HCC INSURANCE HOLDINGS INC/DE/
S-8, 1996-10-18
FIRE, MARINE & CASUALTY INSURANCE
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<PAGE>

 As filed with the Securities and Exchange Commission on October 18, 1996
                                                Registration No. 333-___________
                                                                                

                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C.  20549

                                    FORM S-8
                             REGISTRATION STATEMENT
                        UNDER THE SECURITIES ACT OF 1933

                          HCC INSURANCE HOLDINGS, INC.
             (Exact name of registrant as specified in its charter)

      DELAWARE                               76-0336636
(State of Incorporation)             (I.R.S. Employer Identification No.)

                 13403 NORTHWEST FREEWAY, HOUSTON, TEXAS  77040
              (Address of principal executive offices)  (zip code)

                          HCC INSURANCE HOLDINGS, INC.
                          1995 FLEXIBLE INCENTIVE PLAN
                            (Full title of the plan)

                                            Copies of All Communications to:

       Frank J. Bramanti                           Arthur S. Berner
   13403 Northwest Freeway                  Winstead Sechrest & Minick P.C.
    Houston, Texas  77040                         910 Travis Street
       (713) 462-1000                            Houston, Texas 77002
(Name and address and telephone                     (713) 650-2729
 number, including area code,
   of agent for service)
                                                         
                         CALCULATION OF REGISTRATION FEE

<TABLE>
<CAPTION>
- --------------------------------------------------------------------------------------------------------
                                                    Proposed          Proposed
      Title of                  Amount              Maximum            Maximum           Amount of
     Securities                 Being             Offering Price      Aggregate         Registration 
  Being Registered           Registered(1)         Per Share(2)    Offering Price(2)        Fee
<S>                          <C>                   <C>             <C>                      <C>
- --------------------------------------------------------------------------------------------------------
 Common Stock, $1.00
 par value per share        1,250,000 Shares         $27 1/16       $33,828,125 (1)     $11,664.87
- --------------------------------------------------------------------------------------------------------
</TABLE>
(1)  Pursuant to Rule 416 under the Securities Act of 1933, and amended, this
     registration statement also covers an indeterminate number of shares as may
     be required to cover possible adjustments under the Plan by reason of any
     stock dividend, stock split, share combination, exchange of shares,
     recapitalization, merger, consolidation, separate reorganization or the
     like of or by the Registrant.

(2)  Estimated solely for the purposes of calculating the registration fee
     pursuant to Rule 457(h), based on the average of the high and low prices of
     the Common Stock of the Registrant on the New York Stock Exchange on
     October 16, 1996. 

<PAGE>

     The contents of the Registrant's Registration Statement on Form S-8 
(Registration No. 33-94468) are incorporated herein by reference.

                                     PART II

INFORMATION REQUIRED IN THE REGISTRATION STATEMENT

ITEM 3.  INCORPORATION OF DOCUMENTS BY REFERENCE.

     The following documents (as filed with the Securities and Exchange 
Commission (the "Commission") by the Registrant) are incorporated by 
reference in this Registration Statement:

     (a)  The Registrant's Annual Report on Form 10-K for the fiscal year 
ended December 31, 1995.

     (b)  The Registrant's Quarterly Report on Form 10-Q for the quarter 
ended March 31, 1996.

     (c)  The Registrant's Quarterly Report on Form 10-Q for the quarter 
ended June 30, 1996.

     (d)  The Registrant's current report on Form 8-K dated January 8, 1996.

     (e)  The Registrant's current report on Form 8-K dated April 19, 1996.

     (f)  The Registrant's current report on Form 8-K dated May 24, 1996.

     (g)  All other reports filed by the Registrant pursuant to Section 13(a) 
or 15(d) of the Securities Exchange Act of 1934, as amended (the "Exchange 
Act"), since December 31, 1995.

ITEM 8.  EXHIBITS.

    EXHIBIT NUMBER                           DESCRIPTION    

         4.1           Restated Certificate of Incorporation of  the Registrant,
                       filed with  the Delaware Secretary  of State on  July 23,
                       1996 - filed herewith.

         5             Opinion  of Winstead  Sechrest &  Minick P.C.  as to  the
                       legality of  the  securities  being  registered  -  filed
                       herewith.  

        23.1           Consent  of   Coopers  &  Lybrand,  L.L.P.,   independent
                       certified public accountants - filed herewith.

        23.2           Consent of Winstead  Sechrest & Minick P.C. (included  in
                       the  opinion  filed as  Exhibit 5  to  this  Registration
                       Statement).

        24             Powers of Attorney - filed herewith.

<PAGE>
                                   SIGNATURES

     Pursuant to the requirements of the Securities Act, the Registrant 
certifies that it has reasonable grounds to believe that it meets all of the 
requirements for filing on Form S-8 and has duly caused this Registration 
Statement to be signed on its behalf by the undersigned thereunto duly 
authorized in the City of Houston, State of Texas, on the 9th day of October, 
1996.

                               HCC INSURANCE HOLDINGS, INC.



                                         /S/ STEPHEN L. WAY          *
                                         ---------------------------------
                                         By:  Stephen L. Way
                                              Chairman of the Board and 
                                              Chief Executive Officer

Pursuant to the Securities Act, this Registration Statement has been signed 
below by the following persons in the capacities and on the dates indicated.

SIGNATURE                              TITLE                       DATE
- ---------                              -----                       ----
/S/  STEPHEN L. WAY           Chairman of the Board           October 9, 1996
- -------------------------     and Chief Executive Officer   
Stephen L. Way                (Principal Executive Officer)
 
/S/ STEPHEN J. LOCKWOOD*      President and Director          October 9, 1996
- -------------------------
Stephen J. Lockwood

/S/ FRANK J. BRAMANTI         Executive Vice President,       October 9, 1996
- -------------------------     Secretary and Chief   
 Frank J. Bramanti            Financial Officer
                              (Principal Financial
                              Officer and
                              Principal Accounting
                              Officer)

/S/ JAMES M. BERRY*           Director                        October 9, 1996
- --------------------------
James M. Berry                                   


/S/ PATRICK B. COLLINS*       Director                        October 9, 1996
- --------------------------                
Patrick B. Collins


/S/ J. ROBERT DICKERSON*      Director                        October 9,  1996
- --------------------------                                       
J. Robert Dickerson

                                         2
<PAGE>

/S/ EDWIN H. FRANK            Director                        October 9, 1996
- -------------------------                                             
Edwin H. Frank III


/S/ JOHN L. KAVANAUGH*        Director                        October 9, 1996
- -------------------------                                        
John L. Kavanaugh


/S/ WALTER J. LACK*            Director                       October 9, 1996
- -------------------------
Walter J. Lack                                   


/S/ HUGH T. WILSON*            Director                       October 9,  1996
- -------------------------
Hugh T. Wilson                                  


*By:/S/ FRANK J. BRAMANTI                                     October 9, 1996
    ---------------------
    Frank J. Bramanti
    Attorney-in-Fact

                                              3


<PAGE>
                                                                   EXHIBIT 4.1


                                    RESTATED 
                          CERTIFICATE OF INCORPORATION
                                       OF
                          HCC INSURANCE HOLDINGS, INC.


HCC INSURANCE HOLDINGS, INC., a corporation organized and existing under the 
laws of the State of Delaware (the "Corporation") hereby certifies as follows:

     1. The name of the Corporation is HCC INSURANCE HOLDINGS, INC. which was 
originally incorporated under the name HCC Holdings, Inc., and the original 
Certificate of Incorporation was filed with the Secretary of  State of the 
State of Delaware on March 27, 1991. 

     2. Pursuant to Section 245 of the General Corporation Law of the State 
of Delaware, this Restated Certificate is duly adopted by the Board of 
Directors without a vote of the shareholders.  This Restated Certificate of 
Incorporation only restates and integrates and does not further amend the 
provisions of the Corporation's Certificate of Incorporation, as theretofore 
amended or supplemented, and there is no discrepancy between those provisions 
and the provisions of the Restated Certificate of Incorporation.  

     3. The text of the Restated Certificate of Incorporation is hereby 
restated and integrated to read in its entirety as follows:

                                    ARTICLE I

     The name of the Corporation is HCC INSURANCE HOLDINGS, INC.

                                   ARTICLE II

     The address of its registered office in the State of Delaware is 
Corporation Trust Center, 1209 Orange Street, in the City of Wilmington, 
County of New Castle.  The name of its registered agent at such address is 
The Corporation Trust Company.

                                   ARTICLE III

     The nature of the business or purposes to be conducted or promoted is to 
engage in any lawful act or activity for which corporations may be organized 
under the General Corporation Law of Delaware.

<PAGE>

                                   ARTICLE IV

     The total number of shares of all classes of stock which the Corporation 
shall be authorized to issue is one hundred million (100,000,000) shares of 
common stock, of the par value $1.00 per share ("Common Stock").

(a)  VOTING RIGHTS.  
     
     (1) COMMON STOCK.   Except as set forth herein or as otherwise required 
by law, each outstanding share of Common Stock shall be entitled to vote on 
each matter on which the shareholders of the Corporation shall be entitled to 
vote, and each holder of Common Stock shall be entitled to one vote for each 
share of such stock held by such holder.

(b)  DIVIDENDS.  The Board of Directors of the Corporation may cause 
dividends to be paid to holders of shares of Capital Stock out of funds 
legally available for the payment of dividends.

(c)  LIQUIDATION.  In the event of any voluntary or involuntary liquidation, 
dissolution or winding up of the Corporation, all distributions on the Common 
Stock of the Corporation shall be payable to the holders of shares of Common 
Stock.

                                    ARTICLE V

     No shareholder of the Corporation shall have the right of cumulative 
voting at any election of directors or upon any other matter.  No holder of 
securities of the Corporation shall be entitled as a matter of right, 
preemptive or otherwise, to subscribe for or purchase any securities of the 
Corporation now or hereafter authorized to be issued, or securities held in 
the treasury of the Corporation, whether issued or sold for cash or other 
consideration or as dividend or otherwise.  Any such securities may be issued 
or disposed of by the Board of Directors to such persons on such terms as in 
its discretion it shall deem applicable.

                                   ARTICLE VI     

     The Corporation is to have perpetual existence.

                                   ARTICLE VII

     The Board of Directors of the Corporation is expressly authorized to 
make, alter, or repeal the by-laws of the Corporation.  Elections of 
directors need not be written by ballot.

                                  ARTICLE VIII

     The Corporation reserves the right to amend, alter, change, or repeal 
any provision contained in this Certificate of Incorporation, in the manner 
now or hereafter prescribed by statute, and all rights conferred upon 
shareholders herein are granted subject to this reservation.

                                       2
<PAGE>

                                   ARTICLE IX

(a)  ACTIONS NOT BY OR IN THE RIGHT OF THE CORPORATION.  The Corporation 
shall indemnify its officers and directors and may indemnify its other 
employees or agents to the fullest extent permitted by law if any such person 
was or is a party, or is threatened to be made a party, to any threatened, 
pending, or completed action, suit, or proceeding, whether civil, criminal, 
administrative, arbitrative, or investigative (other than an action by or in 
the right of the corporation ), by reason of the fact that he is or was a 
director, officer, employee, or agent of the corporation, or is or was 
serving at the request of the Corporation as a director, officer, employee, 
or agent of another Corporation, partnership, joint venture, trust, or other 
enterprise, to the fullest extent authorized or permitted by the General 
Corporation Law of Delaware and any other applicable law, as the same exists 
or may hereafter be amended (but, in the case of any such amendment, only to 
the extent that such amendment permits the Corporation to provide broader 
indemnification rights than said law permitted the corporation to provide 
prior to such amendment), against expenses (including attorneys' fees), 
judgments, fines, and amounts paid in settlement actually and reasonably 
incurred by him in connection with such action, suit, or proceeding if he 
acted in good faith and in a manner he reasonably believed to be in or not 
opposed to the best interests of the Corporation, and, with respect to any 
criminal action or proceeding, had no reasonable cause to believe his conduct 
was unlawful.

(b)  ACTION BY OR IN THE RIGHT OF THE CORPORATION.  The Corporation shall 
indemnify its officers and directors and may indemnify its other employees or 
agents to the fullest extent permitted by law if any such person was or is a 
party, or is threatened to be made a party, to any threatened, pending, or 
completed action or suit by or in the right of the Corporation to procure a 
judgment in its favor by reason of the fact that he is or was a director, 
officer, employee, or agent of the Corporation or is or was serving at the 
request of the Corporation as a director, officer, employee, or agent of 
another corporation, partnership, joint venture, trust, or other enterprise, 
to the fullest extent authorized or permitted by the General Corporation Law 
of Delaware and any other applicable law, as the same exists or may hereafter 
be amended (but, in the case of any such amendment, only to the extent that 
such amendment permits the Corporation to provide broader indemnification 
rights than said law permitted the Corporation to provide prior to such 
amendment), against expenses (including attorneys' fees) actually and 
reasonably incurred by him in connection with the defense or settlement of 
such action or suit if he acted in good faith and in a manner he reasonably 
believed to be in or not opposed to the best interest of the Corporation.  
Notwithstanding the foregoing, no indemnification shall be made in respect of 
any claim, issue, or matter as to which such person shall have been adjudged 
to be liable to the Corporation unless and only to the extent that the Court 
of Chancery or the court in which such action or suit was brought shall 
determine upon application that, despite the adjudication of liability but in 
view of the circumstances of the case, such person is fairly and reasonably 
entitled to indemnity for such expenses which the Court of Chancery or such 
other court shall deem proper.

                                     3
<PAGE>

(c)  EXPENSES ALLOWED.  Expenses incurred by an officer or director in 
defending a civil or criminal action, suit, or proceeding shall be paid by 
the Corporation in advance of the final disposition of such action, suit, or 
proceeding upon receipt of an undertaking by or on behalf of such director or 
officer to repay such amount if it shall ultimately be determined that he is 
not entitled to be indemnified by the Corporation as authorized herein or 
otherwise.  Such expense incurred by other employees and agents may be so 
paid upon such terms and conditions, if any, as the Board of Directors deems 
appropriate.

(d)  NOT EXCLUSIVE.  Such right of indemnification shall not be deemed 
exclusive of any other rights to which such person may be entitled under any 
by-law, agreement, vote of stockholders, or otherwise.

                                    ARTICLE X

      No director of the Corporation shall be personally liable to the 
Corporation or any of its shareholders for monetary damages for breach of 
fiduciary duty or as a director, provided however, that the limitation of 
liability contained in this Article X shall not eliminate or limit the 
liability of a director:

     (1)  For any breach of the director's duty of loyalty to the Corporation or
          its shareholders;
     (2)  For acts or omissions not in good faith or which involve intentional
          misconduct or a knowing violation of law;
     (3)  Under Section 174 of the General Corporation Law of Delaware; or
     (4)  For any transaction from which the director derived an improper
          personal benefit.

     If the General Corporation Law of Delaware is amended to authorize 
corporate action further eliminating or limiting the personal liability of 
directors, then the personal liability of a director of the Corporation shall 
be eliminated or limited to the fullest extent permitted by the General 
Corporation Law of Delaware, as so amended.  Any repeal or modification of 
the provisions of this Article X by the shareholders of the Corporation shall 
not adversely affect any right or protection of a director of the Corporation 
existing at the time of such repeal or modification.

IN WITNESS WHEREOF, this Restated Certificate of Incorporation has been 
executed this 17th day of June, 1996 by Frank J. Bramanti, the Corporation's 
authorized officer.

                                   /S/ FRANK J. BRAMANTI                        
                                   ------------------------------
                                   Frank J. Bramanti, Secretary

                                         4

<PAGE>
                                                                   EXHIBIT 5

                    [LETTERHEAD OF WINSTEAD SECHREST & MINICK
                                  APPEARS HERE]





                                                                                

                                October 18, 1996



HCC Insurance Holdings, Inc.
13403 Northwest Freeway
Houston, Texas 77040

 Gentlemen:

     You have requested our opinion as to the legality of the securities of 
HCC Insurance Holdings, Inc. (the "Company") being registered on Form S-8 
(the "Registration Statement") to be filed by the Company with the Securities 
and Exchange Commission pursuant to the Securities Act of 1933, as amended, 
in connection with the HCC Insurance Holdings, Inc. 1995 Flexible Incentive 
Plan, as amended (the "Plan").  You have also requested our opinion as to 
whether such securities will, when sold, be legally issued, fully paid, and 
nonassessable. The securities to be registered in the Registration Statement 
and issued pursuant to the Plan will be up to 2,500,000 shares (the "Shares") 
of Common Stock, $1.00 par value per share, of the Company ("Common Stock"), 
which may be treasury shares or authorized but unissued shares.

     We have examined copies of the Restated Certificate of Incorporation and 
Bylaws of the Company and of the resolutions adopted by shareholders of the 
Company in connection with the adoption of the Plan and the amendments 
thereto. We have also examined such other corporate records and documents, 
certificates of corporate officers, and statutes as we have deemed necessary 
for purposes of this opinion.

     In such examination, we have assumed the genuineness of all signatures, 
the authenticity of all corporate records, documents and instruments 
submitted to us as originals, the conformity to original documents of all 
documents submitted to us as conformed, certified or photostatic copies 
thereof, and the authenticity of the originals of such photostatic, certified 
or conformed copies.  We have assumed compliance both in the past and in the 
future with the terms of the Plan by the Company and its employees, officers, 
and Board of Directors, and that all statements in all certificates of 
officers of the Company submitted are true and correct.  

     Based upon the foregoing and in reliance thereon, we are of the opinion 
that the Shares when issued or sold pursuant to and in accordance with the 
terms of the Plan will be validly issued, fully paid and nonassessable shares 
of Common Stock.

<PAGE>

HCC Insurance Holdings, Inc.
October 18, 1996
Page 2


     We know that we are named in the Registration Statement, and we hereby 
consent to the use of our name in the Registration Statement and to the 
filing of this opinion as Exhibit 5 to the Registration Statement.

                              Very truly yours,

                              WINSTEAD SECHREST & MINICK P.C.



                              By: /S/ ARTHUR S. BERNER 
                                 ---------------------------
                                  Arthur S. Berner




<PAGE>
                                                                    EXHIBIT 23.1

                       CONSENT OF INDEPENDENT ACCOUNTANTS

     We consent to the incorporation by reference in this Registration Statement
of our reports dated March 27, 1996 on our audits of the consolidated financial
statements and financial statement schedules of HCC Insurance Holdings, Inc. and
Subsidiaries as of December 31, 1995 and 1994 and for the years ended
December 31, 1995, 1994 and 1993, included in the annual report on Form 10-K.




                                   /S/ COOPERS & LYBRAND, L.L.P.


Houston, Texas
October 18, 1996


<PAGE>
                                                                      EXHIBIT 24

                                POWER OF ATTORNEY



     KNOW ALL MEN BY THESE PRESENTS, that the undersigned constitutes and
appoints STEPHEN L. WAY and FRANK J. BRAMANTI, 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 HCC Holdings, Inc. 1995
Flexible Incentive 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 attorneys-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 attorneys-in-fact and
agents, or any of them, whether substitute or substitutes, may lawfully do or
cause to be done by virtue hereof.



                              /S/ STEPHEN L. WAY
                              -------------------------------
<PAGE>
                                                                      EXHIBIT 24

                                POWER OF ATTORNEY



     KNOW ALL MEN BY THESE PRESENTS, that the undersigned constitutes and
appoints STEPHEN L. WAY and FRANK J. BRAMANTI, 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 HCC Holdings, Inc. 1995
Flexible Incentive 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 attorneys-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 attorneys-in-fact and
agents, or any of them, whether substitute or substitutes, may lawfully do or
cause to be done by virtue hereof.



                              /S/ STEPHEN L. LOCKWOOD                           
                              -------------------------------
<PAGE>
 
                                                                      EXHIBIT 24

                                POWER OF ATTORNEY



     KNOW ALL MEN BY THESE PRESENTS, that the undersigned constitutes and
appoints STEPHEN L. WAY and FRANK J. BRAMANTI, 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 HCC Holdings, Inc. 1995
Flexible Incentive 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 attorneys-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 attorneys-in-fact and
agents, or any of them, whether substitute or substitutes, may lawfully do or
cause to be done by virtue hereof.



                              /S/ JAMES M. BERRY 
                              -------------------------------
<PAGE>

                                                                      EXHIBIT 24

                                POWER OF ATTORNEY



     KNOW ALL MEN BY THESE PRESENTS, that the undersigned constitutes and
appoints STEPHEN L. WAY and FRANK J. BRAMANTI, 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 HCC Holdings, Inc. 1995
Flexible Incentive 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 attorneys-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 attorneys-in-fact and
agents, or any of them, whether substitute or substitutes, may lawfully do or
cause to be done by virtue hereof.



                              /S/ PATRICK B. COLLINS                            
                              -------------------------------
<PAGE>

                                                                      EXHIBIT 24

                                POWER OF ATTORNEY



     KNOW ALL MEN BY THESE PRESENTS, that the undersigned constitutes and
appoints STEPHEN L. WAY and FRANK J. BRAMANTI, 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 HCC Holdings, Inc. 1995
Flexible Incentive 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 attorneys-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 attorneys-in-fact and
agents, or any of them, whether substitute or substitutes, may lawfully do or
cause to be done by virtue hereof.



                              /S/ J. ROBERT DICKERSON                           
                              -------------------------------
<PAGE>

                                                                      EXHIBIT 24

                                POWER OF ATTORNEY



     KNOW ALL MEN BY THESE PRESENTS, that the undersigned constitutes and
appoints STEPHEN L. WAY and FRANK J. BRAMANTI, 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 HCC Holdings, Inc. 1995
Flexible Incentive 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 attorneys-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 attorneys-in-fact and
agents, or any of them, whether substitute or substitutes, may lawfully do or
cause to be done by virtue hereof.



                              /S/ EDWIN H. FRANK, III                           
                              -------------------------------
<PAGE>
 
                                                                      EXHIBIT 24

                                POWER OF ATTORNEY



     KNOW ALL MEN BY THESE PRESENTS, that the undersigned constitutes and
appoints STEPHEN L. WAY and FRANK J. BRAMANTI, 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 HCC Holdings, Inc. 1995
Flexible Incentive 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 attorneys-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 attorneys-in-fact and
agents, or any of them, whether substitute or substitutes, may lawfully do or
cause to be done by virtue hereof.



                              /S/ JOHN L. KAVANAUGH                             
                              -------------------------------
<PAGE>
 
                                                                      EXHIBIT 24

                                POWER OF ATTORNEY



     KNOW ALL MEN BY THESE PRESENTS, that the undersigned constitutes and
appoints STEPHEN L. WAY and FRANK J. BRAMANTI, 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 HCC Holdings, Inc. 1995
Flexible Incentive 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 attorneys-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 attorneys-in-fact and
agents, or any of them, whether substitute or substitutes, may lawfully do or
cause to be done by virtue hereof.



                              /S/ WALTER J. LACK                                
                              -------------------------------
<PAGE>
 
                                                                      EXHIBIT 24

                                POWER OF ATTORNEY



     KNOW ALL MEN BY THESE PRESENTS, that the undersigned constitutes and
appoints STEPHEN L. WAY and FRANK J. BRAMANTI, 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 HCC Holdings, Inc. 1995
Flexible Incentive 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 attorneys-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 attorneys-in-fact and
agents, or any of them, whether substitute or substitutes, may lawfully do or
cause to be done by virtue hereof.



                              /S/ HUGH T. WILSON                                
                              -------------------------------

 


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