content: <PAGE>
  <TABLE>
  <S><C>
  
                                                                                                             ------------------------
                                                               UNITED STATES                                       OMB APPROVAL
                                                     SECURITIES AND EXCHANGE COMMISSION                      ------------------------
                                                           WASHINGTON, D.C.  20549                           OMB Number:    3235-0101
                                                                                                             Expires:    May 31, 2000
                                                                                                             Estimated average burden
                                                                                                             hours per response...2.0
                                                                   FORM 144
                                                                                                             ------------------------
                                                                                                             ------------------------
                                                                                                                 SEC USE ONLY
                                                                                                             ------------------------
                                                                                                             ------------------------
                                                      NOTICE OF PROPOSED SALE OF SECURITIES                  DOCUMENT SEQUENCE NO.
                                              PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933
                                                                                                             ------------------------
                                                                                                             CUSIP NUMBER
  ATTENTION:  TRANSMIT FOR FILING 3 COPIES OF THIS FORM CONCURRENTLY WITH EITHER PLACING AN ORDER
              WITH A BROKER TO EXECUTE SALE OR EXECUTING A SALE DIRECTLY WITH A MARKET MAKER.
                                                                                                              -----------------------
  ----------------------------------------------------------------------------------------------------------  WORK LOCATION
  1(a)  NAME OF ISSUER (PLEASE TYPE OR PRINT)             (b)  IRS IDENT. NO.      (c)  S.E.C. FILE NO.
  
  HCC INSURANCE HOLDINGS, INC.                                  76-0336636                 0-20766            ------------------------
  ------------------------------------------------------------------------------------------------------------------------------------
  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
  ------------------------------------------------------------------------------------------------------------------------------------
  2(a) NAME OF PERSON FOR WHOSE ACCOUNT   (b)  IRS IDENT. NO  (c)  RELATIONSHIP   (d)  ADDRESS STREET      CITY     STATE    ZIP CODE
       THE SECURITIES ARE TO BE SOLD                               TO ISSUER
  STEPHEN J. LOCKWOOD                          ###-##-####         VICE-CHAIRMAN      27 CONGRESS STREET,  SALEM     MA        01970
                                                                                      SUITE 108
  ------------------------------------------------------------------------------------------------------------------------------------
                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.
  ------------------------------------------------------------------------------------------------------------------------------------
  3(a)                (b)                       SEC USE ONLY  (c)            (d)          (e)           (f)             (g)
      TITLE OF           NAME AND ADDRESS OF    ------------     NUMBER OF      AGGREGATE    NUMBER OF     APPROXIMATE     NAME OF
      THE CLASS          EACH BROKER THROUGH                     SHARES OR      MARKET       SHARES OR     DATE OF SALE    EACH
      OF SECURITIES      WHOM THE SECURITIES    BROKER-DEALER    OTHER UNITS    VALUE        OTHER UNITS   (SEE INSTR.     SECURITIES
      TO BE SOLD         ARE TO BE OFFERED OR   FILE NUMBER      TO BE SOLD     (SEE INSTR.  OUTSTANDING   3(f))           EXCHANGE
                         EACH MARKET MAKER                       (SEE INSTR.    3(d))        (SEE INSTR.)  (MO. DAY  YR.)  (SEE INSTR.
                         WHO IS ACQUIRING THE                    3(c))                       3(e)                          3(g))
                         SECURITIES
  ------------------------------------------------------------------------------------------------------------------------------------
  COMMON                 RAYMOND JAMES &                         100,000      1,925,000(1)   49,213,773     06/19/00       NYSE
                         ASSOCIATES, INC.
                         880 CARILLON
                         PARKWAY
                         ST. PETERSBURG, FL
                         33716
  ------------------------------------------------------------------------------------------------------------------------------------
  INSTRUCTIONS:
  1.  (a)  Name of issuer                                    3.  (a)  Title of the class of securities to be sold
      (b)  Issuer's I.R.S. Identification Number                 (b)  Name and address of each broker through whom the securities
      (c)  Issuer's S.E.C. file number, if any                        are intended to be sold
      (d)  Issuer's address, including zip code                  (c)  Number of shares or other units to be sold (if debt securities,
      (e)  Issuer's telephone number, including area code             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
  2.  (a)  Name of person for whose account the securities       (f)  Approximate date on which the securities are to be sold
           are to be sold                                        (g)  Name of each securities exchange, if any, on which the
      (b)  Such person's I.R.S. identification number,                securities are intended to be sold
           if such person is an entity
      (c)  Such person's relationship to the issuer
           (e.g., officer, director, 10% stockholder,
           or member of immediate family of any of the
           foregoing)
      (d)  Such person's address, including zip code
  
            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.
                                                        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:
  
  ------------------------------------------------------------------------------------------------------------------------------------
                                                                Name of Person from Whom      Amount of
       Title of       Date you     Nature of Acquisition        Acquired (IF GIFT, ALSO       Securities     Date of  Nature of
       the Class      Acquired     Transaction                  GIVE DATE DONOR ACQUIRED)     Acquired       Payment  Payment
  ------------------------------------------------------------------------------------------------------------------------------------
  COMMON               5/24/96     ACQUISITION OF               HCC INSURANCE HOLDINGS, INC.  3,941,565      5/24/96  EXCHANGE OF
                                   LDG MANAGEMENT                                                                     PRIVATE COMPANY
                                   COMPANY, INC.                                                                      STOCK PURSUANT
                                                                                                                      TO MERGER
  ------------------------------------------------------------------------------------------------------------------------------------
  INSTRUCTIONS: 1.   If the securities were purchased and full         2.   If within two years after the acquisition of the
                     payment therefor was not made in cash at               securities the person for whose account they are to be
                     the time of purchase, explain in the table             sold had any short positions, put or other option to
                     or in a note thereto the nature of the                 dispose of securities referred to in paragraph (d)(3)
                     consideration given.  If the consideration             of Rule 144, furnish full information with respect
                     consisted of any note or other obligation,             thereto.
                     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.
  ------------------------------------------------------------------------------------------------------------------------------------
  ------------------------------------------------------------------------------------------------------------------------------------
                                              TABLE II -- SECURITIES SOLD DURING THE PAST 3 MONTHS
  
                       FURNISH THE FOLLOWING INFORMATION AS TO ALL SECURITIES OF THE ISSUER SOLD DURING THE PAST 3 MONTHS
                                         BY THE PERSON FOR WHOSE ACCOUNT THE SECURITIES ARE TO BE SOLD.
  ------------------------------------------------------------------------------------------------------------------------------------
                                                                                                Amount of
           Name and Address of Seller         Title of Securities Sold      Date of Sale        Securities Sold     Gross Proceeds
  ------------------------------------------------------------------------------------------------------------------------------------
  N/A
  ------------------------------------------------------------------------------------------------------------------------------------
  REMARKS:  NOTE 1: BASED ON NYSE CLOSING PRICE ON JUNE 16, 2000 OF $19.25.
  
  INSTRUCTIONS:                                                   ATTENTION:
  See the definition of "person" in paragraph (a) of Rule 144.    THE PERSON FOR WHOSE ACCOUNT THE SECURITIES TO WHICH THIS NOTICE
  Information is to be given not only as to the person for whose  RELATES ARE TO BE SOLD HEREBY REPRESENTS BY SIGNING THIS NOTICE
  account the securities are to be sold but also as to all other  THAT HE DOES NOT KNOW ANY MATERIAL ADVERSE INFORMATION IN REGARD
  persons included in that definition.  In addition, information  TO THE CURRENT AND PROSPECTIVE OPERATIONS OF THE ISSUER OF THE
  shall be given as to sales by all persons whose sales are       SECURITIES TO BE SOLD WHICH HAS NOT BEEN PUBLICLY DISCLOSED.
  required by paragraph (e) of Rule 144 to be aggregated with
  sales for the account of the person filing this notice.
  
  
                     JUNE 19, 2000                                                  /s/ STEPHEN J. LOCKWOOD
      --------------------------------------------------               -------------------------------------------------------
                     DATE OF NOTICE                                                        (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.
  ------------------------------------------------------------------------------------------------------------------------------------
      ATTENTION:  INTENTIONAL MISSTATEMENTS OR OMISSION OF FACTS CONSTITUTE FEDERAL CRIMINAL VIOLATIONS (SEE 18 U.S.C. 1001)
  ------------------------------------------------------------------------------------------------------------------------------------
                                                                                                                       SEC 1147 (7-97)
  </TABLE>
metadata_documents: [{"type": "144", "sequence": "1", "filename": "a144.txt", "description": "FORM 144", "secsgml_size_bytes": 13968}]
text: ------------------------
                                                               UNITED STATES                                       OMB APPROVAL
                                                     SECURITIES AND EXCHANGE COMMISSION                      ------------------------
                                                           WASHINGTON, D.C.  20549                           OMB Number:    3235-0101
                                                                                                             Expires:    May 31, 2000
                                                                                                             Estimated average burden
                                                                                                             hours per response...2.0
                                                                   FORM 144
                                                                                                             ------------------------
                                                                                                             ------------------------
                                                                                                                 SEC USE ONLY
                                                                                                             ------------------------
                                                                                                             ------------------------
                                                      NOTICE OF PROPOSED SALE OF SECURITIES                  DOCUMENT SEQUENCE NO.
                                              PURSUANT TO RULE 144 UNDER THE SECURITIES ACT OF 1933
                                                                                                             ------------------------
                                                                                                             CUSIP NUMBER
  ATTENTION:  TRANSMIT FOR FILING 3 COPIES OF THIS FORM CONCURRENTLY WITH EITHER PLACING AN ORDER
              WITH A BROKER TO EXECUTE SALE OR EXECUTING A SALE DIRECTLY WITH A MARKET MAKER.
                                                                                                              -----------------------
  ----------------------------------------------------------------------------------------------------------  WORK LOCATION
  1(a)  NAME OF ISSUER (PLEASE TYPE OR PRINT)             (b)  IRS IDENT. NO.      (c)  S.E.C. FILE NO.
  
  HCC INSURANCE HOLDINGS, INC.                                  76-0336636                 0-20766            ------------------------
  ------------------------------------------------------------------------------------------------------------------------------------
  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
  ------------------------------------------------------------------------------------------------------------------------------------
  2(a) NAME OF PERSON FOR WHOSE ACCOUNT   (b)  IRS IDENT. NO  (c)  RELATIONSHIP   (d)  ADDRESS STREET      CITY     STATE    ZIP CODE
       THE SECURITIES ARE TO BE SOLD                               TO ISSUER
  STEPHEN J. LOCKWOOD                          ###-##-####         VICE-CHAIRMAN      27 CONGRESS STREET,  SALEM     MA        01970
                                                                                      SUITE 108
  ------------------------------------------------------------------------------------------------------------------------------------
                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.
  ------------------------------------------------------------------------------------------------------------------------------------
  3(a)                (b)                       SEC USE ONLY  (c)            (d)          (e)           (f)             (g)
      TITLE OF           NAME AND ADDRESS OF    ------------     NUMBER OF      AGGREGATE    NUMBER OF     APPROXIMATE     NAME OF
      THE CLASS          EACH BROKER THROUGH                     SHARES OR      MARKET       SHARES OR     DATE OF SALE    EACH
      OF SECURITIES      WHOM THE SECURITIES    BROKER-DEALER    OTHER UNITS    VALUE        OTHER UNITS   (SEE INSTR.     SECURITIES
      TO BE SOLD         ARE TO BE OFFERED OR   FILE NUMBER      TO BE SOLD     (SEE INSTR.  OUTSTANDING   3(f))           EXCHANGE
                         EACH MARKET MAKER                       (SEE INSTR.    3(d))        (SEE INSTR.)  (MO. DAY  YR.)  (SEE INSTR.
                         WHO IS ACQUIRING THE                    3(c))                       3(e)                          3(g))
                         SECURITIES
  ------------------------------------------------------------------------------------------------------------------------------------
  COMMON                 RAYMOND JAMES &                         100,000      1,925,000(1)   49,213,773     06/19/00       NYSE
                         ASSOCIATES, INC.
                         880 CARILLON
                         PARKWAY
                         ST. PETERSBURG, FL
                         33716
  ------------------------------------------------------------------------------------------------------------------------------------
  INSTRUCTIONS:
  1.  (a)  Name of issuer                                    3.  (a)  Title of the class of securities to be sold
      (b)  Issuer's I.R.S. Identification Number                 (b)  Name and address of each broker through whom the securities
      (c)  Issuer's S.E.C. file number, if any                        are intended to be sold
      (d)  Issuer's address, including zip code                  (c)  Number of shares or other units to be sold (if debt securities,
      (e)  Issuer's telephone number, including area code             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
  2.  (a)  Name of person for whose account the securities       (f)  Approximate date on which the securities are to be sold
           are to be sold                                        (g)  Name of each securities exchange, if any, on which the
      (b)  Such person's I.R.S. identification number,                securities are intended to be sold
           if such person is an entity
      (c)  Such person's relationship to the issuer
           (e.g., officer, director, 10% stockholder,
           or member of immediate family of any of the
           foregoing)
      (d)  Such person's address, including zip code
  
            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.
                                                        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:
  
  ------------------------------------------------------------------------------------------------------------------------------------
                                                                Name of Person from Whom      Amount of
       Title of       Date you     Nature of Acquisition        Acquired (IF GIFT, ALSO       Securities     Date of  Nature of
       the Class      Acquired     Transaction                  GIVE DATE DONOR ACQUIRED)     Acquired       Payment  Payment
  ------------------------------------------------------------------------------------------------------------------------------------
  COMMON               5/24/96     ACQUISITION OF               HCC INSURANCE HOLDINGS, INC.  3,941,565      5/24/96  EXCHANGE OF
                                   LDG MANAGEMENT                                                                     PRIVATE COMPANY
                                   COMPANY, INC.                                                                      STOCK PURSUANT
                                                                                                                      TO MERGER
  ------------------------------------------------------------------------------------------------------------------------------------
  INSTRUCTIONS: 1.   If the securities were purchased and full         2.   If within two years after the acquisition of the
                     payment therefor was not made in cash at               securities the person for whose account they are to be
                     the time of purchase, explain in the table             sold had any short positions, put or other option to
                     or in a note thereto the nature of the                 dispose of securities referred to in paragraph (d)(3)
                     consideration given.  If the consideration             of Rule 144, furnish full information with respect
                     consisted of any note or other obligation,             thereto.
                     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.
  ------------------------------------------------------------------------------------------------------------------------------------
  ------------------------------------------------------------------------------------------------------------------------------------
                                              TABLE II -- SECURITIES SOLD DURING THE PAST 3 MONTHS
  
                       FURNISH THE FOLLOWING INFORMATION AS TO ALL SECURITIES OF THE ISSUER SOLD DURING THE PAST 3 MONTHS
                                         BY THE PERSON FOR WHOSE ACCOUNT THE SECURITIES ARE TO BE SOLD.
  ------------------------------------------------------------------------------------------------------------------------------------
                                                                                                Amount of
           Name and Address of Seller         Title of Securities Sold      Date of Sale        Securities Sold     Gross Proceeds
  ------------------------------------------------------------------------------------------------------------------------------------
  N/A
  ------------------------------------------------------------------------------------------------------------------------------------
  REMARKS:  NOTE 1: BASED ON NYSE CLOSING PRICE ON JUNE 16, 2000 OF $19.25.
  
  INSTRUCTIONS:                                                   ATTENTION:
  See the definition of "person" in paragraph (a) of Rule 144.    THE PERSON FOR WHOSE ACCOUNT THE SECURITIES TO WHICH THIS NOTICE
  Information is to be given not only as to the person for whose  RELATES ARE TO BE SOLD HEREBY REPRESENTS BY SIGNING THIS NOTICE
  account the securities are to be sold but also as to all other  THAT HE DOES NOT KNOW ANY MATERIAL ADVERSE INFORMATION IN REGARD
  persons included in that definition.  In addition, information  TO THE CURRENT AND PROSPECTIVE OPERATIONS OF THE ISSUER OF THE
  shall be given as to sales by all persons whose sales are       SECURITIES TO BE SOLD WHICH HAS NOT BEEN PUBLICLY DISCLOSED.
  required by paragraph (e) of Rule 144 to be aggregated with
  sales for the account of the person filing this notice.
  
                     JUNE 19, 2000                                                  /s/ STEPHEN J. LOCKWOOD
      --------------------------------------------------               -------------------------------------------------------
                     DATE OF NOTICE                                                        (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.
  ------------------------------------------------------------------------------------------------------------------------------------
      ATTENTION:  INTENTIONAL MISSTATEMENTS OR OMISSION OF FACTS CONSTITUTE FEDERAL CRIMINAL VIOLATIONS (SEE 18 U.S.C. 1001)
  ------------------------------------------------------------------------------------------------------------------------------------
                                                                                                                       SEC 1147 (7-97)