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                                                                    Exhibit 31.1

                  CERTIFICATION OF PRINCIPAL EXECUTIVE OFFICER
                        PURSUANT TO RULE 13a-14(a) OF THE
                       SECURITIES AND EXCHANGE ACT OF 1934

      I, John W. Hayden, the principal executive officer of The Midland Company,
certify that:

      1.    I have reviewed this quarterly report on Form 10-Q of The Midland
Company;

      2.    Based on my knowledge, this report does not contain any untrue
statement of a material fact or omit to state a material fact necessary to make
the statements made, in light of the circumstances under which such statements
were made, not misleading with respect to the period covered by this report;

      3.    Based on my knowledge, the financial statements, and other financial
information included in this report, fairly present in all material respects the
financial condition, results of operations and cash flows of the registrant as
of, and for, the periods presented in this report;

      4.    The registrant's other certifying officer(s) and I are responsible
for establishing and maintaining disclosure controls and procedures (as defined
in Exchange Act Rules 13a-15(e) and 15d-15(e)) for the registrant and have:

            (a)   designed such disclosure controls and procedures, or caused
      such disclosure controls and procedures to be designed under our
      supervision, to ensure that material information relating to the
      registrant, including its consolidated subsidiaries, is made known to us
      by others within those entities, particularly during the period in which
      this report is being prepared;

            (b)   evaluated the effectiveness of the registrant's disclosure
      controls and procedures and presented in this report our conclusions about
      the effectiveness of the disclosure controls and procedures, as of the end
      of the period covered by this report based on such evaluation; and

            (c)   disclosed in this report any change in the registrant's
      internal control over financial reporting that occurred during the
      registrant's most recent fiscal quarter that has materially affected, or
      is reasonably likely to materially affect, the registrant's internal
      control over financial reporting; and

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      5.    The registrant's other certifying officer(s) and I have disclosed,
based on our most recent evaluation of internal control over financial
reporting, to the registrant's auditors and the audit committee of registrant's
board of directors (or persons performing the equivalent functions):

            (a)   All significant deficiencies and material weaknesses in the
      design or operation of internal control over financial reporting which are
      reasonably likely to adversely affect the registrant's ability to record,
      process, summarize and report financial information; and

            (b)   Any fraud, whether or not material, that involves management
      or other employees who have a significant role in the registrant's
      internal control over financial reporting.

Date: May 5, 2004

                                      /s/John W. Hayden
                                      -----------------------------------
                                      Principal Executive Officer