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 broker to DOCUMENT SEQUENCE NO. execute a sale or executing a sale directly with a market maker. -------------------------- CUSIP NUMBER -------------------------- WORK LOCATION -------------------------- ------------------------------------------------------------------------------------------------------------------------------------ 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 ------------------------------------------------------------------------------------------------------------------------------------ 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) 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 ------------------------------------------------------------------------------------------------------------------------------------ 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) (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)) ------------------------------------------------------------------------------------------------------------------------------ Raymond James & Associates Common 10 S. Riverside Plaza, Suite 1450 $2,730,166 Stock Chicago, IL 60606 100,300 Note 1 ------------------------------------------------------------------------------------------------------------------------------ Raymond James & Associates Common 10 S. Riverside Plaza, Suite 1450 $ 922,758 Stock Chicago, IL 60606 33,900 Note 1 ------------------------------------------------------------------------------------------------------------------------------ ------------------------------------------------------------------------------------------------------------------------------ 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)) ------------------------------------------------------------------------------------------------ Common Stock 61,000,895 12/28/01 NYSE Note 2 ------------------------------------------------------------------------------------------------ ------------------------------------------------------------------------------------------------ ------------------------------------------------------------------------------------------------ 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: --------------------------------------------------------------------------------------------------------------------------------- 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) --------------------------------------------------------------------------------------------------------------------------------- Common HCC Insurance Stock 12/19/01 Exercise of Stock Options Holdings, Inc. 387,500 12/19/01 Cash --------------------------------------------------------------------------------------------------------------------------------- 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. ------------------------------------------------------------------------------------------------------------------------------------ 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. ------------------------------------------------------------------------------------------------------------------------------------ Name and Address of Seller Title of Securities Sold Date of Sale Amount of Gross Proceeds Securities Sold ------------------------------------------------------------------------------------------------------------------------------------ Common Stock 09/27/01 350,000 $ 8,977,115 Stephen L. Way Common Stock 10/11/01 350,000 $ 9,780,120 13403 Northwest Freeway Common Stock 12/19/01 123,400 $3,467,169.80 Houston, Texas 77040 Common Stock 12/20/01 55,400 $1,565,459.96 Common Stock 12/21/01 1,700 $ 46,936.10 Common Stock 12/24/01 2,800 $ 77,707.00 Common Stock 12/27/01 70,000 $1,905,246.00 ------------------------------------------------------------------------------------------------------------------------------------ REMARKS: NOTE 1: BASED UPON NYSE CLOSING PRICE ON 12/27/01 OF $27.22. NOTE 2: SHARES OUTSTANDING AS OF 11/30/01 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. December 28, 2001 ---------------------------------------- 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. -------------------------------------------------------------------------------- ATTENTION: INTERNATIONAL MISSTATEMENTS OR OMISSION OF FACTS CONSTITUTE FEDERAL CRIMINAL VIOLATIONS (SEE 18 U.S.C. 1001). -------------------------------------------------------------------------------- SEC 1147(10-00)