HCC INSURANCE HOLDINGS REPORTS
SALES OF INVESTMENTS

HOUSTON (October 1, 2008) . . .
HCC Insurance Holdings, Inc. (NYSE: HCC) announced today that it had sold all of its positions in the preferred stock of Fannie Mae, Freddie Mac and Wachovia Corporation, and in the securities of American International Group, Inc. and Lehman Brothers Holdings, Inc. during the third quarter of 2008.

HCC’s cash and investments totaled $4.8 billion as of June 30, 2008. During the third quarter of 2008, the Company will have a realized investment loss of $19.4 million before taxes as a result of the sales of the above-mentioned securities and a net realized investment loss of $12.1 million before taxes from all sales of securities transacted during the quarter.

“These sales are in keeping with our policy of maintaining a portfolio of highly rated, conservative investments. There have recently been significant conversations in the financial community regarding industry holdings of certain securities. We are pleased to disclose that investment issues regarding these names are completely behind us,” HCC Chief Executive Officer Frank J. Bramanti said.

HCC also announced that it owns no Washington Mutual, Inc. securities.

Headquartered in Houston, Texas, HCC Insurance Holdings, Inc. (HCC) is a leading international specialty insurance group with offices across the United States and in Belgium, Bermuda, Ireland, Spain and the United Kingdom. HCC has assets of $8.3 billion, shareholders’ equity of $2.6 billion and is rated AA (Very Strong) by Standard & Poor’s and AA (Very Strong) by Fitch Ratings. In addition, HCC’s domestic property and casualty insurance companies are rated A+ (Superior) by A.M. Best Company.

For more information, visit our website at www.hcc.com.

©2005 HCC Insurance Holdings, Inc.