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                                    EXHIBIT 5
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                        Opinion of Baker & Hostetler LLP
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                                                                       Exhibit 5





                                  July 12, 2000





The Progressive Corporation
6300 Wilson Mills Road
Mayfield Village, Ohio 44143

                 Re: The Progressive Retirement Security Program

Gentlemen:

           We have  acted as  counsel to The  Progressive  Corporation,  an Ohio
corporation  (the  "Company"),  in connection  with the  Company's  Registration
Statement on Form S-8 (the "Registration  Statement") filed under the Securities
Act of 1933,  as amended,  relating to the  offering of up to  1,000,000  Common
Shares,  $1.00 par value (the "Common  Shares"),  of the Company pursuant to The
Progressive  Retirement  Security Program (the "Plan") and interests in the Plan
to be offered and sold  pursuant to the Plan. We have examined the Plan and such
documents,  records and matters of law as we deem necessary for purposes of this
opinion and, based thereon, we are of the opinion that:

           1. The  interests in the Plan,  when offered to  participants  in the
Plan in accordance with the terms of the Plan, will be legally issued; and

           2. The Common Shares of the Company which may be issued,  transferred
or sold by the Company to the Plan will be, when issued,  transferred or sold in
accordance with the terms of the Plan, duly  authorized,  legally issued,  fully
paid and  nonassessable  so long as the  issuance  or sale of any  newly  issued
Common  Shares,  or the  transfer or sale of any Common  Shares held as treasury
shares, is duly authorized by the Company's Board of Directors prior to any such
issuance, transfer or sale.

           We hereby  consent to the filing of this  opinion as Exhibit 5 to the
Registration  Statement  on Form S-8 and to the  reference to our firm under the
caption "Legal Matters" in the prospectus  which is a part of such  Registration
Statement.

                                                 Very truly yours,



                                                 Baker & Hostetler LLP