Document:

<PAGE>   1
                                                                    EXHIBIT 4.11

                               GUARANTEE AGREEMENT

                                     Between

                          HCC INSURANCE HOLDINGS, INC.

                                as Guarantor, and

                            FIRST UNION NATIONAL BANK

                                   as Trustee

                                   dated as of

                               September __, 2000

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                                TABLE OF CONTENTS

<TABLE>
<S>                <C>                                                                                        <C>
                                                    ARTICLE I

                                                   DEFINITIONS

Section 1.1.       Definitions.................................................................................1

                                                    ARTICLE II

                                               TRUST INDENTURE ACT

Section 2.1.       Trust Indenture Act; Application............................................................5
Section 2.2.       List of Holders.............................................................................5
Section 2.3.       Reports by the Guarantee Trustee............................................................5
Section 2.4.       Periodic Reports to the Guarantee Trustee...................................................5
Section 2.5.       Evidence of Compliance with Conditions Precedent............................................6
Section 2.6.       Events of Default; Waiver...................................................................6
Section 2.7.       Event of Default; Notice....................................................................6
Section 2.8.       Conflicting Interests.......................................................................6

                                                   ARTICLE III

                                POWERS, DUTIES AND RIGHTS OF THE GUARANTEE TRUSTEE

Section 3.1.       Powers and Duties of the Guarantee Trustee..................................................6
Section 3.2.       Certain Rights of Guarantee Trustee.........................................................8
Section 3.3.       Compensation; Fees..........................................................................9

                                                    ARTICLE IV

                                                GUARANTEE TRUSTEE

Section 4.1.       Guarantee Trustee: Eligibility.............................................................10
Section 4.2.       Appointment, Removal and Resignation of the Guarantee Trustee..............................10

                                                    ARTICLE V

                                                    GUARANTEE

Section 5.1.       Guarantee..................................................................................11
Section 5.2.       Waiver of Notice and Demand................................................................11
Section 5.3.       Obligations Not Affected...................................................................12
Section 5.4.       Rights of Holders..........................................................................12
Section 5.5.       Guarantee of Payment.......................................................................13
Section 5.6.       Subrogation................................................................................13
Section 5.7.       Independent Obligations....................................................................13
</TABLE>

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<TABLE>
<S>                <C>                                                                                        <C>
                                                    ARTICLE VI

                                           COVENANTS AND SUBORDINATION

Section 6.1.       Subordination..............................................................................13
Section 6.2.       Pari Passu Guarantees......................................................................14

                                                   ARTICLE VII

                                                   TERMINATION

Section 7.1.       Termination................................................................................14

                                                   ARTICLE VIII

                                                 INDEMNIFICATION

Section 8.1        Exculpation................................................................................14
Section 8.2        Indemnification............................................................................14

                                                    ARTICLE IX

                                                  MISCELLANEOUS

Section 9.1.       Successors and Assigns.....................................................................15
Section 9.2.       Amendments.................................................................................15
Section 9.3.       Notices....................................................................................15
Section 9.4.       Benefit....................................................................................16
Section 9.5.       Governing Law..............................................................................16
</TABLE>

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                               GUARANTEE AGREEMENT

         This GUARANTEE AGREEMENT, dated as of September __, 2000, is executed
and delivered by HCC INSURANCE HOLDINGS, INC., a Delaware corporation (the
"Guarantor"), and First Union National Bank, a national banking association
organized under the laws of the United States, as trustee (the "Guarantee
Trustee"), for the benefit of the Holders (as defined herein) from time to time
of the Preferred Securities (as defined herein) of HCC Capital Trust I, a
Delaware statutory business trust (the "Issuer").

         WHEREAS, pursuant to an Amended and Restated Trust Agreement (the
"Trust Agreement"), dated as of September __, 2000, the Guarantor, as Depositor,
the Property Trustee and the Delaware Trustee named therein and the Holders from
time to time of undivided beneficial ownership interests in the assets of the
Issuer, the Issuer is issuing up to $___________ aggregate Liquidation Amount of
its preferred securities (Liquidation Amount $__ per preferred security) (the
"Preferred Securities") and $____________ aggregate Liquidation Amount of its
common securities (the "Common Securities") representing undivided beneficial
ownership interests in the assets of the Issuer and having the terms set forth
in the Trust Agreement;

         WHEREAS, the Preferred Securities will be issued by the Issuer and the
proceeds thereof, together with the proceeds from the issuance of the Issuer's
Common Securities, will be used to purchase the Debentures of the Guarantor
which will be deposited with First Union National Bank, as Property Trustee
under the Trust Agreement, as trust assets; and

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

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

                                    ARTICLE I
                                   DEFINITIONS

         Section 1.1. Definitions.

         As used in this Guarantee Agreement, the terms set forth below shall,
unless the context otherwise requires, have the following meanings:

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

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

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<PAGE>   5

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

         (d) all references in this Guarantee Agreement to Articles and Sections
are to Articles and Sections of this Guarantee Agreement unless otherwise
specified;

         (e) a term defined in the Trust Indenture Act has the same meaning when
used in this Guarantee Agreement unless otherwise defined in this Guarantee
Agreement or unless the context otherwise requires;

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

         (g) the masculine, feminine or neuter genders used herein shall include
the masculine, feminine and neuter genders.

         "Affiliate" of any specified Person means any other Person directly or
indirectly controlling or controlled by or under direct or indirect common
control with such specified Person; provided, however, that an Affiliate of the
Guarantor shall not be deemed to include the Issuer. For the purposes of this
definition, "control" when used with respect to any specified Person means the
power to direct the management and policies of such Person, directly or
indirectly, whether through the ownership of voting securities, by contract or
otherwise; and the terms "controlling" and "controlled" have meanings
correlative to the foregoing.

         "Covered Person" means any Holder or beneficial owner of Preferred
Securities.

         "Event of Default" means a default by the Guarantor on any of its
payment or other obligations under this Guarantee Agreement or a default by the
Guarantor in any other obligation hereunder that remains unremedied 30 days.

         "Guarantee Payments" means the following payments or distributions,
without duplication, with respect to the Preferred Securities, to the extent not
paid or made by or on behalf of the Issuer; (i) any accumulated and unpaid
Distributions required to be paid on such Preferred Securities, to the extent
the Issuer shall have funds on hand available therefor at such time, (ii) the
redemption price, including all accumulated and unpaid Distributions to the
Redemption Date with respect to the Preferred Securities called for redemption
by the Issuer, to the extent the Issuer shall have funds on hand available
therefor at such time, and (iii) upon a voluntary or involuntary termination,
winding-up or liquidation of the Issuer, unless Debentures are distributed to
the Holders, the lesser of (a) the aggregate of the Liquidation Amount of $__
per Preferred Security plus accumulated and unpaid Distributions on the
Preferred Securities to the date of payment to the extent the Issuer shall have
funds on hand available to make such payment at such time and (b) the amount of
assets of the Issuer remaining available for distribution to Holders in
liquidation of the Issuer (in either case, the "Liquidation Distribution").

         "Guarantee Trustee" means First Union National Bank, until a Successor
Guarantee Trustee has been appointed and has accepted such appointment pursuant
to the terms of this Guarantee Agreement and thereafter means each such
Successor Guarantee Trustee.

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

         "Indebtedness" means, with respect to any Person, (i) the principal,
premium, if any, and interest in respect of (A) indebtedness of such Person for
money borrowed and (B) indebtedness evidenced by securities, notes, debentures,
bonds or other similar instruments issued by such Person; (ii) all capital lease
obligations of such Person; (iii) all obligations of such Person issued or
assumed as the deferred purchase price of property, all conditional sale
obligations of such Person and all obligations of such Person under any
conditional sale or title retention agreement (but excluding trade accounts
payable and accrued liabilities arising in the ordinary course of business);
(iv) all obligations, contingent or otherwise, of such Person in respect of any
letters of credit, banker's acceptance, security purchase facilities or similar
credit transactions; (v) all obligations in respect of interest rate swap, cap,
floor, collar or other agreements, interest rate future or option contracts,
currency swap agreements, currency future or option contracts and other similar
agreements; (vi) any indebtedness between or among a Person and its Affiliates,
except as provided in (viii)(B) below; (vii) all obligations of the type
referred to in clauses (i) through (vi) of other Persons for the payment of
which such Person is responsible or liable as obligor, guarantor or otherwise;
and (viii) all obligations of the type referred to in clauses (i) through (vii)
of other Persons secured by any lien on any property or asset of such Person
(whether or not such obligation is assumed by such Person), except for (A) any
such indebtedness that is by its terms subordinated to or pari passu with the
Securities, and (B) any indebtedness between or among such Person and its
Affiliates relating to other debt securities and guarantees in respect of those
debt securities issued to (1) any HCC Trust or a trustee of such HCC Trust or
(2) any other trust, or a trustee of such trust, partnership or other entity
affiliated with the Company which is a financing vehicle of the Company (a
"Financing Entity") in connection with the issuance by such Financing Entity of
preferred securities or other securities guaranteed by the Company pursuant to
an instrument that ranks pari passu with, or junior to, the Preferred
Securities.

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

         "Indenture" means the Indenture, dated as of September __, 2000,
between the Guarantor and First Union National Bank, as Indenture Trustee, as
amended or supplemented from time to time.

         "Junior Subordinated Indebtedness" means all Indebtedness of the
Guarantor subordinate and junior to Subordinated Indebtedness and Senior
Indebtedness.

         "List of Holders" has the meaning specified in Section 2.2(a).

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         "Majority in Liquidation Amount of the Preferred Securities" means,
except as provided by the Trust Indenture Act, more than 50% of the Liquidation
Amount of all the then Outstanding Preferred Securities.

         "Officers' Certificate" means, with respect to any Person, a
certificate signed by the Chairman of the Board, the President or a Senior Vice
President, and by the Treasurer, an Assistant Treasurer, the Comptroller, an
Assistant Comptroller, the Secretary or an Assistant Secretary of such Person,
and delivered to the Guarantee Trustee. Any Officers' Certificate delivered with
respect to compliance with a condition or covenant provided for in this
Guarantee Agreement shall include:

                  (a) a statement that each officer signing the Officers'
         Certificate has read the covenant or condition and the definitions
         relating thereto;

                  (b) a brief statement of the nature and scope of the
         examination or investigation undertaken by each officer in rendering
         the Officers' Certificate;

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

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

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

         "Responsible Officer" means, with respect to the Guarantee Trustee, any
Senior Vice President, any Vice President, any Assistant Vice President, the
Secretary, any Assistant Secretary, the Treasurer, any Assistant Treasurer, any
Trust Officer or Assistant Trust officer or any other officer of the Corporate
Trust Department of the above designated officers and also means, with respect
to a particular corporate trust matter, any other officer to whom such matter is
referred because of that officer's knowledge of and familiarity with the
particular subject.

         "Senior Indebtedness" means all Indebtedness of the Guarantor, unless,
in the instrument creating or evidencing the same or pursuant to which the same
is outstanding, it is provided that such obligations are not superior in right
of payment to Subordinated Indebtedness or Junior Subordinated Indebtedness or
to other Indebtedness of the Guarantor which is pari passu with, or subordinated
to, Subordinated Indebtedness or Junior Subordinated Indebtedness.

         "Subordinated Indebtedness" means all Indebtedness of the Guarantor
which is subordinated and junior in right of payment to Senior Indebtedness, but
does not include Junior Subordinated Indebtedness.

         "Successor Guarantee Trustee" means a successor Guarantee Trustee
possessing the qualifications to act as Guarantee Trustee under Section 4.1.

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         "Trust Indenture Act" means the Trust Indenture Act of 1939, as
amended.

                                   ARTICLE II

                               TRUST INDENTURE ACT

         Section 2.1. Trust Indenture Act; Application.

         (a) This Guarantee Agreement is subject to the provisions of the Trust
Indenture Act that are required to be part of this Guarantee Agreement and
shall, to the extent applicable, be governed by such provisions.

         (b) If and to the extent that any provision of this Guarantee Agreement
limits, qualifies or conflicts with the duties imposed by Sections 310 to 317,
inclusive, of the Trust Indenture Act, such imposed duties shall control.

         Section 2.2. List of Holders.

         (a) The Guarantor shall furnish or cause to be furnished to the
Guarantee Trustee (a) semiannually, on or before June 30 and December 31 of each
year, a list, in such form as the Guarantee Trustee may reasonably require, of
the names and addresses of the Holders (the "List of Holders") as of a date not
more than 15 days prior to the delivery thereof, and (b) at such other times as
the Guarantee Trustee may request in writing, within 30 days after the receipt
by the Guarantor of any such request, a List of Holders as of a date not more
than 15 days prior to the time such list is furnished, in each case to the
extent such information is in the possession or control of the Guarantor and is
not identical to a previously supplied List of Holders or has not otherwise been
received by the Guarantee Trustee in its capacity as such. The Guarantee Trustee
may destroy any List of Holders previously given to it on receipt of a new List
of Holders.

         (b) The Guarantee Trustee shall comply with its obligations under
Section 311(a), Section 311(b) and Section 312(b) of the Trust Indenture Act.

         Section 2.3. Reports by the Guarantee Trustee.

         Not later than 60 days following May 15th of each year, commencing May
15, 2001, the Guarantee Trustee shall provide to the Holders such reports as are
required by Section 313 of the Trust Indenture Act, if any, in the form and in
the manner provided by Section 313 of the Trust Indenture Act. The Guarantee
Trustee shall also comply with the requirements of Section 313(d) of the Trust
Indenture Act.

         Section 2.4. Periodic Reports to the Guarantee Trustee.

         The Guarantor shall provide to the Guarantee Trustee, the Securities
and Exchange Commission and the Holders such documents, reports and information,
if any, as required by Section 314 of the Trust Indenture Act and the compliance
certificate required by Section 314 of the Trust Indenture Act, in the form, in
the manner and at the times required by Section 314 of the Trust Indenture Act.
If the Guarantee Trustee is also acting as the Property Trustee under the Trust
Agreement such reports will not be required hereunder.

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         Section 2.5. Evidence of Compliance with Conditions Precedent.

         The Guarantor shall provide to the Guarantee Trustee such evidence of
compliance with such conditions precedent, if any, provided for in this
Guarantee Agreement that relate to any of the matters set forth in Section
314(c) of the Trust Indenture Act. Any certificate or opinion required to be
given by an officer pursuant to Section 314(c)(1) may be given in the form of an
Officers' Certificate.

         Section 2.6. Events of Default; Waiver.

         The Holders of a Majority in Liquidation Amount of the Preferred
Securities may by vote, on behalf of the Holders, waive any past Event of
Default and its consequences. Upon such waiver, any such Event of Default shall
cease to exist, and any Event of Default arising therefrom shall be deemed to
have been cured, for every purpose of this Guarantee Agreement, but no such
waiver shall extend to any subsequent or other default or Event of Default or
impair any right consequent therefrom.

         Section 2.7. Event of Default; Notice.

         (a) The Guarantee Trustee shall, within 90 days after the occurrence of
an Event of Default known to the Guarantee Trustee, transmit by mail, first
class postage prepaid, to the Holders, notices of all such Events of Default
unless such defaults have been cured or waived before the giving of such notice;
provided, that, except in the case of a default in the payment of a Guarantee
Payment, the Guarantee Trustee shall be protected in withholding such notice if
and so long as the Board of Directors, the executive committee or a trust
committee of directors and/or Responsible Officers of the Guarantee Trustee in
good faith determines that the withholding of such notice is in the interests of
the Holders.

         (b) The Guarantee Trustee shall not be deemed to have knowledge of any
Event of Default unless the Guarantee Trustee shall have received written
notice, or a Responsible Officer charged with the administration of the Trust
Agreement shall have obtained written notice, of such Event of Default.

         Section 2.8. Conflicting Interests.

         The Trust Agreement and the Indenture shall be deemed to be
specifically described in this Guarantee Agreement for the purposes of clause
(i) of the first proviso contained in Section 310(b) of the Trust Indenture Act.

                                   ARTICLE III

               POWERS, DUTIES AND RIGHTS OF THE GUARANTEE TRUSTEE

         Section 3.1. Powers and Duties of the Guarantee Trustee.

         (a) This Guarantee Agreement shall be held by the Guarantee Trustee for
the benefit of the Holders, and the Guarantee Trustee shall not transfer this
Guarantee Agreement to any Person except a Holder exercising his or her rights
pursuant to Section 5.4(iv) or to a Successor

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Guarantee Trustee on acceptance by such Successor Guarantee Trustee of its
appointment to act as Successor Guarantee Trustee. The right, title and interest
of the Guarantee Trustee shall automatically vest in any Successor Guarantee
Trustee, upon acceptance by such Successor Guarantee Trustee of its appointment
hereunder, and such vesting and cessation of title shall be effective whether or
not conveyancing documents have been executed and delivered pursuant to the
appointment of such Successor Guarantee Trustee.

         (b) If an Event of Default has occurred and is continuing, the
Guarantee Trustee shall enforce this Guarantee Agreement for the benefit of the
Holders.

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

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

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

                           (A) the duties and obligations of the Guarantee
                  Trustee shall be determined solely by the express provisions
                  of this Guarantee Agreement, and the Guarantee Trustee shall
                  not be liable except for the performance of such duties and
                  obligations as are specifically set forth in this Guarantee
                  Agreement; and

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

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

                  (iii) the Guarantee Trustee shall not be liable with respect
         to any action taken or omitted to be taken by it in good faith in
         accordance with the direction of the Holders

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         of not less than a Majority in Liquidation Amount of the Preferred
         Securities relating to the time, method and place of conducting any
         proceeding for any remedy available to the Guarantee Trustee, or
         exercising any trust or power conferred upon the Guarantee Trustee
         under this Guarantee Agreement; and

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

         Section 3.2. Certain Rights of Guarantee Trustee.

         (a) Subject to the provisions of Section 3.1:

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

                  (ii) Any direction or act of the Guarantor contemplated by
         this Guarantee Agreement shall be sufficiently evidenced by an
         Officer's Certificate unless otherwise prescribed herein.

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

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

                  (v) The Guarantee Trustee shall be under no obligation to
         exercise any of the rights or powers vested in it by this Guarantee
         Agreement at the request or direction of any Holder, unless such Holder
         shall have provided to the Guarantee Trustee such adequate security and
         indemnity as would satisfy a reasonable person in the position of the
         Guarantee Trustee, against the costs, expenses (including attorneys'
         fees and

                                       8
<PAGE>   12

         expenses) and liabilities that might be incurred by it in complying
         with such request or direction, including such reasonable advances as
         may be requested by the Guarantee Trustee; provided, that nothing
         contained in this Section 3.2(a)(v) shall be taken to relieve the
         Guarantee Trustee, upon the occurrence of an Event of Default, of its
         obligation to exercise the rights and powers vested in it by this
         Guarantee Agreement.

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

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

                  (viii) Whenever in the administration of this Guarantee
         Agreement the Guarantee Trustee shall deem it desirable to receive
         instructions with respect to enforcing any remedy or right or taking
         any other action hereunder, the Guarantee Trustee (A) may request
         instructions from the Holders of a Majority in Liquidation Amount of
         the Securities, (B) may refrain from enforcing such remedy or right or
         taking such other action until such instructions are received, and (C)
         shall be protected in acting in accordance with such instructions.

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

         Section 3.3. Compensation; Fees.

         The Guarantor agrees:

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

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

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                                   ARTICLE IV

                                GUARANTEE TRUSTEE

         Section 4.1. Guarantee Trustee: Eligibility.

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

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

                  (ii) be a Person that is eligible pursuant to the Trust
         Indenture Act to act as such and has a combined capital and surplus of
         at least $50,000,000 and shall be a corporation meeting the
         requirements of Section 310(a) of the Trust Indenture Act. If such
         corporation publishes reports of condition at least annually, pursuant
         to law or to the requirements of the supervising or examining
         authority, then, for the purposes of this Section and to the extent
         permitted by the Trust Indenture Act, the combined capital and surplus
         of such corporation shall be deemed to be its combined capital and
         surplus as set forth in its most recent report of condition so
         published.

         (b) If at any time the Guarantee Trustee shall cease to be eligible to
so act under Section 4.1(a), the Guarantee Trustee shall immediately resign in
the manner and with the effect set out in Section 4.2(c).

         (c) If the Guarantee Trustee has or shall acquire any "conflicting
interest" within the meaning of Section 310(b) of the Trust Indenture Act, the
Guarantee Trustee and Guarantor shall in all respects comply with the provisions
of Section 310(b) of the Trust Indenture Act.

         Section 4.2. Appointment, Removal and Resignation of the Guarantee
Trustee.

         (a) Subject to Section 4.2(c), the Guarantee Trustee may be appointed
or removed at any time by the action of the Holders of a Majority in Liquidation
Amount of the Preferred Securities (i) for cause or (ii) if a Debenture Event of
Default (as defined in the Trust Agreement) shall have occurred and be
continuing at any time.

         (b) Subject to Section 4.2(c), the Guarantee Trustee shall have been
appointed or until its removal or resignation. The Guarantee Trustee may resign
from office (without need for prior or subsequent accounting) by an instrument
in writing executed by the Guarantee Trustee and delivered to the Guarantor and
the Holders, which resignation shall not take effect until the Guarantee Trustee
has appointed a Successor Guarantee Trustee. The Guarantee Trustee shall appoint
a successor by requesting from at least three Persons meeting the requirements
of Section 4.1(a) their expenses and charges to serve as the Guarantee Trustee,
and selecting the Person who agrees to the lowest expenses and charges.

                                       10
<PAGE>   14

         (c) The Guarantee Trustee appointed hereunder shall hold office until a
Successor Guarantee Trustee shall have been appointed and shall have accepted
such appointment. No removal or resignation of a Guarantee Trustee shall be
effective until a Successor Guarantee Trustee has been appointed and has
accepted such appointment by written instrument executed by such Successor
Guarantee Trustee and delivered to the Guarantor and, in the case of any
resignation, the resigning Guarantee Trustee.

         (d) If no Successor Guarantee Trustee shall have been appointed and
accepted appointment as provided in this Section 4.2 within 60 days after
delivery to the Holders and the Guarantor of a notice of resignation, the
resigning Guarantee Trustee may petition, at the expense of the Guarantor, any
court of competent jurisdiction for appointment of a Successor Guarantee
Trustee. Such court may thereupon, after prescribing such notice, as it may deem
proper, appoint a Successor Guarantee Trustee.

         (e) If no Successor Guarantee Trustee shall have been appointed and
accepted appointment as provided in this Section 4.2 within 60 days after
delivery to the Guarantor of an instrument of resignation, or if a Guarantee
Trustee shall be removed or become incapable of acting as Guarantee Trustee and
a replacement shall not be appointed prior to such resignation or removal, or if
a vacancy shall occur in the office of Guarantee Trustee for any cause, the
Holders of the Preferred Securities, by the action of the Holders of record of
not less than 25% in aggregate Liquidation Amount of the Preferred Securities
then Outstanding delivered to such Guarantee Trustee, may appoint a Successor
Guarantee Trustee or Trustees. If no successor Guarantee Trustee shall have been
so appointed by the Holders of the Preferred Securities and accepted
appointments, any Holder, on behalf of such Holder and all other similarly
situated, or any other Guarantee Trustee, may petition any court of competent
jurisdiction for the appointment of a successor Guarantee Trustee.

                                    ARTICLE V

                                    GUARANTEE

         Section 5.1. Guarantee.

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

         Section 5.2. Waiver of Notice and Demand.

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

                                       11
<PAGE>   15

         Section 5.3. Obligations Not Affected.

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

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

         (b) the extension of time for the payment by the Issuer of all or any
portion of the Distributions (other than an extension of time for payment of
Distributions that results from the deferral of any interest payment date on the
Debentures as so provided in the Indenture), Redemption Price, Liquidation
Distribution or any other sums payable under the terms of the Preferred
Securities or the extension of time for the performance of any other obligation
under, arising out of, or in connection with, the Preferred Securities;

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

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

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

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

         (g) any other circumstance whatsoever that might otherwise constitute a
legal or equitable discharge or defense of a guarantor, it being the intent of
this Section 5.3 that the obligations of the Guarantor hereunder shall be
absolute and unconditional under any and all circumstances.

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

         Section 5.4. Rights of Holders.

         The Guarantor expressly acknowledges that: (i) this Guarantee Agreement
will be deposited with the Guarantee Trustee to be held for the benefit of the
Holders; (ii) the Guarantee Trustee has the right to enforce this Guarantee
Agreement on behalf of the Holders; (iii) the Holders of a Majority in
Liquidation Amount of the Preferred Securities have the right to direct the
time, method and place of conducting any proceeding for any remedy available to
the Guarantee Trustee in respect of this Guarantee Agreement or exercising any
trust or power

                                       12
<PAGE>   16

conferred upon the Guarantee Trustee under this Guarantee Agreement; and (iv) if
the Guarantee Trustee fails to enforce this Guarantee Agreement after a Holder
has made a written request for the Guarantee Trustee to do so, any Holder may,
to the extent permitted by law, institute a legal proceeding directly against
the Guarantor to enforce its rights under this Guarantee Agreement, without
first instituting a legal proceeding against the Guarantee Trustee, the Issuer
or any other Person. Notwithstanding the foregoing, if the Guarantor has failed
to make a Guarantee Payment, a Holder may directly institute a proceeding
against the Guarantor for enforcement of this Guarantee Agreement for such
payment. The Guarantor waives, any right or remedy to require that any action on
this Guarantee Agreement be brought first against the Issuer or any other Person
or entity before proceeding directly against the Guarantor.

         Section 5.5. Guarantee of Payment.

         This Guarantee Agreement creates a guarantee of payment and not of
collection. This Guarantee Agreement will not be discharged except by payment of
the Guarantee Payments in full (without duplication of amounts theretofore paid
by the Issuer) or upon distribution of Debentures to Holders as provided in the
Trust Agreement.

         Section 5.6. Subrogation.

         The Guarantor shall be subrogated to all (if any) rights of the Holders
against the Issuer in respect of any amounts paid to the Holders by the
Guarantor under this Guarantee Agreement and shall have the right to waive
payment by the Issuer pursuant to Section 5.1; provided, however, that the
Guarantor shall not (except to the extent required by mandatory provisions of
law) be entitled to enforce or exercise any rights which it may acquire by way
of subrogation or any indemnity, reimbursement or other agreement, in all cases
as a result of payment under this Guarantee Agreement, if at the time of any
such payment, any amounts are due and unpaid under this Guarantee Agreement. If
any amount shall be paid to the Guarantor in violation of the preceding
sentence, the Guarantor agrees to hold such amount in trust for the Holders and
to pay over such amount to the Holders.

         Section 5.7. Independent Obligations.

         The Guarantor acknowledges that its obligations hereunder are
independent of the obligations of the Issuer with respect to the Securities and
that the Guarantor shall be liable as principal and as debtor hereunder to make
Guarantee Payments pursuant to the terms of this Guarantee Agreement
notwithstanding the occurrence of any event referred to in subsections (a)
through (g), inclusive, of Section 5.3 hereof.

                                   ARTICLE VI

                           COVENANTS AND SUBORDINATION

         Section 6.1. Subordination.

         This Guarantee Agreement will constitute an unsecured obligation of the
Guarantor and will rank subordinate and junior in right of payment to all Senior
Indebtedness and Subordinated Indebtedness of the Guarantor.

                                       13
<PAGE>   17

         Section 6.2. Pari Passu Guarantees.

         This Guarantee Agreement shall rank pari passu with any similar
Guarantee Agreements issued by the Guarantor on behalf of the holders of
Preferred Securities issued by an HCC Trust (as defined in the Trust Agreement).

                                   ARTICLE VII

                                   TERMINATION

         Section 7.1. Termination.

         This Guarantee Agreement shall terminate and be of no further force and
effect upon (i) full payment of the Redemption Price of all Preferred
Securities, (ii) the distribution of Debentures to the Holders in exchange for
all of the Preferred Securities or (iii) full payment of the amounts payable in
accordance with the Trust Agreement upon liquidation of the Issuer.
Notwithstanding the foregoing, this Guarantee Agreement will continue to be
effective or will be reinstated, as the case may be, if at any time any Holder
must restore payment of any sums paid with respect to Preferred Securities or
this Guarantee Agreement.

                                  ARTICLE VIII
                                 INDEMNIFICATION

         Section 8.1 Exculpation.

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

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

         Section 8.2 Indemnification.

         The Guarantor agrees to indemnify each Indemnified Person for, and to
hold each Indemnified Person harmless against, any loss, liability or expense
incurred without negligence or bad faith on its part, arising out of or in
connection with the acceptance or administration of

                                       14
<PAGE>   18

the trust or trusts hereunder, including the costs and expenses (including
reasonable legal fees and expenses) of defending itself against, or
investigating, any claim or liability in connection with the exercise or
performance of any of its powers or duties hereunder. The provisions of this
Section 8.2 shall survive the termination of this Guarantee Agreement or the
resignation or removal of the Guarantee Trustee.

                                   ARTICLE IX

                                  MISCELLANEOUS

         Section 9.1. Successors and Assigns.

         All guarantees and agreements contained in this Guarantee Agreement
shall bind the successors, assigns, receivers, trustees and representatives of
the Guarantor and shall inure to the benefit of the Holders of the Securities
then outstanding. Except in connection with a consolidation, merger or sale
involving the Guarantor that is permitted under Article 5 of the Indenture and
pursuant to which the assignee agrees in writing to perform the Guarantor's
obligations hereunder, the Guarantor shall not assign its obligations hereunder.

         Section 9.2. Amendments.

         Except with respect to any changes which do not adversely affect the
rights of the Holders in any material respect (in which case no consent of the
Holders will be required), this Guarantee Agreement may only be amended with the
prior approval of the Holders of not less than a Majority in liquidation
preference of all the outstanding Preferred Securities. The provisions of
Article VI of the Trust Agreement concerning meetings of the Holders shall apply
to the giving of such approval.

         Section 9.3. Notices.

         Any notice, request or other communication required or permitted to be
given hereunder shall be in writing, duly signed by the party giving such
notice, and delivered, telecopied or mailed by first class mail as follows:

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

                  First Union National Bank
                  1525 West W.T. Harris Blvd., 3C3
                  Charlotte, North Carolina 28262-1153
                  Facsimile No.:
                  Attention: Corporate Trust Department

                                       15
<PAGE>   19

         (b) if given to the Guarantor, to the address set forth below or such
other address, facsimile number or to the attention of such other Person as the
Guarantor may give notice to the Holders of the Preferred Securities:

                  HCC Insurance Holdings, Inc.
                  13403 Northwest Freeway
                  Houston, Texas 77040
                  Facsimile No.: 713
                  Attention: Corporate Secretary

         (c) if given to the Issuer, in care of the Guarantee Trustee, at the
address of the Guarantee Trustee as set forth in clause (a) above, with a copy
to::

                  HCC Capital Trust I
                  c/o HCC Insurance Holdings, Inc.
                  13403 Northwest Freeway
                  Houston, Texas 77040
                  Facsimile No.: 713
                  Attention: Corporate Secretary

         (d) if given to any Holder, at the address set forth on the books and
records of the Issuer.

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

         Section 9.4. Benefit.

         This Guarantee Agreement is solely for the benefit of the Holders and
is not separately transferable from the Securities.

         Section 9.5. Governing Law.

         THIS GUARANTEE AGREEMENT SHALL BE GOVERNED BY AND CONSTRUED AND
INTERPRETED IN ACCORDANCE WITH THE LAW OF THE STATE OF NEW YORK WITHOUT REGARD
TO THE CONFLICT OF LAW PRINCIPLES THEREOF.

         This instrument may be executed in any number of counterparts, each of
which so executed shall be deemed to be an original, but all such counterparts
shall together constitute but one and the same instrument.

                                       16
<PAGE>   20

         THIS GUARANTEE AGREEMENT is executed as of the date first above
written.

                                         HCC INSURANCE HOLDINGS, INC.

                                         By:
                                            ------------------------------------
                                              Name:
                                              Title:

                                         First Union National Bank,
                                         as Guarantee Trustee

                                         By:
                                            ------------------------------------
                                              Name:
                                              Title

                                       17<PAGE>

FORM OF CERTIFICATE
MONSANTO COMPANY

                                                                     EXHIBIT 4.1

NUMBER                           SHARES

                                 CUSIP NO. 61166W 10 1

[PICTURE OF WOMAN IN FIELD]

COMMON STOCK
$ .01 PAR VALUE

SEE REVERSE FOR CERTAIN DEFINITIONS
INCORPORATED UNDER THE LAWS OF THE STATE OF DELAWARE

This Certifies that

is the owner of

FULLY PAID AND NONASSESSABLE SHARES OF THE COMMON STOCK OF

Monsanto Company (hereinafter referred to as the "Company"), transferable on
the books of the Company by the holder hereof in person or by duly authorized
attorney upon surrender of this certificate properly endorsed. This certificate
and the shares represented hereby are issued and shall be held subject to all of
the provisions of the Certificate of Incorporation, as amended, of the Company
(a copy of which certificate is on file with the Transfer Agent), to all of
which the holder by acceptance hereof assents.

This certificate is not valid until countersigned and registered by the Transfer
Agent and Registrar.

In witness whereof, the Company has caused this certificate to be signed by its
duly authorized officers and its corporate seal to be hereunto affixed.

Dated:

CHIEF EXECUTIVE OFFICER AND SECRETARY

COUNTERSIGNED AND REGISTERED: EQUISERVE TRUST COMPANY, N.A.

TRANSFER AGENT AND REGISTRAR:

BY
AUTHORIZED SIGNATURE

<PAGE>

Monsanto Company will furnish without charge to each stockholder who so requests
a statement or summary of the powers, designations, preferences and relative,
participating, optional or other special rights of each class of stock or series
thereof which Monsanto Company is authorized to issue and of the qualifications,
limitations or restrictions of such preferences and/or rights. Any such request
is to be addressed to the Secretary of Monsanto Company or to the Transfer Agent
named on the face of this certificate.

The following abbreviations, when used in the inscription on the face of this
certificate, shall be construed as though they were written out in full
according to applicable laws and regulations:

TEN COM - as tenants in common
TEN ENT - as tenants by the entireties
JT TEN  - as joint tenants with rights of survivorship
          and not as tenants in common
TOD     - transfer on death direction in event of owner's death,
          to person named on face subject to STA TOD rules.
Additional abbreviations may be used though not in the above list.

UNIF GIFT MIN ACT _________________CUSTODIAN_______________________
                        (Cust)                      (Minor)

                   Under Uniform Gifts to Minors Act

                   _________________________________
                               (STATE)

UNIF TRAN MIN ACT _________________CUSTODIAN_______________________
                        (Cust)                      (Minor)

                   Under Uniform  Transfers to Minors Act

                   _________________________________
                               (STATE)

FOR VALUE RECEIVED                         HEREBY SELL, ASSIGN AND TRANSFER UNTO

__________________________________________________
(Please print or type name and address of assignee)

__________________________________________________

__________________________________________________

_____________________________________________   Social Security or other
                                                Identifying Number of Assignee

                                                ____________________________
_____________________________________________   SHARES

____________________________________________________________________________

SHARES OF THE CAPITAL STOCK REPRESENTED BY THE WITHIN CERTIFICATE AND DO HEREBY
IRREVOCABLY CONSTITUTE AND APPOINT

____________________________________________________________________________

ATTORNEY TO TRANSFER THE SAID STOCK ON THE BOOKS OF THE WITHIN NAMED COMPANY
WITH FULL POWER OF SUBSTITUTION IN THE PREMISES.

DATED

NOTICE: The Signature(s) to this assignment must correspond with the name(s) as
written upon the face of the certificate in every particular, without alteration
or enlargement or any change whatever.

The signature(s) should be guaranteed by an Eligible Guarantor Institution
(Banks, Stockholders, Savings and Loan Associations and Credit Unions with
membership in an approved signature guarantee medallion program), pursuant to
S.E.C. Rule 17Ad-15.

Signature
Signature
Signature(s) guaranteed by

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