Keefe, Bruyette & Woods Insurance Conference September 8, 2011

See Notice About This Presentation Notice About This Presentation ABOUT FORWARD-LOOKING STATEMENTS: This presentation contains certain “forward-looking statements” within the meaning of Section 27A of the Securities Act of 1933 and Section 21E of the Securities Exchange Act of 1934, which are intended to be covered by the safe harbors created by those laws. These forward-looking statements include information about possible or assumed future results of our operations. All statements, other than statements of historical facts, included in this presentation that address activities, events or developments that we expect or anticipate may occur in the future, including such things as growth of our business and operations, business strategy, competitive strengths, goals, plans, future capital expenditures and references to future successes, may be considered forward-looking statements. Also, when we use the words such as “anticipate”, “believe”, “estimate”, “expect”, “intend”, “plan”, “probably” or similar expressions, we are making forward-looking statements. Many risks and uncertainties may have an impact on the matters addressed in these forward-looking statements, which could affect our future financial results and performance. These could cause our results or performance to differ materially from those we express in our forward-looking statements. Although we believe that the assumptions underlying our forward-looking statements are reasonable, any of these assumptions, and therefore also the forward-looking statements based on these assumptions, could themselves prove to be inaccurate. In light of the significant uncertainties inherent in the forward-looking statements that are included in this presentation, our inclusion of this information is not a representation by us or any other person that our objectives and plans will be achieved. Our forward-looking statements speak only at the date made, and we will not update these forward-looking statements unless the securities laws require us to do so. In light of these risks, uncertainties and assumptions, any forward-looking events discussed in this presentation may not occur. PRESENTATION FORMATTING: Certain figures included in this publication have been rounded for presentation and are provided for comparative purposes only. Our periodic reports filed with the Securities and Exchange Commission contain more detailed information, including specific figures. 2

See Notice About This Presentation HCC Overview Specialty insurer since 1974 (NYSE: HCC) headquartered in Houston, TX Non-correlated specialty lines of business underwritten in more than 180 countries Five segments: U.S. Property & Casualty, Professional Liability, Accident & Health, U.S. Surety & Credit and International Financial Strength Ratings of “AA (Very Strong)” by Standard & Poor’s, “AA (Very Strong)” by Fitch Ratings, “A1 (Good Security)” by Moody’s, and “A+ (Superior)” by A.M. Best Company Assets of $9.5 billion, shareholders’ equity of $3.3 billion and market capitalization of $3.5 billion as of June 30, 2011 3

See Notice About This Presentation Characteristics That Make HCC Unique Specialty Insurance businesses with strong long-term fundamentals and market leadership Diversified underwriting portfolio with historically low correlation Consistent track record of underwriting performance and ROE Lowest expense ratio amongst industry peers1 Disciplined balance sheet and risk management practices High quality investment portfolio Broadly experienced team 4 1 As of 6/30/11. Peer group defined as AFG, AGII, CB, MKL, NAVG, ORI, RLI, TRV and WRB.

See Notice About This Presentation YTD 2011 Operating Highlights Japan, New Zealand and United States catastrophe losses in 2011 of $47.7 million after-tax (1.4% of shareholders’ equity)1 Combined ratio excluding cats of 85.0%; 91.9% with cats Expense ratio of 25.9% Accident year combined ratio excluding cats of 82.8%; 89.8% with cats Book value per share of $29.65 as of June 30, 2011 Five-year compounded BVPS growth of 12.4%2 5 1 After reinsurance and all reinstatement premiums. As a percentage of 12/31/10 shareholders’ equity. 2 As of 6/30/11.

See Notice About This Presentation Segment Overview 2010 ($ in millions) 6 1 Total does not include Exited Lines (GWP = $3M; NWP = $1M). Total1 2010 GWP: $ 538 $ 596 $ 762 $ 227 $ 453 $ 2,576 2010 NWP: $ 329 $ 402 $ 761 $ 209 $ 324 $ 2,025 Key Lines: Aviation Small Account E&O Public Risk EPLI Title Residual Value Disability Contingency Kidnap and Ransom Difference In Conditions Occupational Accident Brown Water Marine U.S. D&O International D&O Large Account E&O Fiduciary Fidelity EPLI Medical Stop-loss ST Domestic and International Medical HMO Reinsurance Medical Excess Contract Surety Commercial Surety Bail Bonds Credit Energy Property Treaty Liability Surety Credit Property Ocean Marine A&H HCC U.S. Property & Casualty Professional Liability U.S. Surety & Credit International Accident & Health

See Notice About This Presentation Segment Comparison 2010 ($ in millions) 7 U.S. Property & Casualty Professional Liability Accident & Health U.S. Surety & Credit International Total1 1 Total includes Exited Lines (NEP = $1M). 2010 Net Earned Loss Premium Ratio Aviation $116 55% E&O 95 79 Public Risk 47 62 Other 82 28 U.S. Property & Casualty $340 56% Net Earned Loss Premium Ratio Surety $160 23% Credit 40 42 U.S. Surety & Credit $200 27% Net Earned Loss Premium Ratio U.S. D&O $378 63% International D&O 47 61 Professional Liability $425 62% Net Earned Loss Premium Ratio Energy $53 22% Property Treaty 47 58 Liability 82 43 Surety & Credit 69 42 Other 65 61 International $316 45% Net Earned Loss Premium Ratio Medical Stop-loss $654 74% Other 106 71 Accident & Health $760 73% 2010 Net Earned Loss Premium Ratio Total $2,042 59% 2010 2010 2010 2010

See Notice About This Presentation Segment Comparison YTD 2Q’11 ($ in millions) 8 U.S. Property & Casualty Professional Liability Accident & Health U.S. Surety & Credit International Total YTD 2Q'11 Net Earned Loss Premium Ratio Aviation $55 64% E&O 38 57 Public Risk 23 67 Other 43 47 U.S. Property & Casualty $159 58%  YTD 2Q'11 Net Earned Loss Premium Ratio Surety $81 25% Credit 21 45 U.S. Surety & Credit $102 29% Net Earned Loss Premium Ratio U.S. D&O $180 69% International D&O 23 57 Professional Liability $203 68% Net Earned Loss Premium Ratio Energy $29 60% Property Treaty 38 103 Liability 40 51 Surety & Credit 36 41 Other 25 151 International $168 78% Net Earned Loss Premium Ratio Medical Stop-loss $351 74% Other 50 64 Accident & Health $401 73%  YTD 2Q'11 Net Earned Loss Premium Ratio Total $1,033 66% YTD 2Q'11 YTD 2Q'11 YTD 2Q'11

See Notice About This Presentation Historical Performance 9 1 Peer group defined as AFG, AGII, CB, MKL, NAVG, ORI, RLI, TRV and WRB. Five-year peer average calculated by HCC as simple mean using SEC filings for peer companies. Gross Written Premium ($ in millions) GAAP Underwriting Ratios Net Written Premium ($ in millions) 1 CAGR (2005-2010): 4.8% CAGR (2005-2010): 6.2% 59.2% 59.6% 60.4% 59.7% 59.4% 59.7% 23.7% 23.9% 24.7% 24.3% 25.2% 24.3% 82.9% 83.5% 85.1% 84.0% 84.6% 84.0% 92.1% 57.3% 34.8% 2006 2007 2008 2009 2010 5 year HCC average 5 year peer average Loss Ratio Expense Ratio $2,038 $2,236 $2,451 $2,499 $2,560 $2,579 $1,314 $1,391 $0 $1,000 $2,000 $3,000 $4,000 2005 2006 2007 2008 2009 2010 YTD 2Q'10 YTD 2Q'11 $1,501 $1,813 $1,986 $2,061 $2,046 $2,026 $1,045 $1,149 $0 $1,000 $2,000 $3,000 $4,000 2005 2006 2007 2008 2009 2010 YTD 2Q'10 YTD 2Q'11

See Notice About This Presentation YTD 2Q’11 Underwriting Performance 10 HCC AGII MKL NAVG ORI1 WRB AFG RLI CB TRV Note: Calculated by HCC using 6/30/11 SEC filings for peer companies. 1 Development not disclosed in 6/30/11 SEC filing. Peer Group Comparison – YTD 2Q’11 Combined Ratios NA 91.9% 97.2% 126.6% 94.3% 101.7% 107.0% 122.9% 109.0% 114.6% 73.8% 98.3% 110.1% 113.8% 98.8% 103.1% 97.8% 107.7% 89.8% 125.9% GAAP AY GAAP AY GAAP AY GAAP AY GAAP AY GAAP AY GAAP AY GAAP AY GAAP AY GAAP AY Loss Ratio Net Positive Development Expense Ratio

See Notice About This Presentation Strong BVPS Growth 11 Note: Calculated by HCC based on 5-year rolling average using 6/30/11 and prior SEC filings for peer companies. HCC AGII CB MKL NAVG RLI TRV WRB AFG ORI (4.0%) 0.0% 4.0% 8.0% 12.0% 16.0% 20.0% 0.0 2.0 4.0 6.0 8.0 10.0 12.0 14.0 16.0 18.0 20.0 Average BVPS Growth Standard Deviation

See Notice About This Presentation Effective Catastrophe Management 12 1 PML calculated as of 3/31/11. Based on RMS Cat Model Version 10.0 and internal assessment of PMLs, excluding reinstatement premium. Net After-Tax Probable Maximum Loss (PML)1 for a single event managed to 5% of Shareholders’ Equity Net After-Tax PML as % of Shareholders’ Equity 1.9% 2.9% 2.0% 2.8% 1 in 100 1 in 250 Earthquake Wind

Single Event Limit Below 5% of Shareholders’ Equity See Notice About This Presentation Catastrophe Exposure Management ($ in millions) 13 1 Represents pretax recorded losses from date of event through 6/30/11. Net losses are net of reinsurance and include reinstatement premiums. 2 Gross loss and beginning of year shareholders’ equity are not available. 3 Represents after-tax net losses as a percentage of beginning of year shareholders’ equity. Year Key Catastrophes Gross 1 Net 1 % of SE 3 2011 Japan earthquake/tsunami, New Zealand earthquake and United States tornados $120 $73 1% 2010 Chile and New Zealand earthquakes and Deepwater Horizon rig disaster 77 26 1% 2008 Hurricanes Gustav and Ike 85 8 - 2005 Hurricanes Katrina, Rita and Wilma 385 58 3% 2004 Hurricanes Charley, Frances, Ivan and Jeanne 73 22 1% 2001 9/11 terrorist attack 119 35 4% 1994 Northridge earthquake 5 1 - 1992 Hurricane Andrew 2 NA 1 NA

See Notice About This Presentation Investment Portfolio At June 30, 2011 ($ in millions) 14 1 Available for sale fixed income securities at fair value and held to maturity fixed income securities at cost. 2 Excludes realized and unrealized investment gains and losses. Average Rating AA+ Average Duration 5.3 years Average Life 7.2 years Average Yield2 3.9% Average Tax Equivalent Yield2 4.8% Average Duration 5.1 years Fixed Income Securities1 $ 5,609 Short-term and Other Investments 226 Total Investments $ 5,835 Fixed Income Securities Total Investments

See Notice About This Presentation Investment Analysis At June 30, 2011 ($ in millions) 15 1 % of fair value of fixed income securities. Category Cost Fair Value % of Fixed Income Securities 1 Municipal Bonds - Special Purpose Rev. 1,580 $ 1,630 $ 29% Residential MBS 1,107 1,150 20% Municipal Bonds - General Obligations 998 1,047 19% Corporate 798 824 15% U.S. Government and Agencies 361 371 7% Foreign Government 303 312 5% Commercial Mortgage-Backed Securities 227 236 4% Asset-Backed Securities 41 41 1% Total Fixed Income Investments 5,415 $ 5,611 $ 100%

See Notice About This Presentation Total Value Creation 16 1 Calculated by HCC using 6/30/11 and prior SEC filings for peer companies. Compounded Annual Return on Tangible Book Value per Share, Including Dividends1 1 Year 3 Year 5 Year 10 Year HCC 9.4% 16.0% 15.8% 17.1% AFG 15.1% 24.9% 17.8% 14.3% AGII 3.5% 8.1% NM NM CB 15.1% 15.2% 15.2% 13.0% MKL 8.0% 6.1% 12.4% 14.1% NAVG 5.8% 10.7% 13.3% 12.4% ORI -3.7% -0.6% 0.4% 6.2% RLI 17.0% 13.3% 14.1% 13.4% TRV 9.7% 14.2% 16.1% NM WRB 13.8% 13.0% 14.6% 18.8% Peer Average 9.4% 11.7% 13.0% 13.2%

See Notice About This Presentation Quality Reinsurance Security ($ in millions) 17 1 A.M. Best ratings are as of 6/30/11. 2 Includes paid losses recoverable, outstanding losses recoverable, incurred but not reported losses recoverable and ceded unearned premium. 3 Net recoverables is gross recoverables less total credits (includes letters of credit, cash deposits and other payables). 4 Includes letters of credit, cash deposits and other payables. Reinsurers as of 6/30/11 Reinsurer A.M. Best rating1 Gross recoverable2 Net recoverable3 Transatlantic Re A $ 152 $ 136 Hannover Ruck. A 115 88 Axis Re A 78 70 ACE P&C A+ 63 62 Arch Re A 54 50 Swiss Re America A 45 35 Highly rated reinsurance partners Reserve for uncollectible reinsurance of $2 million at 6/30/11 on over $1 billion of recoverables 45% of gross recoverables at 6/30/11 were collateralized or had available offsets from reinsurers4 Recoverables Declining as % of Equity 82% 80% 57% 39% 40% 34% 31% 34% 20% 40% 60% 80% 100% 2004 2005 2006 2007 2008 2009 2010 YTD 2Q'11

See Notice About This Presentation HCC’s Value Proposition 18 Non-correlated portfolio of business Maintains double-digit margin in very competitive market High quality investment portfolio Strong operating cash flow Experienced management team