#1Alleghany Investor Presentation March 2022#2Strategic Update#3Stable Leadership - Aligned with Long-Term Horizon Otis & Mantis Van Sweringen Robert Young Allan Kirby F.M. Kirby 1929-1937 Founders 1937-1958 21 years 1958-1967 9 years 1967-1992 25 years John J. Burns, Jr. Weston M. Hicks Joe Brandon 1992-2004 12 years 2004 - 2021 17 years 2022- Current ° Strong Team of Executive Leaders Kerry Jacobs - EVP & CFO Chris Dalrymple, General Counsel David Van Geyzel, CEO - Alleghany Capital • John Shannon, CIO • Reeva Bakhshi, Deputy CFO & Treasurer 3#4A Commitment to Good Stewardship "Whatever opportunities, challenges or risks unfold, we are committed to being good stewards of our stockholders' hard-earned savings" - Joe Brandon 2021 Alleghany Stockholder Letter 4#5Our Management Approach Philosophy "Conservatism dominates our management philosophy. We shun investment fads and fashions in favor of acquiring relatively few interests in basic financial, industrial and other enterprises that offer the potential to deliver long-term value to our investors" 1 2 Strategy Own high-quality underwriting franchises - - - Underwrite for profit Grow premiums only when market allows for profitable growth Consistently maintain appropriately prudent loss reserves Invest for total return when risk/reward is attractive 3 Acquire quality businesses at reasonable prices 4 LO 5 - Provide resources, support and oversight to help them grow revenues, profits and returns Maintain a conservative financial and operating risk profile Hold significant unrestricted liquidity for potential opportunities (and downturns) LO 5#6Capital Allocation by Operation Alleghany Capital 1% 2012 PCT Homesite 1% 1% Parent PacificComp 2% CapSpecialty 4% RSUI 21% marketable securities(2 10% Alleghany Capital 12% 2021 Kentucky Trailer. 1% Piedmont <1% PCT Concord 1% 1% Parent marketable securities 16% (2) IPS 1% Wilbert 2% TransRe 61% W&W AFCO Steel 3% Re/Insurance 89% ($ in millions) Stockholders' Equity 6,404 Alleghany Parent Debt(1) Total Capital 699 7,103 Jazwares 3% CapSpecialty. 4% RSUI 18% TransRe 50% Re/Insurance 72% ($ in millions) Stockholders' Equity Alleghany Parent Debt (1) Total Capital 9,187 1,679 $ 10,866 (1) Excludes TransRe senior notes that mature in 2039 and debt at Alleghany Capital. (2) Includes partnerships, Alleghany Capital parent, Alleghany Properties, and other miscellaneous holdings, net of deferred compensation and deferred taxes. 6#7BVPS Growth Over the Cycles Book Value Per Share Growth 9.4% 10.0% 9.0% 8.3% 8.0% 7.0% 7.5% 6.5% 6.0% 5.0% 4.0% 1-YR CAGR 3-YR CAGR 5-YR CAGR 10-YR CAGR $800 $700 $600 $500 $400 $300 Historical Book Value Per Share 8.3% BVPS CAGR since 1999 (1) $675.58 $200 $100 $- 1999 2001 2003 2005 2007 2009 2011 2013 2015 2017 2019 2021 ☐ Commentary Book value per share growth (including dividends) since 1999: 8.3% per year. Growth driven by a combination of underwriting and investment returns, and more recently earnings from Alleghany Capital, partially offset by financial crisis in 2008, significant catastrophe losses, particularly since 2016 and the Pandemic (2) in 2020. Since of end 2016, book value per share plus dividends has grown at a slower rate (about 6.5%). Slower rate of growth mostly due to elevated natural catastrophe and Pandemic loss activity. Since 2016, pre-tax losses of almost $3.0 billion from natural catastrophes and over $400 million related to the Pandemic, mostly in 2020. (1) Includes special dividends of $10.00 per share and $15.00 per share paid in 2018 and 2020, respectively, and assumes proceeds are reinvested in Alleghany book value. (2) The COVID-19 global pandemic is referred to herein as the "Pandemic." 7#8Components of Alleghany 2021 Growth in Book Value $ in millions Alleghany 2021 Growth in Book Value $ millions Net underwriting gain, before catastrophe losses Net current year catastrophe losses (1) Net underwriting gain, after catastrophe losses Alleghany Capital Common equities: Dividend income Net realized and unrealized gains A % 702 (548) 8.0% (6.2%) 154 1.8% 146 1.7% 64 0.7% 400 4.6% 464 5.3% Fixed income: Interest income 306 3.5% Net realized and unrealized gains (254) (2.9%) 52 0.6% Other invested assets Investments sub-total 71 0.8% 587 6.7% Sub-total Interest expense(2) Other net expenses(3) 887 10.2% (68) (0.8%) (95) (1.1%) Total growth in book value before capital transactions 724 8.3% (1) Net current year catastrophe losses are net of reinstatement premiums. (2) Excludes Alleghany Capital's interest expenses, which are included in Alleghany Capital's returns above. (3) Other, net includes corporate administration expenses, re/insurance subsidiary long-term incentive compensation expenses, Alleghany Properties, AIHL Re, and miscellaneous other income and expenses. 8#9Alleghany's Long-Term Book Value Growth Return on Operations (UW margin)x NPE SH Equity Return on Investments on Equities [(Requities) x (SH Equity) Return on Fixed income )] ACC equity fixed income SH Equity [(ACC RoE) SH Equity Interest expense SH Equity Other net expenses SH Equity Pre-tax gain in book value 1-Effective tax rate Book Value Growth 2021 Variables Return on Operations: NPE leverage of 77% Alleghany Capital accounts for approximately 15% of total stockholders' equity; ROE before taxes and after noncontrolling interest of approximately 16% Return on Investments: - Common equities as a percentage of stockholders' equity of 40%; Other invested assets of ~6% of stockholders' equity Fixed income leverage of 203%; book yield on fixed income portfolio of 2.2% at year- end Costs: Interest expense of 0.9% and other net expenses of approximately 1.3% of stockholders' equity ■ Taxes: Alleghany's effective tax rate in 2021 was 20%. UW margin = Underwriting margin NPE = Net premiums earned SH Equity = Stockholders' equity attributable to Alleghany stockholders ACC ROE = Alleghany Capital Corporation's RoE before taxes and after noncontrolling interest Equities = Common equities and other invested assets Fixed income = Debt securities, short-term investments, commercial mortgage loans and cash 9#10Illustrative BVPS Growth Sensitivity (excluding AOCI) ■ Assumes values for non-sensitized variables, except realized and unrealized gains on fixed income securities, are similar to 2021 ■ Assumes stable interest rates and no realized or unrealized gains (losses) on fixed income securities Normalized Combined Ratio Normalized Returns on Common Equity 100% 98% 96% 94% 92% 90% 88% 5% 5.7% 6.9% 8.1% 9.3% 10.5% 11.8% 13.0% 6% 5.9% 7.2% 8.4% 9.6% 10.8% 12.0% 13.3% 7% 6.2% 7.4% 8.6% 9.9% 11.1% 12.3% 13.5% 8% 6.5% 7.7% 8.9% 10.1% 11.4% 12.6% 13.8% 9% 6.8% 8.0% 9.2% 10.4% 11.6% 12.9% 14.1% 10% 7.0% 8.3% 9.5% 10.7% 11.9% 13.1% 14.4% 10#11I. Performance Highlights - 4Q and Full Year 2021#12Alleghany Consolidated Performance ($ in millions) Net Premiums Written Net Investment Income -10% +13% -3% +10% $7,149 $6,344 $1,696 $1,533 Combined Ratio 10 points 5 points 98.9% 102.1% 89.0% 97.2% $540 $491 $131 $127 4Q '20 4Q '21 FY '20 FY '21 4Q'20 4Q '21 FY '20 FY '21 4Q '20 4Q '21 FY '20 FY '21 $159 Net Earnings(1) +225% $516 Adjusted Earnings(1) +917% +164% $1,035 $102 BVPS Growth (2) 2 +172% points $619 $252 4.8% $228 4.5% $96 2.9% points 8.3% 4Q '20 4Q '21 FY '20 FY '21 4Q '20 4Q '21 FY '20 FY '21 4Q'20 4Q'21 FY '20 FY '21 Ex. AOCI: (1) Attributable to Alleghany stockholders. (2) Adjusted for $15/share dividend paid in March 2020. 2.0% 6.0% (2.3)% 12.5% 12#13Summary of 2021 Results ($ in millions) Income Statement 2020 2021 % Change Net Premiums Written $6,344 $7,149 13% Net Investment Income 491 540 10% Underwriting Profit (1) (129) 195 N/M Net Earnings(2) 102 1,035 917% Adjusted Earnings (1) 228 619 172% Alleghany Capital Adjusted Earnings Before Income 154 332 116% Taxes(1) Adjusted Diluted EPS(1) $15.89 $ 44.64 181% Balance Sheet As of 12/31/2020 As of 12/31/2021 % Change Invested Assets and Cash $20,978 $22,849 9% Total Assets 28,927 32,269 12% Book Value Per Share(2) $623.57 $675.58 8% Book Value Per Share ex AOCI(2) $ 591.35 $665.15 13% (1) (2) See Non-GAAP Financial Measures in appendix for full definitions. Attributable to Alleghany shareholders. " ■ Commentary Reinsurance net premiums written growth of 11.2% and Insurance net premiums growth of 17.5% - Excluding the non-renewed large whole account quota share treaty, Reinsurance net premiums written growth of 17.3% Increase in net investment income due to higher dividend and partnership income partially offset by reduced interest income TransRe combined ratio of 99.4%, RSUI combined ratio of 86.7% and CapSpecialty combined ratio of 99.4% Alleghany Capital 2021 revenue increased 51% to $3.7 billion from $2.5 billion; Alleghany Capital adjusted earnings before income taxes increased to $332 million vs. $154 million in 2020 ■ Book value per share at December 31, 2021 was $675.58, an increase of 8.3% from Q4 2020. Excluding AOCI, book value per share increased 12.5%. 13#14Underwriting Performance - 2021 Reinsurance Insurance Casualty & Property Specialty Total RSUI Cap Specialty Total Total Re/Insurance Loss ratio 84.5% 62.3% 69.2% 65.5% 61.0% 64.4% 68.1% Expense ratio 28.1% 31.2% 30.2% 21.2% 38.4% 25.4% 29.1% Combined ratio 112.6% 93.5% 99.4% 86.7% 99.4% 89.8% 97.2% Change vs the prior year (0.1%) (6.3%) (4.2%) (8.9%) (2.3%) (7.4%) (4.9%) Catastrophe activity & prior year development: Current year catastrophe losses 30.7% 0.6% 10.0% 15.4% 0.6% 11.8% 10.4% Net (favorable) unfavorable development in prior year loss (1.4%) (6.0%) (4.5%) (0.5%) 1.5% 0.0% (3.5%) reserves Combined ratio excluding catastrophe losses and prior 83.3% 98.9% 93.9% 71.8% 97.3% 78.0% 90.3% year development Change vs the prior year (2.3%) (1.4%) (2.0%) (2.3%) (3.2%) (2.8%) (2.1%) 14#15Reported Underwriting Profit (Combined Ratio Points) Catastrophe Losses (Combined Ratio Points) Pre-catastrophe Underwriting Profit (Combined Ratio Points) Improved Underwriting Results ($ in millions) 81.5% 86.5% 86.6% 87.5% 87.4% 89.9% 90.0% 92.1% 88.7% +5 points since 2019 86.8% 2012 2013 2014 2015 2016 2017 2018 2019 2020 2021 $ 690 $ 572 $ 591 $ 529 627 $ 502 $ 497 433 $ 673 $ 932 2012 2013 2014 2015 2016 2017 2018 (1) 2019 2020 2021 2.2% 1.5% 3.6% 4.5% 7.3% 10.4% 12.6% 13.2% 13.4% 16.5% $ 470 151 95 $ 62 226 $ 818 $ 658 $ 400 $ 802 $ 737 88.8% 90.1% 89.0% 91.9% 94.1% 97.2% 99.4% 102.1% 103.2% 106.4% 2012 2013 $ 220 421 2014 $ 495 2015 2016 2017 2018 2019 2020 2021 $ 467 $ 401 $ (316) $ (162) 33 $ (129) 195 Note: Underwriting profit and pre-catastrophe underwriting profit are non-GAAP financial measures. Refer to the appendix for further information. 1) Shaded region reflects $415 million, or 6.9 combined ratio points, of 2020 current year catastrophe losses attributable to the Pandemic. 15#16(1) (2) Summary of 4Q 2021 Results ($ in millions) Income Statement 4Q 2020 4Q 2021 % Change Net Premiums Written $1,696 $1,533 -10% Net Investment Income 131 127 -3% Underwriting Profit(¹) 17 205 1,143% Net Earnings (2) 159 516 225% Adjusted Earnings (1) 96 252 164% Alleghany Capital Adjusted Earnings Before Income 77 111 44% Taxes(1) Adjusted Diluted EPS(1) $6.77 $18.46 173% See Non-GAAP Financial Measures in appendix for full definitions. Attributable to Alleghany shareholders. " ■ ■ Commentary Insurance net premiums written growth of 12.9% and Reinsurance premium decline of 16.8% (due to the termination of a certain large whole account quota share treaty) Excluding the non-renewed large whole account quota share treaty, Reinsurance net premiums written growth of 9.6% Decrease in net investment income due to lower interest income and partnership income partially offset by higher dividend income TransRe combined ratio of 90.8%, RSUI combined ratio of 78.1% Alleghany Capital Q4 2021 revenue increased 46% to $1.2 billion from $823 million; Alleghany Capital adjusted earnings before income taxes increased to $111 million vs. $77 million in 4Q 2020 Book value per share at December 31, 2021 was $675.58, an increase of 8.3% from Q4 2020. Excluding AOCI, book value per share increased 12.5%. 16#17Underwriting Performance – 4Q 2021 Reinsurance Insurance Property Casualty & Specialty Total RSUI Cap Specialty Total Total Re/Insurance Loss ratio 55.6% 62.8% 60.7% 57.2% 62.2% 58.3% 60.1% Expense ratio 29.0% 30.6% 30.1% 20.9% 37.6% 24.8% 28.9% Combined ratio 84.6% 93.4% 90.8% 78.1% 99.8% 83.1% 89.0% Change vs the prior year (31.7%) (4.0%) (12.1%) (3.5%) 0.0% (3.1%) (9.9%) Catastrophe activity & prior year development: Current year catastrophe losses 12.0% (0.4%) 3.3% 1.0% 0.3% 0.9% 2.7% Net (favorable) unfavorable development in prior year loss (4.1%) (4.4%) (4.3%) 3.8% reserves 3.3% 3.7% (2.5%) Combined ratio excluding catastrophe losses and prior 76.7% 98.2% 91.8% 73.3% 96.2% 78.5% 88.8% year development Change vs the prior year (4.2%) (2.5%) (3.2%) 1.0% (5.3%) (1.2%) (2.6%) 17#18II. Re/Insurance Operations#19Current Re/Insurance Operations TransRe RSU Acquisition Date: March 6, 2012 July 1, 2003 January 1, 2002 CapSpecialty A Community of Insurance Specialists AC Total Re/Insurance Years Held: ~10 years ~19 years ~20 years ($ in millions) Cumulative Results Over Holding Period Underwriting Profits (Losses) $878 $1,984 ($58) $2,804 Combined Ratio 97.7% 85.6% 101.4% 95.0% Net Premiums Written $39,362 $14,506 $4,305 $58,172 Internal Rate of Return 9.3% 11.7% 5.2% 9.8% Net Dividends $2,081 $1,524 $130 $3,736 Net Cash Invested $1,431 ($896) $112 $647 (1) Cash & Investments $15,209 $4,577 $1,089 $20,892 Investment Leverage 2.8x 2.4x 2.6x 2.7x (1) Shareholders' Equity $5,398 $1,925 $423 $7,769 Note: As of December 31, 2021. (1) Includes AIHL Re. 19#20TransRe Net Premiums Written (FY 2021) Engineering Aviation 1% Marine & 2% Energy 4% Other Specialty 2% Personal Auto / Motor Guaranty 5% 8% A&H 6% Catastrophe Property Property 28% 7% Traditional Casualty 20% Other Property 21% Professional Liability 24% Casualty and $4.9 billion(1) Specialty 72% ☐ Business Overview Market-leading, diversified and global Professional and Casualty reinsurer Long-term relationships with all top tier insurance companies In-force portfolio 75%+ proportional, benefitting more directly from primary market improvements Leads or co-leads more than half of its book Reducing net property catastrophe exposure; more than 30% reduction in predominantly European notional limits at January 1, 2022 renewals FY 2021 Highlights Net premiums written up 11.2%; excluding non-renewed large whole account quota share up 17.3% Underwriting profit of $29 million Combined ratio of 99.4%; ex-catastrophe combined ratio of 89.4% Q4 2021 Underwriting profit of $132 million and combined ratio of 90.8%; strong momentum going into 2022 Taking Advantage of Leading Position in Attractive Casualty Segment; Focused on Reducing Net Property Catastrophe Exposure (1) Excludes a certain large whole account quota share treaty which contributed $496 million to 2021 net premiums written. 20#21TransRe-Renewal Rate Change Estimates Remain Strong Total Currently Estimated Rate Change (1) (%) All Lines: 3% 4% 5% 3% 3% 2% 2018 12% 7% 13% 21% 20% 9% 8% 6% 3% 2019 Underwriting Year ■Traditional Casualty ■ Professional Liability ■ Other Property 12% 8% 7% 2020 14% 14% 10% 10% 9% 6% 2021 ■Catastrophe Property ■ Other (2) Note: Based on data received from cedents as of December 31, 2021. Data excludes a certain large whole account quota share treaty. (1) Estimated primary rate changes plus reinsurance rate changes on excess of loss treaties for the respective treaty year for all renewal treaties globally. Pro rata treaty rate change data based on intermittently provided data from cedents and therefore reflected here with an estimated 6-month lag. (2) Includes personal auto and various specialty lines. 21#22RSUI Underwriting Profit (Cumulative data for 2H 2003 - FY 2021 period) Alternative Structures 1% Property 49% D&O Liability 9% Professional Liability 20% Umbrella / Excess 15% General Liability 6% Cumulative Underwriting Profit: $2.0 billion Business Overview 30+ years dedicated exclusively to wholesale specialty insurance market Proven ability to generate underwriting profit and grow book value through cycles Highly experienced underwriters Nimble and reacts quickly to opportunities Proprietary, in-house developed technology, models and analytical tools Diversified profitable portfolio FY 2021 Highlights Net premiums written up 20.4% Combined ratio of 86.7% Underwriting profit of $164mm Continuing to Take Advantage of Strong E&S Market Opportunities 22#23RSUI - Continued Strong Rate Increases Renewal Rate Change (%) 2% 9% 8% 6% 4% 5% 5% 3% 3% -1% 16% 18% 20% 15% 15% 13% 12% 11% 4% 4% 2018 2019 2020 2021 ■Management Liability (D&O) ■Professional Liability ■General Liability ■Umbrella / Excess ■Property 23#24CapSpecialty Gross Premiums Written (FY 2021) Surety 13% Binding Authority 11% Excess Casualty 7% Professional Liability 23% Specialty Casualty 26% $475 million Healthcare 20% ◉ Business Overview Well-diversified specialty company Focused on small and mid-size businesses Recognized experts in select classes Select distribution Current focus on profitable growth, expense management & technology optimization Exited certain unprofitable lines of business and producer relationships (Property, Binding Authority) FY 2021 Highlights Gross premiums written up 15.5% Combined ratio of 99.4%; 1.6 pts. improvement in expense ratio Fifth consecutive quarter with underwriting profit Focused on Excess and Surplus Lines Casualty Business for Small and Mid-Sized Businesses 24#25CapSpecialty - Achieving Significant Renewal Rate Increases -1% Renewal Rate Change (%) 2% 10% 14% 2018 2019 2020 2021 All Lines (Ex Surety) 45 25#26III. Alleghany Capital#27Alleghany Capital – A Significant Earnings Contributor Strategy Long-term owner and capital provider to leading non- financial businesses Alleghany Capital Revenue (1) (2021) (2) Kentucky. Trailer Concord 4% 3% Piedmont PCT 1% • Partner with entrepreneurial management teams / founders with high integrity, aligned through meaningful ownership interests 6% Wilbert 7% W&W AFCO Steel 28% IPS 24% Jazwares 27% W&W AFCO Steel and Jazwares each generated revenues in excess of $1.0 billion ☐ Acquire market leaders in niche markets, or rapid share gainers in large fragmented markets Accelerate operational efficiency improvements; follow-on capital for growth / add-on acquisitions $3.7 billion 2021 Acquisitions Acquisition: Piedmont Manufacturing Group New Platform May Linesight October MEMORIAL -MONUMENTS- December Acquirer: Alleghany Capital ips $341 million (3) of capital deployed in 2021 Relates to Alleghany Capital product and service revenues. Revenues from May 10, 2021 to December 31, 2021. (1) (2) (3) Equity and debt deployed. Wilbert Commemorating Life with Respect" 27#28Alleghany Capital – Generating Strong Growth ($ in millions) Revenue(1) Adjusted Earnings Before Tax $897 $678 $1,575 $2,289 $2,477 $3,736 $154 $143 $83 $50 $33 $332 2016 2017 2018 2019 2020 2021 2016 2017 2018 2019 2020 2021 Return on Equity(2) 12.3% 8.3% 8.8% 6.0% 4.6% 3.5% 2016 2017 2018 2019 2020 2021 (1) Relates to Alleghany Capital Products and Services revenue. Cash Dividends $27 $19 $20 $82 $61 $133 2016 2017 2018 2019 2020 2021 (2) Return on equity equals Alleghany's share of adjusted earnings / Alleghany Capital's average equity. 28#29(1) Alleghany Capital - FY 2021 Business Updates Company/ Acquired Revenue (¹) / % Owned FY 2021 Business Update W&W | AFCO STEEL 2017 $ 1,038 80% $ 1,028 Jazwares 2016 76% ips $ 886 82% 2015 ◉ ◉ W&W AFCO Steel achieved over $1.0 billion in revenue in 2021 for the first time in its history as revenue increased 31% YoY due to 40% increase in fabrication revenue W&W AFCO Steel's revenue backlog has more than doubled since December 2020 ■ The significant increase in backlog since year-end 2020 was driven by strong new project wins in the infrastructure and technology sectors For the first time in its 24-year history, Jazwares achieved over $1.0 billion in revenue for FY 2021 (vs. $514.5 million in 2020) making it now the #7 largest US toy manufacturer ■ The 100% revenue increase reflects strong demand across multiple products as it gained significant market share with its 3 largest customers (Wal-Mart, Target, and Amazon) ■ Profit margins were slightly impacted by product mix and higher shipping and logistics costs as ocean freight rates increased 2x-5x 2020 prices driven by tight supply chain capacity ◉ ◉ Gross revenue increased 43% YoY driven partially by the acquisition of Linesight On 10/18/2021, IPS acquired Linesight, a Dublin, Ireland-based global consultancy firm providing cost and project management, project controls, risk, scheduling, and procurement services for clients in the data center, technology, and life sciences sectors Project pipeline remains strong with many Pandemic related engineering and construction assignments ongoing FY 2021 Alleghany Capital product and service revenues. Revenues are on 100% basis in $ millions. 29#30(1) (2) Alleghany Capital - FY 2021 Business Updates (continued) Company / Acquired Wilbert Commemorating Life with Respect Revenue (1) / % Owned ■ $261 100% FY 2021 Business Update Despite a tapering of COVID-related demand, revenue increased 45% vs. 2020 ■ Wilbert closed on the acquisition of 100.0% of Memorial Monuments on December 29th 2017 KT KENTUCKY TRAILER 2013 CONCORD HOSPITALITY -ENTERPRISES 2018 $234 78% $ 160 85% Piedmont $103(2) Manufacturing Group 100% 2018 PRECISION CUTTING $39 TECHNOLOGIES 100% 2012 " ◉ ◉ ◉ • Revenue up 13% YoY driven by higher demand for furniture vans and truck bodies, and growth in Europe KT's revenue backlog was at an all-time high in December 2021, more than double the backlog at year end December 2020 Concord's operating performance continues to be impacted by Pandemic-related industry pressure, but recent occupancy and daily rates are trending up 2021 revenue increased 29% as the number of revenue generating hotels increased to 136 from 124 at year-end 2020 On May 10, 2021, Alleghany Capital, through a newly formed subsidiary, Piedmont Manufacturing Group, acquired 100% of Wilbert Plastic Services in a new platform acquisition Piedmont provides injection molded and thermoformed parts and assemblies for leading original equipment manufacturers in a variety of markets Revenue declined 2% vs. 2020 driven largely by declines in Bourn & Koch machine revenue and CID Performance Tooling parts revenue which was negatively impacted by Pandemic-related weakness in the aerospace sector, slightly offset by an increase in Supermill parts revenue ■ Backlog was more than double the prior year FY 2021 Alleghany Capital product and service revenues. Revenues are on 100% basis in $ millions. From May 10, 2021 through December 31, 2021. 30#31IV. Investments#32Investments Are a Significant Part of Our Earnings Power Other Invested Assets 3% Commercial Mortgage Loans 2% Cash & Short-term 9% Portfolio Allocation Equity Securities 16% Debt Securities 70% Avg. Credit 2.60x Quality of Debt Securities: AA- Investment Leverage(1) 2.42x 2.41x 2.36x 2.31x T 2.49x 2.40x 2.29X T 5.3% Total: $22.8 billion 2014 2015 2016 2017 2018 2019 2020 2021 Investment Results Pre-Tax 7.1% 9.3% 2.5% 2.5% 1.0% 2.6% 2.5% 2.8% 3.2% 3.5% 3.5% 2.7% 2.5% 0.1% 2014 2015 2016 2017 Financial statement return on average invested assets 2018 2019 2.8% 2020 2021 Investment book yield (1) Investment leverage is cash and investments / shareholders' equity. (2) Includes net investment income, net realized gains (losses), changes in allowance for credit losses on available for sale securities, change in fair value of equities and change in net unrealized gains (losses) on debt securities. 32#33Investment Return Components (Pre-Tax) ($ in millions) $1,002 $1,719 $485 $1,306 $129 $731 $710 $682 $507 $307 $70 $307 $636 $25 $176 $465 $10 $211 $28 $80 $90 $18 $460 $439 $439 $451 $501 $550 ($5) ($20) ($185) ($229) ($158) ($257) 2014 2015 2016 $491 $540 ($5) ($26) ($111) ($386) 2017 2018 2019 2020 2021 ■Change in unrealized gains (losses) - fixed income ■Change in the fair value of equity securities ■Net realized gains (losses), net of change in allowance for credit losses on available for sale securities ■Net investment income 33 33#34V. Opportunities and Challenges#35Opportunities and Challenges 1 Opportunities Re/insurance subsidiaries well-positioned for profitable growth - Reinsurance market continues to improve Opportunities continue to be strong, especially in casualty and professional liability lines 1 3 70% of TransRe's business is proportional, which will benefit from primary rate increases with a lag 4 3 E&S market opportunity remains significant; RSUI and CapSpecialty continuing to capitalize on opportunity 5 4 5 Continuing rate increases and robust new business; tempered by signs of increasing competition Strong backlogs and order books at Alleghany Capital; improved platform and bolt-on acquisition opportunities Higher rates ease the recent downward pressure on investment income Challenges Impact of potential inflation on asset values Increasing loss costs / inflation in casualty lines Book value (mark-to-market declines in values of bonds held) impact of higher rates Geopolitical and economic uncertainty (e.g. Russia-Ukraine conflict, tax reform) Supply chain and labor market challenges at Alleghany Capital 35#36Key Takeaways ✓ Leading franchise across global reinsurance and specialty insurance ✓ Long-term focus with track record of disciplined underwriting and risk management through insurance and investment cycles • Improving underwriting performance at TransRe driven by attractive rate environment and deliberate portfolio actions RSUI and CapSpecialty capitalizing on attractive E&S market Alleghany Capital is a meaningful contributor to earnings with double-digit return on equity ✓Conservative financial profile and strong capitalization ✔Holding company conservatively capitalized with significant liquidity allowing us to support subsidiaries, manage through downturns, and respond to opportunities ✓ Demonstrated investment capability and performance 36#37Appendix: Company Overview#38A Long History of Investing in Successful Companies • Alleghany holding company formed Nickel Plate, Chesapeake & Ohio, Erie and Pere Marquette Railroads (merged into Penn Central in 1968) Jones Motor Company (sold in 1982) Chicago Title (spun off in 1998/1999) World Minerals (sold in 2005) Alleghany Asset Management (sold to ABN Amro in 2001) 1929 1946 1949 1968 1974 1985 1986 1991 1993 1995 New York Investors MSL Shelby Central Diversified Industries Railroad Services ("IDS") Insurance (sold in 1991) (merged into (sold to Underwriters Reinsurance Company (sold to Swiss Re in 2000) Penn Central in American 1968) Express in 1984) CapSpecialty PacificComp (sold to Copper Point in 2017) TransRe PRECISION CUTTING TECHNOLOGIES jazwares Anew dimension of play W&W | AFCO STEEL Wilbert Commemorating Life with Respect" I Piedmont Manufacturing Group 2002 2003 2007 2008 2012 2013 2014 2015 2017 2018 2021 RSUI Darwin Underwriters established (IPO in 2006 and sold in 2008) Alleghany Capital Corporation KT ips CONCORD HOSPITALITY -ENTERPRISES- KENTUCKY TRAILER Legacy Alleghany Logo Current Alleghany 38#39Strong Leadership Reinsurance Best-in-class, experienced subsidiary leadership Insurance Private Equity TransRe RSLI Kenneth Brandt Phillip McCrorie CapSpecialty A Community of Insurance Specialists Alleghany Capital Jack Sennott David Van Geyzel Udi Toledano ■ President and Chief Executive Officer since May 2021 ■ Joined TransRe in 2006 ■ Chief Executive Officer since January 2022 ■ Joined RSUI in October 2003 Chairman, Chief Executive Officer and President since July 2019 Joined CapSpecialty in July 2019 ■ President and Chief Executive Officer since July 2013 ■ Joined Alleghany in 2007 ■ Chairman since July 2013 ■ Joined Alleghany in 2013 39#40Modest Financial Leverage and Conservative Risk Profile Debt to Capital Holding Company Liquidity(1) ■Other Debt (ACC) ■Senior Notes (millions) 23.1% 19.2% 17.5% $1,687 $1,383 $1,283 $1,122 $1,124 16.3% 14.7% 2017 2018 2019 2020 2021 2017 Peak Zone PML(2) / Shareholders' Equity(3) 2018 2019 2020 2021 Risk Assets(4) / Shareholders' Equity(3) 8.0 % 7.6% 0.58 x 6.3% 7.0% 0.53 X 0.39 x 0.39 x 2018 2019 2020 2021 2018 2019 2020 2021 (1) Holding company liquidity comprised of marketable securities and cash. (2) Reflects net occurrence probable maximum loss ("PML") (after-tax) in a 1-in-250 year event (having a likelihood of being exceeded in any single year of 0.4 percent) for largest single zone peril (e.g. Northeast U.S. Wind for 4Q '21). Attributable to Alleghany shareholders. བྱས་ཆུ་ (3) (4) Risk assets are defined as high yield bonds, below investment grade collateralized loan obligations and bank loans, publicly traded equity securities, private equity and partnership interests. 40#41Non-GAAP Financial Measures This document contains non-GAAP financial measures. Reconciliations of these non-GAAP financial measures to the most direct comparable GAAP measures and related information are provided in our financial supplement and Form 10-K and 10-Q filings, which are available on our website at www.alleghany.com. Adjusted Earnings (And Adjusted Earnings Per Share And Adjusted Return On Average Stockholders' Equity) Adjusted earnings (including in adjusted return on average stockholders' equity) and adjusted earnings per share exclude (on an after-tax basis): (i) change in the fair value of equity securities; (ii) net realized capital gains; (iii) change in allowance for credit losses for available on sale securities; (iv) amortization of intangible assets; and (v) gain on bargain purchase, all as determined in accordance with GAAP. Alleghany uses adjusted earnings and adjusted earnings per share as a supplement to net earnings attributable to Alleghany stockholders and earnings per share, respectively, the most comparable GAAP financial measures, to provide useful additional information to investors by highlighting net earnings and earnings per share attributable to its performance excluding change in the fair value of equity securities, realized capital gains or losses, change in allowance for credit losses on available for sale securities, amortization of intangible assets and gain on bargain purchase. A reconciliation of adjusted earnings and adjusted earnings per share to net earnings attributable to Alleghany stockholders and earnings per share, respectively, is presented within "Adjusted Earnings Reconciliation" on pages 37 and 38 of the Q4 2021 Financial Supplement. Adjusted Earnings Before Income Taxes Adjusted earnings before income taxes represents product and service revenues and net investment income less other operating expenses and interest expense, and does not include: (i) change in the fair value of equity securities; (ii) net realized capital gains; (iii) change in allowance for credit losses on available for sale securities; and (iv) amortization of intangible assets. Because adjusted earnings before income taxes excludes income taxes, change in the fair value of equity securities, net realized capital gains, change in allowance for credit losses on available for sale securities and amortization of intangible assets, it provides an indication of economic performance that is not affected by investment activity, levels of amortization resulting from acquisition accounting or effective tax rates. Alleghany uses adjusted earnings before income taxes as a supplement to earnings before income taxes, the most comparable GAAP financial measure, to evaluate the performance of certain of its noninsurance operating subsidiaries and investments. A reconciliation of adjusted earnings before income taxes to earnings before income taxes is presented on page 23 of the Q4 2021 Financial Supplement. 41#42Non-GAAP Financial Measures (continued) Underwriting Profit Underwriting profit represents net premiums earned less net loss and LAE and commissions, brokerage and other underwriting expenses, all as determined in accordance with GAAP, and does not include: (i) net investment income; (ii) change in the fair value of equity securities; (iii) net realized capital gains; (iv) change in allowance for credit losses on available for sale securities; (v) product and service revenues; (vi) other operating expenses; (vii) corporate administration; (viii) amortization of intangible assets; and (ix) interest expense. Alleghany uses underwriting profit as a supplement to earnings before income taxes, the most comparable GAAP financial measure, to evaluate the performance of its reinsurance and insurance segments and believes that underwriting profit provides useful additional information to investors because it highlights net earnings attributable to Alleghany's reinsurance and insurance segment's underwriting performance. Earnings before income taxes may show a profit despite an underlying underwriting loss, and when underwriting losses persist over extended periods, a reinsurance or an insurance company's ability to continue as an ongoing concern may be at risk. A reconciliation of underwriting profit to earnings before income taxes is presented within "Earnings by Segment" on page 11 through 12 of the Q4 2021 Financial Supplement. Book Value Per Share Excluding Accumulated Other Comprehensive Income ("BVPS ex-AOCI") BVPS ex-AOCI is calculated by dividing: (i) stockholders' equity attributable to Alleghany stockholders less AOCI, all as determined in accordance with GAAP, by (ii) shares outstanding. Alleghany uses BVPS ex-AOCI as a supplement to BVPS, the most comparable GAAP financial measure, in order to better disclose its per share performance by excluding the effects of AOCI, which include the effect of changes in interest rates and credit spreads on its debt securities portfolio, among others. A reconciliation of BVPS to BVPS ex-AOCI is presented within "Book Value Per Share" on page 39 of the Q4 2021 Financial Supplement. 42