HCC INSURANCE HOLDINGS INC/DE/
S-8, 1998-08-17
FIRE, MARINE & CASUALTY INSURANCE
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<PAGE>

  As filed with the Securities and Exchange Commission on August 17, 1998,
                                             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.
                     1996 NONEMPLOYEE DIRECTOR STOCK OPTION PLAN
                               AS RESTATED AND AMENDED 
                               (Full title of the plan)

                                                Copies of All Communications to:

  CHRISTOPHER L. MARTIN, VICE PRESIDENT              ARTHUR S. BERNER, ESQ.
          AND GENERAL COUNSEL                   WINSTEAD SECHREST & MINICK P.C.
        13403 NORTHWEST FREEWAY                   910 TRAVIS STREET, STE 2400
          HOUSTON, TEXAS  77040                       HOUSTON, TEXAS 77002
            (713) 462-1000                                (713) 650-2729
    (Name and address and telephone                                  
     number, including area code,
       of agent for service)
<TABLE>
- -----------------------------------------------------------------------------------------------
                           CALCULATION OF REGISTRATION FEE
- -----------------------------------------------------------------------------------------------
                                                                 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      200,000 Shares (3)       $20            $4,000,000         $1,180
- -----------------------------------------------------------------------------------------------
</TABLE>

(1)  Pursuant to Rule 416 under the Securities Act of 1933, as 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 August
     13, 1998.

(3)  These shares represent the additional shares which were added to the Plan
     pursuant to an amendment which was adopted by the shareholders on May 21,
     1998.
<PAGE>

     The contents of the registration statement on Form S-8, Registration No.
333-14479, as filed on October 18, 1996, are incorporated herein by reference
and shall continue in full force and effect.  This registration statement on
Form S-8 (the "Registration Statement") is being filed for the purpose of
increasing the number of shares of Common Stock for which options may be granted
under the 1996 Nonemployee Director Stock Option Plan as Restated and Amended
(the "Plan") from 250,000 to 450,000, to refile Exhibit 4.1, the Restated
Certificate of Incorporation to include the Certificate of Amendment of
Certificate of Incorporation of the Registrant, and to refile Exhibit 4.4, the
Plan.

                                       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, 1997 and the Quarterly Reports on Form 10-Q for the periods ended
March 31, 1998 and June 30, 1998.

     (b)  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, 1997.

     (c)  The description of the Common Stock contained in the Registrant's
Prospectus filed with the Commission on September 3, 1993 as part of the
Registrant's Registration Statement on Form S-1 (Registration No. 33-67342).

     (d)  All documents subsequently filed by the Registrant pursuant to
Sections 13(a), 13(c), 14, and 15(d) of the Exchange Act prior to the filing of
a post-effective amendment which indicates that all securities offered have been
sold or which deregisters all securities then remaining unsold, shall be deemed
to be incorporated by reference in this Registration Statement and to be part
hereof from the date of filing of such documents.

ITEM 8.  EXHIBITS.

<TABLE>
EXHIBIT NUMBER      DESCRIPTION
<S>                 <C>
     4.1            Restated Certificate of Incorporation and Certificate of
                    Amendment of Certificate of Incorporation of the Registrant,
                    filed with the Delaware Secretary of State on July 23, 1996
                    and May 21, 1998, respectively - filed herewith.

     4.4            HCC Insurance Holdings, Inc. 1996 Nonemployee Director Stock
                    Option Plan as Restated and Amended- filed herewith.   

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

                                         2
<PAGE>

<TABLE>
EXHIBIT NUMBER      DESCRIPTION
<S>                 <C>
     23.1           Consent of PricewaterhouseCoopers LLP, independent certified
                    public accountants - filed herewith.

     23.2           Consent of KPMG Peat Marwick LLP, independent certified
                    public accountants - filed herewith.

     23.3           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.
</TABLE>

                               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 17th day of August,
1998.


                                       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.

<TABLE>
SIGNATURE                             TITLE                           DATE
- ---------                             -----                           ----
<S>                        <C>                                   <C>

/s/ STEPHEN L. WAY      *  Chairman of the Board and             August 17, 1998
- -------------------------  Chief Executive Officer 
Stephen L. Way             (Principal Executive Officer)
                           

/s/ JAMES M. BERRY      *  Director                              August 17, 1998
- -------------------------
James M. Berry

/s/ FRANK J. BRAMANTI      Executive Vice President and          August 17, 1998
- -------------------------  Director
Frank J. Bramanti          



                                        3
<PAGE>


/s/ PATRICK B. COLLINS  *  Director                              August 17, 1998
- -------------------------
Patrick B. Collins

/s/ ROBERT DICKERSON    *  Director                              August 17, 1998
- -------------------------
J. Robert Dickerson

/s/ EDWARD H. ELLIS, JR.*  Senior Vice President and             August 17, 1998
- -------------------------  Chief Financial Officer 
Edward H. Ellis, Jr.       (Chief Accounting Officer)

/s/ EDWIN H. FRANK, III *  Director                              August 17, 1998
- -------------------------
Edwin H. Frank, III

/s/ ALAN W. FULKERSON   *  Director                              August 17, 1998
- -------------------------
Alan W. Fulkerson

/s/ WALTER J. LACK      *  Director                              August 17, 1998
- -------------------------
Walter J. Lack

/s/ STEPHEN J. LOCKWOOD *  Director and Vice Chairman            August 17, 1998
- -------------------------
Stephen J. Lockwood

/s/ JOHN N. MOLBECK, JR.*  President and Director                August 17, 1998
- -------------------------
John N. Molbeck, Jr.

/s/ PETER B. SMITH, JR. *  Executive Vice President and          August 17, 1998
- -------------------------  Director
Peter B. Smith, Jr.        

/s/ HUGH T. WILSON*        Director                              August 17, 1998
- -------------------------
Hugh T. Wilson


*By: /s/ FRANK J. BRAMANTI  
     --------------------------
     Frank J. Bramanti
     Attorney-in-Fact
</TABLE>

                                         4

<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.

<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.

(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 

<PAGE>

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

<PAGE>


                                                                   Exhibit 4.1
                          CERTIFICATE OF AMENDMENT
                                     OF
                        CERTIFICATE OF INCORPORATION
                                     OF
                        HCC INSURANCE HOLDINGS, INC.



     Pursuant to Section 242 of the Delaware General Corporation Law, HCC 
Insurance Holdings, Inc., a corporation organized and existing under and by 
virtue of the General Corporation Law of the State of Delaware (the " 
Corporation"), does hereby certify:

     FIRST:   The Certificate of Incorporation of the Corporation is hereby 
amended by deleting and replacing the first paragraph of Article Four of the 
Certificate of Incorporation.  The new first paragraph of Article Four shall 
read as follows:

                                 "ARTICLE IV

     The total number of shares of all classes of stock which the Corporation 
shall be authorized to issue is two hundred fifty million (250,000,000) 
shares of common stock, of the par value $1.00 per share ("Common Stock")."

     SECOND:   This amendment to the Certificate of Incorporation has been 
duly adopted in accordance with the provisions of Section 242 of the Delaware 
General Corporation Law.

     IN WITNESS WHEREOF, the Corporation has caused this certificate to be 
signed by Christopher L. Martin, its authorized officer, this 21st day of 
May, 1998.

                              
                              HCC INSURANCE HOLDINGS, INC.



                              By:   /s/ CHRISTOPHER L. MARTIN
                                    ---------------------------------------
                                    Christopher L. Martin, Secretary




<PAGE>

                                                                    Exhibit 4.4

                             HCC INSURANCE HOLDINGS, INC.
                     1996 NONEMPLOYEE DIRECTOR STOCK OPTION PLAN
                               AS RESTATED AND AMENDED

1.  PURPOSE

     The HCC INSURANCE HOLDINGS, INC. 1996 NONEMPLOYEE DIRECTOR STOCK OPTION 
PLAN (the "1996 Directors' Plan") is intended to promote the interest of HCC 
Insurance Holdings, Inc., a Delaware corporation (the "Company"), and its 
Shareholders by helping to award and retain highly-qualified independent 
directors, and allowing them to develop a sense of proprietorship and 
personal involvement in the development and financial success of the Company. 
Accordingly, the Company shall grant to members of the Board of Directors 
(the "Board") of the Company who are not employees of the Company or any of 
its subsidiaries ("Nonemployee Directors") the option ("Option") to purchase 
shares of the common stock of the Company ("Stock"), as hereinafter set 
forth. Options granted under the 1996 Director Plans' shall be options which 
do not constitute incentive stock options, within the meaning of Section 
422(b) of the Internal Revenue Code of 1986, as amended. 
 
2.  OPTION AGREEMENTS
 
     Each Option shall be evidenced by a written agreement in the form 
attached to the 1996 Director Plan.
 
3.  ELIGIBILITY OF OPTIONEE
 
     Options may be granted only to individuals who are Nonemployee Directors 
of the Company. Each Nonemployee Director who was serving on the Board of 
Directors of the Company on December 14, 1995, shall receive, as of such date 
and without the exercise of the discretion of any person or persons, an 
Option exercisable for 5,000 shares of Stock. Each individual becoming a 
Nonemployee Director (a "New Member") after April 1, 1997, shall on the date 
of his first election receive an Option exercisable for 12,500 shares of 
Stock (the "New Member Grant"). Such New Member Grant shall be provided from 
this 1996 Directors' Plan or from such other stock option plan which the 
Company has in effect. Each individual who is a Nonemployee Director as of 
the date of the last regularly scheduled Board of Directors meeting to be 
held in each calendar year (the "Date of Grant") and without the exercise of 
the discretion of any person or persons, will be granted an additional Option 
exercisable for 10,000 shares of Stock (subject to adjustment in the same 
manner as provided in Paragraph 7 hereof with respect to shares of Stock 
subject to Options then outstanding). If, as of any date that the 1996 
Directors' Plan is in effect, there are not sufficient shares of Stock 
available under the 1996 Directors' Plan to allow for the grant to each 
Nonemployee Director of an Option for the number of shares provided herein, 
each Nonemployee Director shall receive an Option for a prorata share of the 
total number of shares of Stock then available under the 1996 Directors' 
Plan. All Options granted under the 1996 Directors' Plan shall be at the 
Option price set forth in Paragraph 5 hereof and shall be subject to 
adjustment as provided in Paragraph 7 hereof.

<PAGE>

4.  SHARES SUBJECT TO THE 1996 DIRECTOR PLAN

     The aggregate number of shares which may be issued under Options granted 
under the 1996 Directors' Plan shall not exceed 450,000 shares of Stock. Such 
shares may consist of authorized but unissued shares of Stock or previously 
issued shares of Stock reacquired by the Company.  Any of such shares which 
remain unissued and which are not subject to outstanding Options at the 
termination of the 1996 Directors' Plan shall cease to be subject to the 1996 
Directors' Plan, but, until termination of the 1996 Directors' Plan, the 
Company shall at all times make available a sufficient number of shares to 
meet the requirements of the 1996 Directors' Plan. Should any Option 
hereunder expire or terminate prior to its exercise in full, the shares 
theretofore subject to such Option may again be subject to an Option granted 
under the 1996 Directors' Plan. The aggregate number of shares which may be 
issued under the 1996 Directors' Plan shall be subject to adjustment in the 
same manner as provided in Paragraph 7 hereof with respect to shares of Stock 
subject to Options then outstanding. Exercise of an Option shall result in a 
decrease in the number of shares of Stock which may thereafter be available, 
both for purposes of the 1996 Directors' Plan and for sale to any one 
individual, by the number of shares as to which the Option is exercised.
 
5.  OPTION PRICE AND PERIOD
 
     The purchase price of Stock issued under each Option shall be the 
average of the closing sales price of the Company's Common Stock on the New 
York Stock Exchange ("NYSE") or, if not traded on the NYSE, any other 
securities exchange on which the Stock is traded, for, other than for a new 
Member Grant, the last ten (10) trading days of the calendar year in which 
the Option is granted and for a New Member Grant the ten (10) trading days 
immediately preceding the New Member's election to the Board of Directors. In 
the event the Stock is not publicly traded at the time a determination of the 
purchase price is required to be made hereunder, the determination of the 
purchase price shall be made by the Board in such manner as it deems 
appropriate.  

     Except as otherwise provided herein, each option and all rights or 
obligations thereunder shall expire on the tenth anniversary of the grant 
date (the "Expiration Date"), and shall be subject to earlier termination as 
hereinafter provided.
 
6.  TERM OF 1996 DIRECTOR PLAN
 
     The 1996 Directors' Plan shall be effective on the date the 1996 
Directors' Plan is approved by the Shareholders of the Company. Except with 
respect to Options then outstanding, if not sooner terminated under the 
provisions of Paragraph 7, the 1996 Directors' Plan shall terminate upon and 
no further Options shall be granted after December 31, 2001.

7.  RECAPITALIZATION OR REORGANIZATION
 
     (a) The existence of the 1996 Directors' Plan and the Options granted 
hereunder shall not affect in any way the right or power of the Board or the 
Shareholders of the Company to make or authorize any adjustment, 
recapitalization, reorganization or other change in the Company's capital 
structure or its business, any merger or consolidation of the Company, any 
issue of debt or equity 

<PAGE>

securities, the dissolution or liquidation of the Company or any sale, lease, 
exchange or other disposition of all or any part of its assets or business or 
any other corporate act or proceeding.
 
     (b) The shares with respect to which Options may be granted are shares 
of Stock as presently constituted, but if, and whenever, prior to the 
expiration of an Option theretofore granted, the Company shall effect a 
subdivision or consolidation of shares of Stock or the payment of a stock 
dividend on Stock without receipt of consideration by the Company, the number 
of shares of Stock with respect to which such Option may thereafter be 
exercised (i) in the event of an increase in the number of outstanding shares 
shall be proportionately increased, and the purchase price per share shall be 
proportionately reduced, and (ii) in the event of a reduction in the number 
of outstanding shares shall be proportionately reduced, and the purchase 
price per share shall be proportionately increased.

     (c) If the Company merges or consolidates with one or more corporations 
and the Company shall be the surviving corporation, thereafter upon any 
exercise of this Option the Grantee shall be entitled to purchase under this 
Option, in lieu of the number of shares of Stock as to which Option shall 
then be exercisable, the number and class of shares of stock and securities 
to which the Grantee would have been entitled pursuant to the terms of the 
agreement of merger or consolidation if, immediately prior to such merger or 
consolidation, the Grantee had been the holder of record of the number of 
shares of Stock as to which this Option is then exercisable.  If the Company 
shall not be the surviving corporation in any merger of consolidation, or if 
the Company is dissolved or liquidated, this Option shall expire on the 
effective date of such merger or consolidation or such dissolution or 
liquidation; provided, that nothing herein shall preclude a surviving 
corporation or other corporation into which stock of the Company may be 
converted from assuming or substituting new options for the Option granted 
hereunder, which assumption or substitution may be made without the consent 
of the holder of this Option to such assumption, substitution, merger or 
consolidation, and further provided that immediately prior to such 
expiration, the entire number of shares of Stock for which this Option may be 
exercised shall be accelerated so that Grantee shall have the opportunity to 
exercise the entire unexpired portion of this Option prior to its expiration. 
The Company agrees to give at least 30 days prior notice to Grantee of the 
effective date of any such merger, consolidation, dissolution or liquidation. 
If the Company is acquired by another entity, in any manner, so that 
following such acquisition the Company is a subsidiary of another entity, the 
Company shall be deemed to be not the surviving corporation for purposes of 
this subparagraph (c).
 
     (d) If the Company recapitalizes or otherwise changes its capital 
structure, thereafter upon any exercise of an Option theretofore granted the 
optionee shall be entitled to purchase under such Option, in lieu of the 
number and class of shares of Stock then covered by such Option, the number 
and class of shares of stock and securities to which the optionee would have 
been entitled pursuant to the terms of the recapitalization if, immediately 
prior to such recapitalization, the optionee had been the holder of record of 
the number of shares of Stock then covered by such Option.
 
     (e) Any adjustment provided for in Subparagraphs (b), (c) or (d) above 
shall be subject to any required Shareholder action.  

     (f) Except as hereinbefore expressly provided, the issuance by the 
Company of shares of 

<PAGE>

stock of any class or securities convertible into shares of stock of any 
class, for cash, property, labor or services, upon direct sale, upon the 
exercise of rights or warrants to subscribe therefor, or upon conversion of 
share or obligations of the Company convertible into such shares or other 
securities, and in any case whether or not for fair value, shall not affect, 
and no adjustment by reason thereof shall be made with respect to, the number 
of shares of Stock subject to Options theretofore granted or the purchase 
price per share.
 
8. AMENDMENT OR TERMINATION OF THE 1996 DIRECTORS' PLAN
 
     The Board in its discretion may terminate the 1996 Directors' Plan at 
any time with respect to any shares for which Options have not theretofore 
been granted. The Board shall have the right to alter or amend the 1996 
Directors' Plan or any part thereof from time to time; provided, that no 
change in any Option theretofore granted may be made which would impair the 
rights of the optionee without the consent of such optionee; and provided, 
further, that the Board may not make any alteration or amendment which would 
materially increase the benefits accruing to participants under the 1996 
Directors' Plan, increase the aggregate number of shares which may be issued 
pursuant to the provisions of the 1996 Directors' Plan, change the class of 
individuals eligible to receive Options under the 1996 Directors' Plan or 
extend the term of the 1996 Directors' Plan, without the approval of the 
Shareholders of the Company.  

9. SECURITIES LAWS
 
     (a) The Company shall not be obligated to issue any Stock pursuant to 
any Option granted under the 1996 Directors' Plan at any time when the 
offering of the shares covered by such Option have not been registered under 
the Securities Act of 1933, as amended, (the "Act") and such other state and 
federal laws, rules or regulations as the Company deems applicable and, in 
the opinion of legal counsel for the Company, there is no exemption from the 
registration requirements of such laws, rules or regulations available for 
the offering and sale of such shares.
 
     (b) It is intended that the 1996 Directors' Plan and any grant of an 
Option made to a person subject to Section 16 of the Securities Exchange Act 
of 1934, as amended (the "1934 Act"), meet all of the requirements of Rule 
16b-3, as currently in effect or as hereinafter modified or amended ("Rule 
16b-3"), promulgated under the 1934 Act. If any provision of the 1996 
Directors' Plan or any such Option would disqualify the 1996 Directors' Plan 
or such Option under, or would otherwise not comply with, Rule 16b-3, such 
provision or Option shall be construed or deemed amended to conform to Rule 
16b-3.

10.  VESTING AND EXERCISE OF OPTIONS
 
     (a)  (i)  Except as set forth herein, any Option granted hereunder shall 
be fully exercisable on the first anniversary of the Date of Grant.

          (ii) A New Member Grant shall also be fully exercisable on the 
first anniversary of the Date of Grant in the year such New Member is elected 
to the Board of Directors (without regard to the date a New Member was first 
elected to the Board of Directors).

<PAGE>

     (b) The purchase price of the Stock purchased upon exercise of an option 
shall be paid in full at the time of each exercise of an option and may be 
paid to the Company, either:
 
          (1) in cash (including a check, bank draft or money order); or 

          (2) by the delivery of Stock having a fair market value equal to the
          aggregate Option price; or
 
          (3)  by a combination of cash and Stock.
 
No options shall be exercisable except in respect of whole shares of Stock. 
Upon exercise of an option, the person exercising the option shall be 
entitled to one (1) stock certificate evidencing the shares acquired upon 
such exercise.

     (c) An option granted under the 1996 Directors' Plan shall, by its 
terms, be nontransferable by the Nonemployee Director other than by will or 
by the laws of descent and distribution. During the Nonemployee Director's 
lifetime, the option shall be exercisable only by the Nonemployee Director or 
by the Nonemployee Director's duly appointed guardian or personal 
representative.
 
     (d) If the directorship of the Nonemployee Director is terminated for 
any reason other than (i) Disability (as hereinafter defined) of the 
Nonemployee Director, (ii) death of the Nonemployee Director, or (iii) on 
account of any act of fraud or intentional misrepresentation or embezzlement, 
misappropriation or conversion of assets or opportunities of the Company, or 
cause as determined by the Board of Directors, an option (to the extent 
otherwise exercisable by the Nonemployee Director on the date of such 
termination) shall be exercisable by the Nonemployee Director at any time 
prior to the Expiration Date of the Option or within two (2) months after the 
date of such termination of the directorship, whichever is the shorter period.
 
     (e) If the Nonemployee Director's directorship is terminated by reason 
of Disability, an option (whether or not exercisable on the date of the 
Nonemployee Director's termination of directorship by reason of Disability) 
shall be exercisable by the Nonemployee Director at any time prior to the 
Expiration Date of the option or within six (6) months after the date of such 
termination, whichever is the shorter period. As used herein, the term 
"Disability" shall mean the inability to engage in any substantial gainful 
activity by reason of any medically determinable physical or mental 
impairment which can be expected to last for a continuous period of not less 
than twelve (12) months. The determination of whether or not a Nonemployee 
Director's directorship is terminated by reason of Disability shall be in the 
sole and absolute discretion of the Board. An individual shall not be 
considered Disabled unless he furnishes proof of the existence thereof in 
such form and manner, and at such times, as the Board may require.
 
     (f) If a Nonemployee Director dies while serving as a member of the 
Board or during the six-month period described in subsection (e) above, the 
option shall be exercisable (whether or not exercisable on the date of the 
death of such Nonemployee Director) by the person or persons entitled to do 
so under the Nonemployee Director's will, or, if the Nonemployee Director 
shall fail to make 

<PAGE>

testamentary disposition of said option or shall die intestate, by the 
Nonemployee Director's legal  representative or representatives, at any time 
prior to the Expiration Date of the option or within six (6) months after the 
date of such death, whichever is the shorter period. If a Nonemployee 
Director dies during the two-month period described in subsection (d) above, 
the option shall be exercisable as described above.  

     (g)  The option of a Nonemployee Director shall automatically terminate 
as of the date his directorship is terminated, if the directorship is 
terminated on account of any act of (i) fraud or intentional 
misrepresentation, or (ii) embezzlement, misappropriation or conversion of 
assets or opportunities of the Company or (iii) cause as determined by the 
Board of Directors. 
 
11.  MISCELLANEOUS
 
     (a)  Nothing contained in this 1996 Directors' Plan (nor in any option 
granted pursuant to this 1996 Directors' Plan) shall confer upon any 
Nonemployee Director any right to continue as a member of the Board or 
constitute any contract or agreement or interfere in any way with the right 
of the Company to remove such Nonemployee Director from the Board. Nothing 
contained herein or in any Option Agreement shall affect any other 
contractual rights of a Nonemployee Director.
 
     (b)  An option shall be deemed to be exercised when the Secretary of the 
Company receives written notice of such exercise from the person entitled to 
exercise the option together with payment of the purchase price made in 
accordance with this 1996 Directors' Plan.
 
     (c)  The holder of an option shall not be entitled to the privilege of 
stock ownership as to any shares of Stock not actually issued and delivered 
to the holder. Subject to the provisions of Paragraph 9 above, upon exercise 
of an option for Stock at a time when there is not in effect under the Act a 
registration statement relating to the Stock issuable upon exercise thereof 
or not available for delivery a prospectus meeting the requirements of 
Section 10 of the Act, the holder of the option shall represent and warrant 
in writing to the Company that, inter alia, the shares of Stock purchased are 
being acquired for investment and not with a view to the resale or 
distribution thereof. No shares of Stock shall be issued upon the exercise of 
any option unless and until there shall have been compliance with any then 
applicable requirements of the Securities and Exchange Commission, other 
regulatory agencies having jurisdiction and any exchanges upon which 
securities subject to the option may be listed.
 
     (d)  The 1996 Directors' Plan and the options issued hereunder shall be 
governed by, and construed and enforced in accordance with, the laws of the 
State of Delaware applicable to contracts made and performed within that 
State.  

     (e)  The proceeds received by the Company from the sale of shares 
pursuant to options shall be used for general corporate purposes.  

     (f)  The members of the Board shall not be liable for any act, omission 
or determination taken or made in good faith with respect to the 1996 
Directors' Plan or any option granted under it. 

<PAGE>

     (g)  Any payment or any issuance or transfer of shares of Stock to the 
Nonemployee Director, or to his legal representative, heir, legatee or 
distributee, in accordance with the provisions hereof, shall, to the extent 
thereof, be in full satisfaction of all claims of such persons hereunder. The 
Board may require any Nonemployee Director, legal representative, heir, 
legatee or distributee, as a condition precedent to such payment, to execute 
a release and receipt therefor in such form as it shall determine. 

     (h)  Neither the Board nor the Company guarantees the Stock of the 
Company from loss or depreciation. 
 
     (i) All expenses incident to the administration or termination of the 
1996 Directors' Plan, including, but not limited to, legal and accounting 
fees, shall be paid by the Company.

     (j)  Records of the Company regarding the Nonemployee Director's period 
of service, termination or service and the reason therefor, leaves of 
absence, and other matters shall be conclusive for all purposes hereunder, 
unless determined by the Board to be incorrect.

     (k)  The Company shall, upon request or as may be specifically required 
hereunder, furnish or cause to be furnished all of the information or 
documentation which is necessary or required by the Board to perform its 
duties and functions under the 1996 Directors' Plan.
 
     (l)  The Company assumes no obligation or responsibility to the 
Nonemployee Director or his or her personal representatives, heirs, legatees 
or distributees for any act of, or failure to act on the part of the Board. 

     (m)  Any action required of the Company shall be by resolution of the 
Board or by a person authorized to act by Board resolution.
 
     (n)  If any provision of this 1996 Directors' Plan shall be held to be 
illegal or invalid for any reason, the illegality or invalidity shall not 
affect the remaining provisions hereof, but shall be fully severable and the 
1996 Directors' Plan shall be construed and enforced as if the illegal or 
invalid provision had never been included herein.
 
     (o)  Whenever any notice is required or permitted hereunder, such notice 
must be in writing and personally delivered or sent by mail. Any notice 
required or permitted to be delivered hereunder shall be deemed to be 
delivered on the date on which it is personally delivered in accordance 
herewith. The Company or a Nonemployee Director may change, at any time and 
from time to time, by written notice to the other, the address which it or he 
had theretofore specified for receiving notices. Until it is changed in 
accordance herewith, the Company and each Nonemployee Director shall specify 
as its and his address for receiving notices the address set forth in the 
Option Agreement pertaining to the shares to which such notice relates.
 
     (p)  Any person entitled to notice hereunder may waive such notice. 
 
     (q)  The 1996 Directors' Plan shall be binding upon the Nonemployee 
Director, his or her 

<PAGE>

heirs, legatees and legal representatives, upon the Company, its successors 
and assigns and upon the Board and its successors. 
 
     (r)  The titles and headings of sections and paragraphs are included for 
convenience of reference only and are not to be considered in construction of 
the provisions hereof.
 
     (s)  Words used in the masculine shall apply to the feminine where 
applicable and, wherever the context of this 1996 Directors' Plan dictates, 
the plural shall be read as the singular and the singular as the plural.


<PAGE>

                                                                    Exhibit 5



                               August 12, 1998


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. 1996 Nonemployee Director 
Stock Option Plan as Restated and 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 450,000 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 
amendments thereto and Bylaws of the Company and of the resolutions adopted 
by the 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 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.
August 12, 1998
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 
on Form S-8 of our report dated March 26, 1998, on our audits of the 
consolidated financial statements and financial statement schedules of HCC 
Insurance Holdings, Inc. as of December 31, 1997 and 1996, and for the three 
year period ended December 31, 1997.  Our reports state that they are based 
on the reports of KPMG Peat Marwick LLP, independent certified public 
accountants with respect to their audit of the 1996 and 1995 consolidated 
financial statements and financial statement schedules of AVEMCO Corporation.


PricewaterhouseCoopers LLP

Houston, Texas
August 12, 1998

<PAGE>
                                                                   Exhibit 23.2

                            INDEPENDENT AUDITORS' CONSENT

The Board of Directors and Shareholder
AVEMCO Corporation:

We consent to incorporation by reference in this registration statement on 
Form S-8 of HCC Insurance Holdings, Inc. of our reports dated January 31, 
1997 (February 28, 1997, as to note 12 and February 18, 1998, as to note 14), 
relating to the consolidated balance sheet of AVEMCO Corporation and 
subsidiaries as of December 31, 1996, and the related consolidated statements 
of income, stockholders' equity, and cash flows for each of the years in the 
two-year period ended December 31, 1996, and all related schedules, which 
reports appear in the December 31, 1997 annual report on Form 10-K of HCC 
Insurance Holdings, Inc.


KPMG Peat Marwick LLP

Washington, D.C.
August 12, 1998

<PAGE>
                                                                    Exhibit 24

                                  POWER OF ATTORNEY


     KNOW ALL MEN BY THESE PRESENTS, that the undersigned constitutes and
appoints STEPHEN L. WAY, 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 HCC Insurance
Holdings, Inc. 1997 Flexible Incentive Plan and the Form S-8 Registration
Statement of the Registrant with respect to the HCC Insurance Holdings, Inc.
1996 Nonemployee Director Stock Option Plan as Restated and Amended, 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.




August 17, 1998                    /s/ STEPHEN L. WAY  
                                   ------------------------------------------
                                   Stephen L. Way
<PAGE>
 
                                                                    Exhibit 24

                                  POWER OF ATTORNEY


     KNOW ALL MEN BY THESE PRESENTS, that the undersigned constitutes and
appoints STEPHEN L. WAY, 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 HCC Insurance
Holdings, Inc. 1997 Flexible Incentive Plan and the Form S-8 Registration
Statement of the Registrant with respect to the HCC Insurance Holdings, Inc.
1996 Nonemployee Director Stock Option Plan as Restated and Amended, 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.



August 17, 1998                    /s/ JAMES M. BERRY  
                                   ------------------------------------------
                                   James M. Berry
<PAGE>
 
                                                                    Exhibit 24

                                  POWER OF ATTORNEY


     KNOW ALL MEN BY THESE PRESENTS, that the undersigned constitutes and
appoints STEPHEN L. WAY, 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 HCC Insurance
Holdings, Inc. 1997 Flexible Incentive Plan and the Form S-8 Registration
Statement of the Registrant with respect to the HCC Insurance Holdings, Inc.
1996 Nonemployee Director Stock Option Plan as Restated and Amended, 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.



August 17, 1998                    /s/ FRANK J. BRAMANTI 
                                   ------------------------------------------
                                   Frank J. Bramanti

<PAGE>
                                                                    Exhibit 24

                                  POWER OF ATTORNEY



     KNOW ALL MEN BY THESE PRESENTS, that the undersigned constitutes and
appoints STEPHEN L. WAY, 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 HCC Insurance
Holdings, Inc. 1997 Flexible Incentive Plan and the Form S-8 Registration
Statement of the Registrant with respect to the HCC Insurance Holdings, Inc.
1996 Nonemployee Director Stock Option Plan as Restated and Amended, 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.



August 17, 1998                    /s/ PATRICK B. COLLINS  
                                   ------------------------------------------
                                   Patrick B. Collins
<PAGE>
 
                                                                    Exhibit 24

                                  POWER OF ATTORNEY


     KNOW ALL MEN BY THESE PRESENTS, that the undersigned constitutes and
appoints STEPHEN L. WAY, 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 HCC Insurance
Holdings, Inc. 1997 Flexible Incentive Plan and the Form S-8 Registration
Statement of the Registrant with respect to the HCC Insurance Holdings, Inc.
1996 Nonemployee Director Stock Option Plan as Restated and Amended, 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.



August 17, 1998                    /s/ J. ROBERT DICKERSON    
                                   ------------------------------------------
                                   J. Robert Dickerson
<PAGE>
 
                                                                    Exhibit 24

                                  POWER OF ATTORNEY



     KNOW ALL MEN BY THESE PRESENTS, that the undersigned constitutes and
appoints STEPHEN L. WAY, 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 HCC Insurance
Holdings, Inc. 1997 Flexible Incentive Plan and the Form S-8 Registration
Statement of the Registrant with respect to the HCC Insurance Holdings, Inc.
1996 Nonemployee Director Stock Option Plan as Restated and Amended, 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.



August 17, 1998                    /s/ EDWARD H. ELLIS, JR. 
                                   ------------------------------------------
                                   Edward H. Ellis, Jr.
<PAGE>

                                                                    Exhibit 24

                                  POWER OF ATTORNEY



     KNOW ALL MEN BY THESE PRESENTS, that the undersigned constitutes and
appoints STEPHEN L. WAY, 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 HCC Insurance
Holdings, Inc. 1997 Flexible Incentive Plan and the Form S-8 Registration
Statement of the Registrant with respect to the HCC Insurance Holdings, Inc.
1996 Nonemployee Director Stock Option Plan as Restated and Amended, 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.



August 17, 1998                    /s/ EDWIN H. FRANK, III     
                                   ------------------------------------------
                                   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, 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 HCC Insurance
Holdings, Inc. 1997 Flexible Incentive Plan and the Form S-8 Registration
Statement of the Registrant with respect to the HCC Insurance Holdings, Inc.
1996 Nonemployee Director Stock Option Plan as Restated and Amended, 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.



August 17, 1998                    /s/ ALAN W. FULKERSON 
                                   ------------------------------------------
                                   Alan W. Fulkerson
<PAGE>

                                                                    Exhibit 24

                                  POWER OF ATTORNEY



     KNOW ALL MEN BY THESE PRESENTS, that the undersigned constitutes and
appoints STEPHEN L. WAY, 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 HCC Insurance
Holdings, Inc. 1997 Flexible Incentive Plan and the Form S-8 Registration
Statement of the Registrant with respect to the HCC Insurance Holdings, Inc.
1996 Nonemployee Director Stock Option Plan as Restated and Amended, 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.



August 17, 1998                    /s/ WALTER J. LACK   
                                   ------------------------------------------
                                   Walter J. Lack
<PAGE>

                                                                    Exhibit 24

                                  POWER OF ATTORNEY



     KNOW ALL MEN BY THESE PRESENTS, that the undersigned constitutes and
appoints STEPHEN L. WAY, 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 HCC Insurance
Holdings, Inc. 1997 Flexible Incentive Plan and the Form S-8 Registration
Statement of the Registrant with respect to the HCC Insurance Holdings, Inc.
1996 Nonemployee Director Stock Option Plan as Restated and Amended, 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.



August 17, 1998                    /s/ STEPHEN J. LOCKWOOD  
                                   ------------------------------------------
                                   Stephen J. Lockwood
<PAGE>

 
                                                                    Exhibit 24

                                  POWER OF ATTORNEY



     KNOW ALL MEN BY THESE PRESENTS, that the undersigned constitutes and
appoints STEPHEN L. WAY, 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 HCC Insurance
Holdings, Inc. 1997 Flexible Incentive Plan and the Form S-8 Registration
Statement of the Registrant with respect to the HCC Insurance Holdings, Inc.
1996 Nonemployee Director Stock Option Plan as Restated and Amended, 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.



August 17, 1998                    /s/ JOHN N. MOLBECK, JR.  
                                   ------------------------------------------
                                  John N. Molbeck, Jr.
<PAGE>
 
                                                                     Exhibit 24
                                  POWER OF ATTORNEY



     KNOW ALL MEN BY THESE PRESENTS, that the undersigned constitutes and
appoints STEPHEN L. WAY, 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 HCC Insurance
Holdings, Inc. 1997 Flexible Incentive Plan and the Form S-8 Registration
Statement of the Registrant with respect to the HCC Insurance Holdings, Inc.
1996 Nonemployee Director Stock Option Plan as Restated and Amended, 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.



August 17, 1998                    /s/ PETER B. SMITH, JR.  
                                   ------------------------------------------
                                   Peter B. Smith, Jr.
<PAGE>

                                                                    Exhibit 24

                                  POWER OF ATTORNEY



     KNOW ALL MEN BY THESE PRESENTS, that the undersigned constitutes and
appoints STEPHEN L. WAY, 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 HCC Insurance
Holdings, Inc. 1997 Flexible Incentive Plan and the Form S-8 Registration
Statement of the Registrant with respect to the HCC Insurance Holdings, Inc.
1996 Nonemployee Director Stock Option Plan as Restated and Amended, 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.



August 17, 1998                    /s/ HUGH T. WILSON  
                                   ------------------------------------------
                                   Hugh T. Wilson


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