<PAGE>


                                                                    Exhibit 4.16


===============================================================================







                    PREFERRED SECURITIES GUARANTEE AGREEMENT



                            ST. PAUL CAPITAL TRUST II

























                         DATED AS OF ___________, 200__



===============================================================================

<PAGE>







                                TABLE OF CONTENTS

<TABLE>
<CAPTION>
                                                                                                       PAGE
                                                                                                       ----
<S>                 <C>                                                                                 <C>
                                    ARTICLE I
                         DEFINITIONS AND INTERPRETATION

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

                                   ARTICLE II
                               TRUST INDENTURE ACT

SECTION 2.1         Trust Indenture Act; Application.....................................................5
SECTION 2.2         Lists of Holders of Securities.......................................................5
SECTION 2.3         Reports by the Preferred Guarantee Trustee...........................................5
SECTION 2.4         Periodic Reports to Preferred Guarantee Trustee......................................6
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................................................................7

                                   ARTICLE III
            POWERS, DUTIES AND RIGHTS OF PREFERRED GUARANTEE TRUSTEE

SECTION 3.1         Powers and Duties of the Preferred Guarantee Trustee.................................7
SECTION 3.2         Certain Rights of Preferred Guarantee Trustee........................................8
SECTION 3.3         Not Responsible for Recitals or Issuance of Guarantee...............................10

                                   ARTICLE IV
                           PREFERRED GUARANTEE TRUSTEE

SECTION 4.1         Preferred Guarantee Trustee; Eligibility............................................11
SECTION 4.2         Appointment, Removal and Resignation of Preferred
                    Guarantee Trustees..................................................................11

                                    ARTICLE V
                                    GUARANTEE

SECTION 5.1         Guarantee...........................................................................12
SECTION 5.2         Waiver of Notice and Demand.........................................................12
SECTION 5.3         Obligations Not Affected............................................................13
SECTION 5.4         Rights of Holders...................................................................13
SECTION 5.5         Guarantee of Payment................................................................14
SECTION 5.6         Subrogation.........................................................................14
SECTION 5.7         Independent Obligations.............................................................14
</TABLE>



                                      -i-


<PAGE>


<TABLE>
<CAPTION>
                                                                                                       PAGE
                                                                                                       ----
<S>                 <C>                                                                                 <C>
                                   ARTICLE VI
                    LIMITATION OF TRANSACTIONS; SUBORDINATION

SECTION 6.1         Limitation of Transactions..........................................................15
SECTION 6.2         Ranking.............................................................................15

                                   ARTICLE VII
                                   TERMINATION

SECTION 7.1         Termination.........................................................................16

                                  ARTICLE VIII
                                 INDEMNIFICATION

SECTION 8.1         Exculpation.........................................................................16
SECTION 8.2         Indemnification.....................................................................16

                                   ARTICLE IX
                                  MISCELLANEOUS

SECTION 9.1         Successors and Assigns..............................................................17
SECTION 9.2         Amendments..........................................................................17
SECTION 9.3         Notices.............................................................................18
SECTION 9.4         Benefit.............................................................................18
SECTION 9.5         Governing Law.......................................................................18
</TABLE>


                                      -ii-



<PAGE>





                             CROSS-REFERENCE TABLE*

<TABLE>
<CAPTION>
    Section of                                                                                Section of
Trust Indenture Act                                                                          Guarantee of
 1939, as amended                                                                              Agreement
-------------------                                                                          ------------
<S>                                                                                         <C>
      310(a)......................................................................................4.1(a)
      310(b..................................................................................4.1(c), 2.8
      310(c)................................................................................Inapplicable
      311(a)......................................................................................2.2(b)
      311(b)......................................................................................2.2(b)
      311(c)................................................................................Inapplicable
      312(a)......................................................................................2.2(a)
      312(b)......................................................................................2.2(b)
      313............................................................................................2.3
      314(a).........................................................................................2.4
      314(b)................................................................................Inapplicable
      314(c).........................................................................................2.5
      314(d)................................................................................Inapplicable
      314(e)...............................................................................1.1, 2.5, 3.2
      314(f)....................................................................................2.1, 3.2
      315(a)......................................................................................3.1(d)
      315(b).........................................................................................2.7
      315(c).........................................................................................3.1
      315(d)......................................................................................3.1(d)
      316(a)...............................................................................1.1, 2.6, 5.4
      316(b).........................................................................................5.3
      316(c).........................................................................................8.2
      317(a)................................................................................Inapplicable
      317(b)................................................................................Inapplicable
      318(a)......................................................................................2.1(b)
      318(b).........................................................................................2.1
      318(c)......................................................................................2.1(a)
</TABLE>

      -----------------

      *   This Cross-Reference Table does not constitute part of the Guarantee
          Agreement and shall not affect the interpretation of any of its terms
          or provisions.





<PAGE>



                    PREFERRED SECURITIES GUARANTEE AGREEMENT

     This GUARANTEE AGREEMENT (this "Preferred Securities Guarantee"), dated as
of [__________, 200__], is executed and delivered by The St. Paul Companies,
Inc., a Minnesota corporation (the "Guarantor"), and JPMorgan Chase Bank as
trustee (the "Preferred Guarantee Trustee"), for the benefit of the Holders (as
defined herein) from time to time of the Preferred Securities (as defined
herein) of St. Paul Capital Trust II, a Delaware statutory business trust (the
"Issuer").

     WHEREAS, pursuant to an Amended and Restated Declaration of Trust (the
"Declaration"), dated as of [__________, 200__], among the trustees of the
Issuer named therein, the Guarantor, 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 $[__________] aggregate liquidation preference of
its [ ]% Preferred Securities (stated liquidation amount [$ ] per preferred
security) (the "Preferred Securities") representing preferred undivided
beneficial interests in the assets of the Issuer and having the terms set forth
in the Declaration;

     WHEREAS, as incentive for the Holders to purchase the Preferred Securities,
the Guarantor desires irrevocably and unconditionally to agree, to the extent
set forth in this Preferred Securities Guarantee, to pay to the Holders 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 Preferred Securities
Guarantee for the benefit of the Holders.

                                   ARTICLE I
                         DEFINITIONS AND INTERPRETATION

SECTION 1.1  Definitions and Interpretation

     In this Preferred Securities Guarantee, unless the context otherwise
requires:

     (a) Capitalized terms used in this Preferred Securities 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 Preferred Securities Guarantee has the
same meaning throughout;

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



<PAGE>


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

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

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

         "Authorized Officer" of a Person means any Person that is authorized to
bind such Person.

         "Affiliate" has the same meaning as given to that term in Rule 405 of
the Securities Act of 1933, as amended, or any successor rule thereunder.

         "Business Day" means any day other than a day on which banking
institutions in the City of New York, New York are permitted or required by any
applicable law to close.

         "Corporate Trust Office" means the office of the Preferred Guarantee
Trustee at which the corporate trust business of the Preferred Guarantee Trustee
shall, at any particular time, be principally administered, which office at the
date of execution of this Agreement is located at 450 West 33rd Street, 15th
Floor, New York, NY 10001, Attention: Institutional Trust Services.

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

         "Debentures" means the series of subordinated debt securities of the
Guarantor designated the [ ]% Subordinated Debentures, due [ ] held by the
Institutional Trustee (as defined in the Declaration) of the Issuer.

         "Event of Default" means a default by the Guarantor on any of its
payment or other obligations under this Preferred Securities Guarantee;
provided, however, that, except with respect to a default in payment of any
Guarantee Payments, the Guarantor shall have received notice of default and
shall not have cured such default within 90 days after receipt of such notice.

         "Guarantee Payments" means the following payments or distributions,
without duplication, with respect to the Preferred Securities, to the extent not
paid or made by the Issuer: (i) any accrued and unpaid Distributions (as defined
in Annex I to the Declaration) that are required to be paid on the Preferred
Securities, to the extent the Issuer has funds available therefor, (ii) the
redemption price of [$ ] per Preferred Security, plus all accrued and unpaid
Distributions to the date of redemption (the "Redemption Price"), to the extent
the Issuer has funds available therefor, with respect to any Preferred
Securities called for redemption by the Issuer and (iii) upon a voluntary or



                                      -2-

<PAGE>



involuntary dissolution, winding-up or termination of the Issuer (other than in
connection with the distribution of Debentures to the Holders in exchange for
Preferred Securities as provided in the Declaration or the redemption of all of
the Preferred Securities upon the maturity or redemption of all of the
Debentures as provided in the Declaration) the lesser of (a) the aggregate of
the liquidation amount of [$ ] per Preferred Security and all accrued and unpaid
Distributions on the Preferred Securities to the date of payment, or (b) the
amount of assets of the Issuer remaining for distribution to Holders in
liquidation of the Issuer (in either case, the "Liquidation Distribution").

         "Holder" shall mean any holder, as registered on the books and records
of the Issuer, of any Preferred 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 or any Affiliate of the Guarantor.

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

         "Indenture" means the Subordinated Debt Indenture dated as of
[_________, 200__], among the Guarantor and JPMorgan Chase Bank, as trustee, and
any indenture supplemental thereto pursuant to which the Debentures are to be
issued to the Institutional Trustee of the Issuer.

         "Issuer" has the meaning provided in the preamble.

         "Majority in liquidation amount of the Securities" means, except as
provided by the Trust Indenture Act, a vote by Holder(s), voting separately as a
class, holding Preferred Securities representing 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
the date upon which the voting percentages are determined) of all Preferred
Securities.

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


                                      -3-



<PAGE>


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

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

          (iii) 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

          (iv) 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.

         "Preferred Guarantee Trustee" means JPMorgan Chase Bank, until a
Successor Preferred Guarantee Trustee has been appointed and has accepted such
appointment pursuant to the terms of this Preferred Securities Guarantee and
thereafter means each such Successor Preferred Guarantee Trustee.

         "Responsible Officer" means, with respect to the Preferred Guarantee
Trustee, any officer of the Preferred Guarantee Trustee with direct
responsibility for the administration of this Preferred Securities Guarantee 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.

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

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



                                      -4-


<PAGE>


                                   ARTICLE II
                               TRUST INDENTURE ACT

SECTION 2.1  Trust Indenture Act; Application

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

     (b) if and to the extent that any provision of this Preferred Securities
Guarantee 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  Lists of Holders of Securities

     (a) The Guarantor shall, or shall cause the Institutional Trustee to,
provide the Preferred Guarantee Trustee with a list of the names and addresses
of the Holders (i) on a date not later than the record date for any payment or
other distribution to the Holders hereunder or under the Declaration, and (ii)
at such other times as the Preferred Guarantee Trustee may request in writing,
within 30 days after the receipt by the Guarantor of any such request, as of a
date no more than 14 days before such list of Holders is given to the Preferred
Guarantee Trustee; provided that the Guarantor shall not be obligated to provide
such a list of holders at any time that such list would not differ from the last
such list provided by the Guarantor to the Preferred Guarantee Trustee under
this Section 2.2(a).

     The Preferred Guarantee Trustee may destroy any List of Holders previously
given to it on receipt of a new List of Holders. Unless supplemented, amended or
restated pursuant to this Section 2.2(a), the Preferred Guarantee Trustee shall
be entitled to rely exclusively on the last list of Holders provided to it by
the Guarantor or any Institutional Trustee.

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

SECTION 2.3  Reports by the Preferred Guarantee Trustee.

     Within 60 days after May 15 of each year, the Preferred 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 Preferred Guarantee Trustee shall also
comply with the requirements of Section 313(d) of the Trust Indenture Act.



                                      -5-


<PAGE>

SECTION 2.4  Periodic Reports to Preferred Guarantee Trustee.

         The Guarantor shall provide to the Preferred Guarantee Trustee, the
Securities and Exchange Commission and the Holders such documents, reports and
information as required by Section 314 of the Trust Indenture Act (if any) 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.

SECTION 2.5  Evidence of Compliance with Conditions Precedent.

         The Guarantor shall provide to the Preferred Guarantee Trustee such
evidence of compliance with any conditions precedent, if any, provided for in
this Preferred Securities Guarantee 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 Preferred Securities
may, by vote, on behalf of the Holders of all of the Preferred Securities, 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 Preferred
Securities Guarantee, but no such waiver shall extend to any subsequent or other
default or Event of Default or impair any right consequent thereon.

SECTION 2.7  Event of Default; Notice.

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

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



                                      -6-


<PAGE>



SECTION 2.8  Conflicting Interests.

         The Declaration shall be deemed to be specifically described in this
Preferred Securities Guarantee 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 PREFERRED GUARANTEE TRUSTEE

SECTION 3.1  Powers and Duties of the Preferred Guarantee Trustee.

     (a) This Preferred Securities Guarantee shall be held by the Preferred
Guarantee Trustee for the benefit of the Holders, and the Preferred Guarantee
Trustee shall not transfer its right, title and interest in this Preferred
Securities Guarantee to any Person except a Holder exercising his or her rights
pursuant to Section 5.4(b) or to a Successor Preferred Guarantee Trustee on
acceptance by such Successor Preferred Guarantee Trustee of its appointment to
act as Successor Preferred Guarantee Trustee. The right, title and interest of
the Preferred Guarantee Trustee shall automatically vest in any Successor
Preferred 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 Preferred Guarantee Trustee.

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

     (c) The Preferred Guarantee Trustee, before the occurrence of any Event of
Default and after the curing of all Events of Default that may have occurred,
shall undertake to perform only such duties as are specifically set forth in
this Preferred Securities Guarantee, and no implied covenants shall be read into
this Preferred Securities Guarantee against the Preferred Guarantee Trustee. In
case an Event of Default has occurred (that has not been cured or waived
pursuant to Section 2.6) and is actually known to a Responsible Officer of the
Preferred Guarantee Trustee, the Preferred Guarantee Trustee shall exercise such
of the rights and powers vested in it by this Preferred Securities 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 Preferred Securities Guarantee shall be construed
to relieve the Preferred 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:



                                      -7-


<PAGE>


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



               (B) in the absence of bad faith on the part of the Preferred
          Guarantee Trustee, the Preferred 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 Preferred Guarantee Trustee and substantially
          conforming to the requirements of this Preferred Securities Guarantee;
          but in the case of any such certificates or opinions that by any
          provision hereof are specifically required to be furnished to the
          Preferred Guarantee Trustee, the Preferred Guarantee Trustee shall be
          under a duty to examine the same to determine whether or not they
          substantially conform to the requirements of this Preferred Securities
          Guarantee;

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

          (iii) the Preferred 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 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
     Preferred Guarantee Trustee, or exercising any trust or power conferred
     upon the Preferred Guarantee Trustee under this Preferred Securities
     Guarantee; and


          (iv) no provision of this Preferred Securities Guarantee shall require
     the Preferred 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
     Preferred 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 Preferred Securities Guarantee or indemnity,
     reasonably satisfactory to the Preferred Guarantee Trustee, against such
     risk or liability is not reasonably assured to it.

SECTION 3.2  Certain Rights of Preferred Guarantee Trustee.

     (a) Subject to the provisions of Section 3.1:


          (i) The Preferred 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.



                                      -8-


<PAGE>



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

          (iii) Whenever, in the administration of this Preferred Securities
     Guarantee, the Preferred Guarantee Trustee shall deem it desirable that a
     matter be proved or established before taking, suffering or omitting any
     action hereunder, the Preferred 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 Officers' Certificate which,
     upon receipt of such request, shall be promptly delivered by the Guarantor.

          (iv) The Preferred Guarantee Trustee shall have no duty to see to any
     recording, filing or registration of any instrument (or any rerecording,
     refilling or re-registration thereof).

          (v) The Preferred Guarantee Trustee may consult with counsel, and the
     written 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 Preferred Guarantee Trustee shall have the right at any time to seek
     instructions concerning the administration of this Preferred Securities
     Guarantee from any court of competent jurisdiction.

          (vi) The Preferred Guarantee Trustee shall be under no obligation to
     exercise any of the rights or powers vested in it by this Preferred
     Securities Guarantee at the request or direction of any Holder, unless such
     Holder shall have provided to the Preferred Guarantee Trustee such security
     and indemnity, reasonably satisfactory to the Preferred Guarantee Trustee,
     against the costs, expenses (including attorneys' fees and expenses and the
     expenses of the Preferred 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 Preferred Guarantee Trustee; provided that, nothing
     contained in this Section 3.2(a)(vi) shall be taken to relieve the
     Preferred Guarantee Trustee, upon the occurrence of an Event of Default, of
     its obligation to exercise the rights and powers vested in it by this
     Preferred Securities Guarantee.

          (vii) The Preferred 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 Preferred Guarantee
     Trustee, in its discretion, may make such further inquiry or investigation
     into such facts or matters as it may see fit.



                                      -9-


<PAGE>


          (viii) The Preferred 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 Preferred
     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.

          (ix) Any action taken by the Preferred Guarantee Trustee or its agents
     hereunder shall bind the Holders of the Preferred Securities, and the
     signature of the Preferred 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 Preferred Guarantee
     Trustee to so act or as to its compliance with any of the terms and
     provisions of this Preferred Securities Guarantee, both of which shall be
     conclusively evidenced by the Preferred Guarantee Trustee's or its agent's
     taking such action.

          (x) Whenever in the administration of this Preferred Securities
     Guarantee the Preferred Guarantee Trustee shall deem it desirable to
     receive instructions with respect to enforcing any remedy or right or
     taking any other action hereunder, the Preferred Guarantee Trustee (i) may
     request instructions from the Holders of a Majority in liquidation amount
     of the Preferred Securities, (ii) may refrain from enforcing such remedy or
     right or taking such other action until such instructions are received, and
     (iii) shall be protected in conclusively relying on or acting in accordance
     with such instructions.

     (b) No provision of this Preferred Securities Guarantee shall be deemed to
impose any duty or obligation on the Preferred 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
Preferred 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 Preferred Guarantee Trustee shall be construed to be a duty.

     (c) The Trustee shall not be charged with knowledge of any Event of Default
with respect to the Securities unless (1) a Responsible Officer of the Trustee
shall have actual knowledge of such Event of Default or (2) written notice of
such Event of Default shall have been given to the Trustee by the Company or by
any Holder of Securities.


SECTION 3.3  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 Preferred Guarantee Trustee does not assume
any responsibility for their correctness. The Preferred Guarantee Trustee makes
no representation as to the validity or sufficiency of this Preferred Securities
Guarantee.



                                      -10-


<PAGE>



                                   ARTICLE IV
                           PREFERRED GUARANTEE TRUSTEE

SECTION 4.1  Preferred Guarantee Trustee; Eligibility.

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

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

          (ii) be a corporation 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 a corporation or Person permitted by the
     Securities and Exchange Commission to act as an institutional trustee under
     the Trust Indenture Act, 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 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 4. 1(a)(ii), 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 Preferred Guarantee Trustee shall cease to be
eligible to so act under Section 4.1(a), the Preferred Guarantee Trustee shall
immediately resign in the manner and with the effect set out in Section 4.2(c).

     (c) If the Preferred Guarantee Trustee has or shall acquire any
"conflicting interest" within the meaning of Section 310(b) of the Trust
Indenture Act, the Preferred 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 Preferred Guarantee
            Trustees.

     (a) Subject to Section 4.2(b), the Preferred Guarantee Trustee may be
appointed or removed without cause at any time by the Guarantor.

     (b) The Preferred Guarantee Trustee shall not be removed in accordance with
Section 4.2(a) until a Successor Preferred Guarantee Trustee has been appointed
and has accepted such appointment by written instrument executed by such
Successor Preferred Guarantee Trustee and delivered to the Guarantor.

     (c) The Preferred Guarantee Trustee appointed to office shall hold office
until a Successor Preferred Guarantee Trustee shall have been appointed or until
its removal or resignation. The Preferred Guarantee Trustee may resign from
office by an instrument in writing executed by the Preferred Guarantee Trustee
and delivered to the Guarantor, which resignation shall not take effect until a



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Successor Preferred Guarantee Trustee has been appointed and has accepted such
appointment by instrument in writing executed by such Successor Preferred
Guarantee Trustee and delivered to the Guarantor and the resigning Preferred
Guarantee Trustee, whereupon the resigning Preferred Guarantee Trustee shall be
released and discharged of the trusts and other duties imposed on such trustee
in connection herewith.

     (d) If no Successor Preferred 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, the resigning
Preferred Guarantee Trustee may petition any court of competent jurisdiction for
appointment of a Successor Preferred Guarantee Trustee. Such court may
thereupon, after prescribing such notice, if any, as it may deem proper, appoint
a Successor Preferred Guarantee Trustee.

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

     (f) Upon termination of this Preferred Securities Guarantee or removal or
resignation of the Preferred Guarantee Trustee pursuant to this Section 4.2, the
Guarantor shall pay to the Preferred Guarantee Trustee all amounts accrued and
owing to such Preferred Guarantee Trustee to the date of such termination,
removal or resignation.

                                    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 pursuant to the Declaration or by the
Guarantor pursuant to the Indenture), as and when due, regardless of any
defense, 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.

SECTION 5.2  Waiver of Notice and Demand.

         The Guarantor hereby waives notice of acceptance of this Preferred
Securities 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.



                                      -12-


<PAGE>


SECTION 5.3  Obligations Not Affected.

     The obligations, covenants, agreements and duties of the Guarantor under
this Preferred Securities 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 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, 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 (other than
     an extension of time for payment of Distributions, Redemption Price,
     Liquidation Distribution or other sum payable that results from the
     extension of any interest payment period on the Debentures as 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 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) to the extent permitted by law, 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
consent of, the Guarantor with respect to the happening of any of the foregoing.


SECTION 5.4  Rights of Holders.

     (a) 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 Preferred Guarantee Trustee in
respect of this Preferred Securities Guarantee or exercising any trust or power
conferred upon the Preferred Guarantee Trustee under this Preferred Securities
Guarantee.



                                      -13-


<PAGE>


     (b) If the Preferred Guarantee Trustee fails to enforce its rights under
this Preferred Securities Guarantee, any Holder may directly institute a legal
proceeding against the Guarantor to enforce the Preferred Guarantee Trustee's
rights under this Preferred Securities Guarantee, without first instituting a
legal proceeding against the Issuer, the Preferred Guarantee Trustee or any
other Person or entity.

     (c) A Holder may also directly institute a legal proceeding against the
Guarantor to enforce such Holder's right to receive payment under this Preferred
Securities Guarantee without first (i) directing the Preferred Guarantee Trustee
to enforce the terms of this Preferred Securities Guarantee or (ii) instituting
a legal proceeding directly against the Issuer or any other Person or entity.

SECTION 5.5  Guarantee of Payment.

         This Preferred Securities Guarantee creates a guarantee of payment and
not of collection (i.e., a Covered Person may institute a legal proceeding
directly against the Guarantor to enforce its rights under this Preferred
Securities Guarantee without first instituting a legal proceeding against any
other person or entity). This Preferred Securities Guarantee will not be
discharged except by payment of the Guarantee Payments in full to the extent not
previously paid or upon Distribution to the Holders of the corresponding series
of Debentures as provided in the Declaration.

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 such Holders by the
Guarantor under this Preferred Securities Guarantee; provided, however, that the
Guarantor shall not (except to the extent required by mandatory 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 Preferred Securities Guarantee, if, at the time
of any such payment, any amounts are due and unpaid under this Preferred
Securities 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.

SECTION 5.7  Independent Obligations.

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



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<PAGE>


                                   ARTICLE VI
                    LIMITATION OF TRANSACTIONS; SUBORDINATION

SECTION 6.1  Limitation of Transactions.

         So long as any Preferred Securities remain outstanding, if there shall
have occurred any event that would constitute an Event of Default hereunder or
an Event of Default under the Declaration, then (a) the Guarantor shall not
declare or pay any dividend on, make any distributions with respect to, or
redeem, purchase, acquire or make a liquidation payment with respect to, any of
its capital stock or make any guarantee payment with respect thereto (other than
(i) repurchases, redemptions or other acquisitions of shares of capital stock of
the Guarantor in connection with any employment contract, benefit plan or other
similar arrangement with or for the benefit of employees, officers, directors or
consultants, (ii) as a result of a reclassification of the Guarantor's capital
stock, or the exchange or conversion of any class or series of the Guarantor's
capital stock for any other class or series of the Guarantor's capital stock,
(iii) 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 or (iv) distribution of rights under
any shareholders' rights plan adopted by the Company) and (b) the Guarantor
shall not make any payment of interest on, or principal of (or premium, if any,
on), or repay, repurchase or redeem, any debt securities issued by the Guarantor
which rank pari passu with or junior to the Debentures and the Guarantor shall
not make any guarantee payments with respect thereto (other than pursuant to
this Preferred Security Guarantee); provided, however, the Guarantor may declare
and pay a stock dividend where the dividend stock is the same stock as that on
which the dividend is being paid.

SECTION 6.2  Ranking.

         This Preferred Securities Guarantee will constitute an unsecured
obligation of the Guarantor and will rank (i) subordinate and junior in right of
payment to all Senior Indebtedness (as defined in the Indenture) of the
Guarantor, (ii) pari passu with (A) the most senior preferred or preference
stock now or hereafter issued by the Guarantor, (B) any guarantee now or
hereafter entered into by the Guarantor in respect of any preferred or
preference stock or preferred trust security of any Affiliate of the Guarantor
and (C) those debt securities previously issued and from time to time issued and
outstanding as described in clause (D) of the proviso to the definition of
Senior Indebtedness set forth in the Indenture and (iii) senior to the
Guarantor's common stock.


                                      -15-


<PAGE>



                                   ARTICLE VII
                                   TERMINATION

SECTION 7.1  Termination.

         This Preferred Securities Guarantee shall terminate upon (i) full
payment of the Redemption Price of all Preferred Securities, (ii) the
distribution of the Debentures to the Holders of all of the Preferred Securities
or (iii) full payment of the amounts payable in accordance with the Declaration
upon liquidation of the Issuer. Notwithstanding the foregoing, this Preferred
Securities Guarantee 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
under the Preferred Securities or under this Preferred Securities Guarantee.

                                  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 Preferred Securities
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
Preferred Securities 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 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.

     (a) To the fullest extent permitted by applicable law, the Guarantor shall
indemnify and hold harmless each Indemnified Person from and against any loss,
damage or claim incurred by such Indemnified Person 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 such Indemnified Person
reasonably believed to be within the scope of authority conferred on such
Indemnified Person by this Guarantee Agreement, except that no Indemnified
Person shall be entitled to be indemnified in respect of any loss, damage or
claim incurred by such Indemnified Person by reason of such Indemnified Person's
negligence or willful misconduct with respect to such acts or omissions.



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<PAGE>



     (b) To the fullest extent permitted by applicable law, reasonable expenses
(including legal fees) incurred by an Indemnified Person in defending any claim,
demand, action, suit or proceeding shall, from time to time, be advanced by the
Guarantor prior to the final disposition of such claim, demand, action, suit or
proceeding upon receipt by the Guarantor of an undertaking by or on behalf of
the Indemnified Person to repay such amount if it shall be determined that the
Indemnified Person is not entitled to be indemnified as authorized in Section
8.2(a).

     (c) The obligation to indemnify as set forth in this Section 8.2 shall
survive the termination of this Preferred Securities Guarantee.

     (d) The Guarantor agrees to pay to the Preferred Guarantee Trustee
compensation for its services as shall be mutually agreed upon by the Guarantor
and the Preferred Guarantee Trustee. The Guarantor shall reimburse the Preferred
Guarantee Trustee upon request for all reasonable out-of-pocket expenses
incurred by it, including the reasonable compensation and expenses of the
Preferred Guarantee Trustee's agents and counsel, except any expense as may be
attributable to the negligence of the Preferred Guarantee Trustee.

                                   ARTICLE IX
                                 MISCELLANEOUS

SECTION 9.1  Successors and Assigns.

         All guarantees and agreements contained in this Preferred Securities
Guarantee shall bind the successors, assigns, receivers, trustees and
representatives of the Guarantor and shall inure to the benefit of the Holders
of the Preferred Securities then outstanding.

SECTION 9.2  Amendments.

         Except with respect to any changes that do not adversely affect the
rights of Holders (in which case no consent of Holders will be required), this
Preferred Securities Guarantee may be amended only with the prior approval of
the Holders of not less than a Majority in aggregate liquidation amount
(including the stated amount that would be paid on redemption, liquidation or
otherwise, plus accrued and unpaid Distributions to the date upon which the
voting percentages are determined) of all the outstanding Preferred Securities.
The provisions of Section 12.2 of the Declaration with respect to meetings of
Holders apply to the giving of such approval. This Preferred Securities
Guarantee may not be amended, and no amendment hereof that affects the Preferred
Guarantee Trustee's rights, duties or immunities hereunder or otherwise shall be
effective, unless such amendment is executed by the Preferred Guarantee Trustee
(which shall have no obligation to execute any such amendment, but may do so in
its sole discretion).


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<PAGE>



SECTION 9.3  Notices.

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

     (a) If given to the Preferred Guarantee Trustee, at the Preferred Guarantee
Trustee's mailing address set forth below (or such other address as the
Preferred Guarantee Trustee may give notice of to the Holders): JPMorgan Chase
Bank, 450 West 33rd Street, 15th Floor, New York, NY 10001, Attention:
Institutional Trust Services.

     (b) 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)
St. Paul Companies, Inc., 385 Washington Street, St. Paul, Minnesota 55102,
Attention: Bruce A. Backberg, with a copy to the attention of the Treasurer at
such address.

     (c) If given to any Holder, 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 9.4  Benefit.

         This Preferred Securities Guarantee is solely for the benefit of the
Holders of the Preferred Securities and, subject to Section 3.1(a), is not
separately transferable from the Preferred Securities.

SECTION 9.5  Governing Law.

         THIS PREFERRED SECURITIES GUARANTEE SHALL BE GOVERNED BY, AND CONSTRUED
AND INTERPRETED IN ACCORDANCE WITH, THE LAWS OF THE STATE OF NEW YORK.



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<PAGE>



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


                                       THE ST. PAUL COMNPANIES,INC.,
                                       as Guarantor


                                       By:
                                           -------------------------------------
                                           Name:  Bruce A. Backberg
                                           Title: Senior Vice President





                                       JPMORGAN CHASE BANK,
                                       as Preferred Guarantee Trustee


                                       By:
                                           -------------------------------------
                                           Name:  Joanne Adamis
                                           Title: Authorized Officer





                                      -19-