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                                 Exhibit No. 4.4


              Second Supplemental Indenture dated February 26, 1999

                       between The Progressive Corporation

              and State Street Bank and Trust Company, as Trustee



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                           THE PROGRESSIVE CORPORATION

                                       and

                     STATE STREET BANK AND TRUST COMPANY, as
                                Successor Trustee



                          SECOND SUPPLEMENTAL INDENTURE

                          6-5/8% Senior Notes due 2029


         THIS SECOND SUPPLEMENTAL INDENTURE, dated as of February 26, 1999,
between THE PROGRESSIVE CORPORATION, an Ohio corporation (the "ISSUER") and
STATE STREET BANK AND TRUST COMPANY, a Massachusetts trust company ("SSB"), in
its capacity as Successor Trustee.

                              W I T N E S S E T H:

         WHEREAS, the Issuer entered into an Indenture, dated as of September
15, 1993 (as supplemented by the First Supplemental Indenture, dated as of March
15, 1996, the "INDENTURE"), with the First National Bank of Boston, in its
capacity as Trustee, pursuant to which the Issuer may from time to time issue
its unsecured debentures, notes and other evidences of indebtedness in one or
more series; and

         WHEREAS, the Issuer entered into a Supplemental Indenture, dated as of
March 15, 1996, confirming the succession of SSB as trustee under the Indenture;
and

         WHEREAS, Article Eight of the Indenture provides for various matters
with respect to any series of Securities issued under the Indenture to be
established in an indenture supplemental to the Indenture; and

         WHEREAS, Section 8.1(c) of the Indenture provides that the Issuer, when
authorized by its Board of Directors, and the Trustee may from time to time and
at any time enter into an indenture supplemental to the Indenture to add on to
the covenants of the Issuer certain further covenants, restrictions, conditions
or provisions.
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         NOW THEREFORE:

         In consideration of the premises and other good and valuable
consideration, the parties hereto mutually covenant and agree as follows:


                                    ARTICLE 1
                       RELATION TO INDENTURE; DEFINITIONS

         SECTION 1.01. Integral Part. This Second Supplemental Indenture
constitutes an integral part of the Indenture.

         SECTION 1.02. General Definitions. For all purposes of this Second
Supplemental Indenture:

         (a) capitalized terms used herein without definition shall have the
meanings specified in the Indenture;

         (b) all references herein to Articles and Sections, unless otherwise
specified, refer to the corresponding Articles and Sections of this Second
Supplemental Indenture; and

         (c) the terms "HEREIN", "HEREOF", "HEREUNDER" and other words of
similar import refer to this Second Supplemental Indenture.

         SECTION 1.03. Definitions. The following definitions shall apply to
this Second Supplemental Indenture:

         "CONSOLIDATED TANGIBLE NET WORTH" means, at any date, the total assets
appearing on the consolidated balance sheet of the Issuer and its consolidated
subsidiaries as of the end of the then most recent fiscal quarter of the Issuer,
prepared in accordance with generally accepted accounting principles, less the
sum of (a) the total liabilities appearing on such balance sheet and (b)
intangible assets. "INTANGIBLE ASSETS" means, for the purposes of this
definition, the value, as shown on or reflected in such balance sheet, of (i)
all trade names, trademarks, licenses, patents, copyrights and goodwill, (ii)
organizational costs and (iii) unamortized debt discount and expense, less
unamortized premium.

         "DESIGNATED SECURITIES" means the series of Securities designated by
the Issuer as its "6-5/8% Senior Notes due 2029".

         "DESIGNATED SUBSIDIARY" means (i) Progressive Casualty Insurance
Company, an Ohio

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corporation, so long as it remains a subsidiary of the Issuer, (ii) any other
consolidated subsidiary of the Issuer the assets of which constitute 10% or more
of the Total Assets, and (iii) any subsidiary which is a successor to all or
substantially all of the business or properties of any such subsidiary.

         "TOTAL ASSETS" means, at any date, the total assets appearing on the
consolidated balance sheet of the Issuer and its consolidated subsidiaries as of
the end of the then most recent fiscal quarter of the Issuer, prepared in
accordance with generally accepted accounting principles.

                                    ARTICLE 2
                              ADDITIONAL COVENANTS

         SECTION 2.01. Limitation on Liens. The Issuer will not, nor will it
permit any Designated Subsidiary to, incur, issue, assume or guarantee any
indebtedness for money borrowed if (i) that indebtedness is secured by a pledge,
mortgage, deed of trust or other lien on any shares of stock or indebtedness of
any Designated Subsidiary (a "LIEN"), and (ii) the aggregate amount of the
indebtedness so secured exceeds an amount equal to 15% of the Issuer's
Consolidated Tangible Net Worth, unless the Designated Securities are also
secured equally and ratably with such other indebtedness. For purposes of this
restriction, a "LIEN" will not include the pledge to, or deposit with, any state
or provincial insurance regulatory authorities of any investment securities by
the Issuer or any of its subsidiaries.

         The foregoing restriction shall not apply to indebtedness secured by:

         (a) Liens on any shares of stock or indebtedness of or acquired from a
corporation merged or consolidated with or into, or otherwise acquired by, the
Issuer or a Designated Subsidiary;

         (b) Liens to secure indebtedness of a Designated Subsidiary to the
Issuer or to another Designated Subsidiary, but only as long as such
indebtedness is owned or held by the Issuer or a Designated Subsidiary; and

         (c) Any extension, renewal or replacement (or successive extensions,
renewals or replacements), in whole or in part, of any lien referred to in (a)
and (b).

         SECTION 2.02. Consolidation, Merger, Sale, Conveyance and Lease. The
Issuer will not consolidate or merge with or into any other Person or Persons,
or sell, convey or lease all or substantially all of its property to any other
Person, unless:

         (a) the Person formed by such consolidation, or into which the Issuer
is merged or which acquires or leases all or substantially all of the property
of the Issuer, is a corporation or

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other entity organized under the laws of the United States, any state thereof or
the District of Columbia, and such Person expressly assumes the Issuer's
obligations under the Designated Securities and the Indenture; and

         (b) immediately after giving effect to the transaction, no Event of
Default exists.

         This restriction shall not apply if the Issuer is the Person that
survives any such transaction.

         In the event of a conflict between any provision in this Section and
any provision in Article 9 of the Indenture, Article 9 of the Indenture shall
govern.

                                    ARTICLE 3
                            MISCELLANEOUS PROVISIONS

         SECTION 3.01. Applicability of this Second Supplemental Indenture. The
provisions of this Second Supplemental Indenture will be applicable solely to
the Designated Securities.

         SECTION 3.02. Adoption, Ratification and Confirmation. The Indenture,
as supplemented by this Second Supplemental Indenture, is in all respects hereby
adopted, ratified and confirmed.

         SECTION 3.03. Counterparts. This Second Supplemental Indenture may be
executed in any number of counterparts, each of which when so executed shall be
deemed an original; and all such counterparts shall together constitute but one
and the same instrument.

         SECTION 3.04. GOVERNING LAW. THIS SECOND SUPPLEMENTAL INDENTURE SHALL
BE GOVERNED BY AND CONSTRUED IN ACCORDANCE WITH THE LAWS OF THE STATE OF NEW
YORK.

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         IN WITNESS WHEREOF, the parties hereto have caused this Second
Supplemental Indenture to be duly executed and their respective corporate seals
to be hereunto fixed and attested as of the day and year first written above.


                                            THE PROGRESSIVE CORPORATION

                                            By:
                                               --------------------------------
                                                 W. Thomas Forrester
                                                 Treasurer

Attest:

By:
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     David M. Schneider
     Secretary



                                            STATE STREET BANK AND TRUST
                                               COMPANY, as Successor Trustee

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

Attest:

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

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STATE OF OHIO      )
                   ) ss:
COUNTY OF CUYAHOGA )

         On this __th day of February, 1999, before me personally came W. Thomas
Forrester, to me personally known, who, being by me duly sworn, did depose and
say that he is a resident of Cuyahoga County, Ohio; that he is an officer of THE
PROGRESSIVE CORPORATION, one of the corporations described in and which executed
the above instrument; that he knows the corporate seal of said corporation; that
the seal affixed to said instrument is such corporate seal; that it was so
affixed by authority of the Board of Directors of said corporation, and that he
signed his name thereto by like authority.


                                               --------------------------------
                                               Notary Public
                                               My commission expires:

[Notarial Seal]



STATE OF MASSACHUSETTS )
                       ) ss.:
COUNTY OF SUFFOLK      )

         On this __th day of February, 1999, before me personally came
__________________, to me personally known, who, being by me duly sworn, did
depose and say that he is a resident of Bristol County, Massachusetts; that he
is an authorized officer of STATE STREET BANK AND TRUST COMPANY, one of the
corporations described in and which executed the above instrument; that he knows
the corporate seal of said corporation; that the seal affixed to said
instruments is such corporate seal; that it was so affixed by authority of the
Board of Directors of said corporation, and that he signed her name thereto by
like authority.


                                               --------------------------------
                                               Notary Public
                                               My commission expires:

[Notary Seal]

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