedness of the Company, the amount thereof or payable thereon and all other facts pertinent thereto or to this Article.

    

    

    Section 5.04                          Authorization to Effect Subordination.

    

    

    Each Holder of a Note, by the acceptance thereof, authorizes and directs the Trustee on the Holder’s behalf to take such action as may be necessary or appropriate to effectuate
      the subordination as provided in this Article and appoints the Trustee to act as the Holder’s attorney-in-fact for any and all such purposes. If the Trustee does not file a proper proof of claim or proof of debt in the form required in any proceeding
      referred to in Section 504 of the Base Indenture hereof at least 30 days before the expiration of the time to file such claim, the holders of any Senior Indebtedness or their representatives are hereby authorized to file an appropriate claim for and
      on behalf of the Holders.

    

    

    Section 5.05                          Notice to Trustee.

    

    

    The Company shall give prompt written notice to a responsible officer of the Trustee and to any paying agent of any fact known to the Company which would prohibit the making of
      any payment of monies to or by the Trustee or any Paying Agent pursuant to the provisions of this Article. Notwithstanding the provisions of this Article or any other provision of the Indenture, the Trustee shall not be charged with knowledge of the
      existence of any facts which would prohibit the making of any payment of monies to or by the Trustee in respect of the Notes pursuant to the provisions of this Article, unless and until a responsible officer of the Trustee shall have received written
      notice thereof at the Corporate Trust Office from the Company or a Representative; and before the receipt of any such written notice, the Trustee, subject to Section 601 of the Base Indenture, shall be entitled in all respects to assume that no such
      facts exist; provided that if on a date not fewer than two Business Days prior to the date upon which by the terms hereof any such monies may become payable for any purpose (including the payment of the principal of or interest on any Note) the
      Trustee shall not have received, with respect to such monies, the notice provided for in this Section, then, anything herein contained to the contrary notwithstanding, the Trustee shall have full power and authority to receive such monies and to
      apply the same to the purpose for which they were received, and shall not be affected by any notice to the contrary which may be received by it on or after such prior date.

    
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    Notwithstanding anything in this Article to the contrary, nothing shall prevent any payment by the Trustee to the Holders of monies deposited with it pursuant to Section 401 of
      the Base Indenture, and any such payment shall not be subject to the provisions of Section 5.01 or 5.02.

    

    

    The Trustee, subject to the provisions of Section 601 of the Base Indenture, shall be entitled to rely on the delivery to it of a written notice by a Representative or a Person
      representing himself to be a holder of Senior Indebtedness (or a trustee on behalf of such holder) to establish that such notice has been given by a Representative or a holder of Senior Indebtedness or a trustee on behalf of any such holder or
      holders. In the event that the Trustee determines in good faith that further evidence is required with respect to the right of any Person as a holder of Senior Indebtedness to participate in any payment or distribution pursuant to this Article, the
      Trustee may request such Person to furnish evidence to the reasonable satisfaction of the Trustee as to the amount of Senior Indebtedness held by such Person, the extent to which such Person is entitled to participate in such payment or distribution
      and any other facts pertinent to the rights of such Person under this Article, and if such evidence is not furnished the Trustee may defer any payment to such Person pending judicial determination as to the right of such Person to receive such
      payment.

    

    

    Section 5.06                          Trustee’s Relation to Senior Indebtedness.

    

    

    The Trustee in its individual capacity shall be entitled to all the rights set forth in this Article in respect of any Senior Indebtedness at any time held by it, to the same
      extent as any other holder of Senior Indebtedness, and nothing in Section 613 of the Base Indenture or elsewhere in the Indenture shall deprive the Trustee of any of its rights as such holder. Nothing in this Article shall apply to the Company’s
      obligations to the Trustee under Section 607 of the Base Indenture.

    

    

    With respect to the holders of Senior Indebtedness, the Trustee undertakes to perform or to observe only such of its covenants and obligations as are specifically set forth in
      this Article, and no implied covenants or obligations with respect to the holders of Senior Indebtedness shall be read into the Indenture against the Trustee. The Trustee shall not be deemed to owe any fiduciary duty to the holders of Senior
      Indebtedness and, subject to the provisions of Section 601 of the Base Indenture, the Trustee shall not be liable to any holder of Senior Indebtedness if it shall pay over or deliver to Holders, the Company or any other Person money or assets to
      which any holder of Senior Indebtedness shall be entitled by virtue of this Article or otherwise.

    

    

    Section 5.07                          No Impairment of Subordination.

    

    

    No right of any present or future holder of any Senior Indebtedness to enforce subordination as herein provided shall at any time in any way be prejudiced or impaired by any act
      or failure to act on the part of the Company or by any act or failure to act, in good faith, by any such holder, or by any noncompliance by the Company with the terms, provisions and covenants of the Indenture, regardless of any knowledge thereof
      which any such holder may have or otherwise be charged with.

    
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    Section 5.08                          Article Applicable to Paying Agents.

    

    

    If at any time any Paying Agent other than the Trustee shall have been appointed by the Company and be then acting hereunder, the term “Trustee” as used in this Article shall
      (unless the context otherwise requires) be construed as extending to and including such Paying Agent within its meaning as fully for all intents and purposes as if such Paying Agent were named in this Article in addition to or in place of the
      Trustee; provided, however, that the first paragraph of Section 5.05 shall not apply to the Company or any Affiliate of the Company if it or such Affiliate acts as Paying Agent.

    

    

    Section 5.09                          Senior Indebtedness Entitled to Rely.

    

    

    The holders of Senior Indebtedness (including Designated Senior Indebtedness) shall have the right to rely upon this Article, and no amendment or modification of the provisions
      contained herein shall diminish the rights of such holders unless such holders shall have agreed in writing thereto.

    

    

    ARTICLE VI.

    

    

    MISCELLANEOUS

    

    

    Section 6.01                          Trust Indenture Act.

    

    

    This Supplemental Indenture is subject to the provisions of the Trust Indenture Act that are required to be part of the Indenture and shall, to the extent applicable, be governed
      by such provisions. If any provision of this Supplemental Indenture limits, qualifies, or conflicts with a provision of the Trust Indenture Act that is required under such Act to be a part of and govern this Supplemental Indenture, the latter
      provision shall control.  If any provision of this Supplemental Indenture modifies or excludes any provision of the Trust Indenture Act that may be so modified or excluded, the latter provision shall be deemed to apply to this Supplemental Indenture
      as so modified or excluded, as the case may be. Whenever this Supplemental Indenture refers to a provision of the Trust Indenture Act, the provision is incorporated by reference in and made a part of this Supplemental Indenture.

    

    

    Section 6.02                          Governing Law.

    

    

    This Supplemental Indenture and the Notes shall be governed by and construed in accordance with the law of the state of New York without reference to its principles of conflict
      of laws (other than Section 5-1401 of the General Obligations Law).

    

    

    Section 6.03                          Ratification.

    

    

    The Base Indenture, as supplemented and amended by this Supplemental Indenture, is in all respects ratified and confirmed. The Trustee accepts the trusts created by the Base
      Indenture, as supplemented by this Supplemental Indenture, and agrees to perform the same upon the terms and conditions of the Base Indenture, as supplemented by this Supplemental Indenture.

    

    

    Section 6.04                          Effectiveness.

    

    

    The provisions of this Supplemental Indenture shall become effective as of the date hereof.

    
      23

      
        


    

    

    

    

    

    Section 6.05                          USA PATRIOT Act.

    

    

    The parties hereto acknowledge that, in accordance with Section 326 of the USA PATRIOT Act, the Trustee is required to obtain, verify, and record information that identifies each
      person or legal entity that establishes a relationship or opens an account with the Trustee. The parties to this Supplemental Indenture agree that they will provide the Trustee with such information as it may request in order for the Trustee to
      satisfy the requirements of the USA PATRIOT Act.

    

    

    [Signature page follows]

    
      24

      
        


    

    

    

    

    

    IN WITNESS WHEREOF, the parties hereto have caused this Supplemental Indenture to be duly executed as of the date first above written.

    

    

    

    

    

    

    	 	
            ENTERPRISE FINANCIAL SERVICES CORP

          


    

    

    	 	
            By:

          	
            /s/ Keene S. Turner

          
	 	
            Name:

          	Keene S. Turner
	 	
            Title:

          	
            Executive Vice President and Chief Financial Officer

          


    

    

    

    

    

    

    

    

    

    

    	 	
            U.S. BANK NATIONAL ASSOCIATION, as Trustee

          


    

    

    	 	
            By:

          	
            /s/ George J. Rayzis

          
	 	
            Name:

          	George J. Rayzis
	 	
            Title:

          	
            Vice President

          


    

    

    [Signature Page to First Supplemental Indenture]

    
      25

      
        


    

    

    

    

    

    EXHIBIT A

    

    

    FORM OF NOTE

    

    

    THIS SECURITY AND THE OBLIGATIONS OF THE COMPANY (AS DEFINED HEREIN) AS EVIDENCED HEREBY (1) ARE NOT DEPOSITS WITH OR HELD BY THE COMPANY AND ARE NOT INSURED OR GUARANTEED BY ANY
      FEDERAL AGENCY OR INSTRUMENTALITY, INCLUDING, WITHOUT LIMITATION, THE FEDERAL DEPOSIT INSURANCE CORPORATION, AND (2) ARE SUBORDINATE IN THE RIGHT OF PAYMENT TO THE SENIOR INDEBTEDNESS (AS DEFINED IN THE INDENTURE IDENTIFIED HEREIN).

    

    

    GLOBAL NOTE

    

    

    THIS SECURITY IS A GLOBAL SECURITY WITHIN THE MEANING OF THE INDENTURE HEREINAFTER REFERRED TO AND IS REGISTERED IN THE NAME OF THE DEPOSITARY OR A NOMINEE OF THE DEPOSITARY, WHICH MAY BE TREATED
      BY THE COMPANY, THE TRUSTEE AND ANY AGENT THEREOF AS OWNER AND HOLDER OF THIS SECURITY FOR ALL PURPOSES.

    

    

    UNLESS AND UNTIL IT IS EXCHANGED IN WHOLE OR IN PART FOR THE INDIVIDUAL SECURITIES REPRESENTED HEREBY, THIS GLOBAL SECURITY MAY NOT BE TRANSFERRED EXCEPT AS A WHOLE (I) BY THE DEPOSITARY TO A
      NOMINEE OF THE DEPOSITARY, (II) BY A NOMINEE OF THE DEPOSITARY TO THE DEPOSITARY OR ANOTHER NOMINEE OF THE DEPOSITARY OR (III) BY A NOMINEE OF THE DEPOSITARY OR THE DEPOSITARY TO A SUCCESSOR DEPOSITARY OR A NOMINEE OF SUCH SUCCESSOR DEPOSITARY.
      UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY TO THE ISSUER OR ITS AGENT FOR REGISTRATION OF TRANSFER, EXCHANGE OR PAYMENT AND ANY CERTIFICATE ISSUED IS REGISTERED IN THE NAME OF CEDE & CO.
      OR SUCH OTHER NAME AS REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY (AND ANY PAYMENT IS MADE TO CEDE & CO. OR TO SUCH OTHER ENTITY AS IS REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF THE DEPOSITARY TRUST COMPANY), ANY
      TRANSFER, PLEDGE OR OTHER USE HEREOF FOR VALUE OR OTHERWISE BY OR TO ANY PERSON IS WRONGFUL SINCE THE REGISTERED OWNER HEREOF, CEDE & CO., HAS AN INTEREST HEREIN.

    
      26

      
        


    

    

    

    

    

    ENTERPRISE FINANCIAL SERVICES CORP

    

    

    5.75% Fixed-to-Floating Rate Subordinated Notes due 2030

    

    

    	
            No. 1

          	
            CUSIP: 293712 AB1

          
	 	 
	
            $63,250,000

          	
            ISIN: US293712AB15

          


    

    

    ENTERPRISE FINANCIAL SERVICES CORP, a Delaware corporation (together with any successor Corporation under the Indenture hereinafter referred to, the “Company”), for value
      received, hereby promises to pay to CEDE & CO., or its registered assigns, the principal sum of SIXTY THREE MILLION TWO HUNDRED AND FIFTY THOUSAND DOLLARS ($63,250,000) on June 1, 2030 (the “Stated Maturity Date”), unless redeemed prior to
      such date, and to pay interest thereon (i) from and including May 21, 2020, to but excluding June 1, 2025, unless redeemed prior to such date (such period, the “Fixed Rate Period”), at a rate of 5.75% per annum, semi-annually in arrears on
      June 1 and December 1 of each year, commencing on December 1, 2020 (each such date, a “Fixed Rate Interest Payment Date”) and (ii) from and including June 1, 2025, to but excluding the Stated Maturity Date, unless redeemed on or subsequent to
      June 1, 2025, but prior to the Stated Maturity Date (such period, the “Floating Rate Period”), at a rate equal to Three-Month Term SOFR, reset quarterly, plus 566.0 basis points, or such other rate as may be determined pursuant to the
      Supplemental Indenture hereinafter referred to, quarterly in arrears on March 1, June 1, September 1 and December 1 of each year, commencing on September 1, 2025, and ending on the Stated Maturity Date or earlier Redemption Date (each such date, a “Floating



        Rate Interest Payment Date” and, together with each Fixed Rate Interest Payment Date, each an “Interest Payment Date”). The amount of interest payable on any Fixed Rate Interest Payment Date during the Fixed Rate Period will be computed
      on the basis of a 360-day year consisting of twelve 30-day months, and the amount of interest payable on any Floating Rate Interest Payment Date during the Floating Rate Period will be computed on the basis of a 360-day year and the actual number of
      days elapsed. If any Interest Payment Date or the Stated Maturity Date falls on a day that is not a Business Day, payment may be made on the next succeeding Business Day and no interest on such payment will accrue for the period of such delay;
      provided that if any scheduled Floating Rate Interest Payment Date falls on a day that is not a Business Day and the next succeeding Business Day falls in the next succeeding calendar month, such Floating Rate Interest Payment Date will be
      accelerated to the immediately preceding Business Day, and in each such case the amount payable on such Business Day will include interest accrued to but excluding such Business Day. All percentages used in or resulting from any calculation of
      Three-Month Term SOFR shall be rounded, if necessary, to the nearest one hundred-thousandth of a percentage point, with 0.000005% rounded up to 0.00001%.

    

    

    Payment of the principal of and interest on this Note will be made in such coin or currency of the United States of America as at the time of payment is legal tender for payment
      of public and private debts.

    

    

    Reference is hereby made to the further provisions of this Note set forth on the reverse hereof, which further provisions shall for all purposes have the same effect as if set
      forth at this place.

    
      27

      
        


    

    

    

    

    

    Unless the certificate of authentication hereon has been executed by the Trustee referred to on the reverse hereof by manual signature, this Note shall not be entitled to any benefit under the
      Indenture or be valid or obligatory for any purpose.

    

    

    [Signature page follows.]

    
      28

      
        


    

    

    

    

    

    IN WITNESS WHEREOF, the Company has caused this Note to be signed manually or by facsimile by its duly authorized officer.

    

    

    

    

    

    

    	 	
            ENTERPRISE FINANCIAL SERVICES CORP

          
	 	 	 
	 	
            By:

          	 
	 	
            Name:

          
	 	
            Title:

          


    
      29

      
        


    

    

    

    

    

    TRUSTEE’S CERTIFICATE OF AUTHENTICATION

    

    

    This is one of the Securities of the series designated and referred to in the within-mentioned Indenture.

    

    

    Date of authentication:

    

    

    	 	
            U.S. BANK NATIONAL ASSOCIATION,

          
	 	
            as Trustee

          


    

    

    	 	
            By:

          	 
	 	
            Name:

          
	 	
            Title:

          


    
      30

      
        


    

    

    

    

    

    REVERSE OF NOTE

    

    

    ENTERPRISE FINANCIAL SERVICES CORP

    

    

    5.75% Fixed-to-Floating Rate Subordinated Notes due 2030

    

    

    This Note is one of a duly authorized issue of Securities of the Company of a series designated as the “5.75% Fixed-to-Floating Rate Subordinated Notes due 2030” (the “Notes”)



      initially issued in an aggregate principal amount of $63,250,000 on May 21, 2020.  Such series of Securities has been established pursuant to, and is one of an indefinite number of series of subordinated debt securities of the Company issued or
      issuable under and pursuant to the Subordinated Debt Securities Indenture dated as of May 21, 2020 (the “Base Indenture” and, as the same may from time to time be amended, supplemented or otherwise modified in accordance therewith, including
      by the Supplemental Indenture referred to below, the “Indenture”), between the Company and U.S. Bank National Association, as Trustee (together with any successor trustee, the “Trustee”), as supplemented and amended by the First
      Supplemental Indenture dated as of May 21, 2020, between the Company and the Trustee (the “Supplemental Indenture”), to which Indenture and any other indentures supplemental thereto reference is hereby made for a statement of the respective
      rights, limitations of rights, duties and immunities thereunder of the Company, the Trustee and the Persons in whose names Notes are registered from time to time and of the terms upon which the Notes are, and are to be, authenticated and delivered.
      The terms, conditions and provisions of the Notes are those stated in the Indenture, those made part of the Indenture by reference to the Trust Indenture Act of 1939, as amended (the “Trust Indenture Act”), and those set forth in this Note. To
      the extent that the provisions of this Note modify, supplement or are inconsistent with those of the Indenture, then the provisions of this Note shall govern to the extent that such provisions of this Note are not inconsistent with (i) the provisions
      of the Supplemental Indenture or (ii) the provisions made part of the Indenture by reference to the Trust Indenture Act.

    

    

    All capitalized terms used in this Note and not defined herein that are defined in the Indenture shall have the meanings assigned to them in the Indenture.

    

    

    The indebtedness of the Company evidenced by the Notes, including the principal thereof and interest thereon, (i) to the extent and in the manner set forth in the Indenture, is
      subordinate and subject in right of payment to the prior payment in full of all Senior Indebtedness, whether outstanding at the date hereof or hereafter incurred, on the terms and subject to the terms and conditions set forth in the Indenture, and
      (ii) shall rank pari passu in right of payment with all other Securities and with all other unsecured subordinated indebtedness of the Company that is not by its terms subordinate and subject in right of payment to the prior payment in full of
      debentures, notes, bonds or other evidences of indebtedness of types that include the Notes. Each Holder of this Note, by the acceptance hereof, agrees to and shall be bound by such provisions of the Indenture and authorizes and directs the Trustee
      on such Holder’s behalf to take such actions as may be necessary or appropriate to effectuate the subordination so provided.

    
      31

      
        


    

    

    

    

    

    The Notes are intended to be treated as Tier 2 Capital (or its then-equivalent if the Company were subject to such capital requirement) for purposes of capital adequacy rules or
      regulations of the Board of Governors of the Federal Reserve System (or any successor regulatory authority with jurisdiction over financial or bank holding companies) (the “Federal Reserve”) as applicable to the Company and as the same may be
      amended or supplemented from time to time. If an Event of Default with respect to the Notes shall occur and be continuing, the principal and interest owed on the Notes shall only become due and payable in accordance with the terms and conditions set
      forth in Article V of the Base Indenture and Section 3.02(m) and (n) of the Supplemental Indenture. Accordingly, the Holder has no right to accelerate the maturity of this Note in the event that the Company fails to pay interest on any of the Notes,
      or fails to perform any other obligations under the Notes or in the Indenture that are applicable to the Notes.

    

    

    The Company may, at its option, redeem the Notes, in whole or in part, at a redemption price equal to 100% of the principal amount of the Notes to be redeemed, plus accrued and
      unpaid interest (the “Redemption Price”) to, but excluding, the date of redemption (the “Redemption Date”), on any Interest Payment Date on or after June 1, 2025. The Company may also, at its option, redeem the Notes before the Stated
      Maturity Date, in whole, but not in part, at any time, upon the occurrence of a Tier 2 Capital Event or a Tax Event, or if the Company is required to register as an investment company pursuant to the Investment Company Act of 1940, as amended. Any
      such redemption will be at a redemption price equal to the Redemption Price to, but excluding, the Redemption Date fixed by the Company. No redemption of the Notes by the Company prior to the Stated Maturity Date shall be made without the prior
      approval of the Federal Reserve if such prior approval is or will be required at the scheduled Redemption Date. The provisions of Article XI of the Base Indenture and Section 3.02(g) of the Supplemental Indenture shall apply to the redemption of any
      Notes by the Company.

    

    

    The Notes are not entitled to the benefit of any sinking fund. The Notes are not convertible into or exchangeable for any other securities or property of the Company or any
      Subsidiary of the Company.

    

    

    In the event that any payment on the Notes is subject to withholding of any U.S. federal income tax or other tax or assessment (as a result of a change in law or otherwise), the
      Company will not pay additional amounts with respect to such tax or assessment.

    

    

    The Indenture permits, with certain exceptions as therein provided, the amendment thereof and the modification of the rights and obligations of the Company and the rights of the
      Holders at any time by the Company and the Trustee with the consent of the Holders of at least a majority in principal amount of the outstanding Notes. The Indenture also contains provisions permitting the Holders of specified percentages in
      principal amount of the Notes at the time outstanding, on behalf of the Holders of all Notes, to waive compliance by the Company with certain provisions of the Indenture and to waive certain past Defaults under the Indenture and their consequences.
      Any such consent or waiver by the Holder of this Note shall be conclusive and binding upon such Holder and upon all future Holders of this Note and of any Note issued upon the registration of transfer hereof or in exchange therefor or in lieu hereof,
      whether or not notation of such consent or waiver is made upon this Note.

    
      32

      
        


    

    

    

    

    

    As provided in the Indenture and subject to certain limitations therein set forth, the transfer of this Note is registrable in the Securities Register described in Section 305 of
      the Base Indenture, upon surrender of this Note for registration of transfer at the office or agency of the Company in any place where the principal of and interest on this Note are payable, duly endorsed, or accompanied by a written instrument of
      transfer in form satisfactory to the Company and the Security Registrar and duly executed, by the Holder hereof or its attorney duly authorized in writing, and thereupon one or more new Notes, of authorized denominations and for the same aggregate
      principal amount, will be issued to the designated transferee or transferees.

    

    

    The Notes are issuable only in registered form without coupons in minimum denominations of $1,000 and integral multiples of $1,000 in excess thereof.

    

    

    The Company and the Trustee and any agent of the Company or the Trustee may treat the Person in whose name this Note is registered as the owner hereof for all purposes, whether
      or not this Note is overdue, and neither the Company, the Trustee nor any such agent shall be affected by notice to the contrary.

    

    

    This Security is a global note, represented by one or more permanent global certificates registered in the name of the nominee of The Depository Trust Company (each a “Global
        Note” and collectively, the “Global Notes”). Accordingly, unless and until it is exchanged for individual certificates, this Note may not be transferred except as a whole (i) by The Depository Trust Company (the “Depositary”) to a
      nominee of the Depositary, (ii) by a nominee of the Depositary to the Depositary or another nominee of the Depositary, or (iii) by the Depositary or a nominee of the Depositary to a successor depositary or any nominee of such successor. Ownership of
      beneficial interests in this Security will be shown on, and the transfer of that ownership will be effected only through, records maintained by the applicable Depositary or its nominee (with respect to interests of persons that have accounts with the
      Depositary (“Participants”)) and the records of Participants (with respect to interests of persons other than Participants). Beneficial interests in Notes owned by persons that hold through Participants will be evidenced only by, and transfers
      of such beneficial interests with such Participants will be effected only through, records maintained by such Participants. Except as provided below, owners of beneficial interests in this Note will not be entitled to have any individual certificates
      and will not be considered the owners or Holders thereof under the Indenture.

    

    

    Except in the limited circumstances set forth in the Base Indenture, Participants and owners of beneficial interests in the Global Notes will not be entitled to receive Notes in
      the form of individual certificates and will not be considered Holders. None of the Company, the Trustee, the Security Registrar, the Paying Agent or any of their respective agents will be liable for any delay by the Depositary, its nominee or any
      direct or indirect Participant in identifying the beneficial owners of the related Notes. The Company, the Trustee, the Security Registrar, the Paying Agent and each of their respective agents may conclusively rely on, and will be protected in
      relying on, instructions from the Depositary or its nominee for all purposes, including with respect to the registration and delivery, and the respective principal amounts, of the Notes to be issued.

    

    

    Except as provided in Section 305 of the Base Indenture and Section 3.02(f) of the Supplemental Indenture, beneficial owners of Global Notes will not be entitled to receive
      physical delivery of Notes in the form of individual certificates, and no Global Note will be exchangeable except for another Global Note of like denomination and tenor to be registered in the name of the Depositary or its nominee. Accordingly, each
      person owning a beneficial interest in a Global Note must rely on the procedures of the Depositary and, if such person is not a Participant, on the procedures of the Participant through which such person owns its interest, to exercise any rights of a
      Holder under the Notes.

    
      33

      
        


    

    

    

    

    

    The laws of some jurisdictions may require that certain purchasers of securities take physical delivery of those securities in definitive form. Accordingly, the ability to
      transfer interests in the Notes represented by a Global Note to those persons may be limited. In addition, because the Depositary can act only on behalf of its Participants, who in turn act on behalf of persons who hold interests through
      Participants, the ability of a person having an interest in Notes represented by a Global Note to pledge or transfer such interest to persons or entities that do not participate in the Depositary’s system, or otherwise to take actions in respect of
      such interest, may be affected by the lack of an individual certificate in respect of such interest. None of the Company, the Trustee, the Paying Agent and the Security Registrar will have any responsibility or liability for any aspect of the records
      relating to or payments made on account of Notes by the Depositary, or for maintaining, supervising or reviewing any records of the Depositary relating to the Notes.

    

    

    The Trustee will act as the Company’s Paying Agent with respect to the Notes through its Corporate Trust Office presently located at Two Liberty Place,  50 South 16th Street,
      Suite 2000, Mail Station EX-PA-WBSP, Philadelphia, PA 19102.  The Company may at any time rescind the designation of a Paying Agent, appoint a successor Paying Agent, or approve a change in the office through which any Paying Agent acts.

    

    

    Notices to the Holders of individual certificates will be given to such Holders at their respective addresses in the Register, or in the case of Global Notes, electronic delivery
      in accordance with DTC’s applicable procedures.

    

    

    The Indenture contains provisions setting forth certain conditions to the institution of proceedings by the Holders of Notes with respect to the Indenture or for any remedy under
      the Indenture.

    

    

    This Note shall be governed by and construed in accordance with the law of the state of New York without reference to its principles of conflict of laws (other than Section
      5-1401 of the General Obligations Law).

    
      34

      
        


    

    

    

    

    

    ASSIGNMENT FORM

    

    

    To assign the within Security, fill in the form below:

    

    

    	
            I or we assign and transfer the

          	 
	
            within Security to:

          	 
	 	
            (Insert assignee’s legal name)

          
	 	 
	 	 
	 	
            (Insert assignee’s social security or tax I.D. number)

          
	 	 
	 	 
	 	
            (Print or type assignee’s name, address and zip code)

          


    

    

    and irrevocably appoint the Trustee as agent to transfer this Security on the books of Enterprise Financial Services Corp. The agent may substitute another to act for it.

    

    

    	
            Your Signature:

          	 
	 	
            (Sign exactly as your name appears on the other side of this Security)

          
	 	 
	
            Your Name:

          	 
	 	 
	
            Date:

          	 
	 	 
	
            Signature Guarantee:

          	 


    

    

    SIGNATURE GUARANTEE

    

    

    Signatures must be guaranteed by an “eligible guarantor institution” meeting the requirements of the Security Registrar, which requirements include membership or participation in the Security
      Transfer Agent Medallion Program (“STAMP”) or such other “signature guarantee program” as may be determined by the Security Registrar in addition to, or in substitution for, STAMP, all in accordance with the Securities Exchange Act of 1934, as
      amended.

    

    

    35