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                                                                      Exhibit 24



                                POWER OF ATTORNEY

         KNOW ALL MEN BY THESE PRESENTS, that the undersigned constitutes and
appoints JOHN N. MOLBECK, JR., FRANK J. BRAMANTI and CHRISTOPHER L. MARTIN and
each of them, his true and lawful attorney-in-fact and agent with full power of
substitution and resubstitution for him and in his name, place, and stead, in
any and all capacities, to sign the Form S-8 Registration Statement of HCC
Insurance Holdings, Inc. (the "Registrant") with respect to the J.E. Stone &
Associates, Inc. Employee Savings and Profit Sharing Plan, to sign any and all
amendments to same (including post-effective amendments), and to file same, with
all exhibits thereto, and other documents in connection therewith, with the
Securities and Exchange Commission, and/or any state securities department or
any other federal or state agency or governmental authority, granting unto such
attorney-in-fact and agents, and each of them, full power and authority to do
and perform each and every act and thing requisite and necessary to be done in
and about the premises, as fully to all intents and purposes as he might or
could do in person, hereby ratifying and confirming all that such
attorney-in-fact and agents, or any of them, whether substitute or substitutes,
may lawfully do or cause to be done by virtue hereof.

September 20, 2001                               /s/ James C. Flagg
                                                 -------------------------------
                                                 James C. Flagg, Ph.D.