UNITED STATES                    --------------------------
          SECURITIES AND EXCHANGE COMMISSION                 OMB APPROVAL
                 WASHINGTON, DC 20549                --------------------------
                                                     OMB Number:      3235-0101
                      FORM 144                       Expires:   August 31, 2003
                                                     Estimated average burden
        NOTICE OF PROPOSED SALE OF SECURITIES        hours per response ... 2.0
      PURSUANT TO RULE 144 UNDER THE SECURITIES      --------------------------
                      ACT OF 1933                    --------------------------
                                                        S.E.C. USE ONLY
      ATTENTION: Transmit for filing three copies
                 of this form concurrently with      --------------------------
                 either placing an order with a      DOCUMENT SEQUENCE NO.
                 broker to execute a sale or
                 executing a sale directly           --------------------------
                 with a market maker.                CUSIP NUMBER

                                                     --------------------------
                                                     WORK LOCATION

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 1(a) NAME OF ISSUER (Please type or print)                  (b) I.R.S. IDENT. NO.    (c) S.E.C. FILE NO.
 HCC Insurance Holdings, Inc.                                    76-0336636           0-20766
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 1(d) ADDRESS OF ISSUER                   STREET           CITY           STATE           ZIP CODE             (e) TELEPHONE NO.
                                                                                                            ------------------------
                                                                                                            AREA CODE      NUMBER
 13403 Northwest Freeway                                   Houston        Texas           77040             713           690-7300
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 2(a) NAME OF PERSON FOR WHOSE ACCOUNT   (b) I.R.S. IDENT.     (c) RELATIONSHIP   (d) ADDRESS    STREET    CITY    STATE    ZIP CODE
      THE SECURITIES ARE TO BE SOLD          NO.                   TO ISSUER

      Stephen L. Way                     108-50-6087           Chairman & CEO     13403 Northwest Freeway, Houston, TX   77040
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 INSTRUCTION: The person filing this notice should contact the issuer to obtain
              THE I.R.S. Identification Number and the S.E.C. File Number.

                                                                                                
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       3(a)                            (b)                                                    (c)                  (d)
   TITLE OF THE          NAME AND ADDRESS OF EACH BROKER           S.E.C. USE ONLY     NUMBER OF SHARES         AGGREGATE
     CLASS OF         THROUGH WHOM THE SECURITIES ARE TO BE        ---------------      OR OTHER UNITS           MARKET
    SECURITIES         OFFERED OR EACH MARKET MAKER WHO IS          BROKER-DEALER         TO BE SOLD              VALUE
    TO BE SOLD               ACQUIRING THE SECURITIES                FILE NUMBER       (See instr. 3(c))    (See instr. 3(d))
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Common            Raymond James & Associates                                               400,000            $11,256,000
Stock             10 S. Riverside Plaza, Suite 1450                                                              Note 1
                  Chicago, IL 60606
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       3(a)                (e)                      (f)                    (g)
   TITLE OF THE       NUMBER OF SHARES            APPROXIMATE            NAME OF EACH
     CLASS OF          OR OTHER UNITS             DATE OF SALE            SECURITIES
    SECURITIES           OUTSTANDING           (See instr. 3(f))           EXCHANGE
    TO BE SOLD        (See instr. 3(e))         (Mo.  Day  Yr.)       (See instr. 3(g))
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                        62,004,318                 04/10/02                 NYSE
                          Note 2
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INSTRUCTIONS:
   1.  (a) Name of issuer
       (b) Issuer's I.R.S. Identification Number
       (c) Issuer's S.E.C. file number, if any
       (d) Issuer's address, including zip code
       (e) Issuer's telephone number, including area code

   2.  (a) Name of person for whose account the securities are
           to be sold
       (b) Such person's I.R.S. identification number, if such
           person is an entity
       (c) Such person's relationship to the issuer (e.g.,
           officer, director, 10 percent stockholder, or member
           of immediate family of any of the foregoing)
       (d) Such person's address, including zip code

   3.  (a) Title of the class of securities to be sold
       (b) Name and address of each broker through whom the
           securities are intended to be sold
       (c) Number of shares or other units to be sold (if debt
           securities, give the aggregate face amount)
       (d) Aggregate market value of the securities to be sold
           as of a specified date within 10 days prior to the
           filing of this notice
       (e) Number of shares or other units of the class
           outstanding, or if debt securities the face amount
           thereof outstanding, as shown by the most recent
           report or statement published by the issuer
       (f) Approximate date on which the securities are to be
           sold
       (g) Name of each securities exchange, if any, on which
           the securities are intended to be sold


POTENTIAL PERSONS WHO ARE TO RESPOND TO THE COLLECTION OF INFORMATION CONTAINED
IN THIS FORM ARE NOT REQUIRED TO RESPOND UNLESS THE FORM DISPLAYS A CURRENTLY
VALID OMB CONTROL NUMBER.

                                                                 SEC 1147(10-00)



                         TABLE I--SECURITIES TO BE SOLD
   Furnish the following information with respect to the acquisition of the
   securities to be sold and with respect to the payment of all or any part
            of the purchase price or other consideration therefor:


                                                                                               
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     Title of    Date you    Nature of Acquisition      Name of Person from      Amount of         Date of      Nature of Payment
    the Class    Acquired       Transaction             Whom Acquired            Securities        Payment
                                                        (If gift, also give      Acquired
                                                        date donor acquired)

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Common Stock    04/10/02     Exercise of Stock Options  HCC Insurance Holdings,   200,000           04/10/02         Cash
                                                        Inc.
Common Stock    Various          Original Issue         HCC Insurance Holdings,   200,000           Various          Cash
                                                        Inc.
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INSTRUCTIONS:
 1. If the securities were purchased and full payment therefor was not made in
    cash at the time of purchase, explain in the table or in a note thereto the
    nature of the consideration given. If the consideration consisted of any
    note or other obligation, or if payment was made in installments describe
    the arrangement and state when the note or other obligation was discharged
    in full or the last installment paid.

 2. If within two years after the acquisition of the securities the person for
    whose account they are to be sold had any short positions, put or other
    option to dispose of securities referred to in paragraph (d)(3) of Rule 144,
    furnish full information with respect thereto.

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              TABLE II--SECURITIES SOLD DURING THE PAST 3 MONTHS
     Furnish the following information as to all securities of the issuer
                          sold during the past three
     months by the person for whose account the securities are to be sold.

                                                                                                     
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   Name and Address of Seller             Title of Securities Sold         Date of Sale         Amount of        Gross Proceeds
                                                                                               Securities
                                                                                                  Sold

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REMARKS: Note 1: Based upon NYSE Closing Price on 04/08/02 of $28.14.
         Note 2: Shares Outstanding as of March 15, 2002.

INSTRUCTIONS:
 See the definition of "person" in paragraph (a) of Rule 144. Information is to
 be given not only as to the person for whose account the securities are to be
 sold but also as to all other persons included in that definition. In addition,
 information shall be given as to sales by all persons whose sales are required
 by paragraph (e) of Rule 144 to be aggregated with sales for the account of the
 person filing this notice.

                               April 10, 2002
                    ----------------------------------------
                                DATE OF NOTICE
ATTENTION:
 The person for whose account the securities to which this notice relates are to
 be sold hereby represents by signing this notice that he does not know any
 material adverse information in regard to the current and prospective
 operations of the Issuer of the securities to be sold which has not been
 publicly disclosed.

                              /s/ Stephen L. Way
                    ----------------------------------------
                                  (SIGNATURE)

The notice shall be signed by the person for whose account the securities are
    to be sold. At least one copy of the notice shall be manually signed.
    Any copies not manually signed shall bear typed or printed signatures.

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      ATTENTION: INTENTIONAL MISSTATEMENTS OR OMISSION OF FACTS CONSTITUTE
                    FEDERAL CRIMINAL VIOLATIONS (SEE 18 U.S.C. 1001).
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                                                                 SEC 1147(10-00)