ST PAUL COMPANIES INC /MN/
424B4, 1995-05-10
FIRE, MARINE & CASUALTY INSURANCE
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<PAGE>
                         3,600,000 PREFERRED SECURITIES

                         [LOGO] ST. PAUL CAPITAL L.L.C.
               6% CONVERTIBLE MONTHLY INCOME PREFERRED SECURITIES
                            (CONVERTIBLE MIPS-SM-*)
                   (LIQUIDATION PREFERENCE $50 PER SECURITY)
       GUARANTEED TO THE EXTENT SET FORTH HEREIN BY, AND CONVERTIBLE INTO
                                COMMON STOCK OF,
                          THE ST. PAUL COMPANIES, INC.
                                   ---------

    The  6%  convertible  monthly income  preferred  securities  (the "Preferred
Securities") representing preferred limited liability company interests  offered
hereby  are being  issued by  St. Paul  Capital L.L.C.  ("St. Paul  Capital"), a
Delaware limited liability company. All of the common limited liability  company
interests  of St. Paul  Capital (the "Common Securities")  are owned directly or
indirectly by The St.  Paul Companies, Inc., a  Minnesota corporation ("The  St.
Paul"  or the "Company"). St. Paul Capital  was formed solely for the purpose of
issuing securities and investing the proceeds from the issuance thereof in  debt
securities  of The  St. Paul.  The proceeds from  the offering  of the Preferred
Securities will be used by St. Paul Capital to purchase from The St. Paul its 6%
Convertible Subordinated  Debentures  due 2025  (the  "Convertible  Subordinated
Debentures") having the terms described herein.

    Holders  of the Preferred Securities will  be entitled to receive cumulative
cash distributions  from  St. Paul  Capital  at an  annual  rate of  6%  of  the
liquidation  preference of $50 per Preferred Security, accruing from the date of
original issuance  and  payable monthly  in  arrears on  the  last day  of  each
calendar  month  of  each  year,  commencing  May  31,  1995  ("dividends"). See
"Description of Securities  Offered -- Preferred  Securities -- Dividends".  The
preferred  limited  liability  company interests  represented  by  the Preferred
Securities will have a preference with respect to cash distributions and amounts
payable on liquidation over the  Common Securities owned directly or  indirectly
by The St. Paul.
                                                        (CONTINUED ON NEXT PAGE)
                               ------------------

    SEE  "INVESTMENT CONSIDERATIONS" FOR A  DISCUSSION OF CERTAIN MATERIAL RISKS
TO BE CONSIDERED IN CONNECTION WITH  AN INVESTMENT IN THE PREFERRED  SECURITIES,
INCLUDING  THE PERIOD AND  CIRCUMSTANCES DURING AND UNDER  WHICH PAYMENTS ON THE
PREFERRED SECURITIES AND THE CONVERTIBLE SUBORDINATED DEBENTURES MAY BE DEFERRED
AND THE RELATED FEDERAL INCOME TAX CONSEQUENCES.
                                ----------------

THESE SECURITIES HAVE NOT BEEN APPROVED  OR DISAPPROVED BY THE SECURITIES  AND
  EXCHANGE  COMMISSION  OR  ANY  STATE SECURITIES  COMMISSION  NOR  HAS THE
     SECURITIES AND EXCHANGE COMMISSION OR ANY STATE SECURITIES COMMISSION
       PASSED  UPON  THE  ACCURACY   OR  ADEQUACY  OF  THIS   PROSPECTUS.
          ANY  REPRESENTATION TO  THE CONTRARY IS  A CRIMINAL OFFENSE.
                                 --------------

<TABLE>
<CAPTION>
                                                                                                     PROCEEDS TO
                                                     INITIAL PUBLIC          UNDERWRITING         ST. PAUL CAPITAL
                                                     OFFERING PRICE         COMMISSION (1)             (2)(3)
                                                  ---------------------  ---------------------  ---------------------
<S>                                               <C>                    <C>                    <C>
Per Preferred Security..........................         $ 50.00                  (2)                  $ 50.00
Total(4)........................................      $180,000,000                (2)               $180,000,000
<FN>
- --------------------------
(1)  St. Paul Capital and The St. Paul have agreed to indemnify the Underwriters
     against certain liabilities, including liabilities under the Securities Act
     of 1933, as amended. See "Underwriting".
(2)  In view  of  the fact  that  the proceeds  of  the sale  of  the  Preferred
     Securities  will  ultimately  be  used  by  St.  Paul  Capital  to purchase
     convertible subordinated  debentures  of  The St.  Paul,  the  Underwriting
     Agreement  provides  that The  St. Paul  will pay  to the  Underwriters, as
     compensation ("Underwriters' Compensation"), $1.125 per Preferred  Security
     (or $4,050,000 in the aggregate). See "Underwriting".
(3)  Expenses of the offering which are payable by The St. Paul are estimated to
     be $410,000.
(4)  St.  Paul Capital and The St. Paul  have granted the Underwriters an option
     for 30 days to purchase up to an additional 540,000 Preferred Securities at
     the initial public offering  price per Preferred  Security solely to  cover
     over-allotments.   The  St.   Paul  will   pay  to   the  Underwriters,  as
     Underwriters'  Compensation,  $1.125   per  Preferred  Security   purchased
     pursuant  to this option.  If such option  is exercised in  full, the total
     initial public offering price, underwriting commission and proceeds to  St.
     Paul   Capital   will  be   $207,000,000,  $4,657,500,   and  $207,000,000,
     respectively. See "Underwriting".
</TABLE>

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

    The Preferred  Securities  offered  hereby  are  offered  severally  by  the
Underwriters, as specified herein, subject to receipt and acceptance by them and
subject  to their right to reject any order  in whole or in part. It is expected
that delivery of the Preferred Securities  will be made only in book-entry  form
through the facilities of The Depository Trust Company on or about May 16, 1995.
- --------------------------
* MIPS is a service mark of Goldman, Sachs & Co.

GOLDMAN, SACHS & CO.                                 J.P. MORGAN SECURITIES INC.
                                   ---------

                  The date of this Prospectus is May 9, 1995.
<PAGE>
(CONTINUED FROM PREVIOUS PAGE)

    In  the  event  of the  liquidation  of  St. Paul  Capital,  holders  of the
Preferred Securities will be entitled to  receive for each Preferred Security  a
liquidation  preference of $50 plus accumulated and unpaid dividends to the date
of payment,  subject  to certain  limitations.  See "Description  of  Securities
Offered -- Preferred Securities -- Liquidation Rights".

    Each Preferred Security is convertible in the manner described herein at the
option  of the holder, at  any time prior to  the Conversion Expiration Date (as
hereinafter defined), into shares of Common Stock, without par value, of The St.
Paul ("St. Paul Common Stock") at the  rate of 0.8475 shares of St. Paul  Common
Stock  for each Preferred Security (equivalent to  a conversion price of $59 per
share of St. Paul Common Stock), subject to adjustment in certain circumstances.
Whenever The St. Paul issues shares of St. Paul Common Stock upon conversion  of
Preferred  Securities, The St. Paul will issue,  together with each share of St.
Paul Common Stock, under the circumstances described herein, one Stock  Purchase
Right  (each,  a "Stock  Purchase Right")  entitling  the holder  thereof, under
certain circumstances,  to  purchase shares  of  Series A  Junior  Participating
Preferred  Stock,  without  par value,  of  The  St. Paul.  See  "Description of
Securities  Offered   --  Preferred   Securities  --   Conversion  Rights"   and
"Description  of St. Paul  Capital Stock". The  last reported sale  price of St.
Paul Common Stock, which is listed under the symbol "SPC" on the New York  Stock
Exchange  ("NYSE"), on May 9, 1995 was $48  3/8 per share. See "Market Prices of
St. Paul Common Stock". On and after May 31, 1999, St. Paul Capital may, at  its
option,  cause the conversion  rights of holders of  the Preferred Securities to
expire. St. Paul Capital may  exercise this option only  if for 20 trading  days
within any period of 30 consecutive trading days, including the last trading day
of  such period, the Current Market Price (as defined herein) of St. Paul Common
Stock exceeds 120% of the conversion price of the Preferred Securities,  subject
to  adjustment in  certain circumstances.  In order  to exercise  its conversion
expiration option, St. Paul  Capital must issue a  press release announcing  the
date  upon  which  conversion  rights will  expire  (the  "Conversion Expiration
Date"), prior to  the opening  of business  on the  second trading  day after  a
period  in which the condition in the preceding sentence has been met, but in no
event prior to May 31, 1999. The Conversion Expiration Date shall be a date  not
less  than 30 and not more than 60  days following the date of the press release
described above. See "Description of Securities Offered -- Preferred  Securities
- -- Conversion Rights".

    The  Preferred  Securities  are  also  subject  to  exchange  in  the manner
described herein,  in  whole  but  not in  part,  into  depositary  shares  (the
"Depositary  Shares"),  each representing  ownership of  1/100th  of a  share of
Series C Cumulative Convertible Preferred Stock, without par value  (liquidation
preference  $5000 per share),  of The St.  Paul ("St. Paul  Series C Convertible
Preferred Stock"), deposited with the Depositary (as defined herein) upon a vote
of the holders  of a  majority of the  aggregate liquidation  preference of  all
outstanding  Preferred Securities following the  failure of holders of Preferred
Securities to receive dividends in full for 15 consecutive months (including any
such failure caused  by the  deferral of  interest payments  on the  Convertible
Subordinated  Debentures). Each Depositary Share will entitle the holder thereof
to all proportional rights and preferences of the St. Paul Series C  Convertible
Preferred  Stock (including dividend, voting,  conversion and liquidation rights
and preferences). The St.  Paul Series C Convertible  Preferred Stock will  have
dividend and conversion features substantially similar to those of the Preferred
Securities  (adjusted  proportionately per  Depositary  Share) but  will  not be
subject to  mandatory  redemption. See  "Description  of Securities  Offered  --
Preferred   Securities  --   Optional  Exchange  for   Depositary  Shares",  "--
Description  of  St.  Paul  Series  C  Convertible  Preferred  Stock"  and   "--
Description of Depositary Shares".

    In  the event that, at  any time after the  Conversion Expiration Date, less
than  5%  of  the  Preferred  Securities  remain  outstanding,  such   Preferred
Securities  shall be redeemable at the option  of St. Paul Capital, in whole but
not in part, at a redemption price equal to the liquidation preference for  such
Preferred  Securities  plus accumulated  and  unpaid dividends  (whether  or not
earned or declared). The  Preferred Securities have  no maturity date,  although
they are subject to mandatory redemption upon the

                                       2
<PAGE>
repayment  at  maturity  or  as  a result  of  acceleration  of  the Convertible
Subordinated Debentures and St.  Paul Capital is subject  to dissolution in  the
event  of  a  Special  Event  (as  defined  herein),  as  described  below.  See
"Description of Securities Offered -- Preferred Securities -- Redemption".

    Under certain circumstances following the occurrence of a Special Event, The
St. Paul may cause St.  Paul Capital to be  dissolved and cause the  Convertible
Subordinated  Debentures  to  be distributed  to  the holders  of  the Preferred
Securities. If Convertible Subordinated Debentures  are so distributed, The  St.
Paul  will use its best efforts to have such Convertible Subordinated Debentures
listed on the same exchange on  which the Preferred Securities are then  listed.
See  "Description of Securities Offered -- Preferred Securities -- Special Event
Distribution" and "-- Description of the Convertible Subordinated Debentures".

    The  St.  Paul  will  irrevocably   and  unconditionally  guarantee,  on   a
subordinated  basis and to the extent set forth herein, the payment of dividends
by St. Paul Capital on the Preferred  Securities (but only if and to the  extent
declared  from  funds  of  St. Paul  Capital  legally  available  therefor), the
redemption price (including all accumulated  and unpaid dividends) payable  with
respect  to the Preferred Securities and payments on liquidation with respect to
the Preferred Securities  (but only  to the  extent of  the assets  of St.  Paul
Capital  available for distribution to holders of the Preferred Securities) (the
"Guarantee"). The Guarantee will be unsecured, will be subordinate to all  other
liabilities  of The St. Paul  and will rank PARI PASSU  (I.E., on a parity) with
the most senior preferred or preference stock now or hereafter issued by The St.
Paul. Given  such  subordination, if  The  St. Paul  is  unable to  make  timely
payments  on  the Convertible  Subordinated Debentures,  there is  a substantial
likelihood that  it  would  also  be  unable to  make  timely  payments  on  the
Guarantee.  See  "Description  of  Securities  Offered  --  Description  of  the
Guarantee".

    St. Paul Capital's ability to pay amounts due on the Preferred Securities is
solely dependent upon The St. Paul's ability to make payments on the Convertible
Subordinated  Debentures.   Interest   payment  periods   on   the   Convertible
Subordinated  Debentures are monthly but may be  extended by The St. Paul for up
to 60  months  (a "deferral  of  interest  payments"), in  which  event  monthly
dividend  payments  on the  Preferred Securities  by St.  Paul Capital  would be
deferred (but would continue to compound monthly). Prior to the end of any  such
deferral of interest payments, The St. Paul may further defer interest payments,
provided  that all such deferrals may not exceed 60 months in the aggregate, and
provided further that no  such deferral may extend  the stated maturity date  of
the Convertible Subordinated Debentures. After The St. Paul has paid all accrued
and  unpaid  interest  (including  compound interest)  following  a  deferral of
interest payments, it  may again defer  interest payments for  up to 60  months,
subject  to the  preceding sentence.  At the  end of  such deferral  of interest
payments, The  St. Paul  is required  to  pay all  accrued and  unpaid  interest
(including  compound interest) and upon such repayment St. Paul Capital would be
able to pay  all accumulated and  unpaid dividends on  the Preferred  Securities
(including  Additional Dividends, as  defined herein). If The  St. Paul does not
make interest  payments on  the Convertible  Subordinated Debentures,  St.  Paul
Capital  would  not  be  able  to declare  or  pay  dividends  on  the Preferred
Securities. The Guarantee is a full and unconditional guarantee from the time of
its issuance, but does not  apply to any payment  of dividends unless and  until
such  dividends are declared. The failure of holders of the Preferred Securities
to receive  dividends in  full for  15 consecutive  months (including  any  such
failure   caused  by  a  deferral  of   interest  payments  on  the  Convertible
Subordinated Debentures)  would trigger  the  right of  such holders  to  obtain
Depositary  Shares representing St. Paul Series C Convertible Preferred Stock in
the manner described herein. See "Description of Securities Offered -- Preferred
Securities -- Dividends -- Description of the Guarantee" and "-- Description  of
the Convertible Subordinated Debentures".

    The  Convertible Subordinated Debentures are subordinate in right of payment
to all Senior Indebtedness (as defined under "Description of Securities  Offered
- --  Description of the Convertible Subordinated Debentures -- Subordination") of
The St. Paul. As of March 31, 1995, The St. Paul had approximately $628  million
of  indebtedness constituting Senior  Indebtedness and no  indebtedness or other
obligations  that  would   rank  equally  with   the  Convertible   Subordinated
Debentures.  The Convertible Subordinated  Debentures will not  be guaranteed by
St. Paul Capital Holdings, Inc.

                                       3
<PAGE>
    The Preferred Securities have been approved for listing on the NYSE, subject
to notice of issuance, under the symbol "SPC pfM".

    The Preferred  Securities will  be represented  by a  global certificate  or
certificates  registered in the name of  The Depository Trust Company ("DTC") or
its nominee. Beneficial interests in the Preferred Securities will be shown  on,
and  transfers  thereof will  be effected  only  through, records  maintained by
participants in  DTC.  Except  as  described  herein,  Preferred  Securities  in
certificated  form will not be issued in  exchange for the global certificate or
certificates. See "Description of Securities Offered -- Preferred Securities  --
Book-Entry-Only Issuance -- The Depository Trust Company".

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

    FOR NORTH CAROLINA RESIDENTS: THE COMMISSIONER OF INSURANCE FOR THE STATE OF
NORTH  CAROLINA  HAS  NOT APPROVED  OR  DISAPPROVED  THIS OFFERING  NOR  HAS THE
COMMISSIONER PASSED UPON THE ACCURACY OR ADEQUACY OF THIS PROSPECTUS.

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

    IN CONNECTION WITH THIS OFFERING, THE UNDERWRITERS MAY OVER-ALLOT OR  EFFECT
TRANSACTIONS  WHICH  STABILIZE OR  MAINTAIN THE  MARKET  PRICE OF  THE PREFERRED
SECURITIES OFFERED HEREBY AND ST. PAUL COMMON STOCK AT LEVELS ABOVE THOSE  WHICH
MIGHT OTHERWISE PREVAIL IN THE OPEN MARKET. SUCH TRANSACTIONS MAY BE EFFECTED ON
THE  NYSE, IN  THE OVER-THE-COUNTER  MARKET OR  OTHERWISE. SUCH  STABILIZING, IF
COMMENCED, MAY BE DISCONTINUED AT ANY TIME.

                                       4
<PAGE>
                             AVAILABLE INFORMATION

    The St. Paul is subject to the informational requirements of the  Securities
Exchange  Act  of  1934, as  amended  (the  "Exchange Act"),  and  in accordance
therewith files  reports,  proxy  statements  and  other  information  with  the
Securities and Exchange Commission (the "Commission"). Reports, proxy statements
and  other information filed by The St. Paul  may be inspected and copied at the
public reference facilities maintained by the Commission in Room 1024, 450 Fifth
Street, N.W., Washington, D.C. 20549,  and at the Commission's Regional  Offices
located  at Seven World  Trade Center, 7th  Floor, New York,  New York 10048 and
Citicorp Center, 500 West Madison  Street, Suite 1400, Chicago, Illinois  60661.
Copies  of such materials may  be obtained upon written  request from the Public
Reference Section of the Commission at 450 Fifth Street, N.W., Washington,  D.C.
20549, at prescribed rates. In addition, such material may also be inspected and
copied at the offices of the New York Stock Exchange, Inc., 20 Broad Street, New
York, New York 10005.

    The  St.  Paul  and  St.  Paul Capital  have  filed  with  the  Commission a
registration statement on Form S-3  (together with all amendments and  exhibits,
the "Registration Statement") under the Securities Act of 1933, as amended. This
Prospectus does not contain all of the information set forth in the Registration
Statement,  certain parts of which are omitted  in accordance with the rules and
regulations of the Commission. For further information, reference is hereby made
to the Registration Statement.

    No separate  financial statements  of St.  Paul Capital  have been  included
herein.  The St. Paul and  St. Paul Capital do  not consider that such financial
statements would be  material to  holders of  Preferred Securities  as St.  Paul
Capital  is a newly  organized special purpose entity,  has no operating history
and no independent operations  and is not  engaged in, and  does not propose  to
engage  in,  any activity  other  than as  described  under "St.  Paul Capital".
Further, The St. Paul believes that financial statements of St. Paul Capital are
not material  to  the holders  of  the  Preferred Securities  as  the  Preferred
Securities  have been structured to  provide a guarantee by  The St. Paul of the
Preferred Securities  such that  the holders  of the  Preferred Securities  with
respect  to the payment  of dividends and  amounts upon liquidation, dissolution
and winding-up are at least in the same position VIS-A-VIS the assets of The St.
Paul as a  preferred stockholder of  The St.  Paul. See "St.  Paul Capital"  and
"Description  of Securities Offered -- Preferred Securities", "-- Description of
the Guarantee" and "-- Description of the Convertible Subordinated  Debentures".
The  St.  Paul  beneficially  owns  directly or  indirectly  all  of  the Common
Securities  of  St.  Paul  Capital.  The  preferred  limited  liability  company
interests  represented by the  Preferred Securities will  have a preference with
respect to cash distributions and amounts payable on liquidation over the Common
Securities owned directly or indirectly by The St. Paul.

    Each holder of Preferred Securities will be furnished annually with The  St.
Paul's  Annual Report to Shareholders, containing audited consolidated financial
statements of The St. Paul, as soon as such report is available after the end of
The St. Paul's fiscal year.

                                       5
<PAGE>
                INCORPORATION OF CERTAIN DOCUMENTS BY REFERENCE

    The following documents filed with  the Commission pursuant to the  Exchange
Act are incorporated herein by reference:

        1.    The St.  Paul's  Annual Report  on Form  10-K  for the  year ended
    December 31, 1994.

        2.  The St. Paul's Current Report on Form 8-K, dated January 24, 1995.

        3.  The description  of the Preferred Securities  contained in St.  Paul
    Capital's Registration Statement on Form 8-A, dated April 21, 1995.

        4.   The descriptions  of the St.  Paul Common Stock  and Stock Purchase
    Rights contained in The St. Paul's Registration Statements on Form 8-A, each
    dated October 17, 1991.

    All documents filed by The St. Paul with the Commission pursuant to  Section
13(a),  13(c), 14 or 15(d) of the Exchange Act subsequent to the date hereof and
prior to the termination of the offering described herein shall hereby be deemed
to be incorporated by  reference into this  Prospectus and to  be a part  hereof
from  the date of filing of such documents. Any statement contained herein or in
a document incorporated or deemed to  be incorporated by reference herein  shall
be  deemed to be modified  or superseded for purposes  of this Prospectus to the
extent that a  statement contained  herein or  in any  other subsequently  filed
document  which also  is or  is deemed  to be  incorporated by  reference herein
modifies or  supersedes  such  statement.  Any such  statement  so  modified  or
superseded  shall  not  be  deemed,  except as  so  modified  or  superseded, to
constitute a part of this Prospectus.

    The St. Paul will provide  without charge to each person  to whom a copy  of
this  Prospectus is delivered, on the written  or oral request of such person, a
copy of any or all of the  documents incorporated herein by reference into  this
Prospectus,  other than exhibits  to such information  (unless such exhibits are
specifically incorporated by  reference in such  documents). Requests should  be
directed  to  The St.  Paul Companies,  Inc., 385  Washington Street,  St. Paul,
Minnesota 55102,  Attention: Bruce  A. Backberg,  Vice President  and  Corporate
Secretary, telephone (612) 221-7911.

                                       6
<PAGE>
                               PROSPECTUS SUMMARY

    THE  FOLLOWING SUMMARY  IS QUALIFIED  IN ITS  ENTIRETY BY  THE MORE DETAILED
INFORMATION AND CONSOLIDATED FINANCIAL STATEMENTS (INCLUDING THE NOTES  THERETO)
APPEARING  ELSEWHERE  OR INCORPORATED  BY REFERENCE  IN THIS  PROSPECTUS. UNLESS
OTHERWISE SPECIFIED, REFERENCES HEREIN TO THE "COMPANY" OR "THE ST. PAUL"  REFER
TO  THE ST. PAUL COMPANIES, INC.  AND ITS CONSOLIDATED SUBSIDIARIES. PROSPECTIVE
INVESTORS SHOULD CAREFULLY READ THE ENTIRE PROSPECTUS.

                          THE ST. PAUL COMPANIES, INC.

    The St.  Paul  is a  management  company principally  engaged,  through  its
subsidiaries,   in   three  industry   segments:   property-liability  insurance
underwriting (primarily through its wholly-owned  subsidiary, St. Paul Fire  and
Marine  Insurance Company), insurance brokerage (primarily through its brokerage
subsidiary, Minet)  and investment  banking-asset  management (through  its  77%
stake  in  The John  Nuveen  Company). As  a  management company,  The  St. Paul
oversees the  operations of  its subsidiaries  and provides  them with  capital,
management  and administrative services. According  to "Fortune" magazine's most
recent rankings, in terms  of total assets,  The St. Paul  was the 25th  largest
diversified  financial company  in the  United States  at December  31, 1993. At
March 23, 1995, The St. Paul and its subsidiaries employed approximately  12,900
persons.

    The  St. Paul's primary business  is insurance underwriting, which accounted
for 88% of  consolidated revenues  in 1994. Insurance  brokerage and  investment
banking-asset  management  operations accounted  for 7%  and 5%  of consolidated
revenues, respectively, in 1994.

    The Company's  principal executive  offices are  located at  385  Washington
Street, St. Paul, Minnesota 55102, and its telephone number is (612) 221-7911.

                            ST. PAUL CAPITAL L.L.C.

    St.  Paul Capital is  a limited liability  company formed under  the laws of
Delaware and  is  managed  by The  St.  Paul  and The  St.  Paul's  wholly-owned
subsidiary   St.  Paul  Capital   Holdings,  Inc.  ("St.   Paul  Holdings"  and,
collectively with The St.  Paul, the "Managing  Members"). The Managing  Members
own  all of the Common Securities of St. Paul Capital. The Common Securities are
nontransferable and are and will be beneficially owned directly or indirectly by
the Company. The Managing Members are the  sole members of St. Paul Capital  and
are  also the only  managers of St.  Paul Capital. St.  Paul Capital's principal
executive offices  are located  at 385  Washington Street,  St. Paul,  Minnesota
55102,  telephone:  (612)  221-7911.  The  principal  executive  offices  of the
Managing Members  are located  at  385 Washington  Street, St.  Paul,  Minnesota
55102, telephone: (612) 221-7911.

    Pursuant  to  St.  Paul  Capital's Amended  and  Restated  Limited Liability
Company Agreement (the "L.L.C. Agreement"), the Managing Members have  unlimited
liability  for the debts, obligations and liabilities of St. Paul Capital in the
same manner as a general partner  of a Delaware limited partnership (which  does
not  include obligations to holders of Preferred Securities in their capacity as
such). The holders of Preferred Securities will not be generally liable for  the
debts,  obligations or liabilities of St. Paul Capital solely by reason of being
a member of St.  Paul Capital (subject  to their obligation  to repay any  funds
wrongfully distributed to them).

    St.  Paul  Capital  exists  exclusively  for  the  purposes  of  issuing its
Preferred Securities and Common Securities  and investing the proceeds  thereof,
together  with substantially all the capital contributed by the Managing Members
in respect of the Common Securities, in the Convertible Subordinated Debentures,
and may engage in no other activities now  or in the future. The payment by  St.
Paul Capital of dividends due on the Preferred Securities is solely dependent on
its  receipt of interest payments on the Convertible Subordinated Debentures. To
the extent  that aggregate  interest payments  on the  Convertible  Subordinated
Debentures  exceed  aggregate dividends  on  the Preferred  Securities  and such
dividends have been  paid in full,  St. Paul  Capital may at  times have  excess
funds, which shall be distributed to the Company.

                                       7
<PAGE>
    SEE  "INVESTMENT CONSIDERATIONS" FOR A  DISCUSSION OF CERTAIN MATERIAL RISKS
TO BE CONSIDERED IN CONNECTION WITH  AN INVESTMENT IN THE PREFERRED  SECURITIES,
INCLUDING  THE PERIOD AND  CIRCUMSTANCES DURING AND UNDER  WHICH PAYMENTS ON THE
PREFERRED SECURITIES AND THE CONVERTIBLE SUBORDINATED DEBENTURES MAY BE DEFERRED
AND THE RELATED FEDERAL INCOME TAX CONSEQUENCES.

                                   [GRAPHIC]

    1. ST. PAUL  CAPITAL. The issuer  of the Preferred  Securities is a  special
purpose  Delaware  limited liability  company  formed by  The  St. Paul  and its
wholly-owned subsidiary St. Paul Holdings for the exclusive purposes of  issuing
the  Preferred  Securities  (which will  constitute  all of  St.  Paul Capital's
preferred limited  liability  company  interests)  and  investing  the  proceeds
thereof, together with substantially all the capital contributed by the Managing
Members  in respect  of the Common  Securities, in  the Convertible Subordinated
Debentures. The Managing Members will own  100% of the Common Securities of  St.
Paul Capital. St. Paul Capital will be taxed as a partnership for federal income
tax purposes.

    2. PREFERRED SECURITIES. The Preferred Securities issued by St. Paul Capital
are  preferred limited liability company interests that are convertible into St.
Paul Common Stock. Distributions  on Preferred Securities  are not eligible  for
the dividends received deduction for federal income tax purposes.

    3.  PREFERRED  SECURITIES  PROCEEDS  INVESTED  IN  CONVERTIBLE  SUBORDINATED
DEBENTURES OF THE ST. PAUL. Proceeds of Preferred Securities will be used by St.
Paul Capital to  purchase Convertible  Subordinated Debentures of  The St.  Paul
having  a maturity of 30 years from date of issue and the same economic terms as
the Preferred Securities. The St. Paul  may elect to defer interest payments  on
the Convertible Subordinated Debentures for up to 60 months, but only if The St.
Paul  neither declares nor pays  any dividends on its  capital stock during such
deferral period. If  The St. Paul  defers interest payments  on the  Convertible
Subordinated  Debentures, St. Paul  Capital would be unable  to pay dividends on
the Preferred  Securities.  The  Convertible  Subordinated  Debentures  are  not
guaranteed by St. Paul Holdings.

                                       8
<PAGE>
    4. REPAYMENT OF CONVERTIBLE SUBORDINATED DEBENTURES. The St. Paul repays the
Convertible  Subordinated  Debentures in  cash  or the  Convertible Subordinated
Debentures are converted into St. Paul Common Stock.

    5. OWNERSHIP OF COMMON  SECURITIES AND GUARANTEE.  The Managing Members  own
100%  of the Common Securities of St.  Paul Capital. The St. Paul guarantees, on
an unsecured and subordinated basis, (a)  the payment of dividends (but only  if
and  to  the  extent declared  from  funds  legally available  therefor)  on the
Preferred Securities,  (b) the  payment  of the  redemption price  payable  with
respect  to the Preferred Securities  (but only to the  extent that funds of St.
Paul Capital are  legally available  therefor) and (c)  payments on  liquidation
with  respect to the Preferred Securities (but only to the extent that assets of
St. Paul  Capital  are  available  for  distribution  to  holders  of  Preferred
Securities).

                                  THE OFFERING

<TABLE>
<S>                                 <C>
Securities Offered................  3,600,000  of St. Paul  Capital's 6% Convertible Monthly
                                    Income Preferred Securities, liquidation preference  $50
                                    per security. Additionally, St. Paul Capital and The St.
                                    Paul have granted the Underwriters an option for 30 days
                                    to  purchase  up  to  an  additional  540,000  Preferred
                                    Securities at the initial  public offering price  solely
                                    to cover over-allotments, if any.
Dividends.........................  Dividends on the Preferred Securities will be cumulative
                                    from  the  date of  original  issuance of  the Preferred
                                    Securities and will be payable at the annual rate of  6%
                                    of  the  liquidation  preference  of  $50  per Preferred
                                    Security. Dividends will be  paid monthly in arrears  on
                                    the  last day of each calendar month, commencing May 31,
                                    1995. The proceeds  from the offering  of the  Preferred
                                    Securities  will  be  invested in  the  Convertible Sub-
                                    ordinated Debentures.  Interest payment  periods on  the
                                    Convertible  Subordinated Debentures are monthly but may
                                    be extended from time to time by The St. Paul for up  to
                                    60  months,  in which  event St.  Paul Capital  would be
                                    unable  to  make  monthly   dividend  payments  on   the
                                    Preferred  Securities  during  the  period  of  any such
                                    extension.  During   such   period,  interest   on   the
                                    Convertible   Subordinated   Debentures   will  compound
                                    monthly and Additional Dividends (as defined below) will
                                    continue to  accumulate  on  the  Preferred  Securities.
                                    Selection of such an extended interest payment period is
                                    referred to herein as a "deferral of interest payments".
                                    "Additional  Dividends", as  used herein,  means amounts
                                    payable upon any  dividend arrearages  on the  Preferred
                                    Securities  in  order  to  provide,  in  effect, monthly
                                    compounding on such  dividend arrearages. See  "Dividend
                                    Deferral  Provisions" below.  The failure  of holders of
                                    the Preferred Securities  to receive  dividends in  full
                                    (including  arrearages) for 15  consecutive months would
                                    trigger the right of  such holders to obtain  depositary
                                    shares  (the  "Depositary  Shares"),  each  representing
                                    1/100th of a  share of Series  C Cumulative  Convertible
                                    Preferred  Stock,  without par  value,  of The  St. Paul
                                    (liquidation preference  $5000  per  share)  ("St.  Paul
                                    Series   C  Convertible  Preferred   Stock"),  upon  the
                                    affirmative vote or written consent of the holders of  a
                                    majority of
</TABLE>

                                       9
<PAGE>

<TABLE>
<S>                                 <C>
                                    the  aggregate liquidation preference of the outstanding
                                    Preferred Securities, as described below under "Optional
                                    Exchange  for   Depositary  Shares".   See   "Investment
                                    Considerations -- Option to Defer Payment of Dividends,"
                                    "Investment   Considerations  --   Tax  Consequences  of
                                    Deferral   of   Interest    Payments   on    Convertible
                                    Subordinated  Debentures,"  "Description  of  Securities
                                    Offered -- Description  of the Convertible  Subordinated
                                    Debentures  --  Option to  Defer Interest  Payments" and
                                    "Description  of   Securities   Offered   --   Preferred
                                    Securities -- Optional Exchange for Depositary Shares".
Dividend Deferral Provisions......  The St. Paul has the right, at any time and from time to
                                    time,  to  defer  interest payments  on  the Convertible
                                    Subordinated  Debentures.  Monthly   dividends  on   the
                                    Preferred  Securities  would  be  deferred  by  St. Paul
                                    Capital  (but  would   continue  to  accrue   Additional
                                    Dividends)  during  any such  deferral of  interest pay-
                                    ments. The St. Paul will have the right during any  such
                                    deferral  of interest payments  to make partial payments
                                    of interest and at the end  of such periods may pay  all
                                    interest then accrued and unpaid (together with compound
                                    interest). Upon a partial payment of interest by The St.
                                    Paul,   St.  Paul  Capital  may  pay  partial  PRO  RATA
                                    dividends to holders of  Preferred Securities, and  upon
                                    the  payment of all  accrued and unpaid  interest on the
                                    Convertible Subordinated Debentures, may pay in full all
                                    accumulated and unpaid  dividends (including  Additional
                                    Dividends).  Prior  to  the  end  of  such  deferral  of
                                    interest  payments,  The  St.  Paul  may  further  defer
                                    interest  payments, provided that all such deferrals may
                                    not exceed 60 months in the aggregate nor extend  beyond
                                    the  stated  maturity  of  the  Convertible Subordinated
                                    Debentures. After The St. Paul has paid all accrued  and
                                    unpaid  interest (including compound interest) following
                                    a deferral  of interest  payments,  it may  again  defer
                                    interest  payments for up  to 60 months,  subject to the
                                    preceding sentence. St. Paul  Capital will give  written
                                    notice  of The St. Paul's  deferral of interest payments
                                    to the holders of Preferred Securities no later than the
                                    last date on which  it would be  required to notify  the
                                    NYSE  of  the  record  or payment  date  of  the related
                                    dividend, which  is  currently  10 days  prior  to  such
                                    record  or payment date.  See "Investment Considerations
                                    -- Option to Defer  Payment of Dividends,"  "Description
                                    of   Securities  Offered  --   Preferred  Securities  --
                                    Dividends" and  "Description  of Securities  Offered  --
                                    Description  of the  Convertible Subordinated Debentures
                                    -- Option to Defer Interest Payments". Should a deferral
                                    of interest payments occur, St. Paul Capital, except  in
                                    very  limited  circumstances,  will  continue  to accrue
                                    income for United States income tax purposes, which will
                                    be allocated  to  holders  of  Preferred  Securities  in
                                    advance  of  any  corresponding  cash  distribution. See
                                    "Investment  Considerations  --   Tax  Consequences   of
                                    Deferral    of   Interest    Payments   on   Convertible
                                    Subordinated Debentures" and "Certain Federal Income Tax
                                    Considerations  --   Potential  Deferral   of   Interest
                                    Payment".
</TABLE>

                                       10
<PAGE>

<TABLE>
<S>                                 <C>
Liquidation Preference............  $50  per Preferred Security, plus an amount equal to any
                                    accumulated and unpaid dividends (whether or not  earned
                                    or declared).
Conversion into St. Paul Common
 Stock............................  Each  Preferred  Security is  convertible in  the manner
                                    described below at the option of the holder, at any time
                                    prior to  the  Conversion Expiration  Date  (as  defined
                                    below),  into shares  of St. Paul  Common Stock, without
                                    par value (the "St. Paul Common Stock"), at the rate  of
                                    0.8475   shares  of  St.  Paul  Common  Stock  for  each
                                    Preferred Security (equivalent to a conversion price  of
                                    $59  per  share of  St.  Paul Common  Stock).  Such con-
                                    version price will be  subject to adjustment in  certain
                                    circumstances,  including the payment or distribution by
                                    The  St.   Paul   of   certain   types   of   dividends,
                                    distributions  or other payments to  holders of St. Paul
                                    Common Stock; subdivisions and combinations of St.  Paul
                                    Common  Stock; and certain payments in respect of tender
                                    or exchange  offers  for  St. Paul  Common  Stock.  Such
                                    conversion  price will also be  subject to adjustment in
                                    the event  that  The St.  Paul  is a  party  to  certain
                                    transactions  (including,  without  limitation,  certain
                                    mergers, consolidations, sales  of all or  substantially
                                    all  of the assets of The St. Paul, recapitalizations or
                                    reclassifications  of  St.  Paul  Common  Stock  or  any
                                    compulsory  share exchange) as a  result of which shares
                                    of St. Paul Common Stock are converted into the right ro
                                    receive  securities,   cash  or   other  property.   See
                                    "Description   of   Securities   Offered   --  Preferred
                                    Securities --  Conversion  Rights  --  Conversion  Price
                                    Adjustments  --  General"  and  "  --  Conversion  Price
                                    Adjustments -- Merger, Consolidation  or Sale of  Assets
                                    of The St. Paul".
                                    A holder of a Preferred Security wishing to exercise its
                                    conversion   right   shall   surrender   such  Preferred
                                    Security,  together  with   an  irrevocable   conversion
                                    notice,  to  the  Conversion Agent  (as  defined herein)
                                    acting on behalf of the holders of Preferred Securities,
                                    which  shall  exchange  the  Preferred  Security  for  a
                                    portion  of the Convertible Subordinated Debentures held
                                    by  St.  Paul  Capital  and  immediately  convert   such
                                    Convertible  Subordinated Debentures and any accrued and
                                    unpaid interest thereon  into St. Paul  Common Stock.  A
                                    holder of Preferred Securities should not recognize gain
                                    or  loss upon the exchange  through the Conversion Agent
                                    of Preferred Securities for a proportionate share of the
                                    Convertible Subordinated  Debentures  held by  St.  Paul
                                    Capital.  Except to  the extent  attributable to accrued
                                    but unpaid  interest  on  the  Convertible  Subordinated
                                    Debentures,  a holder should not  recognize gain or loss
                                    upon  the  exchange  through  the  Conversion  Agent  of
                                    Convertible  Subordinated Debentures for St. Paul Common
                                    Stock. See "Certain Federal Income Tax Considerations --
                                    Exchange of Preferred Securities for St. Paul Stock". On
                                    and after  May  31, 1999,  and  provided that  St.  Paul
                                    Capital  is current in  the payment of  dividends on the
                                    Preferred Securities,  St.  Paul  Capital  may,  at  its
                                    option,  cause the  conversion rights of  holders of the
                                    Preferred Securities  to expire.  St. Paul  Capital  may
                                    exercise this
</TABLE>

                                       11
<PAGE>

<TABLE>
<S>                                 <C>
                                    option  only if for 20 trading days within any period of
                                    30 consecutive trading days, including the last  trading
                                    day  of such period, the Current Market Price (as herein
                                    defined) of St.  Paul Common Stock  exceeds 120% of  the
                                    conversion price of the Preferred Securities, subject to
                                    adjustment   in  certain  circumstances.   In  order  to
                                    exercise its  conversion  expiration  option,  St.  Paul
                                    Capital  must issue  a press release  for publication on
                                    the Dow  Jones News  Service announcing  the  Conversion
                                    Expiration  Date prior to the opening of business on the
                                    second trading day after a period in which the condition
                                    in the preceding sentence has been met, but in no  event
                                    prior  to May 31, 1999. The press release shall announce
                                    the Conversion Expiration Date  and provide the  current
                                    conversion   price  and  Current  Market  Price  of  the
                                    Preferred Securities, in  each case as  of the close  of
                                    business  on the trading day  next preceding the date of
                                    the press release.  Written notice  containing the  same
                                    information  set forth in the press release will be sent
                                    by  first-class  mail  to   each  holder  of   Preferred
                                    Securities  not  more  than  four  business  days  after
                                    issuance of the press release. The Conversion Expiration
                                    Date shall be a date not less than 30 and not more  than
                                    60  days following the date of such press release or, if
                                    St.  Paul  Capital  has  not  exercised  its  conversion
                                    expiration  option,  the  earlier  of  the  date  of  an
                                    Exchange Election  referred  to  below  under  "Optional
                                    Exchange  for  Depositary Shares"  or two  business days
                                    prior to the scheduled date for the mandatory redemption
                                    of  the  Preferred   Securities.  See  "Description   of
                                    Securities Offered -- Preferred Securities -- Conversion
                                    Rights".
                                    Whenever The St. Paul issues shares of Common Stock upon
                                    conversion  of Preferred  Securities, The  St. Paul will
                                    issue, together with  each such share  of Common  Stock,
                                    one  Stock Purchase Right  (as defined herein) entitling
                                    the holder  thereof,  under  certain  circumstances,  to
                                    purchase  Series A Preferred  Stock of The  St. Paul (or
                                    other  securities  in  lieu  thereof)  pursuant  to  the
                                    Shareholder  Protection  Rights Agreement,  dated  as of
                                    December 4, 1989, as  amended (the "Rights  Agreement"),
                                    between  The St. Paul and First Chicago Trust Company of
                                    New York,  as Rights  Agent. The  Stock Purchase  Rights
                                    will  expire on December 19,  1999, subject to extension
                                    to December  18,  2002 under  certain  circumstances  or
                                    earlier redemption by The St. Paul.
Redemption........................  If at any time following the Conversion Expiration Date,
                                    less   than  5%  of   the  Preferred  Securities  remain
                                    outstanding,  such   Preferred   Securities   shall   be
                                    redeemable at the option of St. Paul Capital, as a whole
                                    but  not  in  part, at  a  redemption price  of  $50 per
                                    Preferred Security together with accumulated and  unpaid
                                    dividends  (whether  or  not  earned  or  declared) (the
                                    "Redemption Price").  The Preferred  Securities have  no
                                    maturity  date, although  they are  subject to mandatory
                                    redemption upon the  repayment at maturity  (on May  31,
                                    2025)  or as a result of acceleration of the Convertible
                                    Subordinated Debentures. See "Description of  Securities
                                    Offered -- Description of the
</TABLE>

                                       12
<PAGE>

<TABLE>
<S>                                 <C>
                                    Convertible   Subordinated   Debentures  --   Events  of
                                    Default". The  Preferred  Securities are  not  otherwise
                                    redeemable  for any reason, including  in the event that
                                    St. Paul  Capital should  become subject  to federal  or
                                    state  taxation.  To the  extent  that such  taxation or
                                    other events cause St. Paul Capital to have insufficient
                                    funds to  pay full  dividends on  the Preferred  Securi-
                                    ties,  the  holders  will  have  available  to  them the
                                    exchange option described below. Upon the occurrence  of
                                    certain  Tax Events (as defined herein) St. Paul Capital
                                    may  be  dissolved  and  the  Convertible   Subordinated
                                    Debentures  distributed  to  holders  of  the  Preferred
                                    Securities. See "-- Special Event Distribution".
Special Event Distribution........  Upon the occurrence of a Tax Event (as defined  herein),
                                    the  Managing Members may, and upon the occurrence of an
                                    Investment  Company  Event   (as  defined  herein)   the
                                    Managing  Members shall, dissolve  St. Paul Capital and,
                                    after satisfaction of  liabilities to  creditors of  St.
                                    Paul  Capital as  required by applicable  law, cause the
                                    Convertible Subordinated Debentures to be distributed to
                                    the holders of  the Preferred  Securities in  connection
                                    with the liquidation of St. Paul Capital. In the case of
                                    a Special Event that is a Tax Event (as defined herein),
                                    however,  the Managing Members may elect not to dissolve
                                    St. Paul Capital and  to cause the Preferred  Securities
                                    to  remain outstanding.  See "Description  of Securities
                                    Offered  --  Preferred   Securities  --  Special   Event
                                    Distribution"  and  "-- Description  of  the Convertible
                                    Subordinated Debentures".
Optional Exchange for Depositary
 Shares...........................  Upon the failure of holders of the Preferred  Securities
                                    to  receive, for 15 consecutive  months, the full amount
                                    of  dividend  payments  (including  any  arrearages  and
                                    including  any  such  failure caused  by  a  deferral of
                                    interest  payments  on   the  Convertible   Subordinated
                                    Debentures)  the holders of a  majority of the aggregate
                                    liquidation preference of Preferred Securities then out-
                                    standing, voting  as a  class at  a special  meeting  of
                                    members  called for such purpose  or by written consent,
                                    may, at  their option,  direct the  Conversion Agent  to
                                    exchange  all (but not  less than all)  of the Preferred
                                    Securities for Convertible Subordinated Debentures  held
                                    by  St. Paul  Capital, and  to immediately  exchange the
                                    Convertible Subordinated Debentures and any accrued  and
                                    unpaid  interest thereon  on behalf of  such holders for
                                    Depositary Shares, each representing a 1/100th  interest
                                    in a
                                    share  of St. Paul Series  C Convertible Preferred Stock
                                    at the Exchange Price (as defined under "Description  of
                                    Securities    Offered   --   Preferred   Securities   --
                                    Dividends"). Each  Depositary  Share  will  entitle  the
                                    holder  thereof to  a proportionate share  in all rights
                                    and preferences  of the  St. Paul  Series C  Convertible
                                    Preferred  Stock (including dividend, voting, conversion
                                    and liquidation rights  and preferences).  The St.  Paul
                                    Series C Convertible Preferred Stock will have dividend,
                                    conversion  and other terms substantially similar to the
                                    terms   of    the   Preferred    Securities    (adjusted
                                    proportionately    per    Depositary    Share),   except
</TABLE>

                                       13
<PAGE>

<TABLE>
<S>                                 <C>
                                    that, among other things, the holders of St. Paul Series
                                    C Convertible  Preferred Stock  will have  the right  to
                                    elect  two additional directors of The St. Paul whenever
                                    dividends on the St. Paul Series C Convertible Preferred
                                    Stock are in arrears for  18 months (including for  this
                                    purpose  any  arrearage  with respect  to  the Preferred
                                    Securities)  and  the  St.  Paul  Series  C  Convertible
                                    Preferred   Stock  will  not  be  subject  to  mandatory
                                    redemption. A holder of Preferred Securities should  not
                                    recognize  gain or  loss upon  the exchange  through the
                                    Conversion  Agent   of   Preferred  Securities   for   a
                                    proportionate  share  of  the  Convertible  Subordinated
                                    Debentures held  by  St.  Paul Capital.  Except  to  the
                                    extent  attributable to  accrued but  unpaid interest on
                                    the Convertible Subordinated Debentures, a holder should
                                    not recognize gain or loss upon the exchange through the
                                    Conversion Agent of Convertible Subordinated  Debentures
                                    for  Depository Shares. See  "Certain Federal Income Tax
                                    Considerations -- Exchange  of Preferred Securities  for
                                    St.   Paul  Stock".  If  the  Preferred  Securities  are
                                    exchanged for Depositary Shares,  The St. Paul will  use
                                    its best efforts to have the Depositary Shares listed on
                                    the  NYSE or any  other exchange on  which the Preferred
                                    Securities may  then  be  listed.  See  "Description  of
                                    Securities  Offered -- Description of  St. Paul Series C
                                    Convertible  Preferred   Stock"  and   "Description   of
                                    Securities  Offered -- Description of Depositary Shares"
                                    for a description of the principal terms of the St. Paul
                                    Series C Convertible Preferred Stock and the  Depositary
                                    Shares, respectively.
Guarantee.........................  Pursuant to a Guarantee Agreement (the "Guarantee"), The
                                    St.  Paul will irrevocably and unconditionally agree, on
                                    a subordinated basis, to  guarantee the payment in  full
                                    of (a) the dividends (including any Additional Dividends
                                    thereon)  payable by  St. Paul Capital  on the Preferred
                                    Securities, if and to the extent declared from funds  of
                                    St.  Paul  Capital legally  available therefor,  (b) the
                                    redemption price (including  all accumulated and  unpaid
                                    dividends)  of the  Preferred Securities,  to the extent
                                    funds  of  St.  Paul   Capital  are  legally   available
                                    therefor,  and (c) payments  on liquidation with respect
                                    to the Preferred Securities, to the extent the assets of
                                    St. Paul  Capital  are  available  for  distribution  to
                                    holders   of  the  Preferred  Securities.  A  holder  of
                                    Preferred  Securities   may  enforce   The  St.   Paul's
                                    obligations under the Guarantee directly against The St.
                                    Paul,  and The St. Paul waives any right to require that
                                    an action be  brought against  St. Paul  Capital or  any
                                    other person before proceeding against The St. Paul. The
                                    Guarantee  will be unsecured and will be subordinated to
                                    all liabilities of The St. Paul and will rank PARI PASSU
                                    (I.E., on  a  parity)  with the  most  senior  preferred
                                    shares  hereafter issued by The  St. Paul and PARI PASSU
                                    with any guarantee now or hereafter entered into by  The
                                    St. Paul in respect of any preferred or preference stock
                                    of  any affiliate  of The  St. Paul.  On the bankruptcy,
                                    liquidation  or  winding-up   of  The   St.  Paul,   its
                                    obligations  under the Guarantee will rank junior to all
                                    its other liabilities and,  therefore, funds may not  be
                                    available   for   payment  under   the   Guarantee.  See
                                    "Investment Considerations --
</TABLE>

                                       14
<PAGE>

<TABLE>
<S>                                 <C>
                                    Subordinate Obligations Under Guarantee and  Convertible
                                    Subordinated  Debentures," "Investment Considerations --
                                    Dependence  on  Subordinated  Debenture  Payments"   and
                                    "Description of Securities Offered -- Description of the
                                    Guarantee".
Voting Rights.....................  Generally,  holders of the Preferred Securities will not
                                    have any  voting  rights.  However,  upon  an  Event  of
                                    Default  under  the Convertible  Subordinated Debentures
                                    (as described under  "Description of Securities  Offered
                                    --   Description   of   the   Convertible   Subordinated
                                    Debentures -- Events of Default"), a failure by St. Paul
                                    Capital  to  pay  dividends   in  full  (including   any
                                    arrearages)   on   the  Preferred   Securities   for  15
                                    consecutive months (including any such failure caused by
                                    a deferral by The St.  Paul of interest payments on  the
                                    Convertible Subordinated Debentures) or a default by The
                                    St.  Paul  under  the  Guarantee,  the  holders  of  the
                                    Preferred Securities  will be  entitled to  appoint  and
                                    authorize  a special trustee  (the "Special Trustee") to
                                    enforce St. Paul Capital's rights under the  Convertible
                                    Subordinated   Debentures,   enforce   The   St.  Paul's
                                    obligations under  the  Guarantee  and,  to  the  extent
                                    permitted  by  law,  declare and  pay  dividends  on the
                                    Preferred Securities  to the  extent funds  are  legally
                                    available  therefor. The St. Paul  has agreed to execute
                                    and deliver  such  documents  as  may  be  necessary  or
                                    appropriate  for  the  Special Trustee  to  enforce such
                                    rights and obligations. In  addition, if for any  reason
                                    (including  a  deferral  by  The  St.  Paul  of interest
                                    payments on  the  Convertible  Subordinated  Debentures)
                                    holders  of Preferred Securities fail to receive, for 15
                                    consecutive months, the full amount of dividend payments
                                    (including any arrearages), the holders of the Preferred
                                    Securities will be entitled to call a special meeting of
                                    members for the purpose of deciding whether to  exchange
                                    all Preferred Securities then outstanding for Depositary
                                    Shares,  as described above under "Optional Exchange for
                                    Depositary  Shares".  See  "Description  of   Securities
                                    Offered -- Preferred Securities -- Dividends".
Use of Proceeds...................  The proceeds to be received by St. Paul Capital from the
                                    sale of the Preferred Securities will be invested in the
                                    Convertible  Subordinated  Debentures of  The  St. Paul,
                                    which, after paying  the expenses  associated with  this
                                    Offering,  will  use  such funds  for  general corporate
                                    purposes, which  may include  possible acquisitions  and
                                    the  reduction of short-term  indebtedness. Pending such
                                    use, the  net proceeds  may be  temporarily invested  in
                                    short-term debt obligations. See "Use of Proceeds".
Convertible Subordinated
 Debentures.......................  The  Convertible  Subordinated  Debentures  will  have a
                                    maturity of 30 years and will bear interest at the  rate
                                    of  6% per  annum, payable  monthly in  arrears. The St.
                                    Paul has the right to select an interest payment  period
                                    or periods longer than one month (during which period or
                                    periods  interest will compound  monthly), provided that
                                    any  such  deferral  of   interest  payments  will   not
</TABLE>

                                       15
<PAGE>

<TABLE>
<S>                                 <C>
                                    exceed 60 months and provided further that a deferral of
                                    interest  payments may not extend the stated maturity of
                                    the Convertible  Subordinated  Debentures.  Accordingly,
                                    dividend payments on the Preferred Securities may not be
                                    deferred  beyond the stated  maturity of the Convertible
                                    Subordinated Debentures. If The St. Paul defers interest
                                    payments longer than  one month, it  will be  prohibited
                                    from  paying dividends on  any of its  capital stock and
                                    making certain other  restricted payments until  monthly
                                    interest  payments are  resumed and  all accumulated and
                                    unpaid  interest  (including  any  interest  payable  to
                                    effect   monthly   compounding)   on   the   Convertible
                                    Subordinated Debentures is brought current. The St. Paul
                                    will have the  right to  make partial  payments of  such
                                    interest  during  a deferral  of interest  payments. The
                                    failure by The St. Paul to make interest payments during
                                    a deferral of interest  payments would not constitute  a
                                    default  or  an event  of default  under The  St. Paul's
                                    currently  outstanding  indebtedness.  The   Convertible
                                    Subordinated  Debentures are convertible  into shares of
                                    St. Paul  Common  Stock at  the  option of  the  holders
                                    thereof  and  are  exchangeable  for  Depositary  Shares
                                    representing St.  Paul  Series C  Convertible  Preferred
                                    Stock  as described  above under  "Optional Exchange for
                                    Depositary Shares". St. Paul  Capital will covenant  not
                                    to  convert  Convertible Subordinated  Debentures except
                                    pursuant to  a notice  of  conversion delivered  to  the
                                    Conversion  Agent by  a holder  of Preferred Securities.
                                    The  payment  of  the  principal  and  interest  on  the
                                    Convertible  Subordinated Debentures will be subordinate
                                    in right  of  payment  to all  Senior  Indebtedness  (as
                                    defined  under  "Description  of  Securities  Offered --
                                    Description of the  Convertible Subordinated  Debentures
                                    --  Subordination")  of The  St. Paul.  As of  March 31,
                                    1995, The  St. Paul  had  $628 million  of  indebtedness
                                    constituting  Senior Indebtedness and no indebtedness or
                                    other obligations  that  would  rank  equally  with  the
                                    Convertible  Subordinated  Debentures.  See  "Investment
                                    Considerations   --   Subordinate   Obligations    Under
                                    Guarantee  and Convertible  Subordinated Debentures" and
                                    "Investment Considerations -- Dependence on Subordinated
                                    Debenture  Payments".   The   Convertible   Subordinated
                                    Debentures  will not be guaranteed by St. Paul Holdings.
                                    While the Preferred Securities are outstanding, St. Paul
                                    Capital will not have the ability to amend the Indenture
                                    (as defined  below)  or  the terms  of  the  Convertible
                                    Subordinated  Debentures in a way that adversely affects
                                    the holders of the Preferred Securities, or to waive  an
                                    event of default under the Indenture without the consent
                                    of   holders  of   66  2/3%   in  aggregate  liquidation
                                    preference of the Preferred Securities then outstanding.
                                    See "Description of Securities Offered -- Description of
                                    the Convertible Subordinated Debentures --  Modification
                                    of Indenture".
</TABLE>

                                       16
<PAGE>
                      SUMMARY FINANCIAL AND OPERATING DATA

    The selected data presented below under the captions "Income Statement Data"
and  "Balance Sheet Data" for,  and as of the  end of, each of  the years in the
five-year period  ended December  31, 1994,  are derived  from the  consolidated
financial  statements of  the Company,  which consolidated  financial statements
have been  audited  by  KPMG  Peat Marwick  LLP,  independent  certified  public
accountants.  The consolidated financial statements as  of December 31, 1994 and
1993, and for  each of the  years in  the three-year period  ended December  31,
1994,  and the report  thereon, are incorporated by  reference elsewhere in this
prospectus. The  information presented  below  under the  caption  "Underwriting
Operations"  is unaudited. The  financial data for the  three months ended March
31, 1995 and 1994, respectively, have been derived from the Company's  unaudited
consolidated  financial statements, which, in the opinion of management, include
all adjustments (consisting of normal  recurring accruals) necessary for a  fair
presentation of the results of operations and financial position for the periods
and  as of the dates  presented. The results of  operations for the three months
ended March 31,  1995 may not  be indicative  of results for  the entire  fiscal
year. The table should be read in conjunction with "Overview of Results" and the
consolidated   financial  statements  and  the  notes  thereto  incorporated  by
reference in this Prospectus. Numbers of shares and per share figures reflect  a
two-for-one stock split in June 1994.

<TABLE>
<CAPTION>
                                                THREE MONTHS
                                              ENDED MARCH 31,                           YEAR ENDED DECEMBER 31,
                                          ------------------------  ---------------------------------------------------------------
                                             1995         1994         1994         1993         1992         1991         1990
                                          -----------  -----------  -----------  -----------  -----------  -----------  -----------
                                                                (DOLLARS IN THOUSANDS, EXCEPT PER SHARE DATA)
<S>                                       <C>          <C>          <C>          <C>          <C>          <C>          <C>
INCOME STATEMENT DATA:
Premiums earned.........................  $   946,070  $   845,402  $ 3,412,081  $ 3,178,338  $ 3,143,246  $ 3,146,238  $ 2,893,959
Net investment income...................      186,389      168,408      694,594      661,106      666,374      675,604      669,989
Insurance brokerage fees and
 commissions............................       67,061       66,450      303,152      283,680      280,836      284,702      256,354
Investment banking-asset management.....       53,616       53,598      211,789      241,730      218,825      175,610      126,607
Realized gains(1).......................        2,977       21,783       41,974       58,254      155,735       38,008        9,864
Other...................................       11,346        8,134       37,695       37,064       33,676       31,538       48,464
                                          -----------  -----------  -----------  -----------  -----------  -----------  -----------
    Total revenues......................    1,267,459    1,163,775    4,701,285    4,460,172    4,498,692    4,351,700    4,005,237
                                          -----------  -----------  -----------  -----------  -----------  -----------  -----------
Insurance losses and loss adjustment
 expenses...............................      680,439      667,688    2,461,698    2,303,738    2,690,046    2,365,569    2,119,776
Policy acquisition, operating and
 administrative expenses(2).............      427,296      404,269    1,636,428    1,593,063    1,998,156    1,422,511    1,352,034
Interest expense........................       11,578        9,815       39,581       40,765       35,553       35,559       29,522
Income tax expense......................       37,550       17,566      120,750       94,997        7,458      122,999      112,635
Cumulative net benefit of accounting
 changes, net of taxes..................            0            0            0            0       76,483            0            0
                                          -----------  -----------  -----------  -----------  -----------  -----------  -----------
    Net income (loss)...................  $   110,596  $    64,437  $   442,828  $   427,609  $  (156,038) $   405,062  $   391,270
                                          -----------  -----------  -----------  -----------  -----------  -----------  -----------
                                          -----------  -----------  -----------  -----------  -----------  -----------  -----------
Fully diluted net income (loss) per
 common share...........................        $1.23        $0.71        $4.93        $4.73       $(1.94)       $4.50        $4.16
Cash dividends declared per common
 share..................................        $0.40       $0.375        $1.50        $1.40        $1.36        $1.30        $1.20
BALANCE SHEET DATA:
Total assets............................  $17,651,999  $16,741,009  $17,495,820  $17,149,196  $15,392,054  $14,744,717  $13,907,293
Total debt..............................      628,178      584,737      622,624      639,729      566,717      486,779      473,829
Change in unrealized appreciation of
 investments, net of taxes(3)...........      185,960     (311,937)    (574,896)     525,175      (23,815)      55,093      (67,558)
Common shareholders' equity.............    3,008,801    2,690,833    2,732,934    3,005,128    2,202,499    2,532,841    2,196,371
Book value per common share.............        35.67        32.02        32.46        35.47        26.18        29.78        26.00
Number of common shares outstanding.....   84,341,306   84,041,142   84,202,417   84,714,676   84,118,554   85,042,484   84,468,058
UNDERWRITING OPERATIONS:
GAAP underwriting result................  $   (15,452) $   (83,057) $  (113,008) $  (150,255) $  (566,886) $  (163,782) $  (120,730)
Statutory combined ratio:(4)............
  Loss and loss expense ratio...........         71.9         79.0         72.1         72.5         85.6         75.2         73.2
  Underwriting expense ratio............         30.4         31.2         30.2         32.0         32.2         29.4         30.0
                                          -----------  -----------  -----------  -----------  -----------  -----------  -----------
  Combined ratio........................        102.3        110.2        102.3        104.5        117.8        104.6        103.2
                                          -----------  -----------  -----------  -----------  -----------  -----------  -----------
                                          -----------  -----------  -----------  -----------  -----------  -----------  -----------
Combined ratio including policyholders'
 dividends..............................        102.4        110.2        102.3        104.7        118.2        105.0        104.2
                                          -----------  -----------  -----------  -----------  -----------  -----------  -----------
                                          -----------  -----------  -----------  -----------  -----------  -----------  -----------
<FN>
- ----------------------------------------
(1)  1992  realized  gains  include $98  million  from  the sale  of  a minority
     interest in The John Nuveen Company.
(2)  1992  operating  and  administrative   expenses  include  a  $365   million
     write-down  of  the goodwill  associated with  the Company's  investment in
     Minet.
(3)  The change  for  1993 includes  an  increase of  $502  million due  to  the
     adoption   of  Statement   of  Financial  Accounting   Standards  No.  115,
     "Accounting for Certain Investments in Debt and Equity Securities".
(4)  The combined ratio is not  derived from the audited consolidated  financial
     statements.
</TABLE>

                                       17
<PAGE>
                           INVESTMENT CONSIDERATIONS

    PROSPECTIVE  PURCHASERS OF PREFERRED SECURITIES  SHOULD CAREFULLY REVIEW THE
INFORMATION CONTAINED  ELSEWHERE  IN  THIS PROSPECTUS  AND  SHOULD  PARTICULARLY
CONSIDER THE FOLLOWING MATTERS:

SUBORDINATE OBLIGATIONS UNDER GUARANTEE AND CONVERTIBLE SUBORDINATED DEBENTURES

    The St. Paul's obligations under the Convertible Subordinated Debentures are
subordinate and junior in right of payment to all Senior Indebtedness of The St.
Paul.  The St.  Paul's obligations  under the  Guarantee are  subordinate to all
liabilities of The St. Paul  and will rank PARI PASSU  (I.E., on a parity)  with
the most senior preferred shares hereafter issued by The St. Paul and PARI PASSU
with  any guarantee now or hereafter entered into  by The St. Paul in respect of
any preferred or preference stock of any affiliate of The St. Paul. There are no
terms of the  Preferred Securities, the  Convertible Subordinated Debentures  or
the   Guarantee  that  limit   The  St.  Paul's   ability  to  incur  additional
indebtedness, including  indebtedness  that  ranks  senior  to  the  Convertible
Subordinated Debentures and the Guarantee, or the ability of its subsidiaries to
incur additional indebtedness.

    The  Guarantee  is a  full  and unconditional  guarantee  of payment  to the
holders of the Preferred Securities of accumulated and unpaid monthly  dividends
declared  by St.  Paul Capital  from funds  legally available  therefor, amounts
payable on redemption out of funds  legally available therefor, and the  amounts
available  for distribution to holders of Preferred Securities on liquidation of
St. Paul Capital. In each case, payments on the Preferred Securities are covered
by the Guarantee  only to the  extent that St.  Paul Capital has  funds on  hand
legally available therefor and such payments do not otherwise violate applicable
law.  If The  St. Paul  were to  default on  its obligation  to pay  interest or
amounts payable  on  redemption  or maturity  of  the  Convertible  Subordinated
Debentures,  St. Paul Capital would lack legally available funds for the payment
of dividends or amounts payable on  redemption of the Preferred Securities,  and
in such event holders of the Preferred Securities would not be able to rely upon
the  Guarantee for  payment of such  amounts. On the  bankruptcy, liquidation or
winding-up of  The St.  Paul, its  obligations under  the Guarantee  would  rank
junior to all of its liabilities and, therefore, funds might not be available in
such  circumstances  for  payment  pursuant to  the  Guarantee.  The Convertible
Subordinated  Debentures  are   not  guaranteed  by   St.  Paul  Holdings.   See
"Description  of  Securities  Offered  --  Description  of  the  Guarantee"  and
"Description  of   Securities  Offered   --  Description   of  the   Convertible
Subordinated Debentures -- Subordination".

DEPENDENCE ON CONVERTIBLE SUBORDINATED DEBENTURE PAYMENTS

    St. Paul Capital's ability to pay amounts due on the Preferred Securities is
solely dependent upon The St. Paul's ability to make payments on the Convertible
Subordinated  Debentures as and  when required. Since  The St. Paul  is also the
Guarantor of the Preferred Securities, in  the event that St. Paul Capital  were
unable  to make payments on the Preferred Securities as and when required, there
is a substantial likelihood that The St.  Paul would be unable to make  payments
on the Guarantee as and when required.

OPTION TO DEFER PAYMENT OF DIVIDENDS

    The  St.  Paul has  the  right to  extend  interest payment  periods  on the
Convertible Subordinated Debentures for up to 60 months, and, as a  consequence,
monthly  dividends on the Preferred Securities would be deferred (but Additional
Dividends will continue to  accumulate monthly) by St.  Paul Capital during  any
such  deferral of interest  payments. In the  event that The  St. Paul exercises
this right,  neither The  St. Paul  nor any  direct or  indirect  majority-owned
subsidiary  of The  St. Paul (excluding  The John Nuveen  Company ("Nuveen") and
Nuveen's consolidated subsidiaries)  shall declare  or pay any  dividend on,  or
redeem,  purchase, otherwise acquire or make  a liquidation payment with respect
to, any of  its common or  preferred stock  or make any  guarantee payment  with
respect to the foregoing (other than payments under the Guarantee or dividend or
guarantee  payments to  The St.  Paul from  a direct  or indirect majority-owned
subsidiary), during any such deferral  period and until all dividend  arrearages
have  been paid in full. No deferral  of interest payments may extend the stated
maturity  of  the  Convertible  Subordinated  Debentures.  See  "Description  of
Securities  Offered -- Description of the Convertible Subordinated Debentures --
Option to Defer Interest Payments".

                                       18
<PAGE>
TAX CONSEQUENCES OF DEFERRAL OF INTEREST PAYMENTS ON CONVERTIBLE SUBORDINATED
DEBENTURES

    Should a deferral of  interest payments occur, St.  Paul Capital, except  in
very  limited circumstances,  will continue to  accrue income  for United States
federal income tax  purposes which  will be allocated  to holders  of record  of
Preferred  Securities in  advance of any  corresponding cash  distribution. As a
result, such  holders will  include such  interest in  gross income  for  United
States  federal income tax purposes  in advance of the  receipt of cash and will
not receive the cash  related to such  income if such a  holder disposes of  its
Preferred  Securities prior  to the  record date  for payment  of dividends. See
"Certain Federal Income  Tax Considerations  -- Potential  Deferral of  Interest
Payment".

TAX CONSEQUENCES OF AN EXCHANGE FOR DEPOSITARY SHARES

    In  the event  that a deferral  of interest  payments or the  failure to pay
interest continues for more  than 15 months,  the holders of  a majority of  the
aggregate  liquidation preference  of the Preferred  Securities then outstanding
may cause the exchange of all of the Preferred Securities for Depositary  Shares
representing  interests in St. Paul Series  C Convertible Preferred Stock at the
Exchange Price. For a discussion of the taxation of such an exchange to holders,
including the possibility that holders  who exchange their Preferred  Securities
for  Depositary Shares will  be subject to  additional income tax  to the extent
accrued but  unpaid  interest  on the  Convertible  Subordinated  Debentures  is
converted  into  accumulated  and unpaid  dividends  on  the St.  Paul  Series C
Convertible  Preferred  Stock  represented  by  Depositary  Shares  received  in
exchange   for  the  Preferred  Securities,  see  "Certain  Federal  Income  Tax
Considerations -- Exchange of Preferred Securities for St. Paul Stock".

EXPIRATION OF CONVERSION RIGHTS

    On and  after  May  31, 1999,  St.  Paul  Capital may,  subject  to  certain
conditions,  at its option, cause the  conversion rights of holders of Preferred
Securities to expire, provided that St.  Paul Capital is current in the  payment
of  dividends  on the  Preferred  Securities and  the  Current Market  Price (as
defined herein) of St. Paul Common Stock exceeds 120% of the conversion price of
the Preferred Securities for a specified period. See "Description of  Securities
Offered -- Preferred Securities -- Expiration of Conversion Rights".

UNCERTAINTY OF DEDUCTIBILITY OF INTEREST ON THE CONVERTIBLE SUBORDINATED
DEBENTURES

    The  offering of  the Preferred Securities  and the issuance  of the related
Convertible Subordinated  Debentures is  a relatively  novel type  of  financing
transaction.  The Company's  ability to deduct  the interest  on the Convertible
Subordinated  Debentures  depends  upon  whether  the  Convertible  Subordinated
Debentures  are  characterized  as  debt  instruments  for  federal  income  tax
purposes, taking  all the  relevant facts  and circumstances  into account.  The
Company   believes  that  the  Convertible   Subordinated  Debentures  are  debt
instruments for federal income tax purposes and that interest on the Convertible
Subordinated Debentures will, therefore, be deductible by the Company. There  is
no  clear authority on  the appropriate characterization  for federal income tax
purposes of instruments  such as  the Convertible  Subordinated Debentures  when
they  are  issued in  connection  with an  offering  of securities  such  as the
Preferred Securities. If the interest on the Convertible Subordinated Debentures
is not deductible by the Company, the Company would have significant  additional
income tax liabilities. Nondeductability of such interest would constitute a Tax
Event.  Upon the occurrence of  a Tax Event, the  Managing Members may cause St.
Paul Capital to be dissolved  and cause the Convertible Subordinated  Debentures
to  be distributed to the holders of the Preferred Securities in connection with
the liquidation of St. Paul Capital.  See "Description of Securities Offered  --
Preferred  Securities -- Special Event Distribution"  and "-- Description of the
Convertible Subordinated Debentures".

                                       19
<PAGE>
                                USE OF PROCEEDS

    St. Paul  Capital  will  invest  the  proceeds  from  the  Offering  in  the
Convertible  Subordinated  Debentures.  The  St.  Paul,  after  payment  of  the
Underwriters' Compensation and other expenses of the Offering, will use the  net
proceeds  of  $180,000,000  ($207,000,000  if  the  Underwriters' over-allotment
option is  exercised in  full) from  the sale  of the  Convertible  Subordinated
Debentures to St. Paul Capital for general corporate purposes, which may include
possible  acquisitions and the reduction of outstanding commercial paper bearing
interest at rates ranging between 6% and 7%. Pending such use, the net  proceeds
may be temporarily invested in short-term debt obligations.

               RATIO OF EARNINGS TO FIXED CHARGES OF THE COMPANY

<TABLE>
<CAPTION>
                                               THREE MONTHS
                                                  ENDED
                                                MARCH 31,                             YEARS ENDED DECEMBER 31,
                                         ------------------------  ---------------------------------------------------------------
                                            1995         1994         1994         1993        1992(1)       1991         1990
                                            -----        -----        -----        -----     -----------     -----        -----

<S>                                      <C>          <C>          <C>          <C>          <C>          <C>          <C>
Ratio of earnings to fixed charges.....        9.49         5.69         9.99         8.96       --             9.06         9.26
Ratio of earnings to combined fixed
 charges and preferred stock
 dividends.............................        7.53         4.51         7.73         6.99       --             7.06         7.19
<FN>
- ------------------------
(1)  The  1992 loss was  inadequate to cover "fixed  charges" by $229.6 million,
     and "combined  fixed  charges  and preferred  stock  dividends"  by  $248.0
     million.
</TABLE>

Earnings  consist  of income  before  income taxes  plus  fixed charges,  net of
capitalized interest. Fixed charges consist of interest expense before reduction
for capitalized interest and one-third of rental expense, which is considered to
be representative of an interest factor.

                                       20
<PAGE>
                                 CAPITALIZATION

    The following table sets forth the  debt and capitalization of The St.  Paul
at  March 31, 1995, and as adjusted  to reflect the consummation of the offering
made hereby, assuming  no exercise of  the Underwriters' over-allotment  option.
The  table  should  be  read  in  conjunction  with  the  consolidated financial
statements of  The  St. Paul  incorporated  by  reference herein.  See  "Use  of
Proceeds,"   "Selected  Financial  and  Operating  Data,"  and  "Description  of
Securities Offered -- Preferred Securities".

<TABLE>
<CAPTION>
                                                                        MARCH 31, 1995
                                                                   ------------------------
                                                                     ACTUAL    AS ADJUSTED
                                                                   ----------  ------------
                                                                    (DOLLARS IN THOUSANDS)

<S>                                                                <C>         <C>
Commercial paper.................................................  $  284,119   $  284,119
Medium-term notes................................................     204,434      204,434
9 3/8% notes.....................................................      99,974       99,974
Guaranteed ESOP debt.............................................      33,334       33,334
Pound sterling loan notes........................................       6,317        6,317
                                                                   ----------  ------------
    Total debt...................................................     628,178      628,178
                                                                   ----------  ------------
Company-obligated minority interest in St. Paul Capital (holding
 $180 million principal amount Convertible Subordinated
 Debentures).....................................................          --      180,000
Preferred Stock:
Series B convertible preferred stock, 1,450,000 shares
 authorized; 1,012,496 shares issued and outstanding.............     145,709      145,709
Guaranteed obligation -- PSOP....................................    (137,589)    (137,589)
                                                                   ----------  ------------
    Net convertible preferred stock..............................       8,120        8,120
                                                                   ----------  ------------
Common shareholders' equity:
Common stock, without par value, 240,000,000 shares authorized;
 84,202,417 shares issued and outstanding........................     449,863      449,863
Retained earnings................................................   2,436,682    2,436,682
Guaranteed obligation -- ESOP....................................     (40,627)     (40,627)
Unrealized appreciation of investments...........................     199,908      199,908
Unrealized loss on foreign currency translation..................     (37,025)     (37,025)
                                                                   ----------  ------------
    Total common shareholders' equity............................   3,008,801    3,008,801
                                                                   ----------  ------------
    Total capitalization.........................................  $3,645,099   $3,825,099
                                                                   ----------  ------------
                                                                   ----------  ------------
</TABLE>

                                       21
<PAGE>
                     MARKET PRICES OF ST. PAUL COMMON STOCK

    St. Paul Common Stock is traded on  the NYSE under the symbol "SPC". At  May
1,  1995,  there were  7,647  holders of  record of  St.  Paul Common  Stock and
84,373,672 shares outstanding. The following table  sets forth the high and  low
sale  prices for St. Paul Common Stock, as reported by the NYSE, for the periods
indicated. All amounts presented reflect the effect of a two-for-one stock split
in 1994.

<TABLE>
<CAPTION>
                                                                                        CASH
                                                                                      DIVIDEND
CALENDAR YEAR                                                    HIGH        LOW      DECLARED
- --------------------------------------------------------------- -------    -------   -----------
<S>                                                             <C>        <C>       <C>
1993:
  1st Quarter.................................................. $41 5/8    $37 3/4    $     .35
  2nd Quarter..................................................  41 7/16    39 1/4          .35
  3rd Quarter..................................................  46 11/16   40 5/16         .35
  4th Quarter..................................................  48 1/2     43 1/4          .35
1994:
  1st Quarter.................................................. $44 3/8    $38 13/16  $    .375
  2nd Quarter..................................................  41 11/16   37 7/8         .375
  3rd Quarter..................................................  44 1/2     39 1/2         .375
  4th Quarter..................................................  45 1/8     40             .375
1995:
  1st Quarter.................................................. $51        $43 1/2    $     .40
  2nd Quarter (through May 1)..................................  51 7/8     47 3/4           --
</TABLE>

    Cash dividends paid  in 1993 and  1994 were  $1.39 per share  and $1.48  per
share,  respectively. For the price of the St.  Paul Common Stock as of a recent
date, see the cover page of this Prospectus.

                         THE ST. PAUL'S DIVIDEND POLICY

    The St. Paul paid a cash dividend of $.40 per share for the first quarter of
1995 and has declared a cash dividend  of $.40 per share for the second  quarter
of 1995. The St. Paul paid a cash dividend of $.375 per share in respect of each
quarter  of 1994. All amounts have been  adjusted to reflect a two-for-one stock
split in 1994.  The levels  of future  payments will  be determined  by The  St.
Paul's  Board of Directors based on such considerations as the level of earnings
from operations, capital requirements and the financial condition and  prospects
of  The St. Paul. The St. Paul and its majority-owned subsidiaries would also be
prohibited from paying dividends on St. Paul  Common Stock at any time during  a
deferral  of  interest payments  with  respect to  the  Convertible Subordinated
Debentures, when there is an Event of Default (as defined under "Description  of
Securities  Offered -- Description of the Convertible Subordinated Debentures --
Events of Default") under  the Convertible Subordinated  Debentures or when  The
St.  Paul  has  failed to  make  a  payment required  under  the  Guarantee. See
"Description of Securities Offered  -- Description of  the Guarantee --  Certain
Covenants of The St. Paul".

                                       22
<PAGE>
                     SELECTED FINANCIAL AND OPERATING DATA

    The selected data presented below under the captions "Income Statement Data"
and  "Balance Sheet Data" for,  and as of the  end of, each of  the years in the
five-year period  ended December  31, 1994,  are derived  from the  consolidated
financial  statements of  the Company,  which consolidated  financial statements
have been  audited  by  KPMG  Peat Marwick  LLP,  independent  certified  public
accountants.  The consolidated financial statements as  of December 31, 1994 and
1993, and for  each of the  years in  the three-year period  ended December  31,
1994,  and the report  thereon, are incorporated by  reference elsewhere in this
prospectus. The  information presented  below  under the  caption  "Underwriting
Operations"  is unaudited. The  financial data for the  three months ended March
31, 1995 and 1994, respectively, have been derived from the Company's  unaudited
consolidated  financial statements, which, in the opinion of management, include
all adjustments (consisting of normal  recurring accruals) necessary for a  fair
presentation of the results of operations and financial position for the periods
and  as of the dates  presented. The results of  operations for the three months
ended March 31,  1995 may not  be indicative  of results for  the entire  fiscal
year. The table should be read in conjunction with "Overview of Results" and the
consolidated   financial  statements  and  the  notes  thereto  incorporated  by
reference in this Prospectus. Numbers of shares and per share figures reflect  a
two-for-one stock split in June 1994.

<TABLE>
<CAPTION>
                                                THREE MONTHS
                                              ENDED MARCH 31,                           YEAR ENDED DECEMBER 31,
                                          ------------------------  ---------------------------------------------------------------
                                             1995         1994         1994         1993         1992         1991         1990
                                          -----------  -----------  -----------  -----------  -----------  -----------  -----------
                                                                (DOLLARS IN THOUSANDS, EXCEPT PER SHARE DATA)
<S>                                       <C>          <C>          <C>          <C>          <C>          <C>          <C>
INCOME STATEMENT DATA:
Premiums earned.........................  $   946,070  $   845,402  $ 3,412,081  $ 3,178,338  $ 3,143,246  $ 3,146,238  $ 2,893,959
Net investment income...................      186,389      168,408      694,594      661,106      666,374      675,604      669,989
Insurance brokerage fees and
 commissions............................       67,061       66,450      303,152      283,680      280,836      284,702      256,354
Investment banking-asset management.....       53,616       53,598      211,789      241,730      218,825      175,610      126,607
Realized gains(1).......................        2,977       21,783       41,974       58,254      155,735       38,008        9,864
Other...................................       11,346        8,134       37,695       37,064       33,676       31,538       48,464
                                          -----------  -----------  -----------  -----------  -----------  -----------  -----------
    Total revenues......................    1,267,459    1,163,775    4,701,285    4,460,172    4,498,692    4,351,700    4,005,237
                                          -----------  -----------  -----------  -----------  -----------  -----------  -----------
Insurance losses and loss adjustment
 expenses...............................      680,439      667,688    2,461,698    2,303,738    2,690,046    2,365,569    2,119,776
Policy acquisition, operating and
 administrative expenses(2).............      427,296      404,269    1,636,428    1,593,063    1,998,156    1,422,511    1,352,034
Interest expense........................       11,578        9,815       39,581       40,765       35,553       35,559       29,522
Income tax expense......................       37,550       17,566      120,750       94,997        7,458      122,999      112,635
Cumulative net benefit of accounting
 changes, net of taxes..................            0            0            0            0       76,483            0            0
                                          -----------  -----------  -----------  -----------  -----------  -----------  -----------
    Net income (loss)...................  $   110,596  $    64,437  $   442,828  $   427,609  $  (156,038) $   405,062  $   391,270
                                          -----------  -----------  -----------  -----------  -----------  -----------  -----------
                                          -----------  -----------  -----------  -----------  -----------  -----------  -----------
Fully diluted net income (loss) per
 common share...........................        $1.23        $0.71        $4.93        $4.73       $(1.94)       $4.50        $4.16
Cash dividends declared per common
 share..................................        $0.40       $0.375        $1.50        $1.40        $1.36        $1.30        $1.20
BALANCE SHEET DATA:
Total assets............................  $17,651,999  $16,741,009  $17,495,820  $17,149,196  $15,392,054  $14,744,717  $13,907,293
Total debt..............................      628,178      584,737      622,624      639,729      566,717      486,779      473,829
Change in unrealized appreciation of
 investments, net of taxes(3)...........      185,960     (311,937)    (574,896)     525,175      (23,815)      55,093      (67,558)
Common shareholders' equity.............    3,008,801    2,690,833    2,732,934    3,005,128    2,202,499    2,532,841    2,196,371
Book value per common share.............        35.67        32.02        32.46        35.47        26.18        29.78        26.00
Number of common shares outstanding.....   84,341,306   84,041,142   84,202,417   84,714,676   84,118,554   85,042,484   84,468,058
UNDERWRITING OPERATIONS:
GAAP underwriting result................  $   (15,452) $   (83,057) $  (113,008) $  (150,255) $  (566,886) $  (163,782) $  (120,730)
Statutory combined ratio:(4)............
  Loss and loss expense ratio...........         71.9         79.0         72.1         72.5         85.6         75.2         73.2
  Underwriting expense ratio............         30.4         31.2         30.2         32.0         32.2         29.4         30.0
                                          -----------  -----------  -----------  -----------  -----------  -----------  -----------
  Combined ratio........................        102.3        110.2        102.3        104.5        117.8        104.6        103.2
                                          -----------  -----------  -----------  -----------  -----------  -----------  -----------
                                          -----------  -----------  -----------  -----------  -----------  -----------  -----------
Combined ratio including policyholders'
 dividends..............................        102.4        110.2        102.3        104.7        118.2        105.0        104.2
                                          -----------  -----------  -----------  -----------  -----------  -----------  -----------
                                          -----------  -----------  -----------  -----------  -----------  -----------  -----------
<FN>
- ------------------------------
(1)  1992  realized  gains  include $98  million  from  the sale  of  a minority
     interest in The John Nuveen Company.
(2)  1992  operating  and  administrative   expenses  include  a  $365   million
     write-down  of  the goodwill  associated with  the Company's  investment in
     Minet.
(3)  The change  for  1993 includes  an  increase of  $502  million due  to  the
     adoption   of  Statement   of  Financial  Accounting   Standards  No.  115,
     "Accounting for Certain Investments in Debt and Equity Securities".
(4)  The combined ratio is not  derived from the audited consolidated  financial
     statements.
</TABLE>

                                       23
<PAGE>
                              OVERVIEW OF RESULTS

THREE MONTHS ENDED MARCH 31, 1995 AND 1994

    The Company's consolidated net income for the first three months of 1995 was
$110.6 million compared with net income of $64.4 million in the first quarter of
1994.  The improvement over 1994 occurred  in the Company's underwriting segment
and was largely  the result  of a $73.6  million decline  in pretax  catastrophe
losses. The Company's insurance brokerage results deteriorated compared with the
first  quarter  of  1994,  while  investment  banking-asset  management earnings
improved slightly over those in the same period of 1994.

    The Company's operating  earnings, which exclude  after-tax realized  gains,
were  $108.5 million, or $1.20 per share, in the first quarter of 1995, compared
with operating earnings of $49.6 million, or $.55 per share, in the first  three
months of 1994.

    Consolidated  revenues  of  $1.3  billion  for  the  first  quarter  of 1995
increased 9% over 1994  first quarter revenues of  $1.2 billion. An increase  in
insurance  premiums  earned was  the  primary factor  in  the growth  over 1994.
Insurance brokerage  and investment  banking-asset  management revenues  in  the
first  quarter of 1995 were  essentially level with those  in the same period of
1994.

    The St. Paul's consolidated assets at March 31, 1995 totaled $17.7  billion,
and  common  shareholders' equity  was $3.0  billion.  The comparable  totals at
December 31,  1994  were  $17.5  billion and  $2.7  billion,  respectively.  The
increase  in  shareholders' equity  resulted  from the  Company's  first quarter
earnings and  a  $161.4  million  increase (net  of  taxes)  in  the  unrealized
appreciation of the Company's fixed maturities portfolio since the end of 1994.

  UNDERWRITING

    Consolidated written premiums of $916.4 million in the first quarter of 1995
were  14% higher  than first  quarter 1994  premiums of  $804.6 million. Premium
volume in the Company's Reinsurance underwriting operation was nearly double the
comparable 1994 total, primarily due  to favorable market conditions,  additions
of  business resulting from the Company's October  1994 acquisition of a book of
property-liability reinsurance business from  a subsidiary of CIGNA  Corporation
and  a change  in estimated premiums  in the first  quarter of 1994  made in the
ordinary course of business. Commercial written premiums grew 21% over the first
quarter of  1994,  driven by  new  business  in several  classes  of  commercial
coverages. Medical Services written premiums declined 18% from the first quarter
of  1994 due primarily to a  change in policy terms from  six months to one year
for much of the physicians and surgeons segment of the business.

    The consolidated  GAAP  underwriting loss  of  $15.5 million  in  the  first
quarter  of 1995 was a significant improvement  over the first quarter 1994 loss
of $83.1 million. Pretax  catastrophe losses in the  first quarter of 1995  were
$16.1  million, compared with  catastrophe losses of $89.7  million in the first
quarter of 1994,  which were driven  by an earthquake  in California and  winter
storms on the East Coast.

    Pretax  earnings in the  underwriting segment totaled  $160.2 million in the
first quarter of 1995, compared with $88.5 million in the first three months  of
1994,  reflecting the improved underwriting results and a $13.9 million increase
in investment  income.  Total fixed  maturity  investments in  the  underwriting
segment  have increased by  nearly $390 million  in the last  twelve months. The
average yield on taxable fixed maturities purchased in the first quarter of 1995
was 8.5%,  compared  with 6.4%  in  the first  quarter  of 1994.  Taxable  fixed
maturities  have constituted the majority  of the Company's investment pruchases
for the last several years.

  INSURANCE BROKERAGE

    Minet incurred a pretax loss of $14.6 million in the first quarter of  1995,
compared  with  a pretax  loss of  $9.0 million  in the  first quarter  of 1994.
Minet's brokerage fees and commissions in the first quarter were level with  the
same  period in  1994; however, total  expenses increased $7.5  million in 1995.
Salary and related expenses increased $4.9 million, a 9% increase over the level
in the first quarter of 1994,

                                       24
<PAGE>
primarily due to Minet's  ongoing effort to  develop new business  opportunities
through  the  expansion of  its specialty  broker  staff. Minet's  first quarter
revenues are generally lower  than revenues in the  remaining three quarters  of
the year due to the timing of account renewals.

  INVESTMENT BANKING-ASSET MANAGEMENT

    The St. Paul's 77% portion of The John Nuveen Company's first quarter pretax
earnings  was $19.4 million, compared with $17.3 million in the first quarter of
1994. Asset management fees declined slightly compared with the first quarter of
1994, but underwriting and distribution  revenues increased by $5.1 million  due
to inventory positioning profits resulting from more favorable market conditions
in  1995. Total assets under management of  $31.2 billion at March 31, 1995 were
virtually level with the same time in 1994. However, managed assets grew by $1.5
billion since year-end  1994, primarily  due to  an increase  in the  underlying
value of fund investments.

YEARS ENDED DECEMBER 31, 1994 AND 1993

    In  1994,  a year  marked  by highly  competitive  market conditions  in the
property-liability  insurance   industry,   the  Company   achieved   its   best
underwriting  result  since 1988  and recorded  its  second consecutive  year of
record earnings. The  primary contributor  to pretax  earnings in  1994 was  the
underwriting segment, where fundamental improvements in underwriting performance
offset  catastrophe losses that  were the third-worst  in the Company's history.
The St. Paul's insurance brokerage  operation, Minet continued to make  progress
in  realigning  its business  structure,  while a  difficult  market environment
resulted in a decline in the earnings for Nuveen after its record results in the
prior year.

    Net income of  $443 million  in 1994  was the  highest annual  total in  the
Company's history, surpassing 1993's previous record of $428 million. Net income
in  1993 included  an income  tax benefit  of $15  million, or  $0.17 per share,
resulting from the impact of  an increase in the  statutory federal tax rate  on
The St. Paul's deferred tax asset.

    The   Company's  operating   earnings,  which   exclude  after-tax  realized
investment gains, were  $414 million  in 1994,  compared with  earnings of  $387
million in 1993 and a loss of $334 million in 1992.

    Consolidated revenues increased 5% in 1994 to $4.7 billion from $4.5 billion
in  1993, as increases  in premiums earned, net  investment income and insurance
brokerage  fees  and  commissions  more  than  offset  declines  in   investment
banking-asset management revenues and realized gains.

    The St. Paul's consolidated assets totaled $17.5 billion at the end of 1994,
compared  with total assets  of $17.1 billion  at year-end 1993.  A $1.2 billion
underlying increase in  total assets  was partially  offset by  an $848  million
decline  in unrealized appreciation  on the Company's  fixed maturity portfolio,
due to  rising  interest  rates in  1994.  The  St. Paul  adopted  Statement  of
Financial  Accounting  Standards  ("SFAS")  No.  115,  "Accounting  for  Certain
Investments in Debt and Equity Securities,"  as of December 31, 1993, and  began
recording  its fixed maturity portfolio at estimated market value on the balance
sheet. At that time, with interest rates  at a 20-year low, the market value  of
that  portfolio exceeded its  amortized cost by $763  million. The year-end 1994
market value was $85 million below amortized cost. The adoption of SFAS No.  115
had no effect on net income.

  UNDERWRITING

    Consolidated  written premiums  of $3.6 billion  in 1994 grew  14% over 1993
premiums of $3.2 billion. Premium growth was centered in The St. Paul's Personal
& Business Insurance  operation, which included  the results of  Economy Fire  &
Casualty Company ("Economy"), acquired in August 1993, for a full twelve months,
and  in  the  Reinsurance operation,  as  a  result of  price  increases, higher
retentions and new business.

                                       25
<PAGE>
    The following table sets forth The St. Paul's consolidated GAAP underwriting
results and combined  ratios for  the years ended  December 31,  1994, 1993  and
1992,   respectively,  and  the   quarters  ended  March   31,  1995  and  1994,
respectively,  and  illustrates   fundamental  underwriting  performance   after
factoring out the impact of catastrophes in each such period.

<TABLE>
<CAPTION>
                                                        THREE MONTHS
                                                           ENDED                    YEAR ENDED
                                                         MARCH 31,                 DECEMBER 31,
                                                    --------------------  -------------------------------
                                                      1995       1994       1994       1993       1992
                                                    ---------  ---------  ---------  ---------  ---------
                                                                    (DOLLARS IN MILLIONS)
<S>                                                 <C>        <C>        <C>        <C>        <C>
Actual:
  GAAP underwriting results.......................  $     (15) $     (83) $    (113) $    (150) $    (567)
  Combined ratio..................................      102.3      110.2      102.3      104.5      117.8
Adjustment:
  Catastrophe losses..............................  $     (16) $     (90) $    (105) $     (62) $    (305)
  Impact on combined ratio........................        1.7       10.6        3.1        1.9        9.7
                                                    ---------  ---------  ---------  ---------  ---------
Excluding catastrophe losses:
  GAAP underwriting loss..........................  $       1  $       7  $      (8) $     (88) $    (262)
  Combined ratio..................................      100.6       99.6       99.2      102.6      108.1
                                                    ---------  ---------  ---------  ---------  ---------
</TABLE>

    In  1994, an  earthquake in  California, winter  ice storms  and summer hail
storms resulted in increased catastrophe losses over 1993, a year in which major
catastrophes were  relatively few.  Hurricane Andrew  was the  most  significant
catastrophe in 1992, severely impacting results in the underwriting segment.

    The  St. Paul's Reinsurance and  Specialized Commercial operations have been
the primary  contributors  to  the improvement  in  noncatastrophe  underwriting
performance  since  1992. In  both  operations, The  St.  Paul has  undertaken a
variety of pricing and underwriting actions designed to reduce the volatility of
underwriting results and further  improve the quality of  the book of  business.
The  Company's  successful efforts  to  restrain expense  growth  throughout the
underwriting segment  have also  played a  major role  in improved  underwriting
results.  The St. Paul's underwriting expense  ratio improved 1.8 points in 1994
to 30.2 from  32.0 in 1993,  due to improved  organizational efficiency and  the
acquisition  of  Economy. The  Company  continued to  restructure  its principal
insurance underwriting subsidiary St. Paul Fire and Marine Insurance Company  in
1994,  an effort that began  in 1993 with the goal  of creating a more efficient
and customer-focused organization  by streamlining the  processes through  which
The  St. Paul acquires business and provides  service to customers. In 1993, the
Company recorded restructuring charges of  $21 million, primarily consisting  of
severance   and  relocation  expenses.  The  St.  Paul  incurred  no  additional
restructuring charges in 1994.

    Pretax earnings in the  underwriting segment of  $561 million increased  11%
over  1993  pretax  income  of $507  million,  reflecting  improved underwriting
results and increased investment income.  Pretax investment income totaled  $675
million  in 1994, compared with $646 million  and $642 million in 1993 and 1992,
respectively. The increase in 1994 reflected the inclusion of Economy for a full
year. For several years  prior to 1994, investment  income levels were  stagnant
due to a sustained period of falling interest rates.

                                       26
<PAGE>
    The  following table  summarizes written premiums,  underwriting results and
combined ratios for each of The St. Paul's underwriting operations for the  last
three  years and for  the first quarters of  1995 and 1994.  Figures are on GAAP
basis, except for combined ratios, which are not derived from the GAAP financial
statements. Several  reclassifications  have been  made  to the  1993  and  1992
information to conform to the 1994 presentation.

<TABLE>
<CAPTION>
                                                                 UNDERWRITING RESULTS BY OPERATION
                                                           THREE MONTHS                  YEAR ENDED
                                       % OF 1994         ENDED MARCH 31,                DECEMBER 31,
                                        WRITTEN      ------------------------  -------------------------------
                                        PREMIUMS       1995(1)      1994(1)      1994       1993       1992
                                     --------------  -----------  -----------  ---------  ---------  ---------
                                                                       (DOLLARS IN MILLIONS)
<S>                                  <C>             <C>          <C>          <C>        <C>        <C>
Specialized Commercial
  Written premiums.................           30%     $     284    $     263   $   1,086  $   1,000  $   1,058
  Underwriting result..............                   $     (20)   $     (34)  $     (89) $    (116) $    (244)
  Combined ratio...................                       106.7        110.4       107.1      111.9      123.2
                                                     -----------  -----------  ---------  ---------  ---------
Personal & Business Insurance
  Written premiums.................           21%     $     151    $     144   $     747  $     486  $     350
  Underwriting result..............                   $      (7)   $     (11)  $     (35) $     (29) $     (63)
  Combined ratio...................                       104.5        107.5       104.6      105.8      117.7
                                                     -----------  -----------  ---------  ---------  ---------
Medical Services
  Written premiums.................           19%     $     136    $     165   $     690  $     710  $     712
  Underwriting result..............                   $      26    $      34   $     118  $     133  $     152
  Combined ratio...................                        85.2         80.5        80.3       80.0       78.6
                                                     -----------  -----------  ---------  ---------  ---------
Commercial
  Written premiums.................           11%     $     146    $     121   $     418  $     380  $     499
  Underwriting result..............                   $      (4)   $     (34)  $     (54) $     (58) $    (123)
  Combined ratio...................                       102.6        128.1       112.6      115.4      123.9
                                                     -----------  -----------  ---------  ---------  ---------
    Total Fire and Marine
    Written premiums...............           81%     $     717    $     693   $   2,941  $   2,576  $   2,619
    Underwriting result............                   $      (5)   $     (45)  $     (60) $     (70) $    (278)
    Combined ratio.................                       101.1        105.6       101.0      102.6      110.5
                                                     -----------  -----------  ---------  ---------  ---------
Reinsurance
  Written premiums.................           14%     $     156    $      81   $     513  $     431  $     343
  Underwriting result..............                   $      (5)   $     (29)  $     (22) $     (18) $    (241)
  Combined ratio...................                       104.5        134.3       105.1      103.1      166.3
                                                     -----------  -----------  ---------  ---------  ---------
International
  Written premiums.................            5%     $      43    $      31   $     169  $     172  $     180
  Underwriting result..............                   $      (5)   $      (9)  $     (31) $     (62) $     (48)
  Combined ratio...................                       113.5        128.9       117.6      135.9      132.1
                                                     -----------  -----------  ---------  ---------  ---------
    Total
    Written premiums...............          100%     $     916    $     805   $   3,623  $   3,179  $   3,142
    Underwriting result............                   $     (15)   $     (83)  $    (113) $    (150) $    (567)
    Combined ratio:
      Loss and loss expense
       ratio.......................                        71.9         79.0        72.1       72.5       85.6
      Underwriting expense ratio...                        30.4         31.2        30.2       32.0       32.2
                                                     -----------  -----------  ---------  ---------  ---------
      Combined ratio...............                       102.3        110.2       102.3      104.5      117.8
                                                     -----------  -----------  ---------  ---------  ---------
    Combined ratio including
     policyholders' dividends......                       102.4        110.2       102.3      104.7      118.2
                                                     -----------  -----------  ---------  ---------  ---------
</TABLE>

- ------------------------
(1)  During the first quarter of 1995, the commercial underwriting operations of
    Personal &  Business  Insurance  ($27  million  in  written  premiums)  were
    transferred  to  Commercial. This  included the  commercial package  line of
    business and commercial business written  by Economy Fire & Casualty.  First
    quarter 1994 was reclassified to reflect this new presentation. However, the
    annual  information  for  the  years  1994,  1993  and  1992  has  not  been
    reclassified to reflect this change.

                                       27
<PAGE>
  INSURANCE BROKERAGE

    The St. Paul's insurance brokerage subsidiary, Minet, provides insurance and
reinsurance broking and risk advisory services for major corporations and  large
professional organizations worldwide. In recent years, Minet's operating results
have  been negatively impacted by excess capacity in worldwide insurance markets
and the increasing trend  away from commissions  and toward fees  as a basis  of
determining prices for services performed. Minet's pretax loss of $10 million in
1994 represented a slight improvement over 1993 losses of $13 million. Brokerage
fees  and commissions increased 7% to $316 million in 1994, reflecting growth in
Minet's reinsurance and wholesale  brokerage operations and additional  revenues
contributed  by  several  newly  acquired  specialty  brokerage  firms. Expenses
increased in  1994 as  a result  of the  expansion of  retail specialty  broking
teams.

  INVESTMENT BANKING-ASSET MANAGEMENT

    Nuveen,  in which  The St.  Paul held  a 77%  interest at  December 31, 1994
comprises The  St. Paul's  investment banking-asset  management segment.  Nuveen
markets tax-exempt open-end and closed-end (exchange-traded) managed fund shares
and  provides investment advice  to and administers the  business affairs of its
family of managed funds. Nuveen also underwrites and trades municipal bonds  and
tax-exempt unit investment trusts ("UITs") and provides pricing and surveillance
services  to  its UITs.  Rising interest  rates,  declining municipal  new issue
volume and  increased  investor  uncertainty  resulting  from  the  increase  in
interest  rates caused Nuveen's  total revenues to  decline 10% in  1994 to $220
million from  $246  million  in  1993.  Revenues  in  1992  were  $221  million.
Investment  advisory fees earned on managed assets increased slightly over 1993.
Distribution revenues fell by $23 million, or 70%, from 1993 due to the  decline
in  the value of municipal bonds and interests  in UITs held for future sale and
the decline  in new  investment product  sales  in 1994.  The increase  in  1993
revenues  resulted primarily from growth in  asset management fees. Total assets
under management fell to $29.7 billion at  the end of 1994, compared with  $32.7
billion at the end of 1993 and $27.3 billion at the end of 1992.

    Nuveen's  pretax earnings in 1994  of $95 million were  the third highest in
its history.  Earnings in  1993 and  1992  were $112  million and  $98  million,
respectively.  The St. Paul's consolidated  results include Nuveen's earnings to
the extent of  the Company's  ownership percentage.  The St.  Paul's portion  of
Nuveen's  earnings in each of  those years was $72  million, $83 million and $82
million, respectively.

                                       28
<PAGE>
                                    BUSINESS

GENERAL DESCRIPTION

    The St. Paul  is incorporated as  a general business  corporation under  the
laws  of  the  State  of  Minnesota.  The  St.  Paul  Companies,  Inc.  and  its
subsidiaries comprise one of  the oldest insurance  organizations in the  United
States,  dating back to 1853.  The St. Paul is  a management company principally
engaged,   through    its   subsidiaries,    in   three    industry    segments:
property-liability  insurance underwriting (primarily through  St. Paul Fire and
Marine Insurance Company), insurance brokerage (primarily through The St. Paul's
brokerage subsidiary, Minet)  and investment  banking-asset management  (through
the Company's 77 percent stake in Nuveen). As a management company, The St. Paul
oversees  the operations  of its  subsidiaries and  provides them  with capital,
management and administrative services.  According to "Fortune" magazine's  most
recent  rankings, in terms  of total assets,  The St. Paul  was the 25th largest
diversified financial company  in the  United States  at December  31, 1993.  At
March  23, 1995, The St. Paul and its subsidiaries employed approximately 12,900
persons.

    The St. Paul's primary business  is insurance underwriting, which  accounted
for  88% of  consolidated revenues in  1994. Insurance  brokerage and investment
banking-asset management  operations accounted  for 7%  and 5%  of  consolidated
revenues,  respectively, in 1994.  The St. Paul conducts  its business in highly
competitive markets and The St. Paul's results can be affected by many  factors,
including  seasonal trends in premium volume and  the size, number and timing of
catastrophe losses. As a result, net income, operating earnings and consolidated
revenues can vary significantly  from period to period  and interim results  may
not necessarily be representative of the full year results of operations.

    The  St. Paul  depends primarily on  dividends from its  subsidiaries to pay
dividends to its shareholders, service its debt and pay expenses. Various  state
laws and regulations limit the amount of dividends The St. Paul may receive from
St.  Paul Fire and Marine Insurance Company. In 1995, approximately $312 million
will be available for  dividends free from such  restrictions. During 1994,  The
St.  Paul received  cash dividends of  approximately $201 million  from St. Paul
Fire and Marine Insurance Company.

    The following  table  lists  the  sources of  The  St.  Paul's  consolidated
revenues for each of the last three years:

<TABLE>
<CAPTION>
                                                                             PERCENTAGE OF
                                                                         CONSOLIDATED REVENUES
                                                                   ----------------------------------
                                                                      1994        1993        1992
                                                                   ----------  ----------  ----------
<S>                                                                <C>         <C>         <C>
INSURANCE UNDERWRITING OPERATIONS:
  Fire and Marine:
  Specialized Commercial.........................................       21.6%       22.7%       23.4%
  Personal & Business............................................       15.7        10.9         7.6
  Medical Services...............................................       13.6        15.4        16.0
  Commercial.....................................................        8.1         9.4        12.0
                                                                       -----       -----       -----
    Total Fire and Marine........................................       59.0        58.4        59.0
  REINSURANCE....................................................       10.3         8.9         8.0
  INTERNATIONAL..................................................        3.3         4.0         2.9
  Net Investment Income..........................................       14.4        14.5        14.3
  Realized Investment Gains......................................        0.7         1.1         1.3
  Other..........................................................        0.6         0.7         0.5
                                                                       -----       -----       -----
    Total Insurance Underwriting.................................       88.3        87.6        86.0
INSURANCE BROKERAGE..............................................        7.4         7.2         7.3
INVESTMENT BANKING -- ASSET MANAGEMENT...........................        4.7         5.5         4.9
Parent Company and Eliminations..................................       (0.4)       (0.3)        1.8
                                                                       -----       -----       -----
    Total........................................................      100.0%      100.0%      100.0%
                                                                       -----       -----       -----
                                                                       -----       -----       -----
</TABLE>

                                       29
<PAGE>
INSURANCE UNDERWRITING OPERATIONS

    The  St. Paul's insurance  underwriting business is  conducted through three
principal  operations.  The  St.  Paul   conducts  its  U.S.  direct   insurance
underwriting  operations  under the  name St.  Paul Fire  and Marine  ("Fire and
Marine"). Fire  and  Marine underwrites  property  and liability  insurance  and
provides insurance-related products and services to commercial, professional and
individual  customers throughout the  United States. The  St. Paul's reinsurance
business operates under the name St. Paul Re, which underwrites reinsurance  for
North   American  and   international  insurance   companies.  The   St.  Paul's
International Underwriting division offers primary property- liability insurance
coverages in the  United Kingdom  and in other  selected international  markets,
primarily Canada and Western Europe.

    The  primary sources of  the underwriting operations'  revenues are premiums
earned from  insurance  and reinsurance  policies  and income  earned  from  the
investment portfolio. According to the most recent industry statistics published
in "Best's Review" with respect to property-liability insurers doing business in
the  United States,  The St. Paul's  underwriting operations ranked  15th on the
basis of 1993 written premiums. The insurance underwriting business is generally
characterized by mature markets, numerous market participants, and intense price
and other competition. These industry  factors, which are expected to  continue,
make it difficult for the Company to achieve premium growth.

  SPECIALIZED COMMERCIAL

    This  is  the largest  of  Fire and  Marine's  operations, based  on written
premiums, and includes a number of individual underwriting operations  organized
according  to market segments or along product lines. Specialized Commercial, in
general, provides coverage for damage  to the customer's property (fire,  inland
marine  and auto),  liability for  bodily injury  or damage  to the  property of
others (general  liability, auto  liability and  excess), workers'  compensation
insurance,  and  various  professional liability  coverages.  Operations serving
particular market segments consist  of the following: Construction,  Technology,
Financial  Services,  National Accounts  (large  businesses), and  Public Sector
Services (government  entities). The  following operations  are organized  along
specific product lines: The Surety operation underwrites surety bonds, primarily
for  construction  contractors,  which  guarantee  that  third  parties  will be
indemnified against  the nonperformance  of  contractual obligations.  Based  on
estimated  1994  premium  data,  Fire  and  Marine's  surety  operation  is  the
second-largest underwriter  of surety  bonds  in the  United States.  The  Ocean
Marine  operation provides a variety of property and liability insurance related
to ocean  and  inland  waterways  traffic, including  cargo  and  hull  property
protection.  The Professional  Liability operation markets  errors and omissions
coverage for  lawyers,  insurance  agents and  other  nonmedical  professionals,
including  directors  and  officers.  The  Surplus  Lines  operation underwrites
products liability insurance, umbrella and excess liability coverages,  property
insurance for high-risk classes of business, and coverages for unique, sometimes
one-of-a-kind  risks. The Special Property operation provides property insurance
programs for large commercial accounts.

    Specialized Commercial  also  includes  the results  of  Fire  and  Marine's
participation  in insurance  pools and  associations, which  provide specialized
underwriting skills and  risk management  services for the  classes of  business
that  they  underwrite.  These  pools and  associations  serve  to  increase the
underwriting capacity  of the  participating  companies for  insurance  policies
where  the concentration of risk is so high or the amount so large that a single
company could not prudently accept the entire risk.

    Management's strategies  for  1995  vary among  specialty  areas,  based  on
expected  market conditions. In  Ocean Marine, Surplus  Lines, and Public Sector
Services, The St. Paul expects moderate growth as a result of current  favorable
market  conditions.  In  the  Financial  Services,  Professional  Liability  and
Technology sectors, efforts  will focus  on developing new  products that  offer
innovative coverages and superior service, while in the Construction, Surety and
National  Accounts  sectors,  The  St.  Paul's  objective  will  be  to  deliver
high-quality loss control and claim  service and innovative coverage options  to
customers; the Company does not expect significant growth in these areas.

  PERSONAL & BUSINESS INSURANCE

    This  operation  provides  property and  liability  insurance  coverages for
individuals and small-business  owners. For individuals,  a variety of  monoline
and package policies are offered to protect personal

                                       30
<PAGE>
property  such as homes, automobiles  and boats, as well  as to provide coverage
for personal liability. For small-business owners, Personal & Business Insurance
markets  general  commercial  property  and  liability  coverages  for  offices,
retailers  and family restaurants. Economy, a personal insurance underwriter, is
included in this operation and is in the process of being fully integrated  into
Fire and Marine's existing personal insurance operations. The personal and small
commercial  market  environment  is  becoming  increasingly  competitive, making
significant premium growth  unlikely. Consequently, management's  focus in  1995
will be on improving operating efficiency, including further integrating Economy
with  The St.  Paul's other  personal lines  operations, while  maintaining high
customer satisfaction. The Company  intends to lower its  expense ratio in  this
sector as a result of reduced headcount and improved operating efficiencies.

  MEDICAL SERVICES

    Medical  Services underwrites  professional liability,  property and general
liability insurance  for the  health  care industry  delivery system.  Fire  and
Marine  is  the largest  medical liability  insurer in  the United  States, with
premium volume representing  approximately 12%  of the United  States market  in
1993  based on premium data published in "Best's Review". While Medical Services
premium volume  declined slightly  in 1994,  underwriting profit  exceeded  $100
million for the fifth consecutive year. The Company has identified objectives in
several  areas: increasing physicians and surgeons professional liability market
share in states where Medical Services  has either not offered this coverage  or
has  not focused on developing significant  market share; continued expansion in
the long-term care industry; and opportunities arising from the  consolidations,
mergers  and acquisitions  that mark the  current evolving  health care delivery
system. Premium volume in 1995 is expected to be comparable to that in 1994, and
The St.  Paul expects  Medical Services  to  continue to  make a  strong  profit
contribution in 1995.

  COMMERCIAL

    Fire  and  Marine's Commercial  underwriting  operation offers  property and
liability  insurance  to  midsize  commercial  enterprises.  Coverages  marketed
include  package, general  liability, umbrella and  excess liability, commercial
auto and  fire, inland  marine and  workers' compensation.  Commercial  premiums
increased approximately 10% in 1994, and the underwriting loss declined slightly
from  1993. Commercial  will continue  to pursue  new business  while seeking to
maintain its underwriting  discipline. After  the recent  restructuring of  this
operation,  the Company's objective is to maintain a favorable loss ratio and to
reduce the expense ratio, thereby improving results in this line. Due to  market
conditions,  The St. Paul does not  anticipate significant premium growth in the
Commercial line.

  REINSURANCE

    St. Paul  Re  underwrites reinsurance  in  both domestic  and  international
insurance  markets  (referred to  as "assumed  reinsurance"). Reinsurance  is an
agreement between  insurance  companies to  transfer  risks. According  to  data
published  by the Reinsurance Association of America,  St. Paul Re ranked as the
eighth largest U.S. reinsurance underwriter based on written premium volume  for
the  first nine months of 1994. The Company expects additional premium growth as
a result of its  agreement in late  1994 to purchase  the book of  international
property-liability reinsurance from a reinsurance underwriting subsidiary of the
CIGNA  Corporation.  Management intends  to  achieve growth  without sacrificing
pricing adequacy  by  targeting  certain  specific  initiatives.  A  significant
contributor  to premium growth in 1995 will be  accounts taken on as a result of
the purchase of the international book  of business from CIGNA. The  opportunity
for  new and renewal accounts offered by this  book fits well with St. Paul Re's
strategy to expand the scope and characteristics of its international business.

  INTERNATIONAL UNDERWRITING

    The International Underwriting operation includes primary insurance  written
outside  the United  States, mainly  the United  Kingdom, Canada,  Spain and the
Republic of Ireland. It also  includes insurance written for foreign  operations
of  multinational corporations based in the United States, and insurance written
to cover  exposures  in the  United  States for  foreign-based  companies.  This
operation  offers a range of commercial and personal lines products and services
tailored to  meet the  unique  needs of  customers  located outside  the  United
States.    The   Company's    plan   includes   expanding    by   product   line

                                       31
<PAGE>
and geographically, especially in Europe.  In Canada, International will  pursue
several specialty niche markets. In the United Kingdom, new business initiatives
will  focus  on specific  customer groups  in both  the commercial  and personal
market sectors. The reduction of underwriting losses for mature operations is an
objective, along with  new product introduction.  Significant premium growth  is
not anticipated in 1995.

PRINCIPAL MARKETS AND METHODS OF DISTRIBUTION

    Fire and Marine's business is produced primarily through approximately 6,300
independent  insurance agencies and national  insurance brokers. Fire and Marine
maintains 12 regional offices in major  cities throughout the United States  and
90  additional service offices in  the United States to  respond to the needs of
agents, brokers and policyholders.

INSURANCE BROKERAGE OPERATIONS

    The St. Paul's  insurance brokerage segment,  Minet, provides insurance  and
reinsurance  broking and risk advisory services for major corporations and large
professional organizations worldwide. According to  the most recent rankings  in
terms of total 1993 revenues by "Business Insurance," Minet is the tenth largest
international  insurance brokerage organization  in the world.  Based in London,
Minet has  131  offices  throughout  North America,  Europe,  Africa,  Asia  and
Australia.

    Minet  operates through six business units, each focusing on distinct client
groups. GLOBAL PROFESSIONAL  SERVICES provides insurance  brokerage services  to
the  world's largest accounting firms,  as well as law  firms, law societies and
insurance companies.  INTERNATIONAL  RETAIL  serves  clients  in  Asia,  Africa,
Australia  and Europe.  Retail brokers  act on  behalf of  organizations such as
corporations  and  partnerships  by  providing  risk  management  services   and
procuring  insurance  coverages.  INTERNATIONAL BROKING,  through  its wholesale
broking operations, provides access to Lloyd's  of London and other markets  for
the  purpose  of  assembling  underwriting  capacity  for  specialized insurance
programs for clients throughout  the world. Wholesale brokers  act on behalf  of
retail  brokers  by  procuring  specialty  insurance  coverages.  Minet's  NORTH
AMERICAN  operations  include  retail   brokerage  and  advisory  services   for
professional  clients  and  major  industrial  and  service  corporations.  This
business unit  includes  Minet's  U.S.  wholesale  brokerage  network,  Swett  &
Crawford,  which, according to the  most recent rankings in  terms of total 1993
revenues by "Business Insurance", is  the largest wholesale insurance broker  in
the  United  States. REINSURANCE  provides  facultative and  treaty intermediary
services to  insurance  companies  throughout the  world.  MINET  RISK  SERVICES
provides  consulting  and  actuarial  services to  clients  worldwide,  and also
provides management services to captive insurance companies.

    Minet in recent  years has  expanded the  scope of  its specialty  brokerage
operations  by acquiring several small, specialized brokers throughout the world
to complement its existing worldwide client  base and market network. The  focus
will  remain on developing new business opportunities in specialty market niches
where Minet has the expertise to offer value-added services. Minet will continue
to form  new specialty  broker teams  and selectively  pursue acquisitions  that
complement  existing operations.  Expense containment initiatives  will remain a
vital component of  the Company's  efforts toward  achieving profitability.  The
intense  competition that has characterized the insurance brokerage industry for
many years will make it difficult for Minet to increase revenues in 1995.

INVESTMENT BANKING -- ASSET MANAGEMENT OPERATIONS

    Nuveen is The St. Paul's investment banking-asset management subsidiary. The
St. Paul  and  St. Paul  Fire  and Marine  Insurance  Company currently  hold  a
combined 77% interest in Nuveen after selling a minority interest by means of an
initial  public  offering in  1992. Through  John Nuveen  & Co.  Incorporated, a
wholly-owned subsidiary,  Nuveen  markets tax-exempt,  open-end  and  closed-end
(exchange-traded)  managed funds.  Nuveen also underwrites  and trades municipal
bonds and tax-exempt  UITs. Nuveen  markets its  funds and  UITs to  individuals
through  registered  representatives associated  with unaffiliated  national and
regional broker-dealers and other financial organizations. Through its Municipal
Finance Department, the firm also serves  state and local governments and  their
authorities   by  financing  community  projects  through  both  negotiated  and
competitive financings.

                                       32
<PAGE>
    Nuveen Advisory  Corp.,  a wholly-owned  subsidiary  of John  Nuveen  &  Co.
Incorporated,  is  investment adviser  to  the Nuveen-sponsored  open-end mutual
funds and exchange-traded  funds. Nuveen  Institutional Advisory  Corp., also  a
wholly-owned   subsidiary,  is  investment  adviser  to  other  Nuveen-sponsored
exchange-traded funds and also provides investment management services to  trust
funds  established by public utilities for  the decommissioning of nuclear power
plants.

    As the leading sponsor  of tax-free UITs,  Nuveen currently sponsors  trusts
with  assets  of  $16.8 billion  in  50  different national,  state  and insured
portfolios. Nuveen also  manages 21  tax-free, open-end mutual  funds and  money
market  funds with  net assets of  approximately $6 billion  in national, state,
insured  and  money   market  portfolios.   In  addition,   Nuveen  manages   70
exchange-traded  funds with approximately  $24 billion in  net assets, which are
traded on national stock exchanges. Nuveen  has its principal office in  Chicago
and maintains regional sales offices in other cities across the United States.

    Nuveen  is a  recognized market leader  in municipal  investing. The Company
expects that assets under management will begin to grow again as the  volatility
in the municipal market subsides. Material growth is not expected to occur until
such  time as  Nuveen begins  to offer  successful new  investment products once
again.

INVESTMENTS
    Investments are an integral part of  The St. Paul's insurance business.  The
following  table  shows the  composition and  carrying value  of The  St. Paul's
investment portfolio  for the  last three  years, followed  by more  information
about each of the major investment classes.

<TABLE>
<CAPTION>
                                                                   DECEMBER 31,
                                                          -------------------------------
                                                            1994       1993       1992
                                                          ---------  ---------  ---------
                                                               (DOLLARS IN MILLIONS)

<S>                                                       <C>        <C>        <C>
Fixed maturities(1).....................................  $   8,829  $   9,148  $   7,722
Equities................................................        531        549        494
Real estate.............................................        528        489        435
Venture capital.........................................        330        298        231
Short-term investments..................................        898        725        639
Other investments.......................................         47         47         56
                                                          ---------  ---------  ---------
    Total investments...................................  $  11,163  $  11,256  $   9,577
                                                          ---------  ---------  ---------
                                                          ---------  ---------  ---------
<FN>
- ------------------------
(1)  The carrying values for 1994 and 1993 represent market value. The amortized
     costs  for 1994 and 1993 were  $8.9 billion and $8.4 billion, respectively.
     The carrying value for 1992 is stated at amortized cost.
</TABLE>

  FIXED MATURITIES

    Fixed maturities constituted 79% of  The St. Paul's investment portfolio  at
December  31, 1994. The St. Paul determines the mix of its investment in taxable
and tax-exempt securities based  on its current and  projected tax position  and
the  relationship  between  taxable  and  tax-exempt  investment  yields.  As of
December 31, 1994, taxable bonds accounted for 55% of total fixed maturities, up
from  51%  in  1993.  Fixed  maturity  purchases  in  1994  were   predominantly
intermediate-term,  investment-grade taxable securities.  Beginning December 31,
1993, the fixed maturities portfolio was carried on The St. Paul's balance sheet
at estimated market value, with unrealized appreciation and depreciation (net of
taxes) recorded in common shareholders' equity. At December 31, 1994, the pretax
unrealized depreciation on the portfolio totaled $85 million.

                                       33
<PAGE>
    The  fixed  maturities  portfolio  is  managed  conservatively  to   provide
reasonable  return while  limiting exposure to  risks. Approximately  95% of the
fixed maturities portfolio  is rated at  investment grade levels  (I.E., BBB  or
better).  Nonrated securities comprise  the remainder of  the portfolio. Most of
these are  nonrated  municipal  bonds  which, in  management's  view,  would  be
considered of investment-grade quality if rated.

  EQUITIES

    Equity  holdings comprised 5% of The  St. Paul's investments at December 31,
1994, and consist of  a diversified portfolio of  common stocks, which are  held
with  the primary  objective of  achieving capital  appreciation. This portfolio
provided $21 million of  realized investment gains and  $13 million of  dividend
income in 1994, and its carrying value at December 31, 1994 included $30 million
of unrealized appreciation.

  REAL ESTATE

    The St. Paul's real estate holdings, which comprised 5% of total investments
at December 31, 1994, consist primarily of a diversified portfolio of commercial
office  and warehouse buildings  distributed throughout the  United States. This
portfolio produced $28 million of pretax investment income in 1994. The St. Paul
does not invest in real estate mortgages.

  VENTURE CAPITAL

    Securities  of  small  to  medium-size  companies  spanning  a  variety   of
industries  comprised  The  St.  Paul's investments  in  venture  capital, which
accounted for 3% of  total investments at December  31, 1994. These  investments
are  in the form of limited  partnership interests or direct equity investments,
and their carrying value at December 31, 1994 included $69 million of unrealized
appreciation.

  OTHER INVESTMENTS

    The St.  Paul's  portfolio also  includes  short-term securities  and  other
miscellaneous  investments,  which  in  the  aggregate  comprised  8%  of  total
investments at December 31, 1994.

LOSS RESERVES

    Loss reserves are The St. Paul's largest liability. Reserves are established
on an undiscounted basis and reflect the Company's estimates of the total losses
and loss adjustment expenses it will ultimately have to pay under insurance  and
reinsurance  policies. These include losses that  have been incurred but not yet
settled, and losses that have been incurred but not yet reported.

    Reserve estimates reflect  such variables  as past  loss experience,  social
trends  in damage awards, changes in  judicial interpretation of legal liability
and policy coverages, and  inflation. The St. Paul  takes into account not  only
monetary  increases in the cost of what it insures, but also changes in societal
factors that influence jury verdicts and case law and, in turn, claim costs.

    Due to the nature of many insurance coverages offered, which involve  claims
that  may not  be settled  for many  years after  they are  incurred, subjective
judgments as to the  Company's ultimate exposure to  losses are an integral  and
necessary  component  of the  loss reserving  process. Reserves  are continually
reviewed, using a  variety of  statistical and actuarial  techniques to  analyze
current  claim  costs, frequency  and  severity data,  and  prevailing economic,
social and legal factors. Previously  established reserves are adjusted as  loss
experience develops and new information becomes available. These adjustments are
reflected  in the  financial results  for the periods  in which  they were made.
Management believes that the reserves currently established for losses and  Loss
Adjustment Expenses ("LAE") are adequate to cover their eventual costs.

                                       34
<PAGE>
    The  following table presents a reconciliation  of beginning and ending loss
reserves for 1994, 1993 and 1992.

<TABLE>
<CAPTION>
                                                              YEAR ENDED DECEMBER 31,
                                                          -------------------------------
                                                            1994       1993       1992
                                                          ---------  ---------  ---------
                                                               (DOLLARS IN MILLIONS)

<S>                                                       <C>        <C>        <C>
Loss and LAE reserves at beginning of year, as
 reported...............................................  $   9,185  $   8,813  $   8,246
Less reinsurance recoverables on unpaid losses at
 beginning of year......................................     (1,545)    (1,606)    (1,558)
                                                          ---------  ---------  ---------
  Net loss and LAE reserves at beginning of year........      7,640      7,207      6,688
Economy reserves at acquisition.........................         --        280         --
Provision for losses and LAE for claims incurred:
  Current year..........................................      2,790      2,527      2,941
  Prior years...........................................       (328)      (223)      (251)
                                                          ---------  ---------  ---------
    Total incurred......................................      2,462      2,304      2,690
Losses and LAE payments for claims incurred:
  Current year..........................................       (667)      (580)      (708)
  Prior years...........................................     (1,566)    (1,547)    (1,452)
                                                          ---------  ---------  ---------
    Total paid..........................................     (2,233)    (2,127)    (2,160)
Unrealized foreign exchange loss (gain).................         21        (24)       (11)
                                                          ---------  ---------  ---------
    Net loss and LAE reserves at end of year............      7,890      7,640      7,207
Plus reinsurance recoverables on unpaid losses at end of
 year...................................................      1,533      1,545      1,606
                                                          ---------  ---------  ---------
    Loss and LAE reserves at end of year, as reported...  $   9,423  $   9,185  $   8,813
                                                          ---------  ---------  ---------
                                                          ---------  ---------  ---------
</TABLE>

                                       35
<PAGE>
                                ST. PAUL CAPITAL

    St.  Paul Capital is  a limited liability  company formed under  the laws of
Delaware and  is  managed  by The  St.  Paul  and The  St.  Paul's  wholly-owned
subsidiary  St.  Paul  Holdings. The  Managing  Members  own all  of  the Common
Securities of St. Paul  Capital. The Common  Securities are nontransferable  and
are  and will be beneficially  owned directly or indirectly  by the Company. The
Managing Members are the sole members of St. Paul Capital and are also the  only
managers of St. Paul Capital. St. Paul Capital's principal executive offices are
located  at 385 Washington  Street, St. Paul,  Minnesota 55102, telephone: (612)
221-7911. The principal executive offices of the Managing Members are located at
385 Washington Street, St. Paul, Minnesota 55102, telephone: (612) 221-7911.

    Pursuant to the L.L.C. Agreement, the  members of St. Paul Capital that  own
Common  Securities  have  unlimited  liability for  the  debts,  obligations and
liabilities of St. Paul  Capital in the  same manner as a  general partner of  a
Delaware  limited partnership  (which do not  include obligations  to holders of
Preferred Securities  in  their capacity  as  such). The  holders  of  Preferred
Securities   will  not  be  generally  liable  for  the  debts,  obligations  or
liabilities of St. Paul Capital solely by  reason of being a member of St.  Paul
Capital.  (subject to their obligation to repay any funds wrongfully distributed
to them).

    St. Paul  Capital exists  for  the sole  purpose  of issuing  its  Preferred
Securities  and investing the proceeds  thereof, together with substantially all
the capital  contributed  by the  Managing  Members  in respect  of  the  Common
Securities,  in the  Convertible Subordinated Debentures,  and may  engage in no
other activities  now or  in the  future. The  payment by  St. Paul  Capital  of
dividends  due on the Preferred Securities is solely dependent on its receipt of
interest payments on the Convertible Subordinated Debentures. To the extent that
aggregate interest payments  on the Convertible  Subordinated Debentures  exceed
aggregate  dividends on  the Preferred Securities  and such  dividends have been
paid in full, St. Paul  Capital may at times have  excess funds, which shall  be
distributed to the Company.

                       DESCRIPTION OF SECURITIES OFFERED

    The  securities offered hereby  are 6% Convertible  Monthly Income Preferred
Securities of  St.  Paul  Capital  with a  liquidation  preference  of  $50  per
security.  The Preferred  Securities are  convertible at  any time  prior to the
Conversion Expiration  Date, at  the option  of  the holder  and in  the  manner
described  herein, into shares of St. Paul Common Stock at an initial conversion
rate of  0.8475 shares  of St.  Paul Common  Stock for  each Preferred  Security
(equivalent  to a conversion price  of $59 per share  of St. Paul Common Stock),
subject to adjustment  in certain  circumstances. The  Preferred Securities  are
guaranteed, to the extent described herein, by The St. Paul as to dividends, the
Redemption  Price and  cash and other  distributions payable  on liquidation. In
certain circumstances, the holders  of a majority  of the aggregate  liquidation
preference   of  the  Preferred  Securities  then  outstanding  can  direct  the
Conversion Agent to  exchange all  of the Preferred  Securities for  all of  the
Convertible  Subordinated Debentures and immediately  thereafter to exchange the
Convertible Subordinated Debentures and any accrued and unpaid interest thereon,
on behalf of such  holders, for Depositary Shares,  each representing a  1/100th
interest in a share of St. Paul Series C Convertible Preferred Stock.

    The  following  is a  description  of the  material  terms of  the Preferred
Securities; the St. Paul Series C Convertible Preferred Stock and the Depositary
Shares representing  such  stock  for  which the  Preferred  Securities  may  be
exchanged;  the Guarantee pursuant to which The  St. Paul will guarantee, to the
extent described  therein,  certain  payments  with  respect  to  the  Preferred
Securities;  the Convertible Subordinated Debentures  and the Indenture pursuant
to  which  the   Convertible  Subordinated  Debentures   will  be  issued   (the
"Indenture");  and the St. Paul Common Stock into which the Preferred Securities
may be converted.

                                       36
<PAGE>
PREFERRED SECURITIES

    THE FOLLOWING SUMMARY OF THE PRINCIPAL TERMS AND PROVISIONS OF THE PREFERRED
SECURITIES DOES NOT PURPORT TO BE COMPLETE  AND IS SUBJECT TO, AND QUALIFIED  IN
ITS  ENTIRETY BY REFERENCE TO, THE L.L.C.  AGREEMENT, THE FORM OF WHICH HAS BEEN
FILED AS AN EXHIBIT TO THE REGISTRATION STATEMENT OF WHICH THIS PROSPECTUS IS  A
PART.

  GENERAL

    All  of  the  Common  Securities  of  St.  Paul  Capital  are  and  will  be
beneficially owned directly or indirectly by The St. Paul at all times while the
Preferred Securities  are  outstanding.  The  L.L.C.  Agreement  authorizes  and
creates  the Preferred  Securities, which represent  preferred limited liability
company interests in St. Paul  Capital. The preferred limited liability  company
interests  represented by the  Preferred Securities will  have a preference with
respect to cash distributions and amounts payable on the dissolution, winding up
or termination  of St.  Paul Capital  over  the Common  Securities of  St.  Paul
Capital.  The  Preferred  Securities,  as  preferred  limited  liability company
interests, do not have  a par value.  The L.L.C. Agreement  does not permit  the
issuance of other limited liability company interests without the prior approval
of  holders of not less than 66  2/3% of the aggregate liquidation preference of
the Preferred Securities then outstanding.

    Holders of Preferred Securities will have no preemptive rights.

    St. Paul Capital is and will be managed by the Managing Members at all times
while the Preferred Securities are outstanding and the Managing Members are  and
will  be the  sole members  of St. Paul  Capital which  are managers  of St Paul
Capital. Except in  connection with  the appointment  of a  Special Trustee  (as
described  below under "-- Voting Rights"),  holders of the Preferred Securities
will not have the right to remove or replace the Managing Members.

  DIVIDENDS

    Holders of the Preferred Securities  will be entitled to receive  cumulative
cash  distributions from  St. Paul Capital,  accruing from the  date of original
issuance and payable monthly in arrears on  the last day of each calendar  month
of  each year, commencing  May 31, 1995 ("dividends").  The dividends payable on
each Preferred Security will be fixed  at a rate per annum  of $3, or 6% of  the
liquidation  preference of $50.  The amount of dividends  payable for any period
will be computed on the  basis of twelve 30-day months  and a 360-day year  and,
for  any period shorter than a full month,  will be computed on the basis of the
actual number of days elapsed in such period. Payment of dividends is limited to
the funds held by St. Paul  Capital and legally available for distribution.  See
"--  Description of the Convertible Subordinated Debentures -- Interest" and "--
Description of the Guarantee -- General".

    Dividends on the Preferred Securities must  be declared monthly and paid  on
the  last day  of each calendar  month to the  extent that St.  Paul Capital has
funds legally  available for  the payment  of such  dividends and  cash on  hand
sufficient to make such payments. St. Paul Capital's ability to pay dividends on
the  Preferred Securities  is solely  dependent upon  The St.  Paul's payment of
interest on the Convertible  Subordinated Debentures in  which St. Paul  Capital
will  invest the proceeds from the offering  made hereby. If The St. Paul defers
interest payments on the Convertible Subordinated Debentures or otherwise  fails
to  make interest payments on the  Convertible Subordinated Debentures, St. Paul
Capital would  not have  sufficient  funds to  pay  dividends on  the  Preferred
Securities  and therefore would not make such payments. The payment of dividends
(if and to  the extent declared)  is guaranteed by  The St. Paul  as and to  the
extent  set forth under  "-- Description of  the Guarantee". The  Guarantee is a
full and unconditional  guarantee from the  time of its  issuance, but does  not
apply  to any payment of dividends unless and until such dividends are declared.
If The St. Paul  were to default  on its obligation to  pay interest or  amounts
payable  on redemption or  maturity of the  Convertible Subordinated Debentures,
St. Paul Capital would lack legally available funds for the payment of dividends
or amounts payable on redemption of the Preferred Securities, and in such  event
holders of the Preferred Securities would not be able to rely upon the Guarantee
for  payment  of such  amounts.  See "Investment  Considerations  -- Subordinate
Obligations Under Guarantee and Convertible Subordinated Debentures".

                                       37
<PAGE>
    The St. Paul has the right under the Indenture to defer, from time to  time,
interest  payments  on  the Convertible  Subordinated  Debentures for  up  to 60
months. Monthly dividends  on the  Preferred Securities would  be deferred  (but
Additional  Dividends would continue to accumulate  monthly) by St. Paul Capital
during any  such deferral  of  interest payments.  St.  Paul Capital  will  give
written notice of The St. Paul's deferral of interest payments to the holders of
Preferred  Securities no later than the last  date on which it would be required
to notify the NYSE of the record or payment date of the related dividend,  which
is  currently 10  days prior  to such  record or  payment date.  See "Investment
Considerations --  Option  to  Defer  Payment  of  Dividends,"  "Description  of
Securities  Offered  -- Preferred  Securities --  Additional Dividends"  and "--
Description of  the  Convertible  Subordinated Debentures  --  Option  to  Defer
Interest Payments". Any failure by The St. Paul to make interest payments on the
Convertible   Subordinated  Debentures  in  the  absence  of  a  deferral  would
constitute an Event of  Default under the Indenture.  The failure of holders  of
Preferred  Securities to receive  dividends on the  Preferred Securities in full
(including arrearages) for  15 consecutive  months (including  any such  failure
caused  by  a  deferral of  interest  payments on  the  Convertible Subordinated
Debentures) would trigger the  right of holders of  a majority of the  aggregate
liquidation preference of the Preferred Securities then outstanding, voting as a
class  at a  special meeting of  members called  for such purpose  or by written
consent,  to  direct  the  conversion  and  exchange  agent  for  the  Preferred
Securities  (the "Conversion Agent") to exchange all of the Preferred Securities
then  outstanding  for  Convertible  Subordinated  Debentures,  and  immediately
thereafter, to exchange such Convertible Subordinated Debentures and any accrued
and  unpaid interest thereon,  on behalf of the  holders, for Depositary Shares,
each representing 1/100th of a share of St. Paul Series C Convertible  Preferred
Stock,  at the Exchange  Price. "Exchange Price" means  one Depositary Share for
each $50 principal amount of Convertible Subordinated Debentures (which rate  of
exchange  is equivalent to each  of (i) one Depositary  Share for each Preferred
Security, (ii) one share  of St. Paul Series  C Convertible Preferred Stock  for
each  $5,000 principal amount  of Convertible Subordinated  Debentures and (iii)
one share  of  St.  Paul Series  C  Convertible  Preferred Stock  for  each  100
Preferred Securities). See "-- Optional Exchange for Depositary Shares".

    Dividends  declared  on  the Preferred  Securities  will be  payable  to the
holders thereof as they appear on the  books and records of St. Paul Capital  on
the  relevant record dates,  which will be  one Business Day  (as defined below)
prior to  the  relevant  payment  dates. Subject  to  any  applicable  laws  and
regulations  and  the  L.L.C.  Agreement,  each such  payment  will  be  made as
described under "--  Book-Entry-Only Issuance --  The Depository Trust  Company"
below.  In  the  event that  any  date on  which  dividends are  payable  on the
Preferred Securities is not a Business Day, then payment of the dividend payable
on such date will be made on the next succeeding day that is a Business Day (and
without any interest or  other payment in  respect of any  such delay). If  such
Business  Day is in the next succeeding calendar year, however, the payment will
be made on the immediately  preceding Business Day, in  each case with the  same
force  and effect as if made on such  date. A "Business Day" means any day other
than a day on which banking institutions in The City of New York are  authorized
or required by law or executive order to close.

  ADDITIONAL DIVIDENDS

    St.  Paul Capital shall be required  to declare and pay additional dividends
on the  Preferred Securities  upon any  dividend arrearages  in respect  of  the
Preferred Securities in order to provide, in effect, monthly compounding on such
dividend  arrearages  at a  rate of  6%  per annum  compounded monthly  and such
Additional Dividends  shall  accumulate.  The amounts  payable  to  effect  such
monthly   compounding  on  dividend  arrearages  in  respect  of  the  Preferred
Securities are referred to herein as "Additional Dividends".

  CERTAIN RESTRICTIONS ON ST. PAUL CAPITAL

    If accumulated  and unpaid  dividends have  not  been paid  in full  on  the
Preferred Securities, St. Paul Capital may not:

         (i)  pay,  declare or  set aside  for payment,  any dividends  or other
    distributions on any  other limited liability  company interests,  including
    the Common Securities; or

                                       38
<PAGE>
        (ii)  redeem, purchase, or otherwise acquire any other limited liability
    company interests, including the Common Securities;

until, in each case, such time as all accumulated and unpaid dividends on all of
the Preferred Securities, including any Additional Dividends thereon, shall have
been paid in full for all dividend  periods terminating on or prior to the  date
of such payment or the date of such redemption, purchase, or acquisition, as the
case may be.

    If  accumulated and unpaid dividends have been paid in full on the Preferred
Securities for  all prior  whole  dividend periods,  then holders  of  Preferred
Securities  will not  be entitled  to receive  or share  in any  dividends paid,
declared or  set  aside for  payment  on  any other  limited  liability  company
interest in St. Paul Capital, including the Common Securities.

    St. Paul Capital may not issue any other limited liability company interests
without  the  approval  of  holders  of not  less  than  66  2/3  in liquidation
preference of the outstanding  Preferred Securities. In  addition, The St.  Paul
has covenanted in the Guarantee and the Indenture to maintain direct or indirect
ownership  of 100% of the outstanding Common Securities of St. Paul Capital. See
"Description of  the  Guarantee  --  Certain Covenants  of  The  St.  Paul"  and
"Description  of the Convertible Subordinated Debentures -- Certain Covenants of
The St. Paul". St. Paul  Capital does not intend  to issue Common Securities  to
persons  other than the Managing Members. Other than Common Securities issued or
to be  issued to  the  Managing Members  and  the Preferred  Securities  offered
hereby,  St. Paul Capital does not intend  to create or issue additional limited
liability company interests.

  CONVERSION RIGHTS

    GENERAL.  The Preferred Securities will be convertible at any time prior  to
the  Conversion Expiration Date, at the option  of the holder thereof and in the
manner described  below, into  shares of  St. Paul  Common Stock  at an  initial
conversion  rate of 0.8475  shares of St.  Paul Common Stock  for each Preferred
Security (equivalent to a conversion price of  $59 per share of St. Paul  Common
Stock),  subject to  adjustment as  described below  under "--  Conversion Price
Adjustments". The Preferred  Securities will  not be  convertible by  or at  the
option  of The St. Paul or St. Paul Capital. Whenever The St. Paul issues shares
of St. Paul Common Stock upon  conversion of Preferred Securities, The St.  Paul
will  issue, together with each  such share of St.  Paul Common Stock, one Stock
Purchase Right, whether or not such  Stock Purchase Rights shall be  exercisable
at  such time, but only if such Stock Purchase Rights are issued and outstanding
and held  by  other holders  of  St. Paul  Common  Stock (or  are  evidenced  by
outstanding  share certificates representing Common Stock) at such time and have
not expired or been redeemed. The Stock Purchase Rights will expire on  December
19,  1999, subject to extension to December 18, 2002 under certain circumstances
or earlier redemption by The St. Paul. The Rights Agreement provides that, until
the Stock Purchase Rights become exercisable pursuant to the terms of the Rights
Agreement, the Stock Purchase Rights will be transferred with and only with  the
St.  Paul  Common  Stock.  Until  the  time  the  Stock  Purchase  Rights become
exercisable -- at which  time the separate  certificates representing the  Stock
Purchase Rights will be mailed to holders of record of the St. Paul Common Stock
- --  the Stock Purchase Rights will be evidenced by the certificates representing
the related shares of St. Paul Common Stock.

    A holder of a  Preferred Security wishing to  exercise its conversion  right
shall surrender such Preferred Security, together with an irrevocable conversion
notice,  to the Conversion Agent which shall, on behalf of such holder, exchange
the Preferred Security for a portion of the Convertible Subordinated  Debentures
held  by St. Paul Capital and  immediately convert such Convertible Subordinated
Debentures and any  accrued and  unpaid interest  thereon into  St. Paul  Common
Stock.  The St. Paul's delivery upon conversion of the fixed number of shares of
St. Paul Common  Stock into  which the Convertible  Subordinated Debentures  are
convertible  (together  with the  cash payment,  if any,  in lieu  of fractional
shares) shall be deemed  to be the  payment in full of  the principal amount  at
maturity  of the portion of Convertible Subordinated Debentures so converted and
any unpaid interest accrued on  such Convertible Subordinated Debentures at  the
time of such conversion. For a discussion of the taxation of such an exchange to
holders,  including the  possibility that  holders who  exchange their Preferred
Securities for

                                       39
<PAGE>
St. Paul Common  Stock may be  subject to  additional income tax  to the  extent
accrued  but  unpaid  interest  on the  Convertible  Subordinated  Debentures is
converted into accumulated  and unpaid dividends  on the St.  Paul Common  Stock
received  upon  conversion of  the  Preferred Securities,  see  "Certain Federal
Income Tax  Considerations --  Exchange  of Preferred  Securities for  St.  Paul
Stock".  Holders may obtain copies of the required form of the conversion notice
from the Conversion  Agent. Conversion  rights will  terminate at  the close  of
business on the Conversion Expiration Date.

    Holders  of Preferred Securities  on a dividend payment  record date will be
entitled to receive the dividend payable on such securities on the corresponding
dividend  payment  date  notwithstanding   the  conversion  of  such   Preferred
Securities on or after such dividend payment record date and on or prior to such
dividend payment date. Except as provided in the immediately preceding sentence,
St.  Paul Capital will make  no payment or allowance  for accumulated and unpaid
dividends, whether or not in arrears, on converted Preferred Securities. The St.
Paul will make no payment or allowance  for dividends on the shares of St.  Paul
Common Stock issued upon such conversion. Each conversion will be deemed to have
been  effected immediately prior  to the close  of business on  the day on which
notice was received by St. Paul Capital.

    No fractional shares of St. Paul Common Stock will be issued as a result  of
conversion, but in lieu thereof such fractional interest will be paid in cash.

    EXPIRATION OF CONVERSION RIGHTS.  On and after May 31, 1999 and provided St.
Paul Capital is current in the payment of dividends on the Preferred Securities,
including any Additional Dividends thereon, St. Paul Capital may, at its option,
cause  the conversion rights  of holders of Preferred  Securities to expire. St.
Paul Capital may exercise  this option only  if for 20  trading days within  any
period  of 30 consecutive trading  days, including the last  trading day of such
period, the Current Market Price  of St. Paul Common  Stock exceeds 120% of  the
conversion  price of the Preferred Securities,  subject to adjustment in certain
circumstances. In order to exercise  its conversion expiration option, St.  Paul
Capital must issue a press release for publication on the Dow Jones News Service
announcing  the Conversion Expiration  Date prior to the  opening of business on
the second trading day after  a period in which  the condition in the  preceding
sentence  has been met, but in no event prior to May 31, 1999. The press release
shall announce the Conversion Expiration Date and provide the current conversion
price and Current Market Price of St. Paul Common Stock, in each case as of  the
close  of  business on  the trading  day next  preceding the  date of  the press
release.

    Written notice of the  expiration of Conversion  Rights containing the  same
information  set forth in the press release  will be sent by first-class mail to
the holders of the Preferred Securities  not more than four Business Days  after
St.  Paul Capital issues the press  release. The Conversion Expiration Date will
be a date selected by St.  Paul Capital not less than  30 nor more than 60  days
after the date on which St. Paul Capital issues the press release announcing its
intention  to terminate conversion rights of  Preferred Security holders. In the
event that St. Paul Capital does not exercise its conversion expiration  option,
the  Conversion Expiration Date with respect to the Preferred Securities will be
the earlier of  the date of  an Exchange  Election referred to  below under  "--
Optional  Exchange for Depositary  Shares," and two  Business Days preceding the
date set for mandatory redemption of the Preferred Securities.

    The term "Current Market Price" of St.  Paul Common Stock for any day  means
the  last reported  sale price, regular  way on such  day, or, if  no sale takes
place on such day, the average of  the reported closing bid and asked prices  on
such  day, regular  way, in  either case  as reported  on the  NYSE Consolidated
Transaction Tape, or, if the St. Paul Common Stock is not listed or admitted  to
trading  on the NYSE on such day,  on the principal national securities exchange
on which the St. Paul Common Stock is listed or admitted to trading, if the  St.
Paul  Common Stock is listed on a  national securities exchange, or the National
Market System of the  National Association of Securities  Dealers, Inc., or,  if
the St. Paul Common Stock is not quoted or admitted to trading on such quotation
system, on the principal quotation system on which the St. Paul Common Stock may
be  listed or admitted  to trading or quoted,  or, if not  listed or admitted to
trading or quoted on any national  securities exchange or quotation system,  the
average  of the closing bid and asked prices of the St. Paul Common Stock in the
over-the-counter market on the

                                       40
<PAGE>
day in question as reported by the National Quotation Bureau Incorporated, or  a
similar  generally accepted reporting  service, or, if not  so available in such
manner, as furnished by any NYSE member  firm selected from time to time by  the
Board  of Directors of The St. Paul for  that purpose or, if not so available in
such manner, as otherwise determined in good faith by the Board of Directors.

    CONVERSION PRICE  ADJUSTMENTS --  GENERAL.   The  conversion price  will  be
subject  to adjustment in certain events including, without duplication: (i) the
payment of dividends (and other  distributions) payable exclusively in St.  Paul
Common Stock on any class of capital stock of The St. Paul; (ii) the issuance to
all  holders of St. Paul Common Stock of rights or warrants entitling holders of
such rights or warrants to  subscribe for or purchase  St. Paul Common Stock  at
less  than the Current Market Price;  (iii) subdivisions and combinations of St.
Paul Common Stock; (iv)  the payment of dividends  (and other distributions)  to
all  holders of St. Paul Common Stock consisting of evidences of indebtedness of
The  St.  Paul,  securities  or  capital  stock,  cash,  or  assets   (including
securities,  but excluding those rights,  warrants, dividends, and distributions
referred to in clause (iii) and dividends and distributions paid exclusively  in
cash); (v) the payment of dividends (and other distributions) on St. Paul Common
Stock  paid exclusively in cash, excluding (A) cash dividends that do not exceed
the per share  amount of  the immediately  preceding regular  cash dividend  (as
adjusted to reflect any of the events referred to in clauses (i) through (vi) of
this  sentence),  and (B)  cash  dividends if  the  annualized per  share amount
thereof does not exceed 15% of the last sale price of St. Paul Common Stock,  as
reported  on  the  NYSE  Consolidated  Transaction  Tape,  on  the  trading  day
immediately preceding the date of declaration of such dividend; and (vi) payment
in respect of a tender  or exchange offer (other than  an odd-lot offer) by  The
St.  Paul or any subsidiary of The St.  Paul for St. Paul Common Stock in excess
of 10% of the Current Market Price of  St. Paul Common Stock on the trading  day
next  succeeding the last date tenders or exchanges may be made pursuant to such
tender or exchange offer.

    The St. Paul from time to time may reduce the conversion price by any amount
selected by The St. Paul for any period  of at least 20 days, in which case  The
St.  Paul shall give  at least 15 days'  notice of such  reduction. The St. Paul
may, at its option, make such reductions in the conversion price, in addition to
those set forth above,  as the Board  of Directors deems  advisable to avoid  or
diminish  any income tax to holders of  St. Paul Common Stock resulting from any
dividend or distribution of stock (or rights to acquire stock) or from any event
treated as  such  for income  tax  purposes.  See "Certain  Federal  Income  Tax
Considerations -- Adjustment of Conversion Price".

    No  adjustment of the conversion price will be made upon the issuance of any
shares of St. Paul Common Stock pursuant to any present or future plan providing
for the reinvestment of dividends or  interest payable on securities of The  St.
Paul  and the investment  of additional optional  amounts in shares  of St. Paul
Common Stock under  any such plan,  or the issuance  of any shares  of St.  Paul
Common  Stock  or options  or rights  to  purchase such  shares pursuant  to any
present or future employee benefit plan or  program of The St. Paul or  pursuant
to  any  option, warrant,  right,  or exercisable,  exchangeable  or convertible
security outstanding  as  of  the  date  the  Preferred  Securities  were  first
designated. There shall also be no adjustment of the conversion price in case of
the  issuance of any  St. Paul Common  Stock (or securities  convertible into or
exchangeable for St. Paul Common Stock), except as specifically described above.
If any action would require adjustment of the conversion price pursuant to  more
than  one of the anti-dilution provisions, only one adjustment shall be made and
such adjustment shall be  the amount of adjustment  that results in the  highest
absolute  value to  holders of  the Preferred  Securities. No  adjustment in the
conversion price  will  be required  unless  such adjustment  would  require  an
increase  or decrease of at least 1% of the conversion price, but any adjustment
that would otherwise be required to be  made shall be carried forward and  taken
into account in any subsequent adjustment.

    CONVERSION  PRICE ADJUSTMENTS -- MERGER, CONSOLIDATION  OR SALE OF ASSETS OF
THE ST. PAUL.   In the event  that The St.  Paul is a  party to any  transaction
(including,  without  limitation,  a  merger,  consolidation,  sale  of  all  or
substantially  all  of  the  assets   of  The  St.  Paul,  recapitalization   or
reclassification of St. Paul Common Stock or any compulsory share exchange (each
of  the foregoing  being referred to  as a  "Transaction")), in each  case, as a
result of which  shares of St.  Paul Common  Stock shall be  converted into  the
right  (i) in the case  of any Transaction other  than a Transaction involving a
Common Stock

                                       41
<PAGE>
Fundamental Change  (as defined  below), to  receive securities,  cash or  other
property,  each Preferred Security shall thereafter be convertible into the kind
and  amount  of  securities,  cash  and  other  property  receivable  upon   the
consummation  of such Transaction  by a holder  of that number  of shares of St.
Paul Common Stock into  which a Preferred  Security was convertible  immediately
prior  to such  Transaction, or (ii)  in the  case of a  Transaction involving a
Common Stock Fundamental Change, to receive common stock of the kind received by
holders of St. Paul Common  Stock (but in each case  after giving effect to  any
adjustment  discussed below relating to a Fundamental Change if such Transaction
constitutes a Fundamental Change). The holders of Preferred Securities will have
no voting rights with respect to any Transaction described in this section.

    In the event of a Fundamental Change (as defined below), then the conversion
price in effect will  be adjusted immediately after  such Fundamental Change  as
described below. In addition, in the event of a Common Stock Fundamental Change,
each  Preferred Security  shall be convertible  solely into common  stock of the
kind received by holders  of St. Paul  Common Stock as a  result of such  Common
Stock Fundamental Change.

    In  the event of a Fundamental Change, the conversion price will be adjusted
immediately after such Fundamental Change:

         (i) in the case of a  Non-Stock Fundamental Change (as defined  below),
    the  conversion price  of the Preferred  Security will  thereupon become the
    lower of  (A) the  conversion  price in  effect  immediately prior  to  such
    Non-Stock  Fundamental Change,  but after giving  effect to  any other prior
    adjustments, and (B) the result obtained  by multiplying the greater of  the
    Applicable  Price (as defined below) or the then applicable Reference Market
    Price (as defined below) by  a fraction of which  the numerator will be  $50
    and  the denominator will be an  amount per Preferred Security determined by
    the Managing Members in  their sole discretion,  after consultation with  an
    investment banking firm, to be the equivalent of the hypothetical redemption
    price  that would have been applicable  if the Preferred Securities had been
    redeemable during such period; and

        (ii) in the case  of a Common Stock  Fundamental Change, the  conversion
    price of the Preferred Securities in effect immediately prior to such Common
    Stock  Fundamental  Change,  but  after giving  effect  to  any  other prior
    adjustments, will thereupon be adjusted by multiplying such conversion price
    by a fraction of which the numerator  will be the Purchaser Stock Price  (as
    defined  below) and the denominator will  be the Applicable Price; provided,
    however, that in the event of a Common Stock Fundamental Change in which (A)
    100% of the  value of the  consideration received  by a holder  of St.  Paul
    Common  Stock is  common stock  of the  successor, acquiror,  or other third
    party (and  cash,  if any,  is  paid only  with  respect to  any  fractional
    interests  in such common stock resulting from such Common Stock Fundamental
    Change) and (B) all of  the St. Paul Common  Stock will have been  exchanged
    for,  converted into, or acquired for common stock (and cash with respect to
    fractional interests) of the successor, acquiror, or other third party,  the
    conversion  price of the Preferred Securities in effect immediately prior to
    such  Common  Stock  Fundamental  Change  will  thereupon  be  adjusted   by
    multiplying  such conversion price by a fraction of which the numerator will
    be one and the denominator will be  the number of shares of common stock  of
    the  successor, acquiror, or other  third party received by  a holder of one
    share of St. Paul Common Stock as a result of such Common Stock  Fundamental
    Change.

    In  the absence of the provisions of  the L.L.C. Agreement which provide for
an adjustment to the conversion price in  the event of a Fundamental Change,  in
the  case of a Transaction each Preferred Security would become convertible into
the securities, cash, or property receivable by a holder of the number of shares
of St. Paul  Common Stock  into which  such Preferred  Security was  convertible
immediately prior to such Transaction. This change could substantially lessen or
eliminate  the value of  the conversion privilege  associated with the Preferred
Securities. For example, if The  St. Paul were acquired  in a cash merger,  each
Preferred Security would become convertible solely into cash and would no longer
be  convertible into securities  whose value would vary  depending on the future
prospects of The St. Paul and other factors.

                                       42
<PAGE>
    The foregoing  conversion price  adjustments are  designed, in  transactions
involving  a  Fundamental Change  where all  or substantially  all the  St. Paul
Common Stock is converted into securities,  cash, or property and not more  than
50%  of the value received  by the holders of St.  Paul Common Stock consists of
stock listed or admitted for listing subject to notice of issuance on a national
securities exchange or  quoted on  the National  Market System  of the  National
Association  of Securities Dealers, Inc.  (E.G., a Non-Stock Fundamental Change,
as defined below), to increase the securities, cash, or property into which each
Preferred Security is convertible.

    In a  Non-Stock  Fundamental  Change transaction  where  the  initial  value
received  per  share of  St. Paul  Common  Stock (measured  as described  in the
definition of  Applicable  Price  below)  is  lower  than  the  then  applicable
conversion  price  of a  Preferred Security  but  greater than  or equal  to the
"Reference Market Price" (initially $32.25, but subject to adjustment in certain
events as described below), the conversion  price will be adjusted as  described
above  with the  effect that  each Preferred  Security will  be convertible into
securities, cash or property  of the same  type received by  the holders of  St.
Paul  Common Stock in  the transaction but  in an amount  per Preferred Security
determined by The St.  Paul in its sole  discretion, after consultation with  an
investment  banking firm,  to be the  equivalent of  the hypothetical redemption
price that  would have  been applicable  if the  Preferred Securities  had  been
redeemable during such period.

    In  a  Non-Stock  Fundamental  Change transaction  where  the  initial value
received per  share of  St. Paul  Common  Stock (measured  as described  in  the
definition  of Applicable  Price) is lower  than both  the Applicable Conversion
Price of a  Preferred Security and  the Reference Market  Price, the  conversion
price  will be adjusted as described above but calculated as though such initial
value had been the Reference Market Price.

    In a transaction involving a  Fundamental Change where all or  substantially
all  the St. Paul Common  Stock is converted into  securities, cash, or property
and more than 50% of the value received by the holders of St. Paul Common  Stock
consists of listed or National Market System traded common stock (E.G., a Common
Stock  Fundamental  Change, as  defined  below), the  foregoing  adjustments are
designed to provide in effect that (a) where St. Paul Common Stock is  converted
partly  into  such  common stock  and  partly  into other  securities,  cash, or
property, each Preferred Security  will be convertible solely  into a number  of
shares  of such common stock determined so that the initial value of such shares
(measured as  described in  the  definition of  "Purchaser Stock  Price"  below)
equals  the  value  of the  shares  of St.  Paul  Common Stock  into  which such
Preferred Security was convertible immediately before the transaction  (measured
as  aforesaid) and (b) where St. Paul Common Stock is converted solely into such
common stock, each Preferred Security will  be convertible into the same  number
of shares of such common stock receivable by a holder of the number of shares of
St.  Paul  Common  Stock  into which  such  Preferred  Security  was convertible
immediately before such transaction.

    The term "Applicable Price" means (i) in the case of a Non-Stock Fundamental
Change in which the holders of the St. Paul Common Stock receive only cash,  the
amount  of cash received by the holder of one share of St. Paul Common Stock and
(ii) in the event of any other Non-Stock Fundamental Change or any Common  Stock
Fundamental  Change, the average of  the Closing Prices for  the St. Paul Common
Stock during the ten trading days prior to and including the record date for the
determination of the holders of St.  Paul Common Stock entitled to receive  such
securities,   cash,  or  other  property   in  connection  with  such  Non-Stock
Fundamental Change or Common  Stock Fundamental Change or,  if there is no  such
record  date, the date upon which the holders of the St. Paul Common Stock shall
have the right to receive such securities, cash, or other property (such  record
date  or distribution  date being  hereinafter referred  to as  the "Entitlement
Date"), in each case as adjusted in good faith by The St. Paul to  appropriately
reflect  any of the events referred to in  clauses (i) through (vi) of the first
paragraph under "-- Conversion Price Adjustments -- General".

    The term "Closing Price" means  on any day the  reported last sale price  on
such day or in case no sale takes place on such day, the average of the reported
closing  bid and asked prices in each  case on the NYSE Consolidated Transaction
Tape  or,  if  the  stock  is  not  listed  or  admitted  to  trading  on   such

                                       43
<PAGE>
Exchange,  on the principal national securities  exchange on which such stock is
listed or admitted to  trading or if  not listed or admitted  to trading on  any
national securities exchange, the average of the closing bid and asked prices as
furnished  by any NYSE  member firm, selected  by the Managing  Members for that
purpose.

    The term "Common Stock Fundamental  Change" means any Fundamental Change  in
which  more than 50% of the  value (as determined in good  faith by the Board of
Directors of The St. Paul) of the consideration received by holders of St.  Paul
Common  Stock consists  of common  stock that  for each  of the  ten consecutive
trading days prior  to the  Entitlement Date has  been admitted  for listing  or
admitted  for listing  subject to  notice of  issuance on  a national securities
exchange or quoted on the National Market System of the National Association  of
Securities Dealers, Inc.; provided, however, that a Fundamental Change shall not
be a Common Stock Fundamental Change unless either (i) The St. Paul continues to
exist  after  the  occurrence of  such  Fundamental Change  and  the outstanding
Preferred Securities continue  to exist as  outstanding Preferred Securities  or
(ii)  not later than the occurrence  of such Fundamental Change, the outstanding
Preferred Securities are converted into  or exchanged for shares of  convertible
preferred  stock of an entity succeeding to  the business of The St. Paul, which
convertible   preferred   stock   has   powers,   preferences,   and   relative,
participating,  optional, or other rights,  and qualifications, limitations, and
restrictions, substantially similar to those of the Preferred Securities.

    The term "Fundamental  Change" means  the occurrence of  any transaction  or
event  in connection with a  plan pursuant to which  all or substantially all of
the St. Paul Common Stock shall be exchanged for, converted into, acquired  for,
or  constitute solely the  right to receive securities,  cash, or other property
(whether  by   means  of   an  exchange   offer,  liquidation,   tender   offer,
consolidation,   merger,  combination,  reclassification,  recapitalization,  or
otherwise), provided, that, in the case of  a plan involving more than one  such
transaction  or event, for purposes of adjustment of the conversion price of the
Preferred Securities, such Fundamental Change  shall be deemed to have  occurred
when  substantially all  of the  St. Paul Common  Stock has  been exchanged for,
converted into,  or acquired  for  or constitute  solely  the right  to  receive
securities,  cash, or other property, but the adjustment shall be based upon the
highest weighed average per share consideration that a holder of St. Paul Common
Stock could have received  in connection with such  transactions or events as  a
result of which more than 50% of the St. Paul Common Stock was so exchanged.

    The  term "Non-Stock Fundamental Change"  means any Fundamental Change other
than a Common Stock Fundamental Change.

    The term "Purchaser  Stock Price" means,  with respect to  any Common  Stock
Fundamental  Change,  the average  of the  Closing Prices  for the  common stock
received in such Common Stock Fundamental Change for the ten consecutive trading
days prior to and including the Entitlement  Date, as adjusted in good faith  by
The  St. Paul to appropriately reflect any  of the events referred to in clauses
(i) through (vi) of the first  paragraph under "-- Conversion Price  Adjustments
- -- General".

    The  term "Reference Market Price" shall  initially mean $32.25 (which is an
amount equal to 66 2/3% of the reported last sale price for the St. Paul  Common
Stock  on the  NYSE Consolidated Transaction  Tape on  May 9, 1995),  and in the
event of any  adjustment to the  conversion price other  than as a  result of  a
Non-Stock  Fundamental Change, the Reference Market Price shall also be adjusted
so that the ratio of  the Reference Market Price  to the conversion price  after
giving  effect to any such  adjustment shall always be the  same as the ratio of
$32.25 to the initial conversion price of the Preferred Securities.

  OPTIONAL EXCHANGE FOR DEPOSITARY SHARES

    Upon the occurrence of an Exchange Event (as defined below), the holders  of
a  majority of the aggregate liquidation preference of Preferred Securities then
outstanding, voting as a class at a  special meeting of members called for  such
purpose or by written consent, may, at their option, direct the Conversion Agent
to  exchange  all  (but not  less  than  all) of  the  Preferred  Securities for
Convertible Subordinated Debentures and to immediately exchange such Convertible
Subordinated Debentures and any accrued  and unpaid interest thereon, on  behalf
of such holders, for Depositary Shares, each

                                       44
<PAGE>
representing  ownership of a 1/100th of a share of St. Paul Series C Convertible
Preferred Stock at the Exchange Price. If the Preferred Securities are exchanged
for Depositary Shares, the L.L.C. Agreement provides that The St. Paul will  use
its  best efforts  to have  the Depositary  Shares listed  on the  NYSE or other
exchange on which the Preferred Securities may then be listed.

    Each Depositary Share will  entitle the holder  thereof to all  proportional
rights  and preferences  of the  St. Paul  Series C  Convertible Preferred Stock
(including dividend, voting, conversion,  redemption and liquidation rights  and
preferences).  The St. Paul Series C Convertible Preferred Stock issued upon any
such exchange  will  have  terms  substantially similar  to  the  terms  of  the
Preferred  Securities  (adjusted proportionately  per Depositary  Share), except
that, among other things, the holders of St. Paul Series C Convertible Preferred
Stock will have  the right to  elect two  additional directors of  The St.  Paul
whenever  dividends on the St. Paul Series  C Convertible Preferred Stock are in
arrears for 18 months (including for this purpose any arrearage with respect  to
the  Preferred Securities) and will not  be subject to mandatory redemption. See
"-- Description  of St.  Paul  Series C  Convertible  Preferred Stock"  and  "--
Description  of  Depositary  Shares".  The  terms  of  the  St.  Paul  Series  C
Convertible Preferred Stock  provide that all  accumulated and unpaid  dividends
(including  any Additional Dividends)  on the Preferred  Securities that are not
paid at the time of making an Exchange Election shall be treated as  accumulated
and  unpaid dividends on the St. Paul  Series C Convertible Preferred Stock. See
"-- Description  of  St. Paul  Series  C  Convertible Preferred  Stock".  For  a
discussion  of  the  taxation of  such  an  exchange to  holders,  including the
possibility that holders who exchange their Preferred Securities for  Depositary
Shares representing St. Paul Series C Convertible Preferred Stock may be subject
to  additional  income tax  to the  extent  accrued but  unpaid interest  on the
Convertible Subordinated  Debentures is  converted into  accumulated and  unpaid
dividends  on the St.  Paul Series C Convertible  Preferred Stock represented by
the Depositary Shares  received in  exchange for the  Preferred Securities,  see
"Certain  Federal Income Tax Considerations  -- Exchange of Preferred Securities
for St. Paul Stock".

    The  failure  of  holders  of  Preferred  Securities  to  receive,  for   15
consecutive  months, the full amount of dividend payments (including arrearages)
on the Preferred Securities, including any such failure caused by a deferral  of
interest payments on the Convertible Subordinated Debentures, will constitute an
"Exchange  Event". As soon  as practicable, but  in no event  later than 30 days
after the occurrence of an Exchange  Event, the Managing Members will, upon  not
less  than  15  days' written  notice  by  first-class mail  to  the  holders of
Preferred Securities, convene a meeting  of such holders (an "Exchange  Election
Meeting")  for  the purpose  of acting  on the  matter of  whether to  cause the
Conversion Agent  to  exchange all  Preferred  Securities then  outstanding  for
Depositary  Shares representing St. Paul Series C Convertible Preferred Stock in
the manner  described  above. If  the  Managing  Members fail  to  convene  such
Exchange Election Meeting within such 30-day period, the holders of at least 10%
of  the  outstanding  Preferred  Securities will  be  entitled  to  convene such
Exchange Election Meeting. Upon the affirmative vote of the holders of Preferred
Securities representing not less  than a majority  of the aggregate  liquidation
preference  of the Preferred Securities then outstanding at an Exchange Election
Meeting or, in the absence of such meeting, upon receipt by St. Paul Capital  of
written  consents  signed  by  the  holders  of  a  majority  of  the  aggregate
liquidation preference of the outstanding  Preferred Securities, an election  to
exchange  all outstanding Preferred Securities on  the basis described above (an
"Exchange Election") will be deemed to have been made.

    Holders of Preferred  Securities, by purchasing  such Preferred  Securities,
will  be deemed to have agreed to be bound by these optional exchange provisions
in regard to  the exchange of  such Preferred Securities  for Depositary  Shares
representing  St.  Paul  Series  C  Convertible  Preferred  Stock  on  the terms
described above.

  REDEMPTION

    If at any time following the Conversion Expiration Date, less than 5% of the
Preferred  Securities  offered   hereby  remain   outstanding,  such   Preferred
Securities  shall be redeemable at the option  of St. Paul Capital, in whole but
not in part, from time to  time, upon not fewer than  30 nor more than 60  days'

                                       45
<PAGE>
prior  notice, at a redemption price of $50 per Preferred Security together with
accumulated and unpaid dividends (whether or not earned or declared),  including
any Additional Dividends (the "Redemption Price").

    Upon  repayment by The St. Paul  of the Convertible Subordinated Debentures,
including as  a  result of  the  acceleration of  the  Convertible  Subordinated
Debentures  upon the  occurrence of  an "Event  of Default"  described under "--
Description of the  Convertible Subordinated Debentures  -- Events of  Default",
the  Preferred Securities shall be subject to mandatory redemption, in whole but
not in part, by St.  Paul Capital and the proceeds  from such repayment will  be
applied  to redeem the Preferred Securities at the Redemption Price. In the case
of such  acceleration,  the Preferred  Securities  will only  be  redeemed  when
repayment  of the Convertible Subordinated Debentures has actually been received
by St. Paul Capital. The Preferred  Securities are not otherwise redeemable  for
any  reason, including in the event that  St. Paul Capital should become subject
to federal or state taxation. To the  extent that such taxation or other  events
cause  St. Paul Capital to have insufficient  funds to pay full dividends on the
Preferred Securities,  the holders  will  have available  to them  the  exchange
option  described above. Upon  the occurrence of certain  Tax Events (as defined
herein), however,  St.  Paul  Capital  may  be  dissolved  and  the  Convertible
Subordinated  Debentures distributed to holders of Preferred Securities. See "--
Special Event Dissolution".

  SPECIAL EVENT DISTRIBUTION

    If a  Tax  Event (as  defined  below) shall  occur  and be  continuing,  the
Managing  Members may, and if an Investment Company Event (as defined below, and
collectively with a Tax Event, "Special Events") shall occur and be  continuing,
the Managing Members shall, dissolve St. Paul Capital and, after satisfaction of
liabilities  to creditors  of St.  Paul Capital  as required  by applicable law,
cause the Convertible Subordinated Debentures  to be distributed to the  holders
of  the Preferred Securities in  liquidation of St. Paul  Capital, in the manner
described below,  provided that  The  St. Paul  has reasonably  determined  that
holders  will not recognize  gain or loss  for United States  federal income tax
purposes as a result of such distribution. In the case of a Tax Event,  however,
the Managing Members may elect not to dissolve St. Paul Capital and to cause the
Preferred Securities to remain outstanding.

    "Tax  Event" means that the Managing  Members shall have obtained an opinion
of nationally recognized independent tax counsel experienced in such matters  to
the  effect that, as a  result of (a) any amendment  to or change (including any
announced prospective change) in the laws (or any regulations thereunder) of the
United States  or  any political  subdivision  or taxing  authority  thereof  or
therein,  (b) any amendment to or change  in an interpretation or application of
such laws or regulations by any legislative body, court, governmental agency  or
regulatory  authority  (including  the  enactment  of  any  legislation  and the
publication of any  judicial decision  or regulatory determination  on or  after
such  date)  or (c)  any  interpretation or  pronouncement  that provides  for a
position with  respect  to  such  laws or  regulations  that  differs  from  the
generally accepted position on the date of issuance of the Preferred Securities,
which  amendment or change is effective  or such interpretation or pronouncement
is announced on or after the date of issuance of the Preferred Securities, there
is a substantial risk that (i) St. Paul Capital is taxable as a corporation  for
United  States federal  income tax  purposes or  is otherwise  subject to United
States federal income tax with respect  to interest received on the  Convertible
Subordinated  Debentures,  (ii) interest  payable by  The St.  Paul to  St. Paul
Capital on the Convertible  Subordinated Debentures will  not be deductible  for
United  States federal income tax purposes or  (iii) St. Paul Capital is subject
to more than a DE  MINIMIS amount of other  taxes, duties or other  governmental
charges.

    "Investment  Company  Event" means  the  occurrence of  a  change in  law or
regulation or  a change  in official  interpretation or  application of  law  or
regulation  by any  legislative body,  court, governmental  agency or regulatory
authority (a "Change in 1940 Act Law") to the effect that St. Paul Capital is or
will be considered an  "investment company" which is  required to be  registered
under  the Investment Company  Act of 1940,  as amended (the  "1940 Act"), which
Change in 1940 Act Law becomes effective on or after the date of issuance of the
Preferred Securities; provided, that no Investment Company Event shall be deemed
to have occurred if the Managing Members obtain a written opinion of  nationally
recognized independent counsel experienced in practice under the 1940 Act to the
effect that The St. Paul or St. Paul

                                       46
<PAGE>
Capital  has taken reasonable measures, in  its discretion, to avoid such Change
in 1940 Act Law  so that in  the opinion of  such counsel, notwithstanding  such
Change  in 1940 Act Law, St. Paul Capital is not required to be registered as an
"investment company" within the meaning of the 1940 Act.

    Following the dissolution of St. Paul  Capital in connection with a  Special
Event  and the satisfaction of  liabilities to creditors of  St. Paul Capital as
required by  applicable law,  St. Paul  Capital will,  on a  date fixed  by  the
Managing  Members within 90 days following the occurrence of such Special Event,
distribute to each holder of Preferred Securities, in respect of each  Preferred
Security, Convertible Subordinated Debentures having a principal amount equal to
$50.  In addition,  all accumulated  and unpaid  dividends (including Additional
Dividends) on the Preferred  Securities that are  not paid at  the time of  such
dissolution  shall be treated as accrued  and unpaid interest on the Convertible
Subordinated Debentures. The Indenture does not provide for the modification  of
the  terms  of  the Convertible  Subordinated  Debentures in  connection  with a
Special Event. After the date of such distribution, (i) the Preferred Securities
will no  longer be  deemed to  be  outstanding, (ii)  the holders  of  Preferred
Securities  shall cease  to be  members of  St. Paul  Capital; (iii)  DTC or its
nominee, as  the record  holder  of the  Preferred  Securities, will  receive  a
registered  global  certificate  or  certificates  representing  the Convertible
Subordinated Debentures  to be  delivered upon  such distribution  and (iv)  any
certificates  representing Preferred Securities  not held by  DTC or its nominee
will be  deemed  to  represent  Convertible  Subordinated  Debentures  having  a
principal amount equal to the aggregate of the stated liquidation preference of,
and  the accumulated  and unpaid dividends  on, such  Preferred Securities until
such certificates are presented  to The St.  Paul or its  agent for transfer  or
reissuance.  The Indenture provides that  if Convertible Subordinated Debentures
are so  distributed,  The St.  Paul  will use  its  best efforts  to  have  such
Convertible  Subordinated Debentures  listed on  the NYSE  or other  exchange on
which the Preferred Securities may then be listed.

  LIQUIDATION RIGHTS

    In the event of  any voluntary or  involuntary liquidation, dissolution,  or
winding-up  of St. Paul Capital, the holders of Preferred Securities at the time
outstanding will be  entitled to  receive a  liquidation preference  of $50  per
Preferred  Security plus  all accumulated and  unpaid dividends  (whether or not
earned or declared), including any Additional Dividends thereon, to the date  of
payment  (the "Liquidation Distribution") out of  the assets of St. Paul Capital
legally available for distribution to members  prior to any distribution by  St.
Paul  Capital on  its other limited  liability company  interests, including the
Common Securities.

    If, upon  any liquidation  of St.  Paul Capital,  the holders  of  Preferred
Securities are paid in full the aggregate Liquidation Distribution to which they
are  entitled, then such holders will not be entitled to receive or share in any
other assets of St.  Paul Capital thereafter available  for distribution to  any
other  holders  of  limited liability  company  interests in  St.  Paul Capital,
including the Common Securities.

    Pursuant to the L.L.C.  Agreement, St. Paul Capital  shall be dissolved  and
its  affairs shall be wound up upon the earliest to occur of: (i) the expiration
of the period  fixed for  the life  of St.  Paul Capital;  (ii) the  bankruptcy,
retirement,  resignation, expulsion,  dissolution, winding up  or liquidation of
either Managing Member;  (iii) the election  of the Managing  Members, with  the
approval  of the holders of 66 2/3%  of the Preferred Securities; (iv) the entry
of a judicial decree of dissolution; (v) the election of the Managing Members in
connection with  a  Special  Event;  (vi)  the  redemption  of  all  outstanding
Preferred  Securities; or (vii) upon  the written consent of  all members of St.
Paul Capital.

  MERGER, CONSOLIDATION OR SALE OF ASSETS OF THE ST. PAUL AND ST. PAUL CAPITAL

    The St. Paul may  not merge or  consolidate with or  into another entity  or
permit  another entity to merge  or consolidate with or into  it, and may not be
replaced by,  or convey,  transfer or  lease  all or  substantially all  of  its
properties  and  assets  to  another  entity unless  (i)  at  the  time  of such
transaction, no  Event of  Default  (as defined  in  the Indenture)  shall  have
occurred and be continuing, or would occur as a result of such transaction, (ii)
the  survivor of  such merger or  consolidation or  the entity to  which The St.

                                       47
<PAGE>
Paul's assets are sold, transferred or  leased is an entity organized under  the
laws  of the United States or any state  thereof, such entity (if other than The
St. Paul) becomes a party of the L.L.C. Agreement and becomes a Managing Member,
assumes all of The St. Paul's  obligations under the L.L.C. Agreement, and  such
entity  has a net worth equal to at least 10% of the total capital contributions
to St. Paul Capital, (iii)  prior to such transaction,  The St. Paul obtains  an
opinion of nationally recognized independent counsel experienced in such matters
to  the  effect  that St.  Paul  Capital will  continue  to be  classified  as a
partnership for federal income tax purposes  after such transaction and (iv)  in
the  case of any sale, transfer or lease  of all or substantially all of the The
St. Paul's assets that includes St. Paul's interest in St. Paul Capital, The St.
Paul has obtained the  consent to the  transaction of holders  of not less  than
66 2/3% of the aggregate liquidation preference of the Preferred Securities then
outstanding.

    St. Paul Capital may not consolidate, merge with or into, or be replaced by,
or  convey,  transfer or  lease its  properties and  assets substantially  as an
entirety to any entity, except as described below. St. Paul Capital may, (i)  in
order  to avoid federal income  tax or 1940 Act  consequences adverse to The St.
Paul or St. Paul Capital or to the holders of the Preferred Securities,  without
the  consent of the holders of the  Preferred Securities, or (ii) with the prior
approval of holders of  not less than  66 2/3 of  the Preferred Securities  then
outstanding,  consolidate,  merge with  or  into, or  be  replaced by  a limited
liability company, limited partnership or trust organized as such under the laws
of any state of the United States of America; PROVIDED, that (i) such  successor
entity  either (x) expressly assumes all of  the obligations of St. Paul Capital
under the Preferred Securities or  (y) substitutes for the Preferred  Securities
other securities having substantially the same terms as the Preferred Securities
(the  "Successor Securities")  so long  as the  Successor Securities  rank, with
respect to participation in  the profits or assets  of the successor entity,  at
least  as high as the Preferred Securities rank with respect to participation in
the profits  or  assets  of  St.  Paul Capital,  (ii)  The  St.  Paul  expressly
acknowledges such successor entity as the holder of the Convertible Subordinated
Debentures,  (iii) such merger, consolidation, or replacement does not cause the
Preferred Securities  (or  any  Successor  Securities) to  be  delisted  by  any
national  securities  exchange  or  other organization  on  which  the Preferred
Securities are then listed, (iv) such merger, consolidation or replacement  does
not  cause the Preferred  Securities (including any  Successor Securities) to be
downgraded by  any nationally  recognized statistical  rating organization,  (v)
such  merger, consolidation or replacement does not adversely affect the powers,
preferences and other special rights of the holders of the Preferred  Securities
(including  any Successor Securities)  in any material  respect (other than with
respect to any dilution of the holders' interest in the new entity), (vi)  prior
to  such  merger, consolidation  or  replacement The  St.  Paul has  received an
opinion of  nationally  recognized  independent  counsel  to  St.  Paul  Capital
experienced  in such matters  to the effect  that (w) such  transaction will not
cause The St.  Paul, St.  Paul Capital  or such  successor entity  to become  an
"investment  company" required to be registered  under the 1940 Act, (x) holders
of the Preferred  Securities will  not recognize any  gain or  loss for  federal
income  tax purposes as a result of  such transaction, (y) such successor entity
will not  be treated  as an  association taxable  as a  corporation for  federal
income  tax  purposes and  (z) such  transaction will  not adversely  affect the
limited liability of holders of the Preferred Securities.

  VOTING RIGHTS

    Except as  provided below  and under  "-- Description  of the  Guarantee  --
Amendments  and  Assignment," "--  Description  of the  Convertible Subordinated
Debentures -- Modification of  the Indenture" and as  otherwise required by  law
and  provided by the  L.L.C. Agreement, the holders  of the Preferred Securities
will have no voting rights.

    If (i)  St. Paul  Capital fails  to  pay dividends  in full  (including  any
arrearages) on the Preferred Securities for 15 consecutive months (including any
such  failure  caused by  a  determination by  The  St. Paul  to  defer interest
payments on  the  Convertible Subordinated  Debentures  as described  under  "--
Description  of  the  Convertible  Subordinated Debentures  --  Option  to Defer
Interest Payments"); (ii) an Event of Default (as defined under "--  Description
of  the Convertible Subordinated Debentures -- Events of Default") occurs and is
continuing with respect to the Convertible Subordinated Debentures; or (iii) The
St. Paul is in default under any of its payment obligations under the  Guarantee
(as described

                                       48
<PAGE>
under  "-- Description  of the  Guarantee"), then  the holders  of the Preferred
Securities will  be entitled  to  appoint and  authorize  a Special  Trustee  to
enforce St. Paul Capital's rights under the Convertible Subordinated Debentures,
enforce  the rights of  the holders of Preferred  Securities under the Guarantee
and, to the extent permitted by law, declare and pay dividends on the  Preferred
Securities.  For purposes of determining whether  St. Paul Capital has failed to
pay dividends in full  for 15 consecutive months,  dividends shall be deemed  to
remain  in  arrears, notwithstanding  any partial  payments in  respect thereof,
until all accumulated and  unpaid dividends have  been or contemporaneously  are
paid.  Not later  than 30  days after  such right  to appoint  a Special Trustee
arises and upon not less than 15 days' written notice by first-class mail to the
holders of Preferred Securities, the Managing Members will convene a meeting  to
elect  a Special Trustee. If  the Managing Members fail  to convene such meeting
within such  30-day period,  the holders  of 10%  of the  aggregate  liquidation
preference  of the  Preferred Securities  then outstanding  will be  entitled to
convene such meeting. In the  event that, at any  such meeting, holders of  less
than  a  majority in  aggregate liquidation  preference of  Preferred Securities
entitled to  vote  for  the appointment  of  a  Special Trustee  vote  for  such
appointment,  no  Special Trustee  shall be  appointed.  Any Special  Trustee so
appointed shall vacate office immediately if  St. Paul Capital (or The St.  Paul
pursuant  to the Guarantee) shall  have paid in full  all accumulated and unpaid
dividends (and any  Additional Dividends)  on the Preferred  Securities or  such
Event  of  Default  or default,  as  the case  may  be, shall  have  been cured.
Notwithstanding the appointment of any such  Special Trustee, The St. Paul  will
retain  all  rights as  obligor under  the Convertible  Subordinated Debentures,
including the right to defer interest payments as provided under "-- Description
of  the  Convertible  Subordinated  Debentures  --  Option  to  Defer   Interest
Payments",  and  any such  deferral  would not  constitute  a default  under the
Indenture or enable a holder of Preferred Securities to require the payment of a
dividend that has not theretofore been declared.

    In furtherance of  the foregoing,  and without  limiting the  powers of  any
Special  Trustee so appointed and for the  avoidance of any doubt concerning the
powers of the Special Trustee, any Special Trustee, in its own name, in the name
of St.  Paul Capital,  in the  name of  any holder  of Preferred  Securities  or
otherwise,  may institute  or cause  to be  instituted a  proceeding, including,
without limitation, any suit in  equity, an action at  law or other judicial  or
administrative  proceeding, to enforce St. Paul Capital's or any holder's rights
directly against The  St. Paul to  the same extent  as St. Paul  Capital or  any
holder  and on behalf of St. Paul Capital  or any holder, and may prosecute such
proceeding to judgment  or final decree,  and enforce the  same against The  St.
Paul  and collect, out of  the property, wherever situated,  of The St. Paul the
monies adjudged or decreed to be payable in the manner provided by law.

    If any  proposed amendment  to the  L.L.C. Agreement  provides for,  or  the
Managing  Members  otherwise  propose  to  effect,  (x)  any  action  that would
materially adversely affect  the powers,  preferences or special  rights of  the
Preferred  Securities, whether  by way of  amendment to the  L.L.C. Agreement or
otherwise (including, without limitation, the  authorization or issuance of  any
additional  limited liability company interests in St. Paul Capital), or (y) the
dissolution, winding-up  or  termination of  St.  Paul Capital  (other  than  in
connection with the exchange of Depositary Shares representing St. Paul Series C
Convertible  Preferred Stock for Preferred Securities  upon the occurrence of an
Exchange Event or as described under "-- Merger, Consolidation or Sale of Assets
of St. Paul Capital"), then the holders of outstanding Preferred Securities will
be entitled to vote on such amendment or action of the Managing Members (but not
on any other amendment  or action), and  such amendment or  action shall not  be
effective except with the approval of the holders of at least 66 2/3% or more of
the   aggregate  liquidation   preference  of  the   Preferred  Securities  then
outstanding; PROVIDED, HOWEVER, that no such  approval shall be required if  the
dissolution,  winding-up  or  termination of  St.  Paul Capital  is  proposed or
initiated pursuant to the L.L.C. Agreement.

    The rights  attached  to the  Preferred  Securities  will be  deemed  to  be
materially  adversely affected by  the creation or  issue of, and  a vote of the
holders of Preferred Securities will be  required for the creation or issue  of,
any  limited  liability company  interests in  St. Paul  Capital other  than the
interests represented  by the  Preferred  Securities and  the interests  of  the
Managing Members.

                                       49
<PAGE>
    So  long as  any Convertible  Subordinated Debentures  are held  by St. Paul
Capital, the Managing Members shall not (i) direct the time, method and place of
conducting any proceeding  for any remedy  available to the  Special Trustee  or
exercising  any trust or power conferred on  the Special Trustee with respect to
the Convertible Subordinated Debentures, (ii)  waive any past default, which  is
waivable  under the Indenture,  (iii) exercise any  right to rescind  or annul a
declaration that the  principal of all  the Convertible Subordinated  Debentures
shall  be  due  and payable,  (iv)  consent  to any  amendment,  modification or
termination of  the  Convertible Subordinated  Debentures  or of  the  Indenture
without,  in each case, obtaining the prior  approval of the holders of at least
66 2/3%  or  more of  the  aggregate  liquidation preference  of  the  Preferred
Securities  then outstanding, PROVIDED, HOWEVER, that  where a consent under the
Indenture would require  the consent of  each holder affected  thereby, no  such
consent shall be given by the Managing Members without the prior consent of each
holder  of the Preferred  Securities. The Managing Members  shall not revoke any
action previously  authorized or  approved by  a vote  of holders  of  Preferred
Securities, without the approval of holders of Preferred Securities representing
66  2/3%  or  more of  the  aggregate  liquidation preference  of  the Preferred
Securities then outstanding. The  Managing Members shall  notify all holders  of
Preferred  Securities of  any notice of  default received from  the Trustee with
respect to the Convertible Subordinated Debentures.

    Any required approval of holders of  Preferred Securities may be given at  a
meeting  of  such  holders convened  for  such  purpose or  pursuant  to written
consent. St. Paul Capital will cause a notice of any meeting at which holders of
Preferred Securities are entitled to vote, or of any matter upon which action by
written consent of such holders is to be  taken, to be mailed to each holder  of
record  of  Preferred  Securities. Each  such  notice will  include  a statement
setting forth (i) the date of such meeting  or the date by which such action  is
to be taken, (ii) a description of any matter on which such holders are entitled
to  vote  or of  such  matter upon  which written  consent  is sought  and (iii)
instructions for the delivery of proxies or consents.

  BOOK-ENTRY-ONLY ISSUANCE -- THE DEPOSITORY TRUST COMPANY

    DTC will  act as  securities depositary  for the  Preferred Securities.  The
information  in this section concerning DTC and DTC's book-entry system is based
upon information obtained from DTC. The Preferred Securities will be issued only
as fully-registered securities registered in the name of Cede & Co. (as  nominee
for  DTC). One or  more fully-registered global  Preferred Security certificates
will be issued,  representing in  the aggregate  the total  number of  Preferred
Securities, and will be deposited with DTC.

    DTC  is a limited-purpose trust company organized under the New York Banking
Law, a "banking organization" within the meaning of the New York Banking Law,  a
member  of  the  Federal Reserve  System,  a "clearing  corporation"  within the
meaning of  the  New  York  Uniform Commercial  Code  and  a  "clearing  agency"
registered  pursuant to the provisions  of Section 17A of  the Exchange Act. DTC
holds securities that  its participants ("Participants")  deposit with DTC.  DTC
also  facilitates the settlement among  Participants of securities transactions,
such as  transfers  and  pledges, in  deposited  securities  through  electronic
computerized  book-entry changes in  Participants' accounts, thereby eliminating
the need for physical movement  of securities certificates. Direct  Participants
include  securities  brokers  and  dealers,  banks,  trust  companies,  clearing
corporations and certain other organizations ("Direct Participants"). Access  to
the  DTC  system is  also available  to  others such  as securities  brokers and
dealers, banks and trust  companies that clear through  or maintain a  custodial
relationship with a Direct Participant, either directly or indirectly ("Indirect
Participants").

                                       50
<PAGE>
    Purchases  of Preferred Securities within the DTC  system must be made by or
through Direct  Participants, which  will  receive a  credit for  the  Preferred
Securities  on DTC's records. The ownership interest of each actual purchaser of
a Preferred Security (a  "Beneficial Owner") is  in turn to  be recorded on  the
Direct  or Indirect  Participants' records.  Beneficial Owners  will not receive
written confirmation  from DTC  of their  purchases, but  Beneficial Owners  are
expected to receive written confirmations providing details of the transactions,
as  well as periodic statements  of their holdings, from  the Direct or Indirect
Participants through which the Beneficial Owners purchased Preferred Securities.
Transfers of ownership interests in Preferred Securities are to be  accomplished
by  entries made  on the  books of Participants  acting on  behalf of Beneficial
Owners. Beneficial  Owners  will  not receive  certificates  representing  their
ownership  interests in Preferred Securities, except  upon a resignation of DTC,
upon the occurrence of  an Event of Default  under the Convertible  Subordinated
Debentures  or upon a decision by St. Paul Capital to discontinue the book-entry
system for the Preferred Securities.

    DTC has  no knowledge  of  the actual  Beneficial  Owners of  the  Preferred
Securities;  DTC's records reflect only the  identity of the Direct Participants
to whose accounts such Preferred Securities  are credited, which may or may  not
be  the Beneficial Owners. The Participants  will remain responsible for keeping
account of their holdings on behalf of their customers.

    Conveyance  of  notices   and  other   communications  by   DTC  to   Direct
Participants,  by Direct  Participants to  Indirect Participants,  and by Direct
Participants and Indirect Participants to Beneficial Owners will be governed  by
arrangements  among them, subject to any statutory or regulatory requirements as
may be in effect from time to time.

    Redemption notices with respect to the Preferred Securities shall be sent to
Cede & Co.

    Although voting  with respect  to the  Preferred Securities  is limited,  in
those  cases where a  vote is required, neither  DTC nor Cede  & Co. will itself
consent  or  vote  with  respect  to  Preferred  Securities.  Under  its   usual
procedures,  DTC would  mail an  Omnibus Proxy  to St.  Paul Capital  as soon as
possible after  the  record  date.  The  Omnibus  Proxy  assigns  Cede  &  Co.'s
consenting  or voting rights to those  Direct Participants to whose accounts the
Preferred Securities are credited  on the record date  (identified in a  listing
attached to the Omnibus Proxy).

    Dividend  payments on  the Preferred Securities  will be made  to DTC. DTC's
practice is to credit Direct Participants' accounts on the relevant payment date
in accordance with their respective holdings  shown on DTC's records unless  DTC
has  reason to believe that  it will not receive  payments on such payment date.
Payments by  Participants to  Beneficial  Owners will  be governed  by  standing
instructions  and customary  practices and  will be  the responsibility  of such
Participant and not of  DTC, St. Paul  Capital or The St.  Paul, subject to  any
statutory  or regulatory  requirements as  may be in  effect from  time to time.
Payment of  dividends  to  DTC  is  the  responsibility  of  St.  Paul  Capital,
disbursement  of such payments  to Direct Participants  is the responsibility of
DTC, and  disbursement  of  such  payments  to  the  Beneficial  Owners  is  the
responsibility of Direct and Indirect Participants.

    Except as provided herein, a Beneficial Owner in a global Preferred Security
will  not  be entitled  to receive  physical  delivery of  Preferred Securities.
Accordingly, each  Beneficial  Owner must  rely  on  the procedures  of  DTC  to
exercise any rights under the Preferred Securities.

    DTC  may discontinue  providing its  services as  securities depositary with
respect to the Preferred Securities at  any time by giving reasonable notice  to
St.  Paul  Capital. Under  such  circumstances, in  the  event that  a successor
securities depositary is not  obtained, certificates representing the  Preferred
Securities  will be printed and  delivered. If an Event  of Default occurs under
the Convertible  Subordinated  Debentures or  if  St. Paul  Capital  decides  to
discontinue  use  of  the  system  of book-entry  transfers  through  DTC  (or a
successor depositary), certificates representing  the Preferred Securities  will
be printed and delivered.

                                       51
<PAGE>
  TRANSFER AGENT, REGISTRAR AND PAYING, CONVERSION AND EXCHANGE AGENT

    The  Chase Manhattan Bank (National Association) will act as Transfer Agent,
Registrar  and  Paying,  Conversion  and   Exchange  Agent  for  the   Preferred
Securities.

    Registration  of transfers of Preferred  Securities will be affected without
charge by or on behalf of St. Paul Capital, but upon payment (with the giving of
such indemnity as St. Paul Capital may  require) in respect of any tax or  other
government charges which may be imposed in relation to it.

DESCRIPTION OF ST. PAUL SERIES C CONVERTIBLE PREFERRED STOCK

    AS  DESCRIBED  UNDER  "--  PREFERRED  SECURITIES  --  OPTIONAL  EXCHANGE FOR
DEPOSITARY SHARES" ABOVE, THE PREFERRED  SECURITIES MAY BE EXCHANGED IN  CERTAIN
CIRCUMSTANCES   (FOLLOWING  A   PRIOR  EXCHANGE   FOR  CONVERTIBLE  SUBORDINATED
DEBENTURES HELD BY ST. PAUL CAPITAL) FOR DEPOSITARY SHARES REPRESENTING ST. PAUL
SERIES C CUMULATIVE CONVERTIBLE PREFERRED STOCK, WITHOUT PAR VALUE  (LIQUIDATION
PREFERENCE $5000 PER SHARE). THE FOLLOWING DESCRIPTION OF THE PRINCIPAL TERMS OF
THE  ST.  PAUL SERIES  C  CONVERTIBLE PREFERRED  STOCK  DOES NOT  PURPORT  TO BE
COMPLETE AND IS QUALIFIED IN ITS ENTIRETY BY REFERENCE TO THE ST. PAUL'S AMENDED
AND RESTATED ARTICLES  OF INCORPORATION, AS  AMENDED (THE "RESTATED  ARTICLES"),
AND  THE  CERTIFICATE  OF  DESIGNATION  OF THE  ST.  PAUL  SERIES  C CONVERTIBLE
PREFERRED STOCK (THE  "CERTIFICATE OF  DESIGNATION"), FORMS OF  WHICH HAVE  BEEN
FILED  AS EXHIBITS TO THE  REGISTRATION STATEMENT OF WHICH  THIS PROSPECTUS IS A
PART.

    The Board of Directors of The St. Paul has designated, and The St. Paul will
keep available, 36,000 shares (41,400 shares if the Underwriters' over-allotment
option is exercised in  full) of St. Paul  Series C Convertible Preferred  Stock
for  issuance upon exchange  of the Preferred  Securities for Depositary Shares,
each representing 1/100th of a share of St. Paul Series C Convertible  Preferred
Stock  (as described  under "--  Preferred Securities  -- Optional  Exchange for
Depositary Shares" above). At the time the Preferred Securities are issued,  all
corporate action required in connection with the issuance of the St. Paul Series
C  Convertible Preferred Stock  and the deposit thereof  with the Depositary (as
hereinafter defined) upon  the making  of an  Exchange Election  will have  been
taken.  The  L.L.C. Agreement  provides that  The  St. Paul  shall use  its best
efforts to have the Depositary Shares listed  on the NYSE or any other  exchange
on which the Preferred Securities may be listed.

    The  terms of the St. Paul Series C Convertible Preferred Stock -- including
as to  dividends, conversion  and liquidation  preference --  are  substantially
similar  to  those of  the  Preferred Securities  (adjusted  proportionately per
Depositary Share) with the following principal exceptions:

        (a) Accumulated and unpaid dividends (including any Additional Dividends
    thereon) on the Preferred Securities, if any,  at the time of the making  of
    an Exchange Election will become accumulated and unpaid dividends on the St.
    Paul Series C Convertible Preferred Stock;

        (b)  If dividends  are not  paid on  the St.  Paul Series  C Convertible
    Preferred Stock for 18 monthly dividend periods (including for this  purpose
    any  arrearage  with respect  to the  Preferred  Securities), the  number of
    directors of The St. Paul shall be increased by two persons and the  holders
    of  the St. Paul  Series C Convertible  Preferred Stock will  be entitled to
    elect the persons to fill such positions; and

        (c) Dividends on the St. Paul  Series C Convertible Preferred Stock  are
    not  subject  to a  deferral  option, however,  such  dividends need  not be
    declared even if The St. Paul has funds legally available therefor and  cash
    on hand sufficient to pay dividends. In the event that The St. Paul fails to
    declare  dividends on the St. Paul  Series C Convertible Preferred Stock, no
    dividends would be payable on any  other securities of The St. Paul  ranking
    PARI  PASSU (I.E.,  on a  parity) with or  junior to  the St.  Paul Series C
    Convertible Preferred Stock.

    If at any time following the Conversion Expiration Date, less than 5% of the
shares of St.  Paul Series  C Convertible  Preferred Stock  issued following  an
Exchange  Election  remain  outstanding,  such  shares  of  St.  Paul  Series  C
Convertible Preferred Stock shall be redeemable, from time to time, in whole but
not in part, at the option  of The St. Paul at  a redemption price of $5000  per
share  (equivalent to a  redemption price of $50  per Depositary Share) together
with accumulated and unpaid dividends (whether or not earned or declared).

                                       52
<PAGE>
    The St. Paul Series  C Convertible Preferred Stock  will rank senior to  the
St.  Paul Common  Stock and the  Series A Preferred  Stock of The  St. Paul with
respect to the payment  of dividends and  amounts upon liquidation,  dissolution
and winding-up. The St. Paul Series C Convertible Preferred Stock will rank PARI
PASSU (I.E., on a parity) with the Series B Preferred Stock of The St. Paul with
respect to the payment of dividends and amounts upon liquidation, dissolution or
winding-up.  In the event dividends are not paid  in full on either the Series B
Preferred Stock  or the  St.  Paul Series  C  Convertible Preferred  Stock,  the
holders  of the Series B  Preferred Stock and the  St. Paul Series C Convertible
Preferred Stock  will share  ratably with  respect to  any dividend  payment  in
proportion to the respective amounts of the accumulated and unpaid dividends due
on such series of preferred stock. See "Description of St. Paul Capital Stock --
Preferred Shares".

    In  the  event  of  a  voluntary  or  involuntary  bankruptcy,  liquidation,
dissolution or winding-up  of The St.  Paul, the  holders of St.  Paul Series  C
Convertible Preferred Stock are entitled to receive out of the net assets of The
St. Paul, but before any distribution is made on any class of securities ranking
junior  to the St.  Paul Series C  Convertible Preferred Stock,  $5000 per share
(equivalent to $50  per Depositary Share)  in cash plus  accumulated and  unpaid
dividends  (whether or not earned or declared) to the date of final distribution
to  such  holders.  After  payment  of  the  full  amount  of  the   liquidation
distribution  to which  they are  entitled, the  holders of  shares of  St. Paul
Series C  Convertible  Preferred Stock  will  not  be entitled  to  any  further
participation  in any distribution of assets of  The St. Paul. In the event that
the assets  available for  distribution  are insufficient  to  pay in  full  the
liquidation  preference  to the  holders of  the St.  Paul Series  C Convertible
Preferred Stock and any preferred  stock ranking on a  parity with the St.  Paul
Series  C Convertible Preferred  Stock, the holders of  such series of preferred
stock will  share  in  the remaining  assets  of  the St.  Paul,  based  on  the
proportion  of  their  liquidation preference  to  the entire  amount  of unpaid
liquidation preference.

    So long as the Convertible Subordinated Debentures are exchangeable for  the
Depositary  Shares  representing the  St.  Paul Series  C  Convertible Preferred
Stock, The St. Paul may not authorize or issue any other preferred stock ranking
senior to the St. Paul Series C Convertible Preferred Stock without the approval
of the holders of not less than 66 2/3% of the aggregate liquidation  preference
of  the Preferred  Securities then outstanding.  However, no such  vote shall be
required for the issuance by The St. Paul of additional preferred stock  ranking
PARI  PASSU or junior to the St. Paul Series C Convertible Preferred Stock as to
the  payment  of  dividends  and  amounts  upon  liquidation,  dissolution   and
winding-up.

DESCRIPTION OF DEPOSITARY SHARES

    THE  FOLLOWING SUMMARY  OF THE  TERMS OF  THE DEPOSIT  AGREEMENT (AS DEFINED
BELOW), DEPOSITARY SHARES AND DEPOSITARY  RECEIPTS (AS DEFINED BELOW), DOES  NOT
PURPORT  TO BE COMPLETE AND IS SUBJECT TO, AND QUALIFIED IN ITS ENTIRETY BY, THE
PROVISIONS OF THE  DEPOSIT AGREEMENT, THE  FORM OF  WHICH HAS BEEN  FILED AS  AN
EXHIBIT TO THE REGISTRATION STATEMENT OF WHICH THIS PROSPECTUS IS A PART.

    The  St. Paul will  cause to be issued  receipts ("Depositary Receipts") for
Depositary Shares, each of which will represent  1/100th of a share of St.  Paul
Series  C  Convertible  Preferred  Stock.  The  shares  of  St.  Paul  Series  C
Convertible Preferred Stock represented by  Depositary Shares will be  deposited
under  a Deposit Agreement (the "Deposit Agreement")  among The St. Paul and The
Chase Manhattan Bank (National Association)  (the "Depositary") for the  benefit
of  the holders  from time to  time of  the Depositary Receipts.  Subject to the
terms of  the  Deposit Agreement,  each  owner of  a  Depositary Share  will  be
entitled, in proportion to the applicable fraction of a share of St. Paul Series
C  Convertible Preferred Stock represented by  such Depositary Share, to all the
rights and preferences  of the  St. Paul  Series C  Convertible Preferred  Stock
represented  thereby  (including  dividend, voting,  conversion  and liquidation
rights and  preferences).  The  proportionate  liquidation  preference  of  each
Depositary  Share will be $50 plus accumulated  and unpaid dividends to the date
of payment, subject to certain  limitations. The L.L.C. Agreement provides  that
The  St. Paul shall use its best efforts to have the Depositary Shares listed on
the NYSE or any other exchange on which the Preferred Securities may be listed.

  GENERAL

    The Depositary  Shares  will  be evidenced  by  Depositary  Receipts  issued
pursuant to the Deposit Agreement. Upon an Exchange Election by the holders of a
majority in aggregate liquidation preference

                                       53
<PAGE>
of  the Preferred Securities  and immediately following (i)  the exchange by the
Conversion Agent of all (but not less than all) outstanding Preferred Securities
for Convertible  Subordinated Debentures,  (ii)  the issuance  of the  St.  Paul
Series  C Convertible Preferred  Stock and (iii)  the delivery of  such St. Paul
Series C Convertible Preferred Stock to the Depositary, The St. Paul will  cause
the Depositary to issue, on behalf of The St. Paul, the Depositary Shares to the
Conversion  Agent,  for  the  account  of  the  holders,  in  exchange  for such
Convertible Subordinated Debentures. Following  an Exchange Election, copies  of
the  forms of Deposit Agreement and Depositary  Receipt may be obtained from The
St. Paul  or  the Depositary,  upon  request, at  the  principal office  of  the
Depositary  at  which at  any  particular time  its  depositary business  may be
administered (the  "Depositary's  Office"),  which  as of  the  date  hereof  is
4  Chase MetroTech Center, Brooklyn, New  York 11245, Attention: Corporate Trust
Administration.

  DIVIDENDS AND OTHER DISTRIBUTIONS

    The Depositary will  distribute all  dividends or  other cash  distributions
received  in respect of the St. Paul Series C Convertible Preferred Stock to the
record holders  of  Depositary  Shares  in such  amounts  of  such  dividend  or
distribution  as are applicable to the number of such Depositary Shares owned by
such holders,  subject  to  certain  obligations  of  holders  to  file  proofs,
certificates  and other information  and to pay certain  charges and expenses to
the Depositary.

    In the  event of  a distribution  other than  in cash,  the Depositary  will
distribute  property received by  it to the record  holders of Depositary Shares
entitled thereto in  such amounts, as  nearly as practicable,  of such  property
(including  securities) received by it  as are applicable to  the number of such
Depositary Shares  owned by  such  holders, subject  to certain  obligations  of
holders  to file proofs,  certificates and other information  and to pay certain
charges and expenses to the Depositary,  unless The St. Paul determines that  it
is  not feasible to make such distribution, in  which case The St. Paul may sell
such property and distribute the net proceeds from such sale to such holders.

  WITHDRAWAL OF ST. PAUL SERIES C CONVERTIBLE PREFERRED STOCK

    Upon surrender of Depositary Receipts  representing at least 100  Depositary
Shares  at the  Depositary's Office,  a holder is  entitled to  delivery at such
office, to or  upon his order,  of the number  of whole shares  of the St.  Paul
Series C Convertible Preferred Stock and any money or other property represented
by  such Depositary  Shares. Holders  of Depositary  Shares will  be entitled to
receive whole shares of the St. Paul Series C Convertible Preferred Stock on the
basis of one share of St. Paul Series C Convertible Preferred Stock for each 100
Depositary Shares,  but  holders of  such  whole shares  of  St. Paul  Series  C
Convertible   Preferred  Stock  will  not  thereafter  be  entitled  to  receive
Depositary Shares therefor. If the  Depositary Receipts delivered by the  holder
evidence  a number of  Depositary Shares in  excess of the  number of Depositary
Shares representing the number of whole shares of St. Paul Series C  Convertible
Preferred  Stock to be withdrawn, the Depositary  will deliver to such holder at
the same  time  a  new  Depositary Receipt  evidencing  such  excess  number  of
Depositary Shares. The L.L.C. Agreement provides that The St. Paul shall use its
best  efforts to  have the  Depositary Shares  listed on  the NYSE  or any other
exchange on which the Preferred Securities may  be listed. The St. Paul is  not,
however, obligated to cause the St. Paul Series C Convertible Preferred Stock to
be listed on any stock exchange.

  VOTING THE ST. PAUL SERIES C CONVERTIBLE PREFERRED STOCK

    Upon  receipt of notice of any meeting at  which the holders of the St. Paul
Series C Convertible Preferred Stock are  entitled to vote, the Depositary  will
mail  the information contained in such notice  of meeting to the record holders
of the Depositary  Shares relating to  St. Paul Series  C Convertible  Preferred
Stock.  Each record holder of  such Depositary Shares on  the record date (which
will be the same date as the record  date for the St. Paul Series C  Convertible
Preferred  Stock) will be entitled to instruct the Depositary as to the exercise
of the voting rights pertaining to the  amount of St. Paul Series C  Convertible
Preferred  Stock (or fraction  thereof) represented by  such holder's Depositary
Shares. The Depositary will endeavor, insofar as practicable, to vote the amount
of St.  Paul  Series  C  Convertible  Preferred  Stock  (or  fractions  thereof)
represented  by such Depositary Shares in accordance with such instructions, and
The St.  Paul will  agree  to take  all reasonable  action  that may  be  deemed
necessary by the Depositary in

                                       54
<PAGE>
order to enable the Depositary to do so. The Depositary will abstain from voting
shares  of St. Paul Series  C Convertible Preferred Stock  to the extent it does
not  receive  specific  instructions  from  the  holders  of  Depositary  Shares
representing those shares of St. Paul Series C Convertible Preferred Stock.

  CONVERSION OF ST. PAUL SERIES C CONVERTIBLE PREFERRED STOCK

    The  Depositary  Receipts  may be  surrendered  by holders  thereof,  at the
holders' option, at any  time and from  time to time, to  the Depositary at  the
Depositary's  Office or at such other office or to such agents as the Depositary
may designate for such  purpose with written instructions  to the Depositary  to
instruct  The St. Paul to cause conversion  of the whole or fractional shares of
St. Paul  Series C  Convertible Preferred  Stock represented  by the  Depositary
Shares  evidenced by such Receipts  into whole shares of  St. Paul Common Stock,
and The St.  Paul has  agreed that  upon receipt  of such  instructions and  any
amounts  payable  in  respect thereof,  it  will  cause the  delivery  of  (i) a
certificate or certificates evidencing  the number of whole  shares of St.  Paul
Common  Stock  into which  the  St. Paul  Series  C Convertible  Preferred Stock
represented by the  Depositary Shares  evidenced by such  Depositary Receipt  or
Receipts  have been converted, and (ii) any money or other property to which the
holder is entitled. If the Depositary Shares represented by a Depositary Receipt
are to be converted in part only,  a new Depositary Receipt or Receipts will  be
issued for any Depositary Shares not to be converted.

    On  and after May 31, 1999 and provided  that The St. Paul is current in the
payment of dividends on the St.  Paul Series C Convertible Preferred Stock,  The
St.  Paul  may,  at  its  option, cause  the  conversion  rights  of  holders of
Depositary Shares representing St. Paul Series C Convertible Preferred Stock  to
expire. The St. Paul may exercise this option only if for 20 trading days within
any  period of 30  consecutive trading days,  including the last  trading day of
such period, the Current Market Price of  St. Paul Common Stock exceeds 120%  of
the  conversion price of the Depositary Shares, subject to adjustment in certain
circumstances. In order to  exercise its conversion  expiration option, The  St.
Paul  must issue a  press release announcing the  Conversion Expiration Date and
give notice by first-class  mail to holders of  Depositary Shares in the  manner
provided  for holders of Preferred Securities under "-- Description of Preferred
Securities -- Expiration of Conversion  Rights". The Conversion Expiration  Date
will  be a date selected by The St. Paul  which is not less than 30 and not more
than 60 days  after the  date on  which The St.  Paul issues  the press  release
announcing its intention to terminate conversion rights of holders of Depositary
Shares.

  AMENDMENT AND TERMINATION OF THE DEPOSIT AGREEMENT

    The  form of  Depositary Receipt  evidencing the  Depositary Shares  and any
provision of  the Deposit  Agreement may  at any  time be  amended by  agreement
between  The St. Paul and the Depositary. However, any amendment that materially
and adversely alters the rights of the holders of Depositary Shares will not  be
effective  unless such amendment  has been approved  by the holders  of at least
66 2/3% of the Depositary Shares  then outstanding. Each holder of a  Depositary
Share  at  the time  any  amendment becomes  effective  will be  deemed  to have
consented and agreed to such amendment.

    The Deposit Agreement may be terminated by The St. Paul or by the Depositary
if (i) all outstanding Depositary Shares have been redeemed, (ii) there has been
a final distribution in respect of  the St. Paul Series C Convertible  Preferred
Stock  in connection with any liquidation, dissolution  or winding up of The St.
Paul and such  distribution has been  distributed to the  holders of  Depositary
Receipts  or (iii) each share  of St. Paul Series  C Convertible Preferred Stock
shall have been converted into shares of St. Paul Common Stock.

  CHARGES OF DEPOSITARY

    The St. Paul will pay all transfer and other taxes and governmental  charges
arising  solely from the  existence of the  Depositary arrangements, the initial
deposit of the St. Paul Series C Convertible Preferred Stock, the redemption  of
shares  of St.  Paul Series  C Convertible Preferred  Stock and  the issuance of
shares of St. Paul Common Stock upon conversion. The St. Paul will pay the  fees
and  reasonable expenses of the Depositary in connection with the performance of
its duties under the Deposit Agreement. Holders of Depositary Receipts will  pay
any other transfer or other taxes and

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<PAGE>
governmental charges. If, at the request of a holder of Depositary Receipts, the
Depositary incurs charges or other expenses for which it is not otherwise liable
under  the Deposit Agreement,  such holder will  be liable for  such charges and
expenses.

  RESIGNATION AND REMOVAL OF DEPOSITARY

    The Depositary may resign at any time  by delivering to The St. Paul  notice
of  its  election  to do  so,  and  The St.  Paul  may  at any  time  remove the
Depositary, any such resignation or removal to take effect upon the  appointment
of  a successor Depositary, which successor  Depositary must be appointed within
60 days after delivery  of the notice  of resignation or removal  and must be  a
bank  or trust  company having  its principal  office in  the United  States and
having a combined capital and surplus of at least $50 million. In the event  The
St.  Paul fails to appoint such successor  Depositary within such sixty (60) day
period, the Depositary may petition any court of competent jurisdiction for  the
appointment of a successor Depositary.

  MISCELLANEOUS

    The  Depositary will, with the approval of The St. Paul, appoint a Registrar
for registration of the Depositary  Receipts or Depositary Shares in  accordance
with  any requirements of any applicable stock exchange in which the Receipts or
the Depositary  Shares are  listed. The  Registrar will  maintain books  at  the
Depositary's  Office  for  the  registration  and  registration  of  transfer of
Depositary Receipts or at such other place as is approved by The St. Paul and of
which the holders of Depositary Receipts are given reasonable notice.

    The St. Paul will deliver to the Depositary and the Depositary will  forward
to  holders of Depositary  Shares all notices  and reports required  by law, the
rules of  any national  securities exchange  upon which  the St.  Paul Series  C
Convertible  Preferred Stock, the  Depositary Shares or  the Depositary Receipts
are listed or by The St.  Paul's Amended and Restated Articles of  Incorporation
(including  the Certificate of Designation) or Bylaws to be furnished by The St.
Paul to holders of St. Paul Series C Convertible Preferred Stock.

    Neither the Depositary nor The St. Paul  will be liable if either is by  law
or  certain other circumstances beyond its  control prevented from or delayed in
performing its obligations under the  Deposit Agreement. Neither the  Depositary
nor  any agent of the Depositary nor The St. Paul assumes any obligation or will
be subject to any liability under the Deposit Agreement to holders of Depositary
Receipts other  than to  use its  best judgment  and act  in good  faith in  the
performance  of  such  duties  as  are specifically  set  forth  in  the Deposit
Agreement. Neither The St. Paul nor  the Depositary will be obligated to  appear
in, prosecute or defend any legal proceeding in respect of any Depositary Shares
or  any  St.  Paul  Series C  Convertible  Preferred  Stock  unless satisfactory
indemnity is furnished. The St.  Paul and the Depositary  may rely on advice  of
counsel  or accountants, or information provided  by persons presenting St. Paul
Series C Convertible Preferred Stock  for deposit, holders of Depositary  Shares
or  other  persons  believed to  be  authorized  or competent  and  on documents
believed to be genuine.

DESCRIPTION OF THE GUARANTEE

    THE FOLLOWING IS A DESCRIPTION OF THE PRINCIPAL TERMS AND PROVISIONS OF  THE
GUARANTEE  AGREEMENT (THE "GUARANTEE"), WHICH WILL  BE EXECUTED AND DELIVERED BY
THE ST. PAUL FOR THE BENEFIT OF THE  HOLDERS FROM TIME TO TIME OF THE  PREFERRED
SECURITIES.  THE FOLLOWING DESCRIPTION IS QUALIFIED IN ITS ENTIRETY BY REFERENCE
TO SUCH  AGREEMENT, THE  FORM OF  WHICH  HAS BEEN  FILED AS  AN EXHIBIT  TO  THE
REGISTRATION STATEMENT OF WHICH THIS PROSPECTUS IS A PART.

  GENERAL

    Pursuant to the Guarantee, The St. Paul will irrevocably and unconditionally
agree,  on a subordinated basis  and to the extent set  forth therein, to pay in
full to the  holders of  the Preferred  Securities, the  Guarantee Payments  (as
defined  below) (except to the  extent previously paid by  St. Paul Capital), as
and when due, regardless of any  defense, right of set-off or counterclaim  that
St.  Paul Capital may have or assert.  The following payments, to the extent not
paid by St. Paul Capital, are the "Guarantee Payments": (a) any accumulated  and
unpaid  dividends (including  any Additional  Dividends thereon)  that have been
theretofore declared on  the Preferred Securities  from funds legally  available
therefor;  (b) the Redemption Price payable with respect to Preferred Securities
called for redemption by St. Paul Capital

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<PAGE>
out of funds legally available therefor; and (c) upon a liquidation of St.  Paul
Capital,  the lesser of (i) the Liquidation  Distribution and (ii) the amount of
assets of St. Paul  Capital available for distribution  to holders of  Preferred
Securities in liquidation of St. Paul Capital. The St. Paul's obligation to make
a  Guarantee Payment may  be satisfied by  The St. Paul's  direct payment of the
required amounts to  the holders of  Preferred Securities or  by The St.  Paul's
causing St. Paul Capital to pay such amounts to such holders.

    If  The  St.  Paul  fails  to  make  interest  payments  on  the Convertible
Subordinated Debentures purchased  by St.  Paul Capital, St.  Paul Capital  will
have  insufficient  funds  to pay  dividends  on the  Preferred  Securities. The
Guarantee does not  cover payment of  dividends when St.  Paul Capital does  not
have sufficient funds to pay such dividends.

    Because  the Guarantee is a full  and unconditional guarantee of payment and
not of  collection, holders  of the  Preferred Securities  may proceed  directly
against  The St. Paul  as guarantor, rather  than having to  proceed against St.
Paul Capital  before  attempting to  collect  from The  St.  Paul. A  holder  of
Preferred Securities may enforce such obligations directly against The St. Paul,
and  under the Guarantee The St. Paul will  waive any right or remedy to require
that any action  be brought  against St.  Paul Capital  or any  other person  or
entity  before proceeding  against The  St. Paul.  Such obligations  will not be
discharged except by payment of the Guarantee Payments in full.

  CERTAIN COVENANTS OF THE ST. PAUL

    Under the Guarantee, The St. Paul will  covenant and agree that, so long  as
any Preferred Securities remain outstanding, neither The St. Paul nor any direct
or  indirect majority owned subsidiary of The St. Paul (excluding Nuveen and its
consolidated subsidiaries) shall declare or pay any dividend or distribution on,
or redeem, purchase  or otherwise  acquire or  make a  liquidation payment  with
respect   to,  any  of  its  capital  stock   (other  than  as  a  result  of  a
reclassification of capital stock or the exchange or conversion of one class  or
series  of capital stock for  another class or series  of capital stock) or make
any guarantee payments with respect to the foregoing (other than payments  under
the  Guarantee or dividends or guarantee payments to The St. Paul by a direct or
indirect majority owned subsidiary), if at such time The St. Paul has  exercised
its option to defer interest payments on the Convertible Subordinated Debentures
and  such deferral is continuing, The St. Paul is in default with respect to its
payment or other obligations  under the Guarantee or  there shall have  occurred
any  event that, with the giving  of notice or the lapse  of time or both, would
constitute an Event  of Default under  the Convertible Subordinated  Debentures.
The  St.  Paul  will  covenant  to take  all  actions  necessary  to  ensure the
compliance of its subsidiaries with the above covenant.

    The St. Paul will also covenant that, so long as Preferred Securities remain
outstanding, it will (i) not cause or  permit any Common Securities of St.  Paul
Capital  to be transferred,  (ii) maintain direct or  indirect 100% ownership of
all outstanding securities  of St.  Paul Capital  other than  (x) the  Preferred
Securities  and (y) any other securities issued  by St. Paul Capital (other than
the Common Securities) so long as the issuance thereof to persons other than The
St. Paul or any of its subsidiaries  would not cause St. Paul Capital to  become
an  "investment company" required to be  registered under the Investment Company
Act of 1940, as amended, (iii) cause at least 21% of the total value of St. Paul
Capital and at least 21%  of all interests in  the capital, income, gain,  loss,
deduction and credit of St. Paul Capital to be represented by Common Securities,
(iv) not voluntarily dissolve, wind up or liquidate St. Paul Capital (other than
in  connection with  the exchange  of all  outstanding Preferred  Securities for
Depositary Shares  in the  manner described  under "--  Preferred Securities  --
Optional Exchange for Depositary Shares") or either of the Managing Members, (v)
cause  The St. Paul and St. Paul Holdings  to remain the Managing Members of St.
Paul Capital  and timely  perform all  of their  respective duties  as  Managing
Members  of St. Paul Capital (including the duty to declare and pay dividends on
the Preferred  Securities  as  described  under "  --  Preferred  Securities  --
Dividends")  and (vi) use reasonable efforts to cause St. Paul Capital to remain
a  limited  liability  company  and  otherwise  continue  to  be  treated  as  a
partnership for U.S. federal income tax purposes; PROVIDED that The St. Paul may
permit St. Paul Capital to consolidate or merge with

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<PAGE>
or  into or convey, transfer or lease its properties and assets substantially as
an entirety to another entity upon the  terms and subject to the conditions  set
forth under " -- Preferred Securities -- Merger, Consolidation or Sale of Assets
of St. Paul Capital" above.

    As  a part of the Guarantee, The St.  Paul will agree that it will honor all
obligations described  therein relating  to the  conversion or  exchange of  the
Preferred  Securities into  or for  St. Paul  Common Stock  or Depositary Shares
representing St. Paul Series C Convertible Preferred Stock, as described in  "--
Preferred  Securities  --  Conversion  Rights," and  "--  Optional  Exchange for
Depositary Shares".

  SUBORDINATION

    The St. Paul's obligations  under the Guarantee  to make Guarantee  Payments
will  constitute an  unsecured obligation  of The  St. Paul  that will  rank (i)
subordinate and junior in right  of payment to all  liabilities of The St.  Paul
and  the Convertible  Subordinated Debentures, and  (ii) PARI PASSU  (I.E., on a
parity) with the most senior preferred shares now or hereafter issued by The St.
Paul and with any  guarantee now or  hereafter entered into by  The St. Paul  in
respect  of any preferred or  preference stock of any  affiliate of The St. Paul
and (iii) senior  to St.  Paul Common  Stock and any  other class  or series  of
capital  stock issued  by The  St. Paul or  any of  its affiliates  which by its
express  terms  ranks  junior  in  the  payment  of  dividends  and  amounts  on
liquidation,  dissolution, and  winding-up to the  Preferred Securities ("Junior
Stock"). On  the bankruptcy,  liquidation or  winding-up of  The St.  Paul,  its
obligations  under the Guarantee  will rank junior to  all its other liabilities
and, therefore, funds may not be  available for payment under the Guarantee.  As
of  March 31, 1995, The St. Paul  had approximately $628 million of indebtedness
or other obligations constituting Senior  Indebtedness and no indebtedness  that
would rank equally with the Guarantee.

  AMENDMENTS AND ASSIGNMENT

    The  terms of the Guarantee  may be amended only  with the prior approval of
the holders of not less than 66 2/3% of the aggregate liquidation preference  of
the  Preferred Securities  then outstanding.  The manner  of obtaining  any such
approval of holders  of the Preferred  Securities will  be as set  forth in  "--
Preferred  Securities  --  Voting  Rights".  All  provisions  contained  in  the
Guarantee  will   bind  the   successors,  assigns,   receivers,  trustees   and
representatives  of The St. Paul and will inure to the benefit of the holders of
the Preferred Securities. Except in connection with any merger or  consolidation
of  The St. Paul with or  into another entity or any  sale, transfer or lease of
The St. Paul's assets to another entity complying with the provisions under  "--
Consolidation,  Merger or Sale of Assets" below, The St. Paul may not assign its
rights or  delegate  its  obligations  under the  Guarantee  without  the  prior
approval  of the holders of  not less than 66  2/3% of the aggregate liquidation
preference of the Preferred Securities then outstanding.

  TERMINATION

    The St. Paul's  obligation to  make Guarantee Payments  under the  Guarantee
will  terminate as to each  holder of Preferred Securities  and be of no further
force and effect upon (a) full payment of the Redemption Price of such  holder's
Preferred  Securities, (b)  full payment of  the amounts payable  to such holder
upon liquidation of St.  Paul Capital, (c) the  distribution of St. Paul  Common
Stock  to  such holder  in respect  of the  conversion of  all of  such holder's
Preferred Securities  into St.  Paul Common  Stock or  (d) the  distribution  of
Depositary  Shares representing St. Paul Series C Convertible Preferred Stock to
such  holder  in  respect  of  the  exchange  of  the  Convertible  Subordinated
Debentures  for St. Paul  Series C Convertible  Preferred Stock. Notwithstanding
the foregoing,  The  St.  Paul's  obligation to  make  Guarantee  Payments  will
continue  to be effective  or will be  reinstated, as the  case may be,  as to a
holder if at any time  such holder must restore payment  of any sums paid  under
the  Preferred Securities or under the  Guarantee for any reason whatsoever. The
St. Paul will indemnify each  holder and hold it  harmless from and against  any
loss it may suffer in such circumstances.

  CONSOLIDATION, MERGER OR SALE OF ASSETS

    The  Guarantee provides that The  St. Paul may merge  or consolidate with or
into another entity, may permit another  entity to merge or consolidate with  or
into  The St. Paul and  may sell, transfer or lease  all or substantially all of
its assets to another entity if (i) at such time no Event of Default (as defined
in the

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Indenture) shall have occurred and be continuing, or would occur as a result  of
such  merger, consolidation or sale, transfer or  lease and (ii) the survivor of
such merger or consolidation or entity to which The St. Paul's assets are  sold,
transferred or leased is an entity organized under the laws of the United States
or any state thereof, becomes a managing member of St. Paul Capital and causes a
wholly-owned  subsidiary to  become the only  other managing member  of St. Paul
Capital, assumes all of The St. Paul's obligations under the Guarantee and has a
net worth equal to at least 10% of the total contributions to St. Paul Capital.

  GOVERNING LAW

    The Guarantee will be governed by and construed in accordance with the  laws
of the State of New York.

DESCRIPTION OF THE CONVERTIBLE SUBORDINATED DEBENTURES

    THE  FOLLOWING SUMMARY OF PRINCIPAL TERMS  AND PROVISIONS OF THE CONVERTIBLE
SUBORDINATED DEBENTURES IN WHICH  ST. PAUL CAPITAL WILL  INVEST THE PROCEEDS  OF
THE  ISSUANCE AND SALE OF THE PREFERRED  SECURITIES AND SUBSTANTIALLY ALL OF THE
CAPITAL CONTRIBUTED TO ST. PAUL CAPITAL  BY THE MANAGING MEMBERS (THE  "MANAGING
MEMBERS  PAYMENT")  DOES NOT  PURPORT TO  BE  COMPLETE AND  IS QUALIFIED  IN ITS
ENTIRETY BY REFERENCE TO THE INDENTURE AMONG THE ST. PAUL, ST. PAUL CAPITAL  AND
THE CHASE MANHATTAN BANK (NATIONAL ASSOCIATION), AS TRUSTEE (THE "TRUSTEE"), THE
FORM  OF WHICH  HAS BEEN FILED  AS AN  EXHIBIT TO THE  REGISTRATION STATEMENT OF
WHICH THIS PROSPECTUS IS A PART. ALL OF THE CONVERTIBLE SUBORDINATED  DEBENTURES
WILL BE ISSUED UNDER THE INDENTURE.

  GENERAL

    The  Convertible  Subordinated  Debentures  will  be  limited  in  aggregate
principal amount to the sum of the aggregate amount of the proceeds received  by
St.  Paul Capital from the offering made hereby and the Managing Members Payment
less 1% of such sum.

    The entire principal amount of the Convertible Subordinated Debentures  will
become  due and payable, together with  any accrued and unpaid interest thereon,
including Additional Interest  (as defined below),  on the earliest  of May  31,
2025  or the date upon which St. Paul Capital is dissolved, wound-up, liquidated
or terminated.

    The Convertible  Subordinated  Debentures  will  be  issued  only  in  fully
registered  form,  without coupons,  in denominations  of  $50 and  any integral
multiple thereof.  No  service charge  will  be  made for  any  registration  of
transfer  or exchange of  Convertible Subordinated Debentures,  but The St. Paul
may require payment of a sum sufficient  to cover any tax or other  governmental
charge payable in connection therewith.

    The  Convertible Subordinated Debentures will not  be guaranteed by St. Paul
Holdings.

  INTEREST

    The Convertible Subordinated Debentures will bear interest at the rate of 6%
per annum from the original date of issuance, payable monthly in arrears on  the
last  day of each calendar month of each year (each an "Interest Payment Date"),
commencing May 31, 1995. Interest will  compound monthly and will accrue at  the
annual rate of 6% on any interest installment not paid when due.

    The  amount of interest payable for any period will be computed on the basis
of twelve 30-day months and  a 360-day year and, for  any period shorter than  a
full monthly interest period, will be computed on the basis of the actual number
of  days elapsed in such period. In the event that any date on which interest is
payable on the Convertible Subordinated Debentures is not a Business Day, then a
payment of the interest payable on such date will be made on the next succeeding
day which  is a  Business Day  (and without  any interest  or other  payment  in
respect  of any  such delay).  If such  Business Day  is in  the next succeeding
calendar year, however, such payment shall be made on the immediately  preceding
Business  Day, in each  case with the same  force and effect as  if made on such
date.

  OPTION TO DEFER INTEREST PAYMENTS

    The St. Paul shall have the right at  any time and from time to time  during
the  term of the Convertible Subordinated  Debentures to defer interest payments
for up to 60  months during which  period interest will  continue to accrue  and
compound  monthly  (provided  that  a  deferral  of  interest  payments  may not

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<PAGE>
extend the  stated  maturity of  the  Convertible Subordinated  Debentures)  and
during  which The  St. Paul  shall have  the right  to make  partial payments of
interest or at the end of which period  The St. Paul must pay all interest  then
accrued  and unpaid (together  with Additional Interest);  PROVIDED THAT, during
any such deferral of interest  payments neither The St.  Paul nor any direct  or
indirect  majority-owned  subsidiary  of  The  St.  Paul  (excluding  Nuveen and
Nuveen's consolidated subsidiaries)  shall declare  or pay any  dividend on,  or
redeem,  purchase, acquire for value or  make a liquidation payment with respect
to, any of its capital  stock (other than as a  result of a reclassification  of
such  capital stock  or the exchange  or conversion  of one class  or service of
capital stock  for  another  class or  series  of  capital stock)  or  make  any
guarantee  payments with respect to the foregoing (other than payments under the
Guarantee or dividend or  guarantee payments to  The St. Paul  from a direct  or
indirect  majority-owned  subsidiary).  Prior  to the  termination  of  any such
deferral of interest payments, The St. Paul may further defer interest payments,
provided that such deferral  of interest payments  together with any  extensions
thereof  may not exceed 60 months, nor may such extended interest payment period
extend the maturity of  the Convertible Subordinated  Debentures. After The  St.
Paul  has paid all  accrued and unpaid  interest (including Additional Interest)
following any extended  interest payment  period, it may  again extend  interest
payment  periods for  up to  60 months, subject  to the  preceding sentence. The
failure by The St. Paul to make interest payments during a deferral of  interest
payments  would not constitute  a default or  an event of  default under The St.
Paul's currently  outstanding indebtedness.  The St.  Paul shall  give St.  Paul
Capital,  as holder of the Convertible  Subordinated Debentures, and the Trustee
notice of its deferral of interest payments no later than the last date on which
St. Paul Capital would be required to  notify the NYSE of the record or  payment
date of the related dividend, which currently is 10 days prior to such record or
payment  date. St.  Paul Capital  shall give  written notice  of The  St. Paul's
deferral of interest payments to the holders of the Preferred Securities.

  ADDITIONAL INTEREST

    The St. Paul shall be  required to pay any  interest upon interest that  has
not  been paid on the  Convertible Subordinated Debentures monthly. Accordingly,
in such circumstance, The St. Paul will  pay interest upon interest in order  to
provide  for monthly compounding on the Convertible Subordinated Debentures (the
amounts of interest  payable to  effect monthly compounding  on the  Convertible
Subordinated Debentures being referred to herein as "Additional Interest").

  MANDATORY REDEMPTION

    If  St. Paul  Capital redeems  Preferred Securities  in accordance  with the
terms thereof, The St. Paul will redeem Convertible Subordinated Debentures in a
principal amount equal  to the  aggregate stated liquidation  preference of  the
Preferred  Securities so redeemed, together with any accrued and unpaid interest
thereon, including Additional  Interest, if  any. Any payment  pursuant to  this
provision  shall be made prior to 12:00 noon, New York City time, on the date of
such redemption  or at  such other  time on  such earlier  date as  the  parties
thereto shall agree. The Convertible Subordinated Debentures are not entitled to
the  benefit  of any  sinking  fund or,  except as  set  forth above,  any other
provision for mandatory prepayment.

  SUBORDINATION

    The Indenture  provides that  the  Convertible Subordinated  Debentures  are
subordinate  and  junior in  right  of payment  to  all Senior  Indebtedness (as
defined below) of The St. Paul.

    Upon any payment or distribution of assets of the Company to creditors  upon
any  liquidation, dissolution,  winding up,  reorganization, assignment  for the
benefit of creditors, marshalling  of assets or  liabilities or any  bankruptcy,
insolvency  or  similar  proceedings  of  the  Company,  the  holders  of Senior
Indebtedness will be entitled to receive payment  in full of all amounts due  on
or to become due on or in respect of all Senior Indebtedness, before the holders
of  the Convertible Subordinated Debentures are  entitled to receive any payment
(including any payment  to holders  of the  Convertible Subordinated  Debentures
made  in respect of any other  debt subordinated to the Convertible Subordinated
Debentures) on  account of  the  principal of  or  interest on  the  Convertible
Subordinated  Debentures  or on  account of  any  purchase, redemption  or other
acquisition of the Convertible Subordinated Debentures by the Company.

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<PAGE>
    The Company may  not make  any payments on  the account  of the  Convertible
Subordinated  Debentures  or  account of  the  purchase or  redemption  or other
acquisition of the  Convertible Subordinated Debentures,  if there has  occurred
and  is continuing a default in the payment  of the principal of (or premium, if
any) or interest  on any Senior  Indebtedness (a "Senior  Payment Default").  In
addition,  if any default  (other than a  Senior Payment Default),  or any event
which after notice  or lapse  of time  (or both)  would become  a default,  with
respect to certain Senior Indebtedness, permitting after notice or lapse of time
(or  both) the holders thereof  (or a trustee or agent  on behalf of the holders
thereof) to accelerate the  maturity thereof has occurred  and is continuing  (a
"Senior  Nonmonetary Default"),  and the Company  and the  Trustee have received
written notice thereof from the holder of such certain Senior Indebtedness, then
the Company  may  not  make any  payments  on  the account  of  the  Convertible
Subordinated  Debentures  or  account of  the  purchase or  redemption  or other
acquisition  of  the  Convertible  Subordinated  Debentures,  for  a  period  (a
"blockage  period") commencing on  the date the Company  and the Trustee receive
such written notice and ending  on the earlier of (i)  179 days after such  date
and  (ii)  the date,  if any,  on which  the Senior  Indebtedness to  which such
default relates is discharged or such default is waived in writing or  otherwise
cured  or ceases to exist and any acceleration of certain Senior Indebtedness to
which such Senior Nonmonetary Default relates is rescinded or annulled.

    In any event, not more than one blockage period may be commenced during  any
period  of 360  consecutive days,  and there must  be a  period of  at least 181
consecutive days in each period of 360 consecutive days when no blockage  period
is  in effect. Following the  commencement of a blockage  period, the holders of
such certain Senior Indebtedness will be precluded from commencing a  subsequent
blockage  period until  the conditions set  forth in the  preceding sentence are
satisfied. No Senior Nonmonetary Default that  existed or was continuing on  the
date  of commencement of any blockage period with respect to such certain Senior
Indebtedness initiating such blockage period will be, or can be, made the  basis
for  the commencement of  a subsequent blockage period,  unless such default has
been cured for a period of not less than 90 consecutive days.

    By reason of such subordination, in the event of any proceeding of the  type
described  in the preceding  paragraph involving The St.  Paul, creditors of The
St. Paul who are holders of Senior Indebtedness and general unsecured  creditors
of  The St. Paul  may recover more, ratably,  than the holder  or holders of the
Convertible Subordinated Debentures.

    The term "Senior Indebtedness" is defined to mean the principal of, premium,
if any, interest on, and any other payment due pursuant to any of the following,
whether Incurred  (as defined  in the  Indenture) on  or prior  to the  date  of
execution of the Indenture or thereafter Incurred:

        (a) all obligations of The St. Paul for money borrowed;

        (b)  all obligations  of The  St. Paul  evidenced by  notes, debentures,
    bonds or other securities, including obligations Incurred in connection with
    the acquisition of property, assets or businesses;

        (c) all capital lease obligations of The St. Paul;

        (d) all  reimbursement  obligations of  The  St. Paul  with  respect  to
    letters of credit, bankers' acceptances or similar facilities issued for the
    account of The St. Paul;

        (e)  all obligations of The  St. Paul issued or  assumed as the deferred
    purchase price  of property  or services,  including all  obligations  under
    master  lease transactions  pursuant to  which The  St. Paul  or any  of its
    subsidiaries have agreed to be treated as owner of the subject property  for
    federal  income tax purposes (but  excluding trade accounts payable, accrued
    liabilities resulting from the  sale of extended  service plans, or  accrued
    liabilities arising in the ordinary course of business);

        (f)  all payment obligations of The St. Paul under interest rate swap or
    similar agreements or foreign currency hedge, exchange or similar agreements
    at the time of determination, including any such obligations Incurred by The
    St.  Paul solely to act as a  hedge against increases in interest rates that
    may occur under  the terms of  other outstanding variable  or floating  rate
    Indebtedness (as defined in the Indenture) of The St. Paul;

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        (g)  all obligations of the type referred  to in clauses (a) through (f)
    above of another person and all dividends of another person, the payment  of
    which,  in either case, The St. Paul has assumed or guaranteed, or for which
    The St. Paul is  responsible or liable, directly  or indirectly, jointly  or
    severally, as obligor, guarantor or otherwise;

        (h) all compensation payable by The St. Paul to the Trustee; and

        (i)   all amendments, modifications, renewals, extensions, refinancings,
    replacements and  refundings  by  The  St. Paul  of  any  such  Indebtedness
    referred  to in  clauses (a)  through (h)  above (and  of any  such amended,
    modified, renewed, extended, refinanced,  refunded or replaced  indebtedness
    or obligations);
PROVIDED,  HOWEVER, that the following shall not constitute Senior Indebtedness:
(a) any Indebtedness owed to a subsidiary of The St. Paul (other than Nuveen and
its consolidated subsidiaries), (b) any Indebtedness  which by the terms of  the
instrument  creating  or  evidencing  the  same  expressly  provides  that  such
Indebtedness is not superior in right of payment to the Convertible Subordinated
Debentures or (c) any Indebtedness Incurred in violation of the Indenture.  Such
Senior Indebtedness shall continue to be Senior Indebtedness and entitled to the
benefits   of  the  subordination  provisions  irrespective  of  any  amendment,
modification or waiver of any term of such Senior Indebtedness.

    As of  March  31, 1995,  Senior  Indebtedness  of The  St.  Paul  aggregated
approximately  $628 million. The Indenture does not limit The St. Paul's ability
to incur Senior Indebtedness.

  CERTAIN COVENANTS OF THE ST. PAUL

    The St. Paul will  also covenant in  the Indenture that  neither it nor  any
direct  or indirect majority-owned subsidiary of  The St. Paul (excluding Nuveen
and Nuveen's consolidated subsidiaries) will declare or pay any dividend on,  or
redeem,  purchase, acquire for value or  make a liquidation payment with respect
to, any of its capital  stock (other than as a  result of a reclassification  of
capital  stock on the exchange  or conversion of one  class or series of capital
stock for  another class  or series  of  capital stock)  or make  any  guarantee
payments  with respect to the foregoing (other than payments under the Guarantee
or dividends  or  guarantee payments  to  The  St. Paul  from  a  majority-owned
subsidiary)  if at such time (i) there  shall have occurred any event that, with
the giving of notice or the lapse of  time or both would constitute an Event  of
Default  (as defined below) under  the Convertible Subordinated Debentures, (ii)
The St.  Paul  shall  be  in  default with  respect  to  its  payment  or  other
obligations under the Guarantee or (iii) The St. Paul shall have given notice of
its  selection  of  an  extended  interest payment  period  as  provided  in the
Convertible Subordinated Debentures  and such deferral  of interest payments  or
any  extension thereof shall be continuing. The  St. Paul will also covenant for
the benefit of the holders of  the Convertible Subordinated Debentures that,  so
long  as the Preferred Securities  remain outstanding, it will  (i) not cause or
permit any  Common  Securities of  St.  Paul  Capital to  be  transferred,  (ii)
maintain  direct or indirect ownership of all outstanding securities of St. Paul
Capital other than  (x) the Preferred  Securities and (y)  any other  securities
issued  by St. Paul  Capital (other than  the Common Securities)  so long as the
issuance thereof to persons other than The  St. Paul or any of its  subsidiaries
would  not cause St. Paul Capital to  become an "investment company" required to
be registered under the Investment Company Act of 1940, as amended, (iii)  cause
at  least 21% of  the total value  of St. Paul  Capital and at  least 21% of all
interests in the capital, income, gain,  loss, deduction and credit of St.  Paul
Capital  to be represented by Common  Securities, (iv) not voluntarily dissolve,
wind-up or  liquidate  St. Paul  Capital  (other  than in  connection  with  the
exchange  of all outstanding  Preferred Securities for  Depositary Shares in the
manner described  under  "--  Preferred  Securities  --  Optional  Exchange  for
Depositary  Shares") or either of  the Managing Members, (v)  cause The St. Paul
and St. Paul Holdings to remain the Managing Members of St. Paul Capital and  to
timely  perform all of their  respective duties as Managing  Members of St. Paul
Capital (including  the duty  to  declare and  pay  dividends on  the  Preferred
Securities  as described under "-- Preferred Securities -- Dividends"), (vi) use
reasonable efforts  to cause  St. Paul  Capital to  remain a  limited  liability
company  and otherwise continue to be treated  as a partnership for U.S. federal
income tax purposes; PROVIDED that The St.  Paul may permit St. Paul Capital  to
consolidate  or merge with or  into or convey, transfer  or lease its properties
and assets substantially  as an entirety  to another entity  upon the terms  and
subject   to  the  conditions  set  forth  under  "--  Preferred  Securities  --

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<PAGE>
Merger, Consolidations or Sale of Assets  of St. Paul Capital" above, and  (vii)
to   deliver  Depositary  Shares  representing  shares  of  St.  Paul  Series  C
Convertible Preferred Stock  or St. Paul  Common Stock upon  an election by  the
holders  of  the Preferred  Securities to  exchange  or convert  the Convertible
Subordinated Debentures.

  EVENTS OF DEFAULT

    If one or more of  the following events (each  an "Event of Default")  shall
occur and be continuing:

        (a)  failure  to  pay  any  principal  of  the  Convertible Subordinated
    Debentures when due;

        (b)  failure  to  pay  any  interest  on  the  Convertible  Subordinated
    Debentures,  including any  Additional Interest,  when due  and such failure
    continues for a period of  10 days; provided that  a valid extension of  the
    interest  payment period by The  St. Paul shall not  constitute a default in
    the payment of interest for this purpose;

        (c) failure by  The St.  Paul to  deliver shares  of St.  Paul Series  C
    Convertible  Preferred Stock  or St. Paul  Common Stock upon  an election by
    holders of  Preferred  Securities  to exchange  or  convert  such  Preferred
    Securities;

        (d) failure by The St. Paul to perform in any material respect any other
    covenant  in the  Indenture for  the benefit  of the  holders of Convertible
    Subordinated Debentures continued for a period  of 60 days (or, in the  case
    of  the covenants described under "-- Certain Covenants of The St. Paul," 10
    days) after written notice  to The St. Paul  from any holder of  Convertible
    Subordinated Debentures or Preferred Securities;

        (e)  the dissolution, winding-up, liquidation or termination of St. Paul
    Capital (except in the event of a Special Event); or

        (f)  certain events of bankruptcy, insolvency or liquidation of The  St.
    Paul;

then  either the Trustee or  the holders of at  least 25% in aggregate principal
amount of the Convertible Subordinated Debentures then outstanding will have the
right  to  declare  the  principal  of  and  the  interest  on  the  Convertible
Subordinated  Debentures  (including  any  Additional  Interest)  and  any other
amounts payable under  the Convertible Subordinated  Debentures to be  forthwith
due  and payable  and to  enforce the  holders' other  rights as  creditors with
respect to the Convertible Subordinated  Debentures; PROVIDED, HOWEVER, that  if
upon  an  Event of  Default,  the Trustee  or  the holders  of  at least  25% in
aggregate principal  amount  of  the Convertible  Subordinated  Debentures  then
outstanding  fail  to declare  the  payment of  all  amounts on  the Convertible
Subordinated Debentures to  be immediately due  and payable, the  holders of  at
least  25%  in aggregate  liquidation  preference of  Preferred  Securities then
outstanding shall have such right;  PROVIDED, FURTHER, HOWEVER, that after  such
acceleration, but before a judgment or decree based on acceleration, the holders
of   a  majority  in  aggregate  principal  amount  of  outstanding  Convertible
Subordinated Debentures,  or the  holders of  the Preferred  Securities if  they
accelerated  such payment, may,  under certain circumstances,  rescind and annul
such acceleration  if all  Events  of Default,  other  than the  non-payment  of
accelerated  principal, have been cured or  waived as provided in the Indenture.
For  information  as  to  waiver  of  defaults,  see  "--  Modification  of  the
Indenture".   St.  Paul  Capital  is  the  initial  holder  of  the  Convertible
Subordinated  Debentures.   However,   while  the   Preferred   Securities   are
outstanding,  St. Paul Capital has agreed not to waive an Event of Default under
the Indenture without the consent of holders of 66 2/3% in aggregate liquidation
preference of the Preferred Securities then outstanding. Additionally, under the
terms  of  the  Preferred  Securities,  the  holders  of  outstanding  Preferred
Securities  will have the rights described  above under "-- Preferred Securities
- -- Voting  Rights", including  the right  to appoint  a Special  Trustee,  which
Special  Trustee shall be authorized to exercise  the right of St. Paul Capital,
as the holder  of at  least 25% aggregate  principal amount  of the  Convertible
Subordinated  Debentures, to accelerate the  principal amount of the Convertible
Subordinated Debentures and accrued interest (including any Additional Interest)
thereon and to enforce the

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other rights of Holders of the Convertible Subordinated Debentures as  creditors
under  the  Convertible  Subordinated  Debentures.  A  default  under  any other
indebtedness of The St. Paul or St.  Paul Capital would not constitute an  Event
of Default under the Convertible Subordinated Debentures.

    Subject  to the  provision of  the Indenture relating  to the  duties of the
Trustee in case an Event of Default  shall occur and be continuing, the  Trustee
will  be under no obligation  to exercise any of its  rights or powers under the
Indenture at the request or direction of any holders of Convertible Subordinated
Debentures, unless such  holders shall  have offered to  the Trustee  reasonable
indemnity.  Subject to such  provisions for the  indemnification of the Trustee,
the holders  of a  majority in  aggregate principal  amount of  the  Convertible
Subordinated Debentures then outstanding will have the right to direct the time,
method  and place of conducting  any proceeding for any  remedy available to the
Trustee or exercising any trust or power conferred on the Trustee.

    No holder of any Subordinated Debenture will have any right to institute any
proceeding with respect to the Indenture,  or for the appointment of a  receiver
or  trustee,  or  for  any  remedy thereunder,  unless  such  holder  shall have
previously given to the Trustee written notice of a continuing Event of  Default
and,  if St.  Paul Capital  is not the  sole holder  of Convertible Subordinated
Debentures, unless  also the  holders of  at least  25% in  aggregate  principal
amount  of the Convertible  Subordinated Debentures then  outstanding shall have
made written  request,  and offered  reasonable  indemnity, to  the  Trustee  to
institute  such proceeding as  trustee, and the Trustee  shall not have received
from the holders of a majority in aggregate principal amount of the  outstanding
Convertible  Subordinated Debentures a direction  inconsistent with such request
and shall have failed to institute such proceeding within 60 days. However, such
limitations do not  apply to a  suit instituted  by a holder  of a  Subordinated
Debenture  for enforcement of  payment of the  principal of or  interest on such
Subordinated Debenture on or  after the respective due  dates expressed in  such
Subordinated Debenture or of the right to convert such Subordinated Debenture in
accordance with the Indenture.

    The St. Paul will be required to furnish to the Trustee annually a statement
as  to the performance by  The St. Paul of certain  of its obligations under the
Indenture and as to any default of such performance.

  CONVERSION OF THE CONVERTIBLE SUBORDINATED DEBENTURES

    The Convertible  Subordinated Debentures  and any  accrued interest  thereon
will  be convertible into St. Paul Common Stock  at the option of the holders of
the Convertible Subordinated Debentures  at any time on  or before the close  of
business  on the maturity date thereof at the initial conversion price set forth
on the cover page of this Prospectus subject to the conversion price adjustments
described under "-- Preferred Securities -- Conversion Rights". St. Paul Capital
will covenant not to convert Convertible Subordinated Debentures except pursuant
to a notice  of conversion  delivered to  the Conversion  Agent by  a holder  of
Preferred  Securities. Upon surrender of  Preferred Securities to the Conversion
Agent for conversion, St. Paul Capital  will distribute $50 principal amount  of
the Convertible Subordinated Debentures to the Conversion Agent on behalf of the
holder  of every Preferred Security so converted, whereupon the Conversion Agent
will convert such Convertible Subordinated  Debentures and any accrued  interest
thereon  to  St. Paul  Common Stock  on behalf  of such  holder. The  St. Paul's
delivery to the holders of the Convertible Subordinated Debentures (through  the
Conversion  Agent) of the fixed  number of shares of  St. Paul Common Stock into
which the Convertible Subordinated Debentures are convertible (together with the
cash payment, if any, in  lieu of fractional shares)  will be deemed to  satisfy
The  St.  Paul's  obligation to  pay  the  principal amount  of  the Convertible
Subordinated Debentures, and the accrued and unpaid interest attributable to the
period from the last date to which interest has been paid or duly provided for.

  EXCHANGE OF THE CONVERTIBLE SUBORDINATED DEBENTURES

    The Convertible  Subordinated Debentures  and any  accrued interest  thereon
will  be  exchangeable  for Depository  Shares  representing St.  Paul  Series C
Convertible Preferred Stock  upon an Exchange  Event on or  before the close  of
business  on the maturity date thereof at the  rate of 1/100th of a share of St.
Paul Series C Convertible Preferred Stock  for each $50 principal amount of  the
Convertible  Subordinated  Debentures (equivalent  to  an exchange  rate  of one
Depositary Share for each $50 principal of

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<PAGE>
amount of  the  Convertible  Subordinated Debentures).  Accumulated  and  unpaid
dividends  (including Additional Dividends) on  the Preferred Securities will be
treated as accumulated and unpaid dividends on the St. Paul Series C Convertible
Preferred Stock.

  MODIFICATION OF THE INDENTURE

    The Indenture may  be amended  by The  St. Paul,  St. Paul  Capital and  the
Trustee with the consent of the holders of 66 2/3% in aggregate principal amount
of  the outstanding Convertible  Subordinated Debentures PROVIDED,  that no such
modification or  amendment  may, without  the  consent  of the  holder  of  each
outstanding  Subordinated Debenture affected thereby, (a) change the Maturity of
the principal of, or any installment of interest on, any Subordinated Debenture,
(b) reduce the principal amount of, or interest on, any Subordinated  Debenture,
(c) change the place or currency of payment of principal of, or interest on, any
Subordinated  Debenture,  (d)  impair  the  right  to  institute  suit  for  the
enforcement of any payment on or with respect to any Subordinated Debenture, (e)
adversely affect  the  right to  convert  or exchange  Convertible  Subordinated
Debentures,  (f) modify the subordination provisions  in a manner adverse to the
holders of the Convertible Subordinated Debentures, (g) reduce the  above-stated
percentage  of  outstanding  Convertible  Subordinated  Debentures  necessary to
modify or  amend  the  Indenture  or (h)  reduce  the  percentage  of  aggregate
principal  amount of  outstanding Convertible  Subordinated Debentures necessary
for waiver of compliance with certain provisions of the Indenture or for  waiver
of  certain defaults; and PROVIDED FURTHER that, so long as any of the Preferred
Securities remain  outstanding, no  such amendment  may be  made that  adversely
affects the holders of Preferred Securities, and no termination of the Indenture
may  occur, and no  Event of Default  or compliance with  any covenant under the
Indenture  may  be  waived  by  the  holders  of  the  Convertible  Subordinated
Debentures,  without the prior consent of the holders of at least 66 2/3% of the
aggregate liquidation preference  of the Preferred  Securities then  outstanding
unless  and until  the Convertible Subordinated  Debentures and  all accrued and
unpaid interest thereon have been paid in full.

  GOVERNING LAW

    The Indenture and the Convertible  Subordinated Debentures will be  governed
by, and construed in accordance with, the laws of the State of New York.

  INFORMATION CONCERNING THE TRUSTEE

    The  Indenture  contains certain  limitations on  the  right of  the Trustee
should it become  a creditor of  The St. Paul,  to obtain payment  of claims  in
certain cases, or to realize for its own account on certain property received in
respect  of  any  such claim  as  security  or otherwise.  The  Trustee  will be
permitted to engage in certain other  transactions; however, if it acquires  any
conflicting  interest and there is a  default under the Convertible Subordinated
Debentures, it must eliminate such conflict or resign.

    The St. Paul and St. Paul Capital have agreed in the Indenture to  indemnify
and  hold harmless the  Trustee against any  losses or damages  it may suffer as
Trustee.

    The Chase  Manhattan  Bank (National  Association),  the Trustee  under  the
Indenture, also serves as the trustee under an indenture with The St. Paul dated
as  of March 31,  1990 and has  from time to  time engaged in  lending and other
transactions with,  or performed  services for,  The St.  Paul in  the  ordinary
course of business.

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                     DESCRIPTION OF ST. PAUL CAPITAL STOCK

    The  following descriptions of  the Common Stock  and undesignated shares of
the Company are stated in general terms and are in all respects subject to,  and
are  qualified in their  entirety by, reference to  the applicable provisions of
the Company's Amended and  Restated Articles of  Incorporation, as amended,  and
Bylaws,  as  amended, forms  of  which have  been  incorporated by  reference as
exhibits to the Registration Statement of which this Prospectus forms a part.

COMMON STOCK

    The St. Paul  is authorized  to issue  240,000,000 shares  of Common  Stock,
without  par  value  per  share.  Each share  of  Common  Stock  is  entitled to
participate PRO RATA in distributions upon liquidation, subject to the rights of
holders of undesignated shares, and  to one vote on  all matters submitted to  a
vote  of shareholders. The holders of Common Stock may receive cash dividends as
declared by the  Board of  Directors out  of funds  legally available  therefor,
subject  to the  rights of any  holders of undesignated  shares. The outstanding
shares of Common Stock are, and the  shares offered hereby when issued will  be,
fully  paid and  nonassessable. Holders  of Common  Stock have  no preemptive or
similar equity  preservation rights,  and  cumulative voting  of shares  in  the
election  of  directors is  prohibited.  The holders  of  more than  50%  of the
outstanding shares of Common Stock have the voting power to elect all  directors
and,  except as is discussed at "Certain St. Paul Charter and Bylaw Provisions",
to approve mergers, sales of assets and other corporate transactions.

    Each holder of Common Stock is entitled to such dividends as may be declared
by the  Board  of  Directors of  the  Company  out of  funds  legally  available
therefor.  The St. Paul  Companies, Inc. is  a holding company,  and its primary
source for the payment of dividends is dividends from its subsidiaries.  Various
state laws and regulations limit the amount of dividends that may be paid to the
Company  by its insurance subsidiaries.  As of March 31,  1995, $312 million was
available  for  the  payment  of  dividends  to  the  Company  free  from   such
restrictions.

    The  transfer  agent and  registrar  for St.  Paul's  Common Stock  is First
Chicago Trust Company of New York.

UNDESIGNATED SHARES

    The Board of Directors of the Company is authorized, without further  action
by  the  shareholders,  to  establish  from  the  5,000,000  undesignated shares
authorized by the Amended  and Restated Articles of  Incorporation, one or  more
classes and series, to designate each such class and series, to fix the relative
rights  and preferences of each such class  and series and to issue such shares.
Such rights and preferences may be superior  to the St. Paul Common Stock as  to
dividends,  distributions of assets  (upon liquidation or  otherwise) and voting
rights. Undesignated shares may be convertible  into shares of any other  series
or class of stock, including St. Paul Common Stock, of the Company, if the Board
of Directors so determines.

    Pursuant  to such  authority, the Board  of Directors  has designated 41,400
undesignated shares as  St. Paul  Series C  Convertible Preferred  Stock. For  a
description   of  the  St.  Paul  Series  C  Convertible  Preferred  Stock,  see
"Description  of  Securities  Offered  --  Description  of  St.  Paul  Series  C
Convertible Preferred Stock".

STOCK PURCHASE RIGHTS, SERIES A PREFERRED STOCK AND SERIES B PREFERRED STOCK

    Pursuant  to  its  authority  to issue  undesignated  shares,  the  Board of
Directors of the Company has also adopted resolutions authorizing 50,000  shares
of Series A Junior Participating Preferred Stock, without par value (the "Series
A  Preferred Stock"),  and 1,450,000  shares of  Series B  Convertible Preferred
Stock (the "Series B Preferred Stock").

    Shares of the Series A Preferred Stock are purchasable upon the exercise  of
the Stock Purchase Rights, upon the terms and conditions set forth in the Rights
Agreement.  The Stock Purchase Rights will  expire on December 19, 1999, subject
to extension  to  December  18,  2002 under  certain  circumstances  or  earlier
redemption  by The St. Paul. The Rights Agreement provides that, until the Stock
Purchase  Rights  become  exercisable  pursuant  to  the  terms  of  the  Rights
Agreement,  the Stock Purchase Rights will be transferred with and only with the
St.   Paul    Common    Stock.   Until    the    time   the    Stock    Purchase

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Rights  become exercisable --  at which time  separate certificates representing
the Stock Purchase Rights will  be mailed to holders of  record of the St.  Paul
Common  Stock -- the Stock Purchase Rights will be evidenced by the certificates
representing the related shares of St. Paul Common Stock.

    Each share of Series A Preferred Stock,  if and when issued, would be  fully
paid  and  nonassessable.  The holders  of  Series  A Preferred  Stock  would be
entitled to 1,000 votes for each share held of record on all matters voted  upon
by  shareholders and  would not be  able to  cumulate votes for  the election of
directors. Subject to preferential rights,  if any, of any undesignated  shares,
if  and when designated and  issued by the Board  of Directors, each outstanding
share of Series A Preferred Stock would be entitled to receive distributions and
dividends equal to 1,000 times the  aggregate per share amounts declared on  the
Common Stock. Upon liquidation of the Company, the holders of Series A Preferred
Stock  would be entitled to  receive (prior to holders  of Common Stock or other
junior ranking stock)  an aggregate amount  per share equal  to 1,000 times  the
aggregate amount to be distributed per share to holders of Common Stock, subject
to  a maximum of $100 per share plus accrued and unpaid dividends, if any. There
are no redemption, sinking fund, conversion or preemptive rights with respect to
the Series A Preferred Stock. All shares of Series A Preferred Stock have  equal
rights and preferences.

    The  Series B Preferred Stock has been  issued to the Savings Plus Preferred
Stock Ownership Plan Trust established by the Company. All outstanding shares of
Series B  Preferred  Stock are  fully  paid  and nonassessable.  Each  share  of
outstanding Series B Preferred Stock is entitled to the number of votes equal to
the number of shares of Common Stock into which such share of Series B Preferred
Stock  could have been converted on the  record date for determining the holders
of Common Stock entitled to vote  on a particular matter. Currently, each  share
of  Series B  Preferred Stock is  entitled to  four votes per  share. Holders of
outstanding shares of Series B Preferred Stock are entitled to receive when,  as
and  if declared by the Board  of Directors, cumulative quarterly cash dividends
at the annual rate of $11.724 per  share in preference and in priority over  the
Common  Stock  and Series  A Preferred  Stock. Upon  liquidation, each  share of
Series B Preferred  Stock would have  a preference  of $100 per  share over  the
Common  Stock and  Series A  Preferred Stock.  The Series  B Preferred  Stock is
redeemable by the  Company at the  following redemption prices  per share  which
apply  if  redemption  occurs  during  the twelve  month  period  ending  on and
including December 31 on each of the following years:

<TABLE>
<CAPTION>
YEAR                                           REDEMPTION PRICE PER SHARE
- --------------------------------------------  ----------------------------
<S>                                           <C>
1995........................................           $   149.52
1996........................................               148.22
1997........................................               146.92
1998........................................               145.62
1999 and thereafter.........................               144.30
</TABLE>

plus accumulated and unpaid  dividends, without interest,  to and excluding  the
date fixed for redemption. The Series B Preferred Stock may be converted, at any
time  and from  time to time,  at the  option of the  holder into  the number of
shares of Common Stock  of the Company determined  by dividing $144.30 for  each
share  of Series B  Preferred to be  converted by the  then effective conversion
price per share  of Common Stock.  Currently, each share  of Series B  Preferred
Stock is convertible into four shares of Common Stock. There are no sinking fund
provisions or preemptive rights with respect to the Series B Preferred Stock.

                 CERTAIN ST. PAUL CHARTER AND BYLAWS PROVISIONS

    In  addition to  the Rights  Agreement, the  Company's Amended  and Restated
Articles of Incorporation and  Bylaws contain provisions  that may discourage  a
third  party from seeking to acquire the  Company or to commence a proxy contest
or other takeover-related action.

    Article V of the  Company's Amended and  Restated Articles of  Incorporation
requires  the affirmative  vote of  the holders  of at  least two-thirds  of the
voting power of all voting shares of the Company for the approval, authorization
or adoption of any plan  of merger; plan of  exchange; sale, lease, transfer  or
other  disposition of  all or  substantially all  of the  Company's property and
assets not in the usual  and regular course of  business; or dissolution of  the
Company.   The   affirmative  vote   of  at   least   one-half  of   the  voting

                                       67
<PAGE>
power of all voting shares is  required for amendments to the Company's  Amended
and  Restated Articles of Incorporation, except for amendments to Article V, for
which the  affirmative vote  of at  least  two-thirds of  all voting  shares  is
required.

    The Company's Bylaws contain certain procedural requirements with respect to
the  nomination of directors  by stockholders that  require, among other things,
delivery of  notice by  such  stockholders to  the  corporate secretary  of  the
Company  not later than 60 days prior to the date of the stockholders meeting at
which such nomination is to be considered, PROVIDED, HOWEVER, that in the  event
that  less than 70 days' notice or prior  disclosure of the date of this meeting
is given or made to shareholders, notice  by the shareholders to be timely  must
be  so received not later  than the close of business  on the 10th day following
the date on  which such notice  of the date  of the meeting  was mailed or  such
public  disclosure was  made. The Bylaws  do not  provide that a  meeting of the
Board of Directors may be called by stockholders.

    The effect of  these provisions may  be to deter  attempts either to  obtain
control  of the Company or to acquire a substantial amount of its stock, even if
such  a  proposed   transaction  were   at  a  significant   premium  over   the
then-prevailing market value of the Common Stock, or to deter attempts to remove
the  Board of  Directors and management  of the  Company, even though  some or a
majority of  the  holders  of  Common  Stock may  believe  such  actions  to  be
beneficial.

                   CERTAIN FEDERAL INCOME TAX CONSIDERATIONS

GENERAL

    This  section  is a  summary  of certain  United  States federal  income tax
considerations that  may  be relevant  to  prospective purchasers  of  Preferred
Securities  and  represents  the opinion  of  Sullivan &  Cromwell,  special tax
counsel to The St. Paul and St.  Paul Capital, insofar as it relates to  matters
of  law and legal conclusions. This section  is based upon current provisions of
the Internal  Revenue  Code of  1986,  as  amended (the  "Code"),  existing  and
proposed  regulations thereunder  and current  administrative rulings  and court
decisions, all of which are subject to change. Subsequent changes may cause  tax
consequences to vary substantially from the consequences described below.

    No  attempt has  been made  in the  following discussion  to comment  on all
United States  federal  income tax  matters  affecting purchasers  of  Preferred
Securities.  Moreover, the discussion  is directed only  to holders of Preferred
Securities who are  individual citizens or  residents of the  United States  who
hold   the  Preferred  Securities  as  capital  assets,  and  has  only  limited
application  to   corporations,  estates,   trusts  and   non-resident   aliens.
Accordingly,  each prospective purchaser of Preferred Securities should consult,
and should depend  on, his  or her  own tax  advisor in  analyzing the  federal,
state,  local  and  foreign  tax  consequences  of  the  purchase,  ownership or
disposition of Preferred Securities.

INCOME FROM PREFERRED SECURITIES

    In the  opinion  of  Sullivan  &  Cromwell,  St.  Paul  Capital  will  be  a
partnership  for federal  income tax purposes.  Accordingly, each  holder of St.
Paul  Capital  Preferred  Securities  (a  "Preferred  Securityholder")  will  be
required  to include in gross income the Preferred Securityholder's distributive
share of the  net income of  St. Paul  Capital. Such income  will generally  not
exceed  the dividends received  on such Preferred  Securities, except in limited
circumstances as described below under "Potential Deferral of Interest Payment".
No portion of such income will be eligible for the dividends received deduction.

DISPOSITION OF PREFERRED SECURITIES

    Gain or loss will be recognized on a sale of Preferred Securities, including
a redemption for cash, equal to  the difference between the amount realized  and
the Preferred Securityholder's tax basis for the Preferred Securities sold. Gain
or  loss recognized by a  Preferred Securityholder on the  sale or exchange of a
Preferred Security  held  for  more  than one  year  will  generally  constitute
long-term  capital  gain or  loss.  Subject to  the  discussion below  under "--
Potential Deferral  of  Interest  Payments",  the  adjusted  tax  basis  of  the
Preferred Securities sold will generally equal the amount paid for the Preferred
Securities.

                                       68
<PAGE>
RECEIPT OF CONVERTIBLE SUBORDINATED DEBENTURES UPON LIQUIDATION OF ST. PAUL
CAPITAL

    Under  certain circumstances, as described under the caption "Description of
the  Preferred   Securities   --  Special   Event   Distribution",   Convertible
Subordinated  Debentures  may  be distributed  to  Preferred  Securityholders in
liquidation of St. Paul Capital. Under current United States federal income  tax
law,  such  a distribution  would  be treated  as  a non-taxable  exchange. Each
Preferred Securityholder would have  an aggregate tax  basis in the  Convertible
Subordinated  Debentures  equal  to such  holder's  aggregate tax  basis  in its
Preferred Securities. A holder's holding period in the Convertible  Subordinated
Debentures  so received  in liquidation  of St.  Paul Capital  would include the
period for which the Preferred Securities were held by such holder.

ST. PAUL CAPITAL INFORMATION RETURNS AND AUDIT PROCEDURES

    The Managing  Members  of  St.  Paul Capital  will  furnish  each  Preferred
Securityholder  with  a  Schedule K-1  each  year setting  forth  such Preferred
Securityholder's allocable  share of  income for  the prior  calendar year.  The
Managing  Members  are  required  to  furnish  such  Schedule  K-1  as  soon  as
practicable following the end of the year, but in any event prior to March 31.

    Any person who holds Preferred Securities as a nominee for another person is
required to  furnish to  St. Paul  Capital (a)  the name,  address and  taxpayer
identification  number of the beneficial owner  and the nominee; (b) information
as to whether the beneficial owner is (i)  a person that is not a United  States
person,  (ii)  a  foreign  government,  an  international  organization  or  any
wholly-owned agency  or  instrumentality of  either  the foregoing  or  (iii)  a
tax-exempt  entity; (c) the amount and description of Preferred Securities held,
acquired or transferred for  the beneficial owner;  and (d) certain  information
including  the dates  of acquisitions and  transfers, means  of acquisitions and
transfers, and acquisition  cost for  purchases, as well  as the  amount of  net
proceeds  from sales. Brokers and financial institutions are required to furnish
additional information, including  whether they  are United  States persons  and
certain  information on Preferred Securities they  acquire, hold or transfer for
their own accounts. A penalty  of $50 per failure (up  to a maximum of  $100,000
per calendar year) is imposed by the Code for failure to report such information
to  St. Paul Capital. The nominee is required to supply the beneficial owners of
the Preferred Securities with the information furnished to St. Paul Capital.

POTENTIAL DEFERRAL OF INTEREST PAYMENTS

    Under the Indenture, The St. Paul has the option to defer interest  payments
on  the Convertible Subordinated  Debentures for up  to 60 months.  In the event
that interest payments are  deferred, St. Paul Capital  will continue to  accrue
income  equal  to the  amount of  the interest  payment  due at  the end  of the
deferred interest payment period,  on an economic basis  over the length of  the
deferred interest payment period.

    Accrued  income will be allocated  to holders of record  on the Business Day
preceding the last  day of each  calendar month without  any corresponding  cash
distribution  at that time. As a result,  holders of record during a deferral of
interest payments  will include  interest  in gross  income  in advance  of  the
receipt  of cash, and any such holders who dispose of Preferred Securities prior
to the  record date  for the  payment of  dividends following  such deferral  of
interest  will include interest  in gross income  but will not  receive any cash
related thereto from  St. Paul Capital.  The tax basis  of a Preferred  Security
will  be increased  by the  amount of  any interest  that is  included in income
without a receipt of cash, and will be decreased again when and if such cash  is
subsequently received from St. Paul Capital.

EXCHANGE OF PREFERRED SECURITIES FOR ST. PAUL STOCK

    A  Preferred  Securityholder  should not  recognize  gain or  loss  upon the
exchange,  through  the  Conversion  Agent,   of  Preferred  Securities  for   a
proportionate  share of the Convertible Subordinated Debentures held by St. Paul
Capital. Except to the extent attributable to accrued but unpaid interest on the
Convertible Subordinated  Debentures,  a  Preferred  Securityholder  should  not
recognize  gain or  loss upon the  conversion, through the  Conversion Agent, of
Convertible Subordinated  Debentures for  St. Paul  Common Stock  or  Depositary
Shares  representing St. Paul Series C  Convertible Preferred Stock. A Preferred
Securityholder will recognize gain, however, upon the receipt of cash in lieu of
a fractional share of  St. Paul Common Stock  or Depositary Shares  representing
St.  Paul  Series C  Convertible Preferred  Stock  equal to  the amount  of cash
received less the Preferred Securityholder's tax basis in

                                       69
<PAGE>
such fractional share. A  Preferred Securityholder's tax basis  in the St.  Paul
Common Stock or the Depositary Shares representing St. Paul Series C Convertible
Preferred  Stock received upon exchange and conversion should generally be equal
to  the  Preferred  Securityholder's  tax  basis  in  the  Preferred  Securities
delivered  to the  Conversion Agent  for exchange  (plus any  accrued but unpaid
interest on the  Convertible Subordinated Debentures  included in the  Preferred
Securityholder's  income as a result of  the exchange, minus the basis allocated
to  any   fractional  share   for   which  cash   is  received).   A   Preferred
Securityholder's  holding period in the St.  Paul Common Stock or the Depository
Shares representing St. Paul Series C Convertible Preferred Stock received  upon
exchange  and  conversion  should  generally begin  on  the  date  the Preferred
Securityholder acquired  the Preferred  Securities delivered  to the  Conversion
Agent for exchange.

ADJUSTMENT OF CONVERSION PRICE

    Treasury  Regulations promulgated under Section 305  of the Code would treat
St. Paul Capital  (and, thus,  Preferred Securityholders) as  having received  a
constructive distribution from The St. Paul in the event the conversion ratio of
the Convertible Subordinated Debentures were adjusted if (i) as a result of such
adjustment,  the proportionate  interest of  St. Paul  Capital in  the assets or
earnings and profits of The St. Paul were increased and (ii) the adjustment  was
not made pursuant to a bona fide, reasonable antidilution formula. An adjustment
in  the conversion ratio would not be considered made pursuant to such a formula
if the adjustment was made to compensate for certain taxable distributions  with
respect  to the  stock into  which the  Convertible Subordinated  Debentures are
convertible. Thus, under  certain circumstances, a  reduction in the  conversion
price for the Convertible Subordinated Debentures is likely to be taxable to St.
Paul  Capital as a dividend to the extent of the current or accumulated earnings
and profits of  The St.  Paul. Preferred  Securityholders would  be required  to
include  their allocable share of such constructive dividend in gross income but
would not receive any  cash related thereto. In  addition, the failure to  fully
adjust  the  conversion  price  of the  Convertible  Subordinated  Debentures to
reflect distributions of  stock dividends with  respect to the  St. Paul  Common
Stock  may result in  a taxable dividend to  the holders of  the St. Paul Common
Stock.

    Similarly, under  Section 305  of the  Code, adjustments  to the  conversion
price  of the  St. Paul  Series C Convertible  Preferred Stock,  which may occur
under certain circumstances, may result in deemed dividend income to holders  of
the Depositary Shares representing St. Paul Series C Convertible Preferred Stock
if   such  adjustments  are  not  made  pursuant  to  a  bona  fide,  reasonable
antidilution formula, and  failure to  make such adjustments  to the  conversion
price  of the St. Paul Series C Convertible Preferred Stock may result in deemed
dividend income to holders of the St. Paul Common Stock.

UNITED STATES ALIEN HOLDERS

    Ownership  of   Preferred   Securities  by   nonresident   aliens,   foreign
corporations  and other foreign persons raises tax considerations unique to such
persons and may have substantially adverse tax consequences to them.  Therefore,
prospective  investors who are foreign persons or which are foreign entities are
urged to consult with  their U.S. tax  advisors as to  whether an investment  in
Preferred  Securities  represents an  appropriate investment  in light  of those
unique tax considerations and possible adverse tax consequences.

BACKUP WITHHOLDING AND INFORMATION REPORTING

    In general, information  reporting requirements  will apply  to payments  to
noncorporate  United States  holders of  the proceeds  of the  sale of Preferred
Securities, St. Paul  Series C Convertible  Preferred Stock or  St. Paul  Common
Stock  within the United States  and "backup withholding" at  a rate of 31% will
apply to such payments if the United States holder fails to provide an  accurate
taxpayer identification number.

    THE  FEDERAL INCOME TAX  DISCUSSION SET FORTH ABOVE  IS INCLUDED FOR GENERAL
INFORMATION AND  MAY NOT  BE  APPLICABLE DEPENDING  UPON A  HOLDER'S  PARTICULAR
SITUATION.  HOLDERS SHOULD  CONSULT THEIR TAX  ADVISORS WITH RESPECT  TO THE TAX
CONSEQUENCES TO THEM OF THE PURCHASE, OWNERSHIP AND DISPOSITION OF THE PREFERRED
SECURITIES, INCLUDING THE TAX CONSEQUENCES UNDER STATE, LOCAL, FOREIGN AND OTHER
TAX LAWS AND THE POSSIBLE EFFECTS OF CHANGES IN FEDERAL OR OTHER TAX LAWS.

                                       70
<PAGE>
                                  UNDERWRITING

    Subject to the terms and conditions of the Underwriting Agreement, St.  Paul
Capital  has agreed to sell to each of the Underwriters named below, and each of
such Underwriters, for whom Goldman, Sachs & Co. and J.P. Morgan Securities Inc.
are acting as representatives,  has severally agreed to  purchase from St.  Paul
Capital,  the respective number  of Preferred Securities  set forth opposite its
name below:

<TABLE>
<CAPTION>
                                                                          NUMBER OF PREFERRED
                              UNDERWRITER                                      SECURITIES
- ------------------------------------------------------------------------  --------------------
<S>                                                                       <C>
Goldman, Sachs & Co.....................................................         1,320,000
J.P. Morgan Securities Inc..............................................         1,320,000
Dain Bosworth Incorporated..............................................            96,000
Kemper Securities, Inc..................................................           192,000
C.J. Lawrence/Deutsche Bank Securities Corporation......................            96,000
Morgan Stanley & Co. Incorporated.......................................           192,000
Piper Jaffray Inc.......................................................            96,000
Salomon Brothers Inc....................................................           192,000
Stifel, Nicolaus & Company, Incorporated................................            96,000
                                                                                ----------
    Total...............................................................         3,600,000
                                                                                ----------
                                                                                ----------
</TABLE>

    Under  the  terms  and  conditions   of  the  Underwriting  Agreement,   the
Underwriters  are committed  to take and  pay for all  such Preferred Securities
offered hereby, if any are taken.

    The Underwriters propose to offer the Preferred Securities in part  directly
to  the public at the initial public offering  price set forth on the cover page
of this Prospectus, and in part to certain securities dealers at such price less
a concession of $.675  per Preferred Security. The  Underwriters may allow,  and
such  dealers may  reallow, a  concession not  in excess  of $.10  per Preferred
Security to  certain brokers  and dealers.  After the  Preferred Securities  are
released  for sale to the public, the offering price and other selling terms may
from time to time be varied by the representatives.

    In view  of the  fact  that the  proceeds from  the  sale of  the  Preferred
Securities  will  be  used  by  St. Paul  Capital  to  purchase  the Convertible
Subordinated Debentures of  The St.  Paul, the  Underwriting Agreement  provides
that  The St. Paul will pay as Underwriters' Compensation a commission of $1.125
per Preferred Security.

    The St. Paul and  St. Paul Capital have  granted the Underwriters an  option
exercisable  for 30 days after the date of  this Prospectus to purchase up to an
aggregate  of   540,000  additional   Preferred  Securities   solely  to   cover
over-allotments,  if  any.  If the  Underwriters  exercise  their over-allotment
option, the Underwriters have severally  agreed, subject to certain  conditions,
to  purchase  approximately  the  same percentage  thereof  that  the  number of
Preferred Securities to be purchased by each of them, as shown in the  foregoing
table, bears to the Preferred Securities offered.

    The  St. Paul and St. Paul Capital  have agreed not to offer, sell, contract
to sell, or otherwise dispose of any shares of St. Paul Common Stock, any  other
capital  stock  of  The  St.  Paul,  any  other  security  convertible  into  or
exercisable or exchangeable for St. Paul Common Stock or any such other  capital
stock  or debt securities substantially  similar to the Convertible Subordinated
Debentures for a period of  180 days after the  date of this Prospectus  without
the  prior written consent of the  representatives, except for (a) the Preferred
Securities offered  hereby, (b)  St. Paul  Common  Stock or  St. Paul  Series  C
Convertible  Preferred Stock issued or delivered  upon conversion or exchange of
the Convertible Subordinated Debentures, (c) securities issued or delivered upon
conversion, exchange  or  exercise of  any  other  securities of  The  St.  Paul
outstanding  on or delivered upon conversion,  exchange or exercise of any other
securities of  The St.  Paul outstanding  on the  date of  this Prospectus,  (d)
securities  issued pursuant to The  St. Paul's stock option  or other benefit or
incentive plans  maintained for  its officers,  directors or  employees, or  (e)
securities   issued  in   connection  with  mergers,   acquisitions  or  similar
transactions.

                                       71
<PAGE>
    In compliance with Article III, Section 34 of the Rules of Fair Practice  of
the  National Association of Securities Dealers,  Inc. (the "NASD"), no sales of
Preferred Securities may be made by  any NASD member to a discretionary  account
without the prior written approval of the transaction by the customer.

    Certain  of the  Underwriters are  customers of,  or engage  in transactions
with, and from time to  time have performed services for,  The St. Paul and  its
subsidiaries and associated companies in the ordinary course of business.

    Prior  to this Offering, there  has been no public  market for the Preferred
Securities. The Preferred Securities have been approved for listing on the NYSE,
subject to notice of issuance, under the symbol "SPC pfM".

    The St.  Paul and  St. Paul  Capital have  agreed to  indemnify the  several
Underwriters  against  certain  liabilities,  including  liabilities  under  the
Securities Act of 1933, as amended.

                           VALIDITY OF THE SECURITIES

    The validity  of  the  Preferred Securities,  the  Convertible  Subordinated
Debentures,  the Guarantee, the St. Paul Common Stock, the Stock Purchase Rights
and the St. Paul Series C  Convertible Preferred Stock issuable upon  conversion
or  exchange of the Convertible Subordinated  Debentures will be passed upon for
The St. Paul by Andrew I. Douglass, Senior Vice President and General Counsel of
The St.  Paul, St.  Paul, Minnesota,  and  for the  Underwriters by  Sullivan  &
Cromwell, New York, New York. Sullivan & Cromwell may rely on Mr. Douglass as to
all  matters of Minnesota law  and each of Mr.  Douglass and Sullivan & Cromwell
may rely on Richards,  Layton & Finger,  Wilmington, Delaware, special  Delaware
counsel  to The St. Paul and St. Paul Capital, as to the matters of Delaware law
relating to the validity of the  Preferred Securities and certain other  matters
covered  by such  firm's opinion.  Certain matters as  to Minnesota  law will be
passed on by Oppenheimer Wolff & Donnelly, Minneapolis, Minnesota. In  addition,
certain  matters as to United States taxation  will be passed upon by Sullivan &
Cromwell as special tax counsel to the  Company and St. Paul Capital. At May  8,
1995, Mr. Douglass beneficially owned 10,161 shares of St. Paul Common Stock and
held  options to  purchase 7,000  shares of  St. Paul  Common Stock.  Sullivan &
Cromwell have from time to time rendered certain legal services to The St. Paul.

                                    EXPERTS

    The consolidated financial statements of the Company as of December 31, 1994
and 1993, and for each of the years in the three-year period ended December  31,
1994,  and  the  related  financial  statement  schedules,  are  incorporated by
reference  herein  from  the  Company's   Annual  Report  on  Form  10-K.   Such
consolidated financial statements and related financial statement schedules have
been audited by KPMG Peat Marwick LLP, independent certified public accountants,
as  stated  in their  reports incorporated  by reference  herein, and  have been
incorporated by reference herein in reliance upon the reports of such firm given
upon their authority as experts in accounting and auditing. The reports of  KPMG
Peat Marwick LLP on the December 31, 1994, consolidated financial statements and
related  financial  statement  schedules  refer  to  changes  in  the  method of
accounting for certain investments, reinsurance, income taxes and postretirement
benefits other than pensions.

                                       72
<PAGE>
                             INDEX OF DEFINED TERMS

<TABLE>
<CAPTION>
                                                                                                           PAGE FIRST
DEFINED TERM                                                                                                 DEFINED
- --------------------------------------------------------------------------------------------------------  -------------
<S>                                                                                                       <C>
1940 Act................................................................................................           46
Additional Dividends....................................................................................            9
Additional Interest.....................................................................................           60
Applicable Price........................................................................................           43
Beneficial Owner........................................................................................           51
blockage period.........................................................................................           61
Business Day............................................................................................           38
Certificate of Designation..............................................................................           52
Change in 1940 Act Law..................................................................................           46
Closing Price...........................................................................................           43
Code....................................................................................................           68
Commission..............................................................................................            5
Common Securities.......................................................................................            1
Common Stock Fundamental Change.........................................................................           44
Company.................................................................................................            1
Conversion Agent........................................................................................           38
Conversion Expiration Date..............................................................................            2
Convertible MIPS........................................................................................            1
Convertible Subordinated Debentures.....................................................................            1
Current Market Price....................................................................................           40
deferral of interest payments...........................................................................            3
Deposit Agreement.......................................................................................           53
Depositary..............................................................................................           53
Depositary Receipts.....................................................................................           53
Depositary Shares.......................................................................................            2
Depositary's Office.....................................................................................           54
Direct Participants.....................................................................................           50
dividends...............................................................................................            1
DTC.....................................................................................................            4
Economy.................................................................................................           25
Entitlement Date........................................................................................           43
Event of Default........................................................................................           63
Exchange Act............................................................................................            5
Exchange Election.......................................................................................           45
Exchange Election Meeting...............................................................................           45
Exchange Event..........................................................................................           45
Exchange Price..........................................................................................           38
Fire and Marine.........................................................................................           30
Fundamental Change......................................................................................           44
Guarantee...............................................................................................            3
Guarantee Payments......................................................................................           56
Indenture...............................................................................................           36
Indirect Participants...................................................................................           50
Interest Payment Date...................................................................................           59
Investment Company Event................................................................................           46
LAE.....................................................................................................           34
Junior Stock............................................................................................           58
L.L.C. Agreement........................................................................................            7
Liquidation Distribution................................................................................           47
</TABLE>

                                       73
<PAGE>
<TABLE>
<CAPTION>
                                                                                                           PAGE FIRST
DEFINED TERM                                                                                                 DEFINED
- --------------------------------------------------------------------------------------------------------  -------------
<S>                                                                                                       <C>
Managing Members Payment................................................................................           59
Managing Members........................................................................................            7
NASD....................................................................................................           72
Non-Stock Fundamental Change............................................................................           44
Nuveen..................................................................................................           18
NYSE....................................................................................................            2
Participants............................................................................................           50
Preferred Securities....................................................................................            1
Preferred Securityholder................................................................................           68
Purchaser Stock Price...................................................................................           44
Redemption Price........................................................................................           12
Reference Market Price..................................................................................           44
Registration Statement..................................................................................            5
Restated Articles.......................................................................................           52
Rights Agreement........................................................................................           12
Senior Indebtedness.....................................................................................           61
Senior Nonmonetary Default..............................................................................           61
Senior Payment Default..................................................................................           61
Series A Preferred Stock................................................................................           66
Series B Preferred Stock................................................................................           66
SFAS....................................................................................................           25
Special Event...........................................................................................           46
Special Trustee.........................................................................................           15
St. Paul Capital........................................................................................            1
St. Paul Common Stock...................................................................................            2
St. Paul Holdings.......................................................................................            7
St. Paul Series C Convertible Preferred Stock...........................................................            2
Convertible Subordinated Debentures.....................................................................            1
Stock Purchase Rights...................................................................................            2
Tax Event...............................................................................................           46
The St. Paul............................................................................................            1
Transaction.............................................................................................           41
Trustee.................................................................................................           59
UITs....................................................................................................           28
Underwriters' Compensation..............................................................................            1
</TABLE>

                                       74
<PAGE>
- --------------------------------------------------------------------------------
- --------------------------------------------------------------------------------

    NO  PERSON  HAS BEEN  AUTHORIZED  TO GIVE  ANY  INFORMATION OR  TO  MAKE ANY
REPRESENTATIONS OTHER THAN THOSE CONTAINED IN THIS PROSPECTUS, AND, IF GIVEN  OR
MADE,  SUCH INFORMATION OR REPRESENTATION MUST NOT BE RELIED UPON AS HAVING BEEN
AUTHORIZED. THIS  PROSPECTUS  DOES  NOT  CONSTITUTE AN  OFFER  TO  SELL  OR  THE
SOLICITATION  OF AN  OFFER TO  BUY ANY SECURITIES  OTHER THAN  THE SECURITIES TO
WHICH IT RELATES OR AN OFFER TO SELL OR THE SOLICITATION OF AN OFFER TO BUY SUCH
SECURITIES IN ANY CIRCUMSTANCES IN WHICH SUCH OFFER OR SOLICITATION IS UNLAWFUL.
NEITHER THE DELIVERY OF THIS PROSPECTUS NOR ANY SALE MADE HEREUNDER SHALL, UNDER
ANY CIRCUMSTANCES, CREATE ANY IMPLICATION THAT  THERE HAS BEEN NO CHANGE IN  THE
AFFAIRS  OF THE ST. PAUL AND ST. PAUL  CAPITAL SINCE THE DATE HEREOF OR THAT THE
INFORMATION CONTAINED HEREIN IS CORRECT AS OF ANY TIME SUBSEQUENT TO ITS DATE.

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

                               TABLE OF CONTENTS

<TABLE>
<CAPTION>
                                                   PAGE
                                                 ---------
<S>                                              <C>
Available Information..........................          5
Incorporation of Certain Documents by
 Reference.....................................          6
Prospectus Summary.............................          7
Investment Considerations......................         18
Use of Proceeds................................         20
Ratio of Earnings to Fixed Charges of the
 Company.......................................         20
Capitalization.................................         21
Market Prices of St. Paul Common Stock.........         22
The St. Paul's Dividend Policy.................         22
Selected Financial and Operating Data..........         23
Overview of Results............................         24
Business.......................................         29
St. Paul Capital...............................         36
Description of Securities Offered..............         36
Description of St. Paul Capital Stock..........         66
Certain St. Paul Charter and Bylaws
 Provisions....................................         67
Certain Federal Income Tax Considerations......         68
Underwriting...................................         71
Validity of the Securities.....................         72
Experts........................................         72
Index of Defined Terms.........................         73
</TABLE>

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<PAGE>
                         3,600,000 PREFERRED SECURITIES

                            ST. PAUL CAPITAL L.L.C.

                         6% CONVERTIBLE MONTHLY INCOME
                              PREFERRED SECURITIES

                            GUARANTEED TO THE EXTENT
                      SET FORTH HEREIN BY, AND CONVERTIBLE
                             INTO COMMON STOCK OF,

                          THE ST. PAUL COMPANIES, INC.

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                                     [LOGO]

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                              GOLDMAN, SACHS & CO.

                          J.P. MORGAN SECURITIES INC.

                      REPRESENTATIVES OF THE UNDERWRITERS


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