FORM 4 Check this box if no longer subject to Section 16. Form 4 or Form 5 obligations may continue. See Instruction 1(b).

UNITED STATES SECURITIES AND EXCHANGE COMMISSION Washington, D.C. 20549 STATEMENT OF CHANGES IN BENEFICIAL OWNERSHIP OF SECURITIES Filed pursuant to Section 16(a) of the Securities Exchange Act of 1934, Section 17(a) of the Public Utility Holding Company Act of 1935 or Section 30(h) of the Investment Company Act of 1940

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1. Name and Address of Reporting Person * Penny Pamela J   2. Issuer Name and Ticker or Trading Symbol HCC INSURANCE HOLDINGS INC/DE/ [HCC] 5. Relationship of Reporting Person(s) to Issuer (Check all applicable) _____ Director _____ 10% Owner __X__ Officer (give title below) _____ Other (specify below) EVP & Chief Accounting Officer (Last) (First) (Middle) C/O HCC INSURANCE HOLDINGS, INC., 13403 NORTHWEST FREEWAY 3. Date of Earliest Transaction (Month/Day/Year) 11/19/2008 (Street) HOUSTON, TX 77040 4. If Amendment, Date Original Filed(Month/Day/Year) 6. Individual or Joint/Group Filing(Check Applicable Line) _X_ Form filed by One Reporting Person ___ Form filed by More than One Reporting Person (City) (State) (Zip) Table I - Non-Derivative Securities Acquired, Disposed of, or Beneficially Owned

1.Title of Security (Instr. 3) 2. Transaction Date (Month/Day/Year) 2A. Deemed Execution Date, if any (Month/Day/Year) 3. Transaction Code (Instr. 8) 4. Securities Acquired (A) or Disposed of (D) (Instr. 3, 4 and 5) 5. Amount of Securities Beneficially Owned Following Reported Transaction(s) (Instr. 3 and 4) 6. Ownership Form: Direct (D) or Indirect (I) (Instr. 4) 7. Nature of Indirect Beneficial Ownership (Instr. 4) Code V Amount (A) or (D) Price

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Table II - Derivative Securities Acquired, Disposed of, or Beneficially Owned
(e.g., puts, calls, warrants, options, convertible securities)

1. Title of Derivative Security (Instr. 3)

2. Conversion or Exercise Price of Derivative Security

3. Transaction Date (Month/Day/Year)

3A. Deemed Execution Date, if any (Month/Day/Year)

4. Transaction Code (Instr. 8)

5. Number of Derivative Securities Acquired (A) or Disposed of (D) (Instr. 3, 4, and 5)

6. Date Exercisable and Expiration Date (Month/Day/Year)

7. Title and Amount of Underlying Securities (Instr. 3 and 4)

8. Price of Derivative Security (Instr. 5)

9. Number of Derivative Securities Beneficially Owned Following Reported Transaction(s) (Instr. 4)

10. Ownership Form of Derivative Security: Direct (D) or Indirect (I) (Instr. 4)

11. Nature of Indirect Beneficial Ownership (Instr. 4)

Code

V

(A)

(D)

Date Exercisable

Expiration Date

Title

Amount or Number of Shares

Option to Purchase (1)

$ 19.73

(2)

08/26/2010

Common Stock

37,500

30,000

D

Option to Purchase (3)

$ 27.56

(4)

07/22/2011

Common Stock

35,000

35,000

D

Option to Purchase (1)

$ 31.11

(5)

03/02/2013

Common Stock

50,000

50,000

D

Option to Purchase (6)

$ 20.86

11/19/2008

A

100,000

(7)

11/19/2014

Common Stock

100,000

$ 20.86

100,000

D

Reporting Owners

Reporting Owner Name / Address	Relationships
	Director	10% Owner	Officer	Other
Penny Pamela J C/O HCC INSURANCE HOLDINGS, INC. 13403 NORTHWEST FREEWAY HOUSTON, TX 77040			EVP & Chief Accounting Officer

Signatures

Edward H. Ellis, Jr. as Attorney in Fact for Pamela J. Penny		11/21/2008
**Signature of Reporting Person		Date

Explanation of Responses:

*	If the form is filed by more than one reporting person, see Instruction 4(b)(v).
**	Intentional misstatements or omissions of facts constitute Federal Criminal Violations. See 18 U.S.C. 1001 and 15 U.S.C. 78ff(a).
(1)	Option to purchase granted pursuant to the 2001 Flexible Incentive Plan.
(2)	The options vest equally annually beginning 8/26/05 @ 7,500 shares per year.
(3)	Option to purchase granted pursuant to the 2004 Flexible Incentive Plan.
(4)	The options vest equally annually beginning 7/22/06 @ 7,000 shares per year.
(5)	The options vest equally annually beginning 3/2/08 @ 10,000 shares per year.
(6)	Option to purchase granted pursuant to the 2008 Flexible Incentive Plan.
(7)	The options vest equally annually beginning 11/19/09 @ 20,000 shares per year.

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