EXHIBIT 10.02




                               GUARANTEE AGREEMENT

                                TOWER GROUP, INC.

                           Dated as of March 31, 2006





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                                TABLE OF CONTENTS

                                                                            Page



                                    ARTICLE I
                         DEFINITIONS AND INTERPRETATION

SECTION 1.1.    Definitions and Interpretation.................................1

                                   ARTICLE II
               POWERS, DUTIES AND RIGHTS OF THE GUARANTEE TRUSTEE

SECTION 2.1.    Powers and Duties of the Guarantee Trustee.....................4

SECTION 2.2.    Certain Rights of the Guarantee Trustee........................5

SECTION 2.3.    Not Responsible for Recitals or Issuance of Guarantee..........7

SECTION 2.4.    Events of Default; Waiver......................................7

SECTION 2.5.    Events of Default; Notice......................................8

                                   ARTICLE III
                              THE GUARANTEE TRUSTEE

SECTION 3.1.    The Guarantee Trustee; Eligibility.............................8

SECTION 3.2.    Appointment, Removal and Resignation of the Guarantee Trustee..9

                                   ARTICLE IV
                                    GUARANTEE

SECTION 4.1.    Guarantee......................................................9

SECTION 4.2.    Waiver of Notice and Demand...................................10

SECTION 4.3.    Obligations Not Affected......................................10

SECTION 4.4.    Rights of Holders.............................................11

SECTION 4.5.    Guarantee of Payment..........................................11

SECTION 4.6.    Subrogation...................................................11

SECTION 4.7.    Independent Obligations.......................................12

SECTION 4.8.    Enforcement...................................................12

                                    ARTICLE V
                    LIMITATION OF TRANSACTIONS; SUBORDINATION

SECTION 5.1.    Limitation of Transactions....................................12

SECTION 5.2.    Ranking.......................................................13

                                   ARTICLE VI
                                   TERMINATION

SECTION 6.1.    Termination...................................................13

                                       -i-

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                                   ARTICLE VII
                                 INDEMNIFICATION

SECTION 7.1.    Exculpation...................................................14

SECTION 7.2.    Indemnification...............................................14

SECTION 7.3.    Compensation; Reimbursement of Expenses.......................15

                                  ARTICLE VIII
                                  MISCELLANEOUS

SECTION 8.1.    Successors and Assigns........................................16

SECTION 8.2.    Amendments....................................................16

SECTION 8.3.    Notices.......................................................16

SECTION 8.4.    Benefit.......................................................17

SECTION 8.5.    Governing Law.................................................17

SECTION 8.6.    Counterparts..................................................17




                                      -ii-

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                               GUARANTEE AGREEMENT
                               -------------------

     This GUARANTEE AGREEMENT (the "Guarantee"),  dated as of March 31, 2006, is
executed  and  delivered  by Tower  Group,  Inc.,  a Delaware  corporation  (the
"Guarantor"),  and Wells  Fargo  Delaware  Trust  Company,  a  national  banking
association  with its principal  place of business in the State of Delaware,  as
trustee (the  "Guarantee  Trustee"),  for the benefit of the Holders (as defined
herein) from time to time of the Capital Securities (as defined herein) of Tower
Group Statutory Trust V, a Delaware statutory trust (the "Issuer").

     WHEREAS,  pursuant to an Amended  and  Restated  Declaration  of Trust (the
"Declaration"),  dated as of March 31, 2006, among the trustees named therein of
the Issuer,  Tower Group, Inc., as sponsor, and the Holders from time to time of
undivided  beneficial  interests  in the  assets of the  Issuer,  the  Issuer is
issuing on the date hereof securities, having an aggregate liquidation amount of
up to $20,000,000, designated the Capital Securities; and

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

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

                                    ARTICLE I
                         DEFINITIONS AND INTERPRETATION

SECTION 1.1. Definitions and Interpretation.
             -------------------------------

In this Guarantee, unless the context otherwise requires:

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

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

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

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

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

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

<PAGE>


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

          "Corporate Trust Office" means the office of the Guarantee  Trustee at
which the  corporate  trust  business of the  Guarantee  Trustee  shall,  at any
particular  time,  be  principally  administered,  which  office  at the date of
execution  of this  Guarantee  is  located  at 919  Market  Street,  Suite  700,
Wilmington, DE 19801.

          "Covered Person" means any Holder of Capital Securities.

          "Debentures" means the junior subordinated  debentures of Tower Group,
Inc.,  designated the Junior  Subordinated Debt Securities due 2036, held by the
Institutional Trustee (as defined in the Declaration) of the Issuer.

          "Event of Default" has the meaning set forth in Section 2.4.

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

          "Guarantee Trustee" means Wells Fargo Delaware Trust Company,  until a
Successor Guarantee Trustee has been appointed and has accepted such appointment
pursuant to the terms of this Guarantee and thereafter means each such Successor
Guarantee Trustee.

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

          "Indemnified  Person"  means the Guarantee  Trustee  (including in its
individual  capacity),  any Affiliate of the Guarantee Trustee, or any officers,
directors,   shareholders,   members,  partners,   employees,   representatives,
nominees, custodians or agents of the Guarantee Trustee.

                                      -2-
<PAGE>


          "Indenture" means the Indenture,  dated as of March 31, 2006,  between
the Guarantor and Wells Fargo  Delaware  Trust  Company,  not in its  individual
capacity but solely as trustee, and any indenture  supplemental thereto pursuant
to which the  Debentures  are to be issued to the  Institutional  Trustee of the
Issuer.

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

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

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

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

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

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

          (c) a statement  that each such 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 such  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 officer  within the  Corporate  Trust Office of the  Guarantee  Trustee with
direct  responsibility  for the  administration  of any matters relating to this
Guarantee,  including any vice  president,  any assistant  vice  president,  any
secretary,  any assistant secretary, the treasurer, any assistant treasurer, any
trust officer or other  officer of the  Corporate  Trust Office of the Guarantee
Trustee  customarily  performing  functions similar to those performed by any 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.

                                      -3-
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          "Successor  Guarantee  Trustee"  means a successor  Guarantee  Trustee
possessing the qualifications to act as Guarantee Trustee under Section 3.1.

          "Trust  Securities"  means  the  Common  Securities  and  the  Capital
Securities.

                                   ARTICLE II
               POWERS, DUTIES AND RIGHTS OF THE GUARANTEE TRUSTEE

SECTION 2.1. Powers and Duties of the Guarantee Trustee.
             -------------------------------------------

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

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

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

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

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

                                      -4-
<PAGE>


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

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

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

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

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

SECTION 2.2. Certain Rights of the Guarantee Trustee.
             ----------------------------------------

          (a) Subject to the provisions of Section 2.1:

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

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

                                      -5-
<PAGE>


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

               (iv)  The  Guarantee  Trustee  shall  have  no duty to see to any
          recording,  filing or  registration of any instrument or other writing
          (or any rerecording, refiling or reregistration thereof).

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

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

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

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

                                      -6-
<PAGE>


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

               (x)  Whenever  in  the   administration  of  this  Guarantee  the
          Guarantee Trustee shall deem it desirable to receive instructions with
          respect to  enforcing  any remedy or right or taking any other  action
          hereunder, the Guarantee Trustee (A) may request instructions from the
          Holders of a Majority in liquidation amount of the Capital 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 conclusively relying on or acting in accordance with such
          instructions.

               (xi) The  Guarantee  Trustee  shall not be liable  for any action
          taken,  suffered,  or  omitted  to be  taken by it in good  faith  and
          reasonably believed by it to be authorized or within the discretion or
          rights or powers conferred upon it by this Guarantee.

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

SECTION 2.3. Not Responsible for Recitals or Issuance of Guarantee.
             ------------------------------------------------------

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

SECTION 2.4. Events of Default; Waiver.
             --------------------------

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

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

                                      -7-
<PAGE>


SECTION 2.5. Events of Default; Notice.
             --------------------------

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

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

                                  ARTICLE III
                              THE GUARANTEE TRUSTEE

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

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

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

                                      -8-
<PAGE>


SECTION 3.2. Appointment, Removal and Resignation of the Guarantee Trustee.
             --------------------------------------------------------------

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

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

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

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

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

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

                                   ARTICLE IV
                                    GUARANTEE

SECTION 4.1. Guarantee.
             ----------

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

                                      -9-
<PAGE>


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

SECTION 4.2. Waiver of Notice and Demand.
             ----------------------------

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

SECTION 4.3. Obligations Not Affected.
             -------------------------

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

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

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

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

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

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

                                      -10-
<PAGE>


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

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

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

SECTION 4.4. Rights of Holders.
             ------------------

          (a) The  Holders of a Majority  in  liquidation  amount of the Capital
     Securities  have  the  right  to  direct  the  time,  method  and  place of
     conducting any proceeding for any remedy available to the Guarantee Trustee
     in respect of this  Guarantee  or to direct  the  exercise  of any trust or
     power conferred upon the Guarantee Trustee under this Guarantee;  provided,
     however, that (subject to Sections 2.1 and 2.2) the Guarantee Trustee shall
     have the right to  decline to follow any such  direction  if the  Guarantee
     Trustee  shall  determine  that the actions so  directed  would be unjustly
     prejudicial  to the  Holders not taking  part in such  direction  or if the
     Guarantee Trustee being advised by legal counsel determines that the action
     or  proceeding  so directed may not  lawfully be taken or if the  Guarantee
     Trustee  in good faith by its board of  directors  or  trustees,  executive
     committee or a trust committee of directors or trustees and/or  Responsible
     Officers  shall  determine  that the action or proceeding so directed would
     involve the Guarantee Trustee in personal liability.

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

SECTION 4.5. Guarantee of Payment.
             ---------------------

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

SECTION 4.6. Subrogation.
             ------------

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

                                      -11-
<PAGE>


SECTION 4.7. Independent Obligations.
             ------------------------

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

SECTION 4.8. Enforcement.
             ------------

          A Beneficiary may enforce the  Obligations of the Guarantor  contained
in Section 4.1 (b) directly against the Guarantor,  and the Guarantor waives any
right or remedy to require that any action be brought  against the Issuer or any
other person or entity before proceeding against the Guarantor.

          The  Guarantor  shall  be  subrogated  to all  rights  (if any) of any
Beneficiary   against  the  Issuer  in  respect  of  any  amounts  paid  to  the
Beneficiaries by the Guarantor under this Guarantee; provided, however, that the
Guarantor shall not (except to the extent  required by applicable  provisions of
law) be entitled to enforce or exercise any rights that it may acquire by way of
subrogation or any indemnity,  reimbursement or other agreement, in all cases as
a result of payment  under  this  Guarantee,  if,  after  giving  effect to such
payment, any amounts are due and unpaid under this Guarantee.

                                   ARTICLE V
                    LIMITATION OF TRANSACTIONS; SUBORDINATION

SECTION 5.1. Limitation of Transactions.
             ---------------------------

          So long as any Capital  Securities  remain  outstanding,  if (a) there
shall have  occurred and be  continuing an Event of Default or (b) the Guarantor
shall have selected an Extension  Period as provided in the Declaration and such
period, or any extension thereof,  shall have commenced and be continuing,  then
the Guarantor may not (x) declare or pay any dividends or  distributions  on, or
redeem, purchase, acquire, or make a liquidation payment with respect to, any of
the  Guarantor's  capital  stock or (y)  make any  payment  of  principal  of or
interest  or  premium,  if any,  on or  repay,  repurchase  or  redeem  any debt
securities of the Guarantor  that rank pari passu in all respects with or junior
in interest to the  Debentures  (other than (i) payments  under this  Guarantee,
(ii) repurchases,  redemptions or other  acquisitions of shares of capital stock
of the Guarantor (A) in connection with any employment contract, benefit plan or
other  similar  arrangement  with or for the  benefit of one or more  employees,
officers,   directors,  or  consultants,  (B)  in  connection  with  a  dividend
reinvestment  or stockholder  stock purchase plan or (C) in connection  with the
issuance of capital stock of the Guarantor (or  securities  convertible  into or
exercisable  for  such  capital  stock),  as  consideration  in  an  acquisition

                                      -12-
<PAGE>


transaction  entered into prior to the occurrence of the Event of Default or the
applicable  Extension Period, (iii) as a result of any exchange or conversion of
any class or series of the Guarantor's  capital stock (or any capital stock of a
subsidiary of the Guarantor) for any class or series of the Guarantor's  capital
stock or of any class or series of the Guarantor's indebtedness for any class or
series  of the  Guarantor's  capital  stock,  (iv) the  purchase  of  fractional
interests in shares of the Guarantor's  capital stock pursuant to the conversion
or exchange  provisions of such capital stock or the security being converted or
exchanged,   (v)  any   declaration  of  a  dividend  in  connection   with  any
stockholder's  rights plan, or the issuance of rights,  stock or other  property
under any  stockholder's  rights plan, or the redemption or repurchase of rights
pursuant thereto, or (vi) any dividend in the form of stock,  warrants,  options
or other rights where the dividend  stock or the stock issuable upon exercise of
such  warrants,  options or other  rights is the same stock as that on which the
dividend is being paid or ranks pari passu with or junior to such stock).

SECTION 5.2. Ranking.
             --------

          This  Guarantee  will  constitute  an  unsecured   obligation  of  the
Guarantor  and will  rank  subordinate  and  junior in right of  payment  to all
present and future  Senior  Indebtedness  (as defined in the  Indenture)  of the
Guarantor. By their acceptance thereof, each Holder of Capital Securities agrees
to the  foregoing  provisions  of this  Guarantee  and the other terms set forth
herein.

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

                                   ARTICLE VI
                                   TERMINATION

SECTION 6.1. Termination.
             ------------

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

                                      -13-
<PAGE>


                                  ARTICLE VII
                                 INDEMNIFICATION

SECTION 7.1. Exculpation.
             ------------

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

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

SECTION 7.2. Indemnification.
             ----------------

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

          (b) Promptly after receipt by an Indemnified Person under this Section
     7.2 of notice of the commencement of any action,  such  Indemnified  Person
     will,  if a claim in respect  thereof is to be made  against the  Guarantor
     under this Section 7.2, notify the Guarantor in writing of the commencement
     thereof;  but the failure so to notify the  Guarantor  (i) will not relieve
     the Guarantor  from liability  under  paragraph (a) above unless and to the
     extent that the Guarantor  did not otherwise  learn of such action and such
     failure  results in the forfeiture by the Guarantor of  substantial  rights
     and defenses and (ii) will not, in any event,  relieve the  Guarantor  from
     any  obligations to any Indemnified  Person other than the  indemnification
     obligation provided in paragraph (a) above. The Guarantor shall be entitled
     to appoint counsel of the Guarantor's choice at the Guarantor's  expense to
     represent the Indemnified Person in any action for which indemnification is
     sought (in which case the Guarantor shall not thereafter be responsible for
     the fees and expenses of any separate  counsel  retained by the Indemnified
     Person or Persons except as set forth below); provided,  however, that such
     counsel shall be satisfactory to the  Indemnified  Person.  Notwithstanding

                                      -14-
<PAGE>


     the  Guarantor's  election to appoint  counsel to represent the Indemnified
     Person in any action, the Indemnified Person shall have the right to employ
     separate counsel  (including  local counsel),  and the Guarantor shall bear
     the reasonable  fees, costs and expenses of such separate  counsel,  if (i)
     the use of counsel  chosen by the  Guarantor to represent  the  Indemnified
     Person would  present  such  counsel with a conflict of interest,  (ii) the
     actual or potential  defendants  in, or targets of, any such action include
     both the Indemnified  Person and the Guarantor and the  Indemnified  Person
     shall have reasonably  concluded that there may be legal defenses available
     to it  and/or  other  Indemnified  Persons  which  are  different  from  or
     additional to those  available to the Guarantor,  (iii) the Guarantor shall
     not  have  employed  counsel  satisfactory  to the  Indemnified  Person  to
     represent the  Indemnified  Person within a reasonable time after notice of
     the  institution of such action or (iv) the Guarantor  shall  authorize the
     Indemnified  Person  to  employ  separate  counsel  at the  expense  of the
     Guarantor. The Guarantor will not, without the prior written consent of the
     Indemnified  Persons,  settle or  compromise or consent to the entry of any
     judgment with respect to any pending or threatened claim,  action,  suit or
     proceeding  in  respect of which  indemnification  or  contribution  may be
     sought  hereunder  (whether  or not the  Indemnified  Persons are actual or
     potential  parties  to  such  claim  or  action)  unless  such  settlement,
     compromise or consent includes an unconditional release of each Indemnified
     Person  from all  liability  arising  out of such  claim,  action,  suit or
     proceeding.

SECTION 7.3. Compensation; Reimbursement of Expenses.
             ----------------------------------------

          The Guarantor agrees:

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

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

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

                                      -15-
<PAGE>


                                  ARTICLE VIII
                                  MISCELLANEOUS

SECTION 8.1. Successors and Assigns.
             -----------------------

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

SECTION 8.2. Amendments.
             -----------

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

SECTION 8.3. Notices.
             --------

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

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

              Wells Fargo Delaware Trust Company
              919 Market Street
              Suite 700
              Wilmington, DE 19801
              Attention: Corporate Trust Division
              Telecopy: 302-575-2006
              Telephone: 302-575-2005

                                      -16-
<PAGE>


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

              Tower Group, Inc.
              120 Broadway, 14th Floor
              New York, New York 10271-1699
              Attention: Francis M. Colalucci
              Telecopy: (212) 271-5492
              Telephone: (212) 655-2146

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

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

SECTION 8.4. Benefit.
             --------

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

SECTION 8.5. Governing Law.
             --------------

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

SECTION 8.6. Counterparts.
             -------------

          This Guarantee may contain more than one  counterpart of the signature
page and this  Guarantee may be executed by the affixing of the signature of the
Guarantor and the Guarantee Trustee to any of such counterpart  signature pages.
All of such  counterpart  signature  pages shall be read as though one, and they
shall have the same force and effect as though all of the  signers  had signed a
single signature page.

                                      -17-
<PAGE>


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

                                        TOWER GROUP, INC.,
                                        as Guarantor


                                        By:  /s/ Francis M. Colalucci
                                            ------------------------------------
                                        Name:  Francis M. Colalucci
                                              ----------------------------------
                                        Title:  Senior Vice President and Chief
                                               ---------------------------------
                                                Financial Officer
                                               ---------------------------------



                                        WELLS FARGO DELAWARE TRUST
                                        COMPANY, as Guarantee Trustee


                                        By:  /s/ Ann Roberts Dukart
                                            ------------------------------------
                                        Name:  Ann Roberts Dukart
                                              ----------------------------------
                                        Title: Vice President
                                               ---------------------------------



                                      -18-