<PAGE>
                                                                     Exhibit 4.1

                           [Form of Face of Security]

                          [Fixed Rate Medium-Term Note]

REGISTERED                                          PRINCIPAL AMOUNT (and
No. FXR - __________                                Specified Currency if other
CUSIP NO.: __________                               than U.S. dollars):


                  [Insert if the Security is to be a Global Security -- THIS
SECURITY IS A SECURITY IN PERMANENT GLOBAL FORM WITHIN THE MEANING OF THE
INDENTURE HEREINAFTER REFERRED TO AND IS REGISTERED IN THE NAME OF A DEPOSITARY
OR A NOMINEE THEREOF. THIS SECURITY MAY NOT BE EXCHANGED IN WHOLE OR IN PART FOR
A SECURITY REGISTERED, AND NO TRANSFER OF THIS SECURITY IN WHOLE OR IN PART MAY
BE REGISTERED, IN THE NAME OF ANY PERSON OTHER THAN SUCH DEPOSITARY OR A NOMINEE
THEREOF, EXCEPT IN THE LIMITED CIRCUMSTANCES DESCRIBED IN THE INDENTURE.

                  UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED
REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY, A NEW YORK CORPORATION ("DTC"),
TO THE ST. PAUL COMPANIES, INC. OR ITS AGENT FOR REGISTRATION OF TRANSFER,
EXCHANGE OR PAYMENT, AND ANY CERTIFICATE ISSUED IS REGISTERED IN THE NAME OF
CEDE & CO. OR IN SUCH OTHER NAME AS IS REQUESTED BY AN AUTHORIZED REPRESENTATIVE
OF DTC (AND ANY PAYMENT IS MADE TO CEDE & CO. OR TO SUCH OTHER ENTITY AS IS
REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF DTC), ANY TRANSFER, PLEDGE OR OTHER
USE HEREOF FOR VALUE OR OTHERWISE BY OR TO ANY PERSON IS WRONGFUL INASMUCH AS
THE REGISTERED OWNER HEREOF, CEDE & CO., HAS AN INTEREST HEREIN.]

                          THE ST. PAUL COMPANIES, INC.

                           MEDIUM-TERM NOTE, SERIES D

SPECIFIED CURRENCY:                 EXCHANGE RATE
                                    AGENT:


ORIGINAL ISSUE                      INTEREST RATE:
DATE:


<PAGE>
STATED MATURITY                     REDEMPTION
DATE:                               COMMENCEMENT DATE:


REDEMPTION PERIODS                  REPAYMENT DATE:
AND PRICES:


REPAYMENT PERIODS                   AUTHORIZED DENOMINATIONS:(only applicable if
AND PRICES:                         different from $1,000 and integral multiples
                                    of $1,000 after that or Specified Currency
                                    is other than U.S. dollars)

DEFAULT RATE:                       OID DEFAULT
(Only applicable if                 AMOUNT:  (Only applicable if
Security issued at                  Security issued at original
original issue discount)            issue discount)


                  THE ST. PAUL COMPANIES, INC., a corporation duly organized and
existing under the laws of the State of Minnesota (herein called the "Company",
which term includes any successor Person under the Indenture hereinafter
referred to), for value received, hereby promises to pay to [Insert if the
Security is to be a Global Security -- CEDE & Co., as nominee for The Depository
Trust Company ("DTC")],     , or registered assigns, the principal sum of

                  (any such currency or composite currency being hereinafter
referred to as a "Specified Currency") on the Stated Maturity Date shown above
or, together with any premium thereon, upon any applicable Redemption or
Repayment Date specified above, [If the Security is to bear interest prior to
Maturity, insert -- and to pay interest thereon from the Original Issue Date
shown above or from the most recent Interest Payment Date to which interest has
been paid or duly provided for, semi-annually on May 15 and November 15 of each
year and on the Maturity Date, commencing on the first such Interest Payment
Date next succeeding the Original Issue Date, provided, however, that if the
Original Issue Date is after a Regular Record Date and before the Interest
Payment Date immediately following such Regular Record Date, interest payments
will commence on the second Interest Payment Date following the Original Issue
Date, at the rate per annum set forth above, until the principal hereof is paid
or made available for payment. The interest so payable, and punctually paid or
duly provided for, on any Interest Payment Date will, as provided in such
Indenture, be paid to the Person in whose name this Security (or one or more
Predecessor Securities) is registered at the close of business on the Regular
Record Date for such interest, which shall be the May 1 or November 1 (whether
or not a Business Day (as defined below)), as the case may be, next preceding
the May 15 and November 15 Interest Payment Dates; provided, however, that
interest

<PAGE>
payable at maturity or upon earlier redemption or repayment will be payable to
the Person to whom principal shall be payable. Any such interest not so
punctually paid or duly provided for will forthwith cease to be payable to the
registered Holder on such Regular Record Date and may either be paid to the
Person in whose name this Security (or one or more Predecessor Securities) is
registered at the close of business on a Special Record Date for the payment of
such Defaulted Interest to be fixed by the Trustee, notice whereof shall be
given to the Holder of this Security not less than 10 days prior to such Special
Record Date, or be paid at any time in any other lawful manner not inconsistent
with the requirements of any securities exchange on which the Securities of the
series evidenced by this Security may be listed, and upon such notice as may be
required by such exchange, all as more fully provided in said Indenture.] [If
the Security is not to bear interest prior to Maturity, insert -- The principal
of this Security shall not bear interest except in the case of a default in
payment of principal upon acceleration, upon redemption or at Stated Maturity
and in such case the overdue principal and any overdue premium shall bear
interest at the Default Rate per annum specified above (to the extent that the
payment of such interest shall be legally enforceable), from the dates such
amounts are due until they are paid or made available for payment. Interest on
any overdue principal or premium shall be payable on demand. Any such interest
on overdue principal or premium which is not paid on demand shall bear interest
at the Default Rate specified above (to the extent that the payment of such
interest on interest shall be legally enforceable) from the date of such demand
until the amount so demanded is paid or made available for payment. Interest on
any overdue interest shall be payable upon demand.]

                  Payment of principal of (and premium, if any) and interest on
this Security will be made in the Specified Currency shown above, except as
provided below. The Holder of a Security denominated in a Specified Currency
other than U.S. dollars may elect to receive all such payments in U.S. dollars
by delivery of a written request to the Paying Agent, in the case of any
interest payment due on an Interest Payment Date, on or prior to the applicable
Record Date, or, in the case of any other payment, on or prior to the Special
Record Date, if one has been established, or otherwise on the due date for such
payment, and must be made at least fifteen calendar days prior to such payment
due date. Such written request may be in writing (mailed or hand delivered) or
by cable, telex or other form of facsimile transmission. Such election shall
remain in effect unless such request is revoked on or prior to the applicable
Record Date or the date fifteen days prior to such payment due date.

                  Notwithstanding the foregoing, any nominee of DTC, as Holder,
will be deemed to have elected to receive all payments on a Security denominated
other than in U.S. dollars, in U.S. dollars, except to the extent that such
Holder requests, in accordance with the then current policies of DTC, that such
payments be made in the Specified Currency, and to such extent payments on such
Security will be made in the Specified Currency.

                  If the Holder has elected to receive payments in U.S. dollars,
payment in respect of such Security will be based upon the exchange rate as
determined by the

                                      -3-
<PAGE>
Exchange Rate Agent based on the highest firm bid quotation for U.S. dollars
received by such Exchange Rate Agent as of 11:00 A.M., New York City time, on
the second Business Day next preceding the applicable payment date from three
recognized foreign exchange dealers in The City of New York, one of which may be
the Exchange Rate Agent, for purchase by the quoting dealer of the Specified
Currency for U.S. dollars for settlement on such payment date of the aggregate
amount of the Specified Currency payable to all Holders of Securities electing
to receive U.S. dollar payments and at which the applicable dealer commits to
execute a contract. All currency exchange costs will be borne by the Holders of
such Securities by deductions from such payments. If three such bid quotations
are not available on the second Business Day preceding the payment of principal
(and premium, if any) or interest with respect to any Security, such payment
will be made in the Specified Currency. The term "Business Day" means each
Monday, Tuesday, Wednesday, Thursday and Friday which is (i) not a day on which
banking institutions in The City of New York generally are authorized or
obligated by law, regulation or executive order to close; (ii) if the security
is denominated in a Specified Currency other than U.S. dollars or euros, it must
also not be a day on which banking institutions are authorized or obligated by
law, regulation or executive order to close in the financial center of the
country issuing the Specified Currency; and (iii) if the Specified Currency is
euro, any day on which the Trans-European Automated Real-Time Gross Settlement
Express Transfer (TARGET) System, or any successor system is open for business
(a Euro Business Day).

                  Payment of the principal of (and premium, if any) and interest
on this Security due at maturity or upon earlier redemption or repayment to be
made in U.S. dollars will be made by wire transfer in immediately available
funds upon surrender of this Security at the Corporate Trust Office of the
Trustee in the Borough of Manhattan, The City of New York, or such other payment
office of a Paying Agent, provided that this Security is presented to the Paying
Agent in time for the Paying Agent to make such payment in accordance with its
normal procedures. Payments of interest to be made in U.S. dollars (other than
interest payable at maturity or upon earlier redemption or repayment) will be
made by check mailed to the address of the Person entitled thereto as it appears
in the Security Register, or by wire transfer to such account as may have been
appropriately designated to the Paying Agent at least 5 business days prior to
the payment due date by such Person.

                  Unless otherwise specified above, payments of interest and
principal (and premium, if any) with respect to any Security made in a Specified
Currency other than U.S. dollars will be made by wire transfer in immediately
available funds to an account with a bank located in the country issuing the
Specified Currency or in another jurisdiction acceptable to the Company and the
Paying Agent as shall have been designated at least 5 business days prior to the
Interest Payment Date or stated maturity, redemption or repayment date, as the
case may be, by the registered Holder of this Security on the relevant Regular
Record Date or maturity, redemption or repayment date, provided, however, that,
in the case of payment of principal of (and premium, if any) and any interest
due at maturity or upon earlier redemption or repayment, this Security is


                                      -4-
<PAGE>
presented to the Paying Agent in time for the Paying Agent to make such payments
in such funds in accordance with its normal procedures. Such designation shall
be made by filing the appropriate information with the Paying Agent, and, unless
revoked, or in the case of a Security held registered to a nominee of DTC, not
later than the time required by then-current policies of DTC, any such
designation made with respect to any Security by a registered Holder will remain
in effect with respect to any further payments with respect to this Security
payable to such Holder. If a payment with respect to this Security cannot be
made by wire transfer because the required designation has not been received by
the Paying Agent on or before the requisite date or for any other reason, a
notice will be mailed to the Holder at its registered address requesting a
designation pursuant to which such wire transfer can be made and, upon the
Paying Agent's receipt of such a designation, such payment will be made within 5
business days of such receipt. The Company will pay any administrative costs
imposed by banks in connection with making payments by wire transfer, but any
tax, assessment or governmental charge imposed upon payment will be borne by the
Holder hereof in respect of which payments are made. Any late payments made in
these circumstances will be treated under the Indenture as if made on the due
date, and no interest will accrue on late payment from the due date to the date
paid.

                  [If the Security is to be a Global Security -- Payment of
principal of (and premium, if any) and interest due on this Security will be
made to DTC or its nominee, as the case may be, as the sole registered owner and
the sole Holder of this Security for all purposes under the Indenture.]

                  If the Security is denominated in other than U.S. dollars and
the Specified Currency is not available due to the imposition of exchange
controls or other circumstances beyond the Company's control or is no longer
used by the government of the relevant country (unless otherwise replaced by the
euro), then the Company will be entitled to satisfy its obligations to Holders
by making payments in U.S. dollars on the basis of the most recently available
Exchange Rate. The "Exchange Rate" means the noon buying rate in The City of New
York for such cable transfers for such Specified Currency. Any payment made
under the circumstances and in a manner described above will not constitute an
Event of Default under the Indenture.

                  If the Specified Currency shown above is converted into or
replaced by another currency pursuant to law having general and direct
applicability in the jurisdiction which issued that Specified Currency (which
may include European Community law), any payments in respect of this Security
otherwise required to be made in such Specified Currency shall be made in the
currency into or by which such Specified Currency has been so converted or
replaced, based on the conversion or equivalency rate prescribed by law having
general and direct applicability in such jurisdiction (which may include
European Community law), and such Specified Currency shall not be deemed to be
unavailable to the Company solely by reason of any such conversion or
replacement.


                                      -5-
<PAGE>
                  If any currency is introduced in the jurisdiction issuing the
Specified Currency on the basis of legally enforceable equivalency to such
Specified Currency pursuant to law having general and direct applicability in
such jurisdiction (which may include European Community law) in preparation for
conversion of such Specified Currency into, or replacement of such Specified
Currency by, such other currency, the Company shall be entitled, at its option,
to make any payments in respect of this Security otherwise required to be made
in such Specified Currency in such other currency based on the equivalency rate
prescribed by law having general and direct applicability in such jurisdiction
(which may include European Community law). Making payments in accordance with
this or the preceding paragraph shall not, by itself, constitute a default in
the Company's obligations to make such payments. No occurrence of a currency
conversion, replacement or introduction of a type described in this paragraph or
the preceding paragraph involving the Specified Currency shall, by itself,
entitle the Company to avoid its obligations under this Security or entitle the
Company or any Holder of this Security to recession of the purchase and sale of
this Security or to reformation of any of the terms hereof on the grounds of
impossibility or impracticality of performance, frustration of purpose or
otherwise.

                  [If the Security is to be a Global Security -- This Security
may not be transferred except as a whole by a nominee of the Depositary to the
Depositary, or another nominee of the Depositary or by the Depositary or any
such nominee to a successor of the Depositary or a nominee of such successor.
This Security is exchangeable for Securities of this series in definitive
registered form only as provided in this paragraph. If (i) the Depositary
notifies the Company that it is unwilling, unable or no longer qualified to
continue as Depositary for this Security, (ii) the Company in its sole
discretion determines that this Security shall be so exchangeable or
transferable for Securities of this series in definitive registered form and
executes and delivers to the Security Registrar a Company Order providing that
this Security shall be so exchangeable or transferable, or (iii) an event shall
have happened and be continuing which, after notice or lapse of time, or both,
would become an Event of Default with respect to the Securities of the series of
which this Security is a part, this Security shall be exchangeable for
Securities of this series in definitive registered form, provided, however, that
the definitive Securities so issued in exchange for this Security shall be in
denominations of $1,000 and any integral multiple of $1,000 in excess thereof
or, if this Security is denominated in a Specified Currency, in the
denominations indicated on the face hereof, and be of like aggregate principal
amount and tenor as the portion of this Security to be exchanged. Except as
provided above, owners of beneficial interests in this Security will not be
entitled to receive physical delivery of Securities in definitive registered
form and will not be considered the Holders thereof for any purpose under the
Indenture.

                  Upon exchange of any portion of this Security for one or more
Securities of this series in definitive registered form, the Trustee or the
Security Registrar, as the case may be, shall cancel this Security and issue a
new Security or Securities of this Series and of like tenor for the remaining
principal amount. Except as otherwise provided herein or in the Indenture, until
exchanged in full for one or more Securities of

                                      -6-
<PAGE>
this series in definitive registered form, this Security shall in all respects
be subject to and entitled to the same benefits and conditions under the
Indenture as a duly authenticated and delivered Security of this series in
definitive registered form.]

                  REFERENCE IS HEREBY MADE TO THE FURTHER PROVISIONS OF THIS
SECURITY SET FORTH ON THE REVERSE HEREOF, WHICH FURTHER PROVISIONS SHALL FOR ALL
PURPOSES HAVE THE SAME EFFECT AS IF SET FORTH AT THIS PLACE.

                  Unless the certificate of authentication hereon has been
executed by the Trustee or by its Authenticating Agent by manual signature, this
Security shall not be entitled to any benefit under the Indenture or be valid or
obligatory for any purpose.


                                      -7-
<PAGE>
                  IN WITNESS WHEREOF, the Company has caused this instrument to
be duly executed under its corporate seal.

Dated:                                      THE ST. PAUL COMPANIES, INC.


                                            By:
                                               --------------------------------
                                                   Authorized Officer

Attest:


----------------------------
Corporate Secretary

[SEAL]
                     TRUSTEE'S CERTIFICATE OF AUTHENTICATION

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

                                             JPMORGAN CHASE BANK
                                             as Trustee

                                             By:
                                               --------------------------------
                                                   Authorized Officer


                                      -8-
<PAGE>
                          [Form of Reverse of Security]

                          [Fixed Rate Medium-Term Note]

                          THE ST. PAUL COMPANIES, INC.
                           MEDIUM-TERM NOTE, Series D

                  This Security is one of a duly authorized issue of securities
of the Company (herein called the "Securities"), issued and to be issued in one
or more series under an Indenture, dated as of March 12, 2002 herein called the
"Indenture" (which term shall have the meaning assigned to it in such
instrument), between the Company and JPMorgan Chase Bank, as trustee (herein
called the "Trustee", which term includes any successor trustee under the
Indenture), and reference is hereby made to the Indenture for a statement of the
respective rights, limitations of rights, duties and immunities thereunder of
the Company, the Trustee and the Holders of the Securities and of the terms upon
which the Securities are, and are to be, authenticated and delivered. This
Security is one of the Securities of the series designated on the face hereof.
The Securities of this series may be issued from time to time in an aggregate
principal amount of up to $500,000,000 or its equivalent in other currencies or
composite currencies, may mature at different times, bear interest, if any, at
different rates, be redeemable at different times or not at all, be issued at an
original issue discount, and be denominated in different currencies; provided,
however, that the foregoing limit may be increased or decreased by the Company,
if in the future it determines that it may want to sell additional Securities of
this series or other securities.

                  Interest payments for this Security with respect to any
Interest Payment Date or date of maturity, redemption or repayment will include
interest accrued to but excluding such Interest Payment Date or date of
maturity, redemption or repayment, as the case may be. Interest payments for
this Security shall be computed and paid on the basis of a 360-day year of
twelve 30-day months.

                  If any Interest Payment Date or the Maturity Date (or date of
redemption or repayment) of this Security falls on a day that is not a Business
Day, the required payment of principal, premium, if any, and/or interest will be
made on the next succeeding Business Day as if made on the date such payment was
due, and no interest will accrue on such payment for the period from and after
such Interest Payment Date or the Maturity Date (or date of redemption or
repayment), as the case may be, to the date of such payment on the next
succeeding Business Day.

                  This Security is not convertible or subject to any sinking
fund, and unless a Redemption Commencement Date, Redemption Periods and
Redemption Prices are specified on the face hereof, this Security is not subject
to redemption prior to the Stated Maturity Date shown above. If so specified,
this Security is subject to redemption upon not less than 30 nor more than 60
days' notice by mail, as a whole or in part, at the

                                      R-1
<PAGE>
election of the Company, during the Redemption Periods and at the Redemption
Prices specified on the face hereof, plus interest accrued to the Redemption
Date, but interest installments whose Stated Maturity is on or prior to such
Redemption Date will be payable to the Holders of this Security, or one or more
Predecessor Securities, of record at the close of business on the relevant
Regular Record Dates referred to on the face hereof, all as provided in the
Indenture.

                  In the event of redemption of this Security in part only, a
new Security or Securities of this series and of like tenor and for a principal
amount equal to the unredeemed portion will be issued in the name of the Holder
hereof upon the cancellation hereof.

                  This Security is not subject to repayment prior to the Stated
Maturity Date shown above unless a Repayment Date, Repayment Periods and
Repayment Prices are specified above. If so specified, this Security is subject
to repayment at the option of the Holder hereof upon the terms set forth above
by completing the form for the Option to Elect Repayment that is attached.

                  In the event of repayment of this Security in part only, a new
Security or Securities of this series and of like tenor and for a principal
amount equal to the unpaid portion will be issued to the registered Holder upon
the cancellation hereof.

                  If an Event of Default with respect to the Securities of this
series shall occur and be continuing, an amount of principal of the Securities
of this series may be declared due and payable in the manner and with the effect
provided in the Indenture.

                  If this Security is an Original Issue Discount Security, (i)
if an Event of Default with respect to the Securities of this series shall have
occurred and be continuing, the amount of principal of this Security which may
be declared due and payable in the manner and with the effect provided in the
Indenture, shall be determined in the manner set forth under "OID Default
Amount" on the face hereof, and (ii) in the case of a default of payment in
principal upon acceleration, redemption or at maturity hereof, in lieu of any
interest otherwise payable, the overdue principal of this Security shall bear
interest at a rate of interest per annum equal to the Default Rate stated on the
face hereof (to the extent that the payment of such interest shall be legally
enforceable), which shall accrue from the date of such acceleration, redemption
or maturity, as the case may be, to the date payment has been made or duly
provided for or such default has been waived in accordance with the terms of the
Indenture. Upon payment (i) of the amount of principal so declared due and
payable and (ii) of interest on any overdue principal, premium and overdue
interest (in each case to the extent that the payment of such interest shall be
legally enforceable) all of the Company's obligations in respect of the payment
of the principal of and premium and interest, if any, on the Securities of this
series shall terminate.


                                      R-2
<PAGE>
                  The Indenture contains provisions for defeasance at any time
of (i) the entire indebtedness of this Security or (ii) certain restrictive
covenants with respect to this Security, in each case upon compliance with
certain conditions set forth in the Indenture.

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

                  No reference herein to the Indenture and no provision of this
Security or of the Indenture shall alter or impair the obligation of the
Company, which is absolute and unconditional, to pay the principal of and any
premium, and interest on this Security at the times, places and rate, and in the
coin or currency, herein prescribed.

                  As provided in the Indenture and subject to certain
limitations therein set forth (including, in the case of a Global Security,
certain additional limitations), the transfer of this Security is registrable in
the Security Register, upon surrender of this Security for registration of
transfer at the office or agency of the Company in any place where the principal
of and any premium and interest on this Security is payable, duly endorsed by,
or accompanied by a written instrument of transfer in a form satisfactory to the
Company and the Security Registrar duly executed by the Holder hereof or his
attorney duly authorized in writing, and thereupon one or more new Securities of
this series and of like tenor, of authorized denominations and for the same
aggregate principal amount, will be issued to the designated transferee or
transferees.

                  The Securities of this series are issuable only in registered
form, without coupons, in denominations of (i) if denominated in U.S. dollars,
$1,000 and any integral multiple of $1,000 in excess thereof or (ii) if this
Security is denominated in a Specified Currency other than U.S. dollars, in the
denominations indicated on the face hereof, equivalent to $1,000 and integral
multiples of $1,000 in excess thereof, using an exchange rate equal to the noon
buying rate in The City of New York for cable transfers for such Specified
Currency on the first Business Day immediately preceding the date on which the
Company accepts the offer to buy such Security, unless otherwise specified
above. The Securities of this series may be issued, in whole or in part, in the
form of one or more Global Securities bearing the legend specified in the
Indenture regarding certain

                                      R-3
<PAGE>
restrictions on registration of transfer and exchange and issued to DTC or its
nominee and registered in the name of DTC or such nominee. As provided in the
Indenture and subject to certain limitations (including, in the case of any
Global Security, certain additional limitations) therein set forth, Securities
of this series are exchangeable for a like aggregate principal amount of
Securities of this series and of like tenor if a different authorized
denomination, as requested by the Holder surrendering the same.

                  No service charge shall be made for any such registration of
transfer or exchange of Securities as provided above, but the Company may
require payment of a sum sufficient to cover any tax or other governmental
charge payable in connection therewith.

                  Prior to due presentment of a Security of this series for
registration of transfer, the Company, the Trustee and any agent of the Company
or the Trustee may treat the Person in whose name this Security is registered as
the owner hereof for all purposes, whether or not this Security is overdue, and
neither the Company, the Trustee nor any such agent shall be affected by notice
to the contrary.

                  All terms used in this Security which are defined in the
Indenture and not herein otherwise defined shall have the meanings assigned to
them in the Indenture.


                                      R-4
<PAGE>
                                  ABBREVIATIONS

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

                  TEN COM -         as tenants in common

                  TEN ENT -         as tenants by the entireties

                  JT TEN  -         as joint tenants with right of
                                    survivorship and not as tenants
                                    in common

                  UNIF GIFT MIN ACT -       __________Custodian___________
                                            (Cust)              (Minor)

                                              Uniform Gifts to Minor Acts
                                             _____________________________
                                                     (State)

                  Additional abbreviations may also be used though not in the
         above list.


                                      R-5
<PAGE>
                                   ASSIGNMENT

                  FOR VALUE RECEIVED, the undersigned hereby sell(s), assign(s)
and transfer(s) unto

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

                        (PLEASE INSERT SOCIAL SECURITY OR
                         IDENTIFYING NUMBER OF ASSIGNEE)

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

                     (PLEASE PRINT OR TYPE NAME AND ADDRESS
                     INCLUDING POSTAL ZIP CODE OF ASSIGNEE)

the within Security and all rights thereunder, hereby irrevocably constituting
and appointing

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

to transfer said Security on the books of the Company, with full power of
substitution in the premises.

Dated:
      -------------------------


         NOTE: The signature to this assignment must correspond with the name as
         written upon the face of the within Security in every particular,
         without alteration or enlargement or any change whatever.


                                      R-6

<PAGE>
                            OPTION TO ELECT REPAYMENT

                  The undersigned hereby irrevocably requests and instructs the
Company to repay the within Security (or portion thereof specified below)
pursuant to its terms at the applicable Repayment Price, together with interest
to the Repayment Date, to the undersigned at

                  ___________________________________________________________

                  ___________________________________________________________

                  ___________________________________________________________

                 (Please Print or Typewrite Name and Address of the Undersigned)

and specify the denomination or denominations (which shall not be less than the
minimum authorized denomination) of the Securities to be issued to the
undersigned for the portion of the within Security not being repaid (in the
absence of any such specification, one such Security will be issued for the
portion not being repaid):__________________________.

                  Dated:   ___________________



                  NOTE: The signature to this assignment must correspond with
the name as written upon the face of the within Security in every particular,
without alteration or enlargement or any change whatever.


                                      R-7

<PAGE>
                                                                     Exhibit 4.2

                           [Form of Face of Security]

                [Floating Rate - No OID (Resetting Daily, Weekly
                      Monthly, Quarterly, Semi-Annually or

                           Annually) Medium-Term Note]


REGISTERED                                             PRINCIPAL AMOUNT (and
NO. FLR- ____________                                  Specified Currency if
CUSIP NO.: __________                                  other than U.S. dollars)
                                                       [$]--------------



                          THE ST. PAUL COMPANIES, INC.

                           MEDIUM-TERM NOTE, SERIES D

                  [Insert if the Security is to be a Global Security -- THIS
SECURITY IS A SECURITY IN PERMANENT GLOBAL FORM WITHIN THE MEANING OF THE
INDENTURE HEREINAFTER REFERRED TO AND IS REGISTERED IN THE NAME OF A DEPOSITARY
OR A NOMINEE THEREOF. THIS SECURITY MAY NOT BE EXCHANGED IN WHOLE OR IN PART FOR
A SECURITY REGISTERED, AND NO TRANSFER OF THIS SECURITY IN WHOLE OR IN PART MAY
BE REGISTERED, IN THE NAME OF ANY PERSON OTHER THAN SUCH DEPOSITARY OR A NOMINEE
THEREOF, EXCEPT IN THE LIMITED CIRCUMSTANCES DESCRIBED IN THE INDENTURE.

                  UNLESS THIS CERTIFICATE IS PRESENTED BY AN AUTHORIZED
REPRESENTATIVE OF THE DEPOSITORY TRUST COMPANY, A NEW YORK CORPORATION ("DTC"),
TO THE ST. PAUL COMPANIES, INC. OR ITS AGENT FOR REGISTRATION OF TRANSFER,
EXCHANGE OR PAYMENT, AND ANY CERTIFICATE ISSUED IS REGISTERED IN THE NAME OF
CEDE & CO. OR IN SUCH OTHER NAME AS IS REQUESTED BY AN AUTHORIZED REPRESENTATIVE
OF DTC (AND ANY PAYMENT IS MADE TO CEDE & CO. OR TO SUCH OTHER ENTITY AS IS
REQUESTED BY AN AUTHORIZED REPRESENTATIVE OF DTC), ANY TRANSFER, PLEDGE OR OTHER
USE HEREOF FOR VALUE OR OTHERWISE BY OR TO ANY PERSON IS WRONGFUL INASMUCH AS
THE REGISTERED OWNER HEREOF, CEDE & CO., HAS AN INTEREST HEREIN.]
<PAGE>
STATED MATURITY DATE:                                   ORIGINAL ISSUE DATE:



SPECIFIED CURRENCY:                                     EXCHANGE RATE AGENT:



INITIAL INTEREST RATE:                                  INTEREST RATE BASIS:



INDEX MATURITY:                                         INDEX CURRENCY (if other
                                                        than U.S. dollars):



SPREAD (plus or minus):                                 SPREAD MULTIPLIER:



MINIMUM INTEREST RATE:                                  MAXIMUM INTEREST RATE:



AUTHORIZED DENOMINATIONS                                REGULAR RECORD DATES:
(only applicable if different from
$1,000 and integral multiples of
$1,000 after that or Specified
Currency is other than U.S. dollars):

INTEREST RESET PERIOD:                                  INTEREST RESET DATES:



INTEREST PAYMENT DATES:                                 CALCULATION DATES:



INTEREST DETERMINATION                                  CALCULATION AGENT (if
DATES:                                                  other than JPMorgan
                                                        Chase Bank):

                                       -2-
<PAGE>
REDEMPTION COMMENCEMENT DATE:                           REDEMPTION PERIODS AND
                                                        PRICES:

REPAYMENT DATE:                                         REPAYMENT PERIODS AND
                                                        PRICES:


DESIGNATED LIBOR PAGE:                                  DESIGNATED CMT MATURITY
                                                        INDEX:


DESIGNATED CMT TELERATE                                 OTHER/ADDITIONAL TERMS:
PAGE:

                  THE ST. PAUL COMPANIES, INC., a corporation duly organized and
existing under the laws of the State of Minnesota (herein called the "Company",
which term includes any successor Person under the Indenture hereinafter
referred to), for value received, hereby promises to pay to [Insert if the
Security is to be a Global Security -- CEDE & Co., as nominee for The Depository
Trust Company ("DTC")] or registered assigns, the principal sum of
                  (any such currency or composite currency being hereinafter
referred to as a "Specified Currency") on the Stated Maturity Date shown above
or, together with any premium thereon, upon any applicable Redemption or
Repayment Date specified above, and to pay interest thereon from the Original
Issue Date shown above or from the most recent Interest Payment Date to which
interest has been paid or duly provided for, on the Interest Payment Dates set
forth above and on the Maturity Date, commencing on the first such Interest
Payment Date next succeeding the Original Issue Date, provided, however, that if
the Original Issue Date is after a Regular Record Date and before the Interest
Payment Date immediately following such Regular Record Date, interest payments
will commence on the second Interest Payment Date following the Original Issue
Date, at the rate per annum determined in accordance with the provisions
hereinafter set forth, depending on the Interest Rate Basis specified above,
until the principal hereof is paid or made available for payment. The interest
so payable, and punctually paid or duly provided for, on any Interest Payment
Date will, as provided in such Indenture, be paid to the Person in whose name
this Security (or one or more Predecessor Securities) is registered at the close
of business on the Regular Record Date for such interest, which shall be the
fifteenth calendar day (whether or not a Business Day (as defined on the reverse
hereof)), next preceding each Interest Payment Date; provided, however, that
interest payable at maturity or upon earlier redemption or repayment will be
payable to the Person to whom principal shall be payable. Any such interest not
so punctually paid or duly provided for will forthwith cease to be payable to
the registered Holder on such Regular Record Date and may either be paid to the
Person in whose name

                                      -3-
<PAGE>
this Security (or one or more Predecessor Securities) is registered at the close
of business on a Special Record Date for the payment of such Defaulted Interest
to be fixed by the Trustee, notice whereof shall be given to the Holder of this
Security not less than 10 days prior to such Special Record Date, or be paid at
any time in any other lawful manner not inconsistent with the requirements of
any securities exchange on which the Securities of the series evidenced by this
Security may be listed, and upon such notice as may be required by such
exchange, all as more fully provided in said Indenture.

                  Payment of principal of (and premium, if any) and interest on
this Security will be made in the Specified Currency shown above, except as
provided below. The Holder of a Security denominated in a Specified Currency
other than U.S. dollars may elect to receive all such payments in U.S. dollars
by delivery of a written request to the Paying Agent, in the case of any
interest payment due on an Interest Payment Date, on or prior to the applicable
Record Date, or, in the case of any other payment, on or prior to the Special
Record Date, if one has been established, or otherwise on the due date for such
payment, and must be made at least fifteen calendar days prior to such payment
due date. Such written request may be in writing (mailed or hand delivered) or
by cable, telex or other form of facsimile transmission. Such election shall
remain in effect unless such request is revoked on or prior to the applicable
Record Date or the date fifteen days prior to such payment due date.

                  Notwithstanding the foregoing, any nominee of DTC, as Holder,
will be deemed to have elected to receive all payments on a Security denominated
other than in U.S. dollars, in U.S. dollars, except to the extent that such
Holder requests, in accordance with the then current policies of DTC, that such
payments be made in the Specified Currency, and to such extent payments on such
Security will be made in the Specified Currency.

                  If the Holder has elected to receive payments in U.S. dollars,
payment in respect of such Security will be based upon the exchange rate as
determined by the Exchange Rate Agent based on the highest firm bid quotation
for U.S. dollars received by such Exchange Rate Agent as of 11:00 A.M., New York
City time, on the second Business Day next preceding the applicable payment date
from three recognized foreign exchange dealers in The City of New York, one of
which may be the Exchange Rate Agent, for purchase by the quoting dealer of the
Specified Currency for U.S. dollars for settlement on such payment date of the
aggregate amount of the Specified Currency payable to all Holders of Securities
electing to receive U.S. dollar payments and at which the applicable dealer
commits to execute a contract. All currency exchange costs will be borne by the
Holders of such Securities by deductions from such payments. If three such bid
quotations are not available on the second Business Day preceding the payment of
principal (and premium, if any) or interest with respect to any Security, such
payment will be made in the Specified Currency.

                  Payment of the principal of (and premium, if any) and interest
on this Security due at maturity or upon earlier redemption or repayment to be
made in U.S. dollars will be made by wire transfer in immediately available
funds upon surrender of

                                      -4-
<PAGE>
this Security at the Corporate Trust Office of the Trustee in the Borough of
Manhattan, The City of New York, or such other payment office of a Paying Agent,
provided that this Security is presented to the Paying Agent in time for the
Paying Agent to make such payment in accordance with its normal procedures.
Payments of interest to be made in U.S. dollars (other than interest payable at
maturity or upon earlier redemption or repayment) will be made by check mailed
to the address of the Person entitled thereto as it appears in the Security
Register, or by wire transfer to such account as may have been appropriately
designated to the Paying Agent at least 5 business days prior to the payment due
date by such Person.

                  Unless otherwise specified above, payments of interest and
principal (and premium, if any) with respect to any Security made in a Specified
Currency other than U.S. dollars will be made by wire transfer in immediately
available funds to an account with a bank located in the country issuing the
Specified Currency or in another jurisdiction acceptable to the Company and the
Paying Agent as shall have been designated at least 5 business days prior to the
Interest Payment Date or stated maturity, redemption or repayment date, as the
case may be, by the registered Holder of this Security on the relevant Regular
Record Date or maturity, redemption or repayment date, provided, however, that,
in the case of payment of principal of (and premium, if any) and any interest
due at maturity or upon earlier redemption or repayment, this Security is
presented to the Paying Agent in time for the Paying Agent to make such payments
in such funds in accordance with its normal procedures. Such designation shall
be made by filing the appropriate information with the Paying Agent, and, unless
revoked, or in the case of a Security held registered to a nominee of DTC, not
later than the time required by then-current policies of DTC, any such
designation made with respect to any Security by a registered Holder will remain
in effect with respect to any further payments with respect to this Security
payable to such Holder. If a payment with respect to this Security cannot be
made by wire transfer because the required designation has not been received by
the Paying Agent on or before the requisite date or for any other reason, a
notice will be mailed to the Holder at its registered address requesting a
designation pursuant to which such wire transfer can be made and, upon the
Paying Agent's receipt of such a designation, such payment will be made within 5
business days of such receipt. The Company will pay any administrative costs
imposed by banks in connection with making payments by wire transfer, but any
tax, assessment or governmental charge imposed upon payment will be borne by the
Holder hereof in respect of which payments are made. Any late payments made in
these circumstances will be treated under the Indenture as if made on the due
date, and no interest will accrue on late payment from the due date to the date
paid.

                  [If the Security is to be a Global Security -- Payment of
principal of (and premium, if any) and interest due on this Security will be
made to DTC or its nominee, as the case may be, as the sole registered owner and
the sole Holder of this Security for all purposes under the Indenture.]

                  If the Security is denominated in other than U.S. dollars and
the Specified Currency is not available due to the imposition of exchange
controls or other

                                      -5-
<PAGE>
circumstances beyond the Company's control, or is no longer used by the
government of the relevant country (unless otherwise replaced by the euro) then
the Company will be entitled to satisfy its obligations to Holders by making
payments in U.S. dollars on the basis of the most recently available Exchange
Rate. The "Exchange Rate" means the noon buying rate in the City of New York for
cable transfers for such Specified Currency. Any payment made under the
circumstances and in a manner described above will not constitute an Event of
Default under the Indenture.

                  If the Specified Currency shown above is converted into or
replaced by another currency pursuant to law having general and direct
applicability in the jurisdiction which issued that Specified Currency (which
may include European Community law), any payments in respect of this Security
otherwise required to be made in such Specified Currency shall be made in the
currency into or by which such Specified Currency has been so converted or
replaced, based on the conversion or equivalency rate prescribed by law having
general and direct applicability in such jurisdiction (which may include
European Community law), and such Specified Currency shall not be deemed to be
unavailable to the Company solely by reason of any such conversion or
replacement.

                  If any currency is introduced in the jurisdiction issuing the
Specified Currency on the basis of legally enforceable equivalency to such
Specified Currency pursuant to law having general and direct applicability in
such jurisdiction (which may include European Community law) in preparation for
conversion of such Specified Currency into, or replacement of such Specified
Currency by, such other currency, the Company shall be entitled, at its option,
to make any payments in respect of this Security otherwise required to be made
in such Specified Currency in such other currency based on the equivalency rate
prescribed by law having general and direct applicability in such jurisdiction
(which may include European Community law). Making payments in accordance with
this or the preceding paragraph shall not, by itself, constitute a default in
the Company's obligations to make such payments. No occurrence of a currency
conversion, replacement or introduction of a type described in this paragraph or
the preceding paragraph involving the Specified Currency shall, by itself,
entitle the Company to avoid its obligations under this Security or entitle the
Company or any Holder of this Security to recession of the purchase and sale of
this Security or to reformation of any of the terms hereof on the grounds of
impossibility or impracticality of performance, frustration of purpose or
otherwise.

                  [If the Security is to be a Global Security -- This Security
may not be transferred except as a whole by a nominee of the Depositary to the
Depositary, or another nominee of the Depositary or by the Depositary or any
such nominee to a successor of the Depositary or a nominee of such successor.
This Security is exchangeable for Securities of this series in definitive
registered form only as provided in this paragraph. If (i) the Depositary
notifies the Company that it is unwilling, unable or no longer qualified to
continue as Depositary for this Security, (ii) the Company in its sole
discretion determines that this Security shall be so exchangeable

                                      -6-
<PAGE>
or transferable for Securities of this series in definitive registered form and
executes and delivers to the Security Registrar a Company Order providing that
this Security shall be so exchangeable or transferable, or (iii) an event shall
have happened and be continuing which, after notice or lapse of time, or both,
would become an Event of Default with respect to the Securities of the series of
which this Security is a part, this Security shall be exchangeable for
Securities of this series in definitive registered form, provided, however, that
the definitive Securities so issued in exchange for this Security shall be in
denominations of $1,000 and any integral multiple of $1,000 in excess thereof
or, if this Security is denominated in a Specified Currency, in the
denominations indicated on the face hereof, and be of like aggregate principal
amount and tenor as the portion of this Security to be exchanged. Except as
provided above, owners of beneficial interests in this Security will not be
entitled to receive physical delivery of Securities in definitive registered
form and will not be considered the Holders thereof for any purpose under the
Indenture.

                  Upon exchange of any portion of this Security for one or more
Securities of this series in definitive registered form, the Trustee or the
Security Registrar, as the case may be, shall cancel this Security and issue a
new Security or Securities of this Series and of like tenor for the remaining
principal amount. Except as otherwise provided herein or in the Indenture, until
exchanged in full for one or more Securities of this series in definitive
registered form, this Security shall in all respects be subject to and entitled
to the same benefits and conditions under the Indenture as a duly authenticated
and delivered Security of this series in definitive registered form.]

                  REFERENCE IS HEREBY MADE TO THE FURTHER PROVISIONS OF THIS
SECURITY SET FORTH ON THE REVERSE HEREOF, WHICH FURTHER PROVISIONS SHALL FOR ALL
PURPOSES HAVE THE SAME EFFECT AS IF SET FORTH AT THIS PLACE.

                  Unless the certificate of authentication hereon has been
executed by the Trustee or by its Authenticating Agent by manual signature, this
Security shall not be entitled to any benefit under the Indenture or be valid or
obligatory for any purpose.


                                      -7-
<PAGE>
                  IN WITNESS WHEREOF, the Company has caused this instrument to
be duly executed under its corporate seal.

Dated:                                    THE ST. PAUL COMPANIES, INC.


                                          By:
                                             ----------------------------------
                                                 Authorized Officer

Attest:


----------------------------
Corporate Secretary

[SEAL]




                     TRUSTEE'S CERTIFICATE OF AUTHENTICATION

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

                                          JPMORGAN CHASE BANK
                                          as Trustee

                                          By:
                                             ----------------------------------
                                              Authorized Officer


                                      -8-