Exhibit 99.1

HCC INSURANCE HOLDINGS REPORTS EARNINGS
FOR THE FIRST QUARTER OF 2010

HOUSTON (May 4, 2010) . . .

HCC Insurance Holdings, Inc. (NYSE: HCC) today released results for its first quarter ended March 31, 2010.

Net earnings for the first quarter of 2010 were $71.4 million, compared with $83.2 million during the first quarter of 2009. Net earnings per diluted share were $0.62 for the first quarter of 2010, compared to $0.73 for the same quarter of 2009. The 2010 results included pretax losses, net of reinsurance, of $20.6 million stemming from several catastrophes, the largest of which was the Chilean earthquake. The catastrophe losses reduced net earnings by $0.12 per share.

The GAAP combined ratio for the first quarter of 2010 was 90.3%, compared to 87.3% for the same quarter of 2009. The first quarter 2010 accident year combined ratio was 89.3%, which included 4.0 percentage points of catastrophe losses. Book value per share increased to $26.91 at March 31, 2010, compared to $26.58 at December 31, 2009. The Company’s annualized return on average equity for the first quarter of 2010 was 9.3%.

For the first quarter of 2010, the gross written premium of HCC’s insurance company subsidiaries increased 3% to $622.5 million, compared to $602.4 million for the same quarter of 2009. Net written premium increased to $498.3 million in 2010, compared with net written premium of $491.3 million in 2009. Net earned premium increased to $509.6 million for the first quarter of 2010, compared to $502.4 million for the same quarter of 2009.

“HCC has continued to produce excellent underwriting performance and control expenses despite the continued competition for premium and the quarter’s catastrophes,” John N. Molbeck, Jr., HCC President and Chief Executive Officer said.

During the first quarter of 2010 and 2009, HCC had net adverse prior year reserve development of $5.0 million and $4.7 million, respectively. The adverse reserve development principally related to the group life, accident and health line of business.

Other operating income was $9.9 million and $22.9 million in the first quarter of 2010 and 2009, respectively. The 2010 quarter included an $8.0 million gain related to the commutation of a mortgage impairment insurance contract that had been accounted for as a derivative financial instrument. The 2009 quarter included $20.5 million from the commutation of a reinsurance contract with MGIC.

Investment income increased during the first quarter of 2010 to $49.2 million, compared to $45.2 million a year earlier, reflecting an increased amount of invested assets. HCC’s fixed income securities generated $48.6 million in investment income in 2010, versus $45.4 million in 2009. The Company’s fixed income investments increased 14% from March 31, 2009 to $4.9 billion at March 31, 2010.

As of March 31, 2010, HCC’s fixed income securities portfolio had an average rating of AA+, an average duration of 5.0 years and an average tax equivalent yield of 5.0%. HCC recognized no other-than-temporary impairment losses on the portfolio in the first quarter of 2010.

The Company’s liquidity position remains strong and its shareholders’ equity was a record $3.1 billion at March 31, 2010. HCC has a $575.0 million revolving loan facility with $553.4 million of available capacity at March 31, 2010, which expires in December 2011. The Company generated $42.5 million of cash flow from operating activities in the first quarter of 2010, compared to $133.6 million in the first quarter of 2009, with the difference primarily due to increased paid losses, the timing of premium payments to reinsurers, and lower net earnings. The Company held $636.5 million of cash and short-term investments at the end of the quarter.

As of March 31, 2010, total investments were $5.5 billion, total assets were $8.9 billion, and the Company’s debt to total capital ratio was 8.8%.

HCC participated in the Transocean placement, as well as the placement for one of the co-venture partners. Due to the complexity of this tragic loss, the Company does not yet have an estimate of its gross loss. HCC has purchased significant facultative reinsurance for this loss and expects its net loss will be minimal.

For further information about HCC’s results, the supplemental financial schedules are accessible on the Company’s website at http://www.hcc.com, as well as directly in the Investor Relations section of HCC’s website at http://ir.hcc.com.

(Note: If clicking on the above links does not open in a new web page, please cut and paste the above URLs into your browser’s address bar.)

HCC will hold an open conference call beginning at 8:00 a.m. Central Daylight Time on Wednesday, May 5. To participate, the number for domestic calls is (800) 374-0290 and the number for international calls is (706) 634-0161. In addition, there will be a live webcast available on a listen-only basis that can be accessed through the HCC website at www.hcc.com. The webcast replay will be archived in the Investor Relations section of the HCC website through Friday, August 6, 2010.

Headquartered in Houston, Texas, HCC Insurance Holdings, Inc. is a leading international specialty insurance group with offices across the United States and in the United Kingdom, Spain and Ireland. As of March 31, 2010, HCC had assets of $8.9

2

billion and shareholders’ equity of $3.1 billion. HCC’s major domestic and international insurance companies have a financial strength rating of “AA (Very Strong)” from Standard & Poor’s Corporation. HCC’s major domestic insurance companies have a financial strength rating of “AA (Very Strong)” from Fitch Ratings, “A1 (Good Security)” from Moody’s Investors Service, Inc., and “A+ (Superior)” by A.M. Best Company, Inc.

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

Contact:	Jonathan Lee, HCC Director of Investor Relations
	Telephone: (713) 996-1156

Forward-looking statements contained in this press release are made under “safe harbor” provisions of the Private Securities Litigation Reform Act of 1995 and involve a number of risks and uncertainties. The types of risks and uncertainties which may affect the Company are set forth in its periodic reports filed with the Securities and Exchange Commission.

* * * *

3

HCC Insurance Holdings, Inc. and Subsidiaries
Financial Highlights
(Unaudited, in thousands except per share data)

	Three months ended
	March 31,
	2010			2009
Gross written premium	$	622,496		$	602,387
Net written premium		498,251			491,250
Net earned premium		509,587			502,388
Fee and commission income		20,993			30,294
Net investment income		49,249			45,218
Other operating income		9,906			22,896
Total revenue		594,260			600,738
Net earnings		71,354			83,170
Earnings per share (diluted)	$	0.62		$	0.73
Weighted-average shares outstanding (diluted) (millions)		114.1			113.3
GAAP net loss ratio		64.1	%		62.8	%
GAAP combined ratio		90.3	%		87.3	%
Paid loss ratio		60.4	%		54.0	%

	March 31,			December 31,
	2010			2009
Total investments	$	5,519,315		$	5,456,229
Total assets		8,867,669			8,834,391
Shareholders’ equity		3,093,828			3,031,183
Debt to total capital ratio		8.8	%		9.0	%
Book value per share	$	26.91		$	26.58

S-1

HCC Insurance Holdings, Inc. and Subsidiaries
Consolidated Balance Sheets
(Unaudited, in thousands)

	March 31,			December 31,
	2010			2009
ASSETS
Investments:
Fixed income securities — available for sale, at fair value	$	4,802,585		$	4,538,073
Fixed income securities — held to maturity, at amortized cost		135,619			102,792
Short-term investments		576,576			810,673
Other investments		4,535			4,691
Total investments		5,519,315			5,456,229
Cash		59,892			129,460
Restricted cash and cash investments		146,512			146,133
Premium, claims and other receivables		641,341			600,332
Reinsurance recoverables		1,028,948			1,016,411
Ceded unearned premium		261,256			270,436
Ceded life and annuity benefits		60,603			61,313
Deferred policy acquisition costs		209,083			208,463
Goodwill		821,698			822,006
Other assets		119,021			123,608
Total assets	$	8,867,669		$	8,834,391
LIABILITIES
Loss and loss adjustment expense payable	$	3,495,705		$	3,492,309
Life and annuity policy benefits		60,603			61,313
Reinsurance balances payable		157,735			182,661
Unearned premium		1,022,950			1,044,747
Deferred ceding commissions		67,876			71,595
Premium and claims payable		174,164			154,596
Notes payable		298,522			298,483
Accounts payable and accrued liabilities		496,286			497,504
Total liabilities		5,773,841			5,803,208
SHAREHOLDERS’ EQUITY
Common stock		119,650			118,724
Additional paid-in capital		923,666			914,339
Retained earnings		2,033,063			1,977,254
Accumulated other comprehensive income		116,248			119,665
Treasury stock		(98,799	)		(98,799	)
Total shareholders’ equity		3,093,828			3,031,183
Total liabilities and shareholders’ equity	$	8,867,669		$	8,834,391

S-2

HCC Insurance Holdings, Inc. and Subsidiaries
Consolidated Statements of Earnings
(Unaudited, in thousands except per share data)

	Three months ended
	March 31,
	2010		2009
REVENUE
Net earned premium	$	509,587	$	502,388
Fee and commission income		20,993		30,294
Net investment income		49,249		45,218
Other operating income		9,906		22,896
Net realized investment gain		4,525		3,055
Other-than-temporary impairment loss:
Total loss		—		(3,113	)
Portion recognized in equity, before tax		—		—
Net loss recognized in earnings		—		(3,113	)
Total revenue		594,260		600,738
EXPENSE
Loss and loss adjustment expense, net		326,521		315,566
Policy acquisition costs, net		92,656		88,692
Other operating expense		66,668		68,998
Interest expense		5,390		4,639
Total expense		491,235		477,895
Earnings before income tax expense		103,025		122,843
Income tax expense		31,671		39,673
Net earnings	$	71,354	$	83,170
Basic earnings per share data:
Net earnings per share	$	0.62	$	0.73
Weighted-average shares outstanding (millions)		113.7		112.8
Diluted earnings per share data:
Net earnings per share	$	0.62	$	0.73
Weighted-average shares outstanding (millions)		114.1		113.3
Cash dividends declared, per share	$	0.135	$	0.125

S-3

HCC Insurance Holdings, Inc. and Subsidiaries
Consolidated Statements of Cash Flows
(Unaudited, in thousands)

	Three months ended
	March 31,
	2010			2009
Operating activities
Net earnings	$	71,354		$	83,170
Adjustments to reconcile net earnings to net cash provided by operating activities:
Change in premium, claims and other receivables		(24,890	)		(28,719	)
Change in reinsurance recoverables		(21,839	)		(29,973	)
Change in ceded unearned premium		7,548			(217	)
Change in loss and loss adjustment expense payable		28,921			67,544
Change in reinsurance balances payable		(23,913	)		11,481
Change in unearned premium		(17,600	)		(11,335	)
Change in premium and claims payable, net of restricted cash		19,413			8,859
Change in accounts payable and accrued liabilities		(18,215	)		(7,556	)
Stock-based compensation expense		3,080			4,783
Depreciation and amortization expense		3,971			3,579
(Gain) loss on investments		(5,011	)		1,020
Other, net		19,657			30,966
Cash provided by operating activities		42,476			133,602
Investing activities
Sales of available for sale fixed income securities		67,689			119,092
Maturity or call of available for sale fixed income securities		115,793			69,280
Maturity or call of held to maturity fixed income securities		8,260			85,821
Cost of available for sale fixed income securities acquired		(381,704	)		(210,093	)
Cost of held to maturity fixed income securities acquired		(44,901	)		(59,515	)
Change in short-term investments		223,947			(177,715	)
Proceeds from sales of strategic and other investments		—			48,579
Payments for purchase of businesses, net of cash received		(36,348	)		(32,966	)
Proceeds from sale of subsidiary		14,851			—
Other, net		(3,824	)		(3,482	)
Cash used by investing activities		(36,237	)		(160,999	)
Financing activities
Advances on line of credit		—			80,000
Sale of common stock		7,173			2,090
Payments on convertible notes		(64,472	)		—
Purchase of common stock		—			(35,464	)
Dividends paid		(15,460	)		(14,182	)
Other, net		(3,048	)		619
Cash provided (used) by financing activities		(75,807	)		33,063
Net increase (decrease) in cash		(69,568	)		5,666
Cash at beginning of year		129,460			27,347
Cash at end of period	$	59,892		$	33,013

S-4

HCC Insurance Holdings, Inc. and Subsidiaries
Gross Written Premium
(Unaudited, in thousands)

	Three months ended
	March 31,
	2010		2009		Change
Diversified financial products
D&O (1)	$	84,168	$	94,284		(11	)%
E&O (2)		56,348		62,359		(10	)
Other		16,412		25,774		(36	)
U.S. Surety & Credit		54,021		44,133		22
International Surety & Credit		21,305		18,562		15
		232,254		245,112		(5	)
Group life, accident & health
Medical Stop-loss		161,766		159,486		1
Other Medical		22,318		31,606		(29	)
Other		22,298		25,901		(14	)
		206,382		216,993		(5	)
Aviation		37,521		41,952		(11	)
London market account
Energy		16,582		14,814		12
Property treaty		37,630		—	nm
Other		39,750		29,935		33
		93,962		44,749		110
Other specialty lines
Public Risk		16,712		19,934		(16	)
HCC Lloyd’s		17,602		11,222		57
Other		18,021		22,421		(20	)
		52,335		53,577		(2	)
Discontinued lines		42		4	nm
Total	$	622,496	$	602,387		3	%

(1)		Includes D&O and related professional liability insurance underwritten by HCCG and D&O insurance for non-profit organizations underwritten by PIA.
(2)		Includes Miscellaneous E&O, Architects and Engineers E&O, and Diversified Financial Products insurance underwritten by PIA, as well as E&O insurance underwritten in the United Kingdom and Spain.
nm	–	Not meaningful comparison

S-5

HCC Insurance Holdings, Inc. and Subsidiaries
Net Written Premium
(Unaudited, in thousands)

	Three months ended
	March 31,
	2010		2009		Change
Diversified financial products
D&O (1)	$	55,956	$	67,467		(17	)%
E&O (2)		47,963		54,652		(12	)
Other		12,921		21,832		(41	)
U.S. Surety & Credit		47,419		42,402		12
International Surety & Credit		19,636		17,010		15
		183,895		203,363		(10	)
Group life, accident & health
Medical Stop-loss		161,766		159,484		1
Other Medical		22,318		31,606		(29	)
Other		5,148		7,966		(35	)
		189,232		199,056		(5	)
Aviation		26,021		30,611		(15	)
London market account
Energy		9,842		6,177		59
Property treaty		35,257		—	nm
Other		23,451		20,217		16
		68,550		26,394	nm
Other specialty lines
Public Risk		9,205		15,116		(39	)
HCC Lloyd’s		16,273		9,681		68
Other		5,033		7,025		(28	)
		30,511		31,822		(4	)
Discontinued lines		42		4	nm
Total	$	498,251	$	491,250		1	%

(1)		Includes D&O and related professional liability insurance underwritten by HCCG and D&O insurance for non-profit organizations underwritten by PIA.
(2)		Includes Miscellaneous E&O, Architects and Engineers E&O, and Diversified Financial Products insurance underwritten by PIA, as well as E&O insurance underwritten in the United Kingdom and Spain.
nm	–	Not meaningful comparison

S-6

HCC Insurance Holdings, Inc. and Subsidiaries
Net Earned Premium
(Unaudited, in thousands)

	Three months ended
	March 31,
	2010		2009		Change
Diversified financial products
D&O (1)	$	92,918	$	82,802		12	%
E&O (2)		53,893		59,405		(9	)
Other		11,826		10,976		8
U.S. Surety & Credit		46,749		44,492		5
International Surety & Credit		18,189		16,409		11
		223,575		214,084		4
Group life, accident & health
Medical Stop-loss		161,766		159,483		1
Other Medical		25,021		33,053		(24	)
Other		6,855		8,552		(20	)
		193,642		201,088		(4	)
Aviation		28,943		32,814		(12	)
London market account
Energy		16,187		9,235		75
Property treaty		6,754		—	nm
Other		13,227		14,439		(8	)
		36,168		23,674		53
Other specialty lines
Public Risk		11,490		8,620		33
HCC Lloyd’s		10,185		10,790		(6	)
Other		5,542		11,314		(51	)
		27,217		30,724		(11	)
Discontinued lines		42		4	nm
Total	$	509,587	$	502,388		1	%

(1)		Includes D&O and related professional liability insurance underwritten by HCCG and D&O insurance for non-profit organizations underwritten by PIA.
(2)		Includes Miscellaneous E&O, Architects and Engineers E&O, and Diversified Financial Products insurance underwritten by PIA, as well as E&O insurance underwritten in the United Kingdom and Spain.
nm	–	Not meaningful comparison

S-7

HCC Insurance Holdings, Inc. and Subsidiaries
Net Investment Income and Unrealized Gain (Loss)
(Unaudited, in thousands)

	Three months ended
	March 31,
	2010			2009
Sources of net investment income:
Fixed income securities
Taxable	$	26,868		$	25,105
Exempt from U.S. income taxes		21,731			20,333
Total fixed income securities		48,599			45,438
Short-term investments		190			884
Other		1,508			(52	)
Total investment income		50,297			46,270
Investment expense		(1,048	)		(1,052	)
Net investment income	$	49,249		$	45,218
Unrealized gain on available for sale fixed income securities:
Increase in unrealized gain for period, before tax	$	7,572		$	45,351
Unrealized gain at:
March 31, 2010	$	163,883
December 31, 2009	$	156,311

S-8

HCC Insurance Holdings, Inc. and Subsidiaries
Net Loss Ratios
(Unaudited, in thousands)

	Three months ended					Three months ended					Twelve months ended
	March 31, 2010					March 31, 2009					December 31, 2009
	Net Earned		Loss			Net Earned		Loss			Net Earned		Loss
	Premium		Ratio			Premium		Ratio			Premium		Ratio
Diversified financial products
D&O (1)	$	92,918		63.1	%	$	82,802		60.7	%	$	371,650		61.2	%
E&O (2)		53,893		57.1			59,405		55.2			234,768		49.6
Other		11,826		34.2			10,976		50.0			39,123		43.4
U.S. Surety & Credit		46,749		26.5			44,492		30.5			182,627		29.9
International Surety & Credit		18,189		44.0			16,409		53.0			68,162		50.9
		223,575		50.9			214,084		51.8			896,330		50.2
Group life, accident & health
Medical Stop-loss		161,766		73.9			159,483		72.6			633,572		71.7
Other Medical		25,021		76.9			33,053		88.7			134,161		86.0
Other		6,855		54.2			8,552		57.1			29,887		43.6
		193,642		73.6			201,088		74.6			797,620		73.0
Aviation		28,943		56.6			32,814		61.3			129,626		56.6
London market account
Energy		16,187		77.8			9,235		29.5			49,116		24.0
Property treaty		6,754		177.0			—		—			—		—
Other		13,227		80.7			14,439		48.8			54,043		41.5
		36,168		97.4			23,674		41.3			103,159		33.1
Other specialty lines
Public Risk		11,490		70.0			8,620		68.8			39,986		66.3
HCC Lloyd’s		10,185		61.2			10,790		67.4			40,273		69.1
Other		5,542		78.7			11,314		103.4			30,114		49.6
		27,217		68.5			30,724		81.0			110,373		62.8
Discontinued lines		42	nm				4	nm				127	nm
Total	$	509,587		64.1	%	$	502,388		62.8	%	$	2,037,235		59.7	%

(1)		Includes D&O and related professional liability insurance underwritten by HCCG and D&O insurance for non-profit organizations underwritten by PIA.
(2)		Includes Miscellaneous E&O, Architects and Engineers E&O, and Diversified Financial Products insurance underwritten by PIA, as well as E&O insurance underwritten in the United Kingdom and Spain.
nm	–	Not meaningful comparison

S-9

HCC Insurance Holdings, Inc. and Subsidiaries
Subprime Liability Exposure
March 31, 2010

• As of March 31, the Company had 77 “non-Side A only” D&O, E&O and Fiduciary Liability claims and 17 “Side A only” D&O claims relating to subprime issues.

• Of the D&O claims reported, four are on primary policies with gross policy limits totaling $20 million. The remaining D&O claims are on excess policies.

• The average policy limit on the “non-Side A only” claims is $13.3 million gross and $9.1 million net, with an average attachment point of $85 million.

• The average policy limit for “Side A only” claims is $14.2 million gross and $11.3 million net, with an average attachment point of $159 million.

• Based upon the Company’s present knowledge, HCC believes the ultimate subprime related losses will be contained within the current overall reserves for D&O, E&O and Fiduciary Liability business.

S-10