ALLEGHANY CORPORATION AND SUBSIDIARIES FINANCIAL SUPPLEMENT

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1 Alleghany FINANCIAL SUPPLEMENT Three Months Ended and Twelve Months Ended December 31, 2018 (Unaudited) Investor Contact: Kerry Jacobs Phone: (212) This report is for informational purposes only. It should be read in conjunction with documents filed by Alleghany Corporation with the U.S. Securities and Exchange Commission, including the company's Annual Reports on Form 10-K and Quarterly Reports on Form 10-Q. PAGE 1

2 Forward-Looking Statements Certain statements contained in this Financial Supplement may be deemed to be forward-looking statements within the meaning of the Private Securities Litigation Reform Act of Forward-looking statements may be identified by the use of words such as may, will, expect, project, estimate, anticipate, plan, believe, potential, should or the negative versions of those words or other comparable words. Forward-looking statements do not relate solely to historical or current facts, rather they are based on management s expectations as well as certain assumptions and estimates made by, and information available to, management at the time. These statements are not guarantees of future performance. These forward-looking statements are based upon Alleghany s current expectations and are subject to a number of uncertainties and risks that could significantly affect current plans, anticipated actions and Alleghany s future financial condition and results. Factors that could cause these forward-looking statements to differ, possibly materially, from that currently contemplated include: significant weather-related or other natural or man-made catastrophes and disasters; the cyclical nature of the property and casualty reinsurance and insurance industries; changes in market prices of Alleghany's significant equity investments and changes in value of Alleghany's debt securities portfolio; adverse loss development for events insured by Alleghany's reinsurance and insurance subsidiaries in either the current year or prior years; the long-tail and potentially volatile nature of certain casualty lines of business written by Alleghany's reinsurance and insurance subsidiaries; the cost and availability of reinsurance; the reliance by Alleghany's reinsurance and insurance operating subsidiaries on a limited number of brokers; legal, political, judicial and regulatory changes; increases in the levels of risk retention by Alleghany's reinsurance and insurance subsidiaries; changes in the ratings assigned to Alleghany's reinsurance and insurance subsidiaries; claims development and the process of estimating reserves; exposure to terrorist acts and acts of war; the willingness and ability of Alleghany's reinsurance and insurance subsidiaries' reinsurers to pay reinsurance recoverables owed to Alleghany's reinsurance and insurance subsidiaries; the uncertain nature of damage theories and loss amounts; the loss of key personnel of Alleghany's reinsurance or insurance operating subsidiaries; fluctuation in foreign currency exchange rates; the failure to comply with the restrictive covenants contained in the agreements governing Alleghany's indebtedness; the ability to make payments on, or repay or refinance, Alleghany's debt; risks inherent in international operations; and difficult and volatile conditions in the global market. Additional risks and uncertainties include general economic and political conditions, including the effects of a prolonged U.S. or global economic downturn or recession; changes in costs; variations in political, economic or other factors; risks relating to conducting operations in a competitive environment; effects of acquisition and disposition activities, inflation rates, or recessionary or expansive trends; changes in interest rates; extended labor disruptions, civil unrest, or other external factors over which we have no control; changes in our plans, strategies, objectives, expectations, or intentions, which may happen at any time at our discretion; and other factors discussed in Alleghany s most recent Annual Report on Form 10-K and subsequent filings with the Securities and Exchange Commission, or the SEC. All forward-looking statements speak only as of the date they are made and are based on information available at that time. Alleghany does not undertake any obligation to update or revise any forward-looking statements to reflect subsequent circumstances or events. PAGE 2

3 FINANCIAL SUPPLEMENT TABLE OF CONTENTS Page I. FINANCIAL SUMMARY 10 Year Financial Summary 5 Historical Growth in Book Value per Share 6 Consolidated Financial Highlights 7 II. III. IV. CONSOLIDATED RESULTS Consolidated Statements of Earnings - Consecutive Quarters 8 Consolidated Statements of Earnings - Year to Date 9 Premiums Written 10 SEGMENT RESULTS Consolidated Underwriting Results - Current Quarter 11 Consolidated Underwriting Results - Prior Year Quarter 12 Consolidated Underwriting Results - Current Year to Date 13 Consolidated Underwriting Results - Prior Year to Date 14 Alleghany Capital Results - Quarter to Date 15 Alleghany Capital Results - Year to Date 16 BALANCE SHEET DETAILS Condensed Consolidating Balance Sheets 17 Condensed Consolidating Balance Sheets - Alleghany Capital 18 Consolidated Total Investment Portfolio 19 Debt Securities Portfolio Credit Quality 20 Net Investment Income 21 Financial Statement Portfolio Return 22 Annualized Investment Book Yield 23 Loss and Loss Adjustment Expenses (LAE) 24 Capital Structure and Leverage Ratios 25 V. OTHER Share Repurchase Detail 26 Basic and Diluted Earnings per Share Information - Consecutive Quarters 27 Basic and Diluted Earnings per Share Information - Year to Date 28 Return on Average Stockholders' Equity - Consecutive Quarters 29 Return on Average Stockholders' Equity - Year to Date 30 Book Value per Share 31 Consolidated Changes in Stockholders' Equity 32 Catastrophe Exposure 33 Non-GAAP Financial Measures 34 Operating Earnings Reconciliation 35 Energy-Related Holdings 36 Alleghany Capital Noninsurance Revenue 37 Alleghany Capital Condensed Consolidating Statements of Cash Flows 38 PAGE 3

4 BASIS OF PRESENTATION Presentation All financial information contained herein is unaudited. Certain amounts may not reconcile exactly due to rounding differences. Unless otherwise noted, all data is in millions of U.S. dollars, except for share, per share, percentage and ratio information. Definitions References in this financial supplement (the "Financial Supplement") to the "Company," "Alleghany," "we," "us," and "our" refer to Alleghany Corporation and its consolidated subsidiaries unless the context otherwise requires. In addition, unless the context otherwise requires, references to, "TransRe" are to our wholly-owned reinsurance holding company subsidiary Transatlantic Holdings, Inc. and its subsidiaries; "AIHL" are to our wholly-owned insurance holding company subsidiary Alleghany Insurance Holdings LLC; "RSUI" are to our wholly-owned subsidiary RSUI Group, Inc. and its subsidiaries; "CapSpecialty" are to our wholly-owned subsidiary CapSpecialty, Inc. and its subsidiaries; "PacificComp" are to our former wholly-owned subsidiary Pacific Compensation Corporation and its subsidiary, which were sold on December 31, 2017; AIHL Re are to our wholly-owned subsidiary AIHL Re LLC; "Roundwood" are to our wholly-owned subsidiary Roundwood Asset Management LLC; SORC are to our wholly-owned subsidiary Stranded Oil Resources Corporation and its subsidiaries; Alleghany Capital are to our wholly-owned subsidiary Alleghany Capital Corporation and its subsidiaries; Bourn & Koch are to our majority-owned subsidiary Bourn & Koch, Inc. and its subsidiary; "Kentucky Trailer are to our majority-owned subsidiary R.C. Tway Company, LLC and its subsidiaries; IPS are to our majority-owned subsidiary IPS-Integrated Project Services, LLC and its subsidiaries; Jazwares are to our majority-owned subsidiary Jazwares, LLC and its subsidiaries and affiliates; W&W AFCO Steel are to our majority-owned subsidiary WWSC Holdings, LLC and its subsidiaries; Concord are to our majority-owned subsidiary CHECO Holdings, LLC and its subsidiaries; and Alleghany Properties are to our wholly-owned subsidiary Alleghany Properties Holdings LLC and its subsidiaries. PAGE 4

5 10 YEAR FINANCIAL SUMMARY (1) (in millions, except per share data) Cash and invested assets $ 4,447.2 $ 4,881.9 $ 4,911.6 $ 18,976.4 $ 19,490.5 $ 19,440.6 $ 18,307.7 $ 18,705.3 $ 19,639.1 $ 18,561.9 Net loss and loss adjustment expense reserves 1, , , , , , , , , ,392.9 All debt and preferred stock , , , , , , ,669.0 Common Stockholders' Equity ("CSE") attributable to Alleghany stockholders (2) 2, , , , , , , , , ,692.7 Common shares outstanding Net invested assets per share $ $ $ $ 1, $ 1, $ 1, $ 1, $ 1, $ 1, $ 1, Percent increase (decrease) 6.0% 6.2% 5.2% 88.5% 3.8% 4.2% (1.1%) 2.9% 5.5% (1.8%) Book value per common share (2) $ $ $ $ $ $ $ $ $ $ Percent increase (decrease) 10.3% 10.4% 5.2% 10.8% 8.9% 12.7% 4.4% 6.0% 7.4% (4.6%) Net premiums written $ $ $ $ 3,723.9 $ 4,287.4 $ 4,497.5 $ 4,489.2 $ 5,091.8 $ 4,965.9 $ 5,048.4 Change in unearned premiums (27.1) 9.1 (48.2) (86.9) (258.9) (116.0) (10.9) (72.2) Net premiums earned $ $ $ $ 3,733.0 $ 4,239.2 $ 4,410.6 $ 4,230.3 $ 4,975.8 $ 4,955.0 $ 4,976.2 Underwriting profit (loss) $ $ $ 49.5 $ $ $ $ $ $ (316.4) $ (161.5) Net investment income Net realized capital gains (3) net of other than temporary impairment losses (233.5) Total investment results $ $ $ $ $ $ $ $ $ $ Net earnings attributable to Alleghany stockholders Special dividend (2) (154.0) Other changes in CSE (7.2) (126.5) 2,775.9 (108.4) (129.6) (479.0) (71.7) (706.9) Increase (decrease) in CSE $ $ $ 16.8 $ 3,478.1 $ $ $ 81.3 $ $ $ (821.4) Combined Ratio 84.7% 83.0% 93.4% 94.1% 90.1% 88.8% 89.0% 91.9% 106.4% 103.2% (1) Amounts have been adjusted for subsequent common stock dividends. (2) 2018 amount reflects a reduction of $154.0 million ($10 per share) related to the payment of a special dividend on March 15, (3) Includes changes in fair value of equity securities commencing in the first quarter of See Note 1(r) to Notes to Consolidated Financial Statements set forth in Part I, Item II, Item 8, Financial Statements and Supplementary Data of Alleghany s Report on Form 10-K for the year ended December 31, 2018 for additional information regarding the adoption of certain new investment accounting guidance. PAGE 5

6 HISTORICAL GROWTH IN BOOK VALUE PER SHARE Growth in Book Value Per Share Annual Growth: As of Year-End Book Annual Y Stock BVPS vs Y Stock Value Per Year 1Q 2Q 3Q 4Q BVPS Price S&P 500 S&P 500 Price Share % 0.9% (3.3%) 1.7% 0.2% (5.9%) (22.1%) 22.3% $ $ x % 3.8% 1.3% 6.4% 11.9% 27.9% 28.7% (16.7%) x % 3.7% (1.3%) 6.0% 12.0% 30.8% 10.9% 1.1% x % 0.6% (1.9%) 3.2% 4.3% 1.6% 4.9% (0.6%) x % 2.3% 2.8% 3.6% 14.8% 30.6% 15.8% (1.0%) x % 3.8% 3.9% 2.9% 15.2% 12.8% 5.5% 9.7% x % 2.1% (6.7%) (1.8%) (5.0%) (28.4%) (37.0%) 32.0% x 2009 (0.3%) 2.7% 5.2% 2.4% 10.3% (0.2%) 26.5% (16.2%) x % (0.2%) 3.9% 4.0% 10.4% 13.2% 15.1% (4.7%) x % (0.3%) (4.0%) 4.5% 5.2% (5.0%) 2.1% 3.1% x % 1.6% 4.8% (2.5%) 10.8% 17.6% 16.0% (5.2%) x % (1.8%) 3.4% 3.1% 8.9% 19.2% 32.4% (23.5%) x % 4.8% 1.0% 2.1% 12.7% 15.9% 13.7% (1.0%) x % 0.3% (0.5%) 2.1% 4.4% 3.1% 1.4% 3.0% x % 1.9% 2.4% (1.9%) 6.0% 27.2% 12.0% (6.0%) x % 3.1% (2.7%) 3.9% 7.4% (2.0%) 21.8% (14.4%) x % (1) 2.8% 2.8% (8.4%) (2.8%) (1) 6.3% (1) (4.4%) 1.6% x Compound Annual Growth Rates (through December 31, 2018): 5 Year 5.4% 9.6% 8.5% 10 Year 7.2% 9.1% 13.1% Since December 31, % 8.5% 6.8% Price- to-book Ratio (1) Adjusted to reflect a $10 per share special dividend payment on March 15, PAGE 6

7 CONSOLIDATED FINANCIAL HIGHLIGHTS ($ in millions, except share and per share data) As of As of December 31, 2018 December 31, 2017 Change HIGHLIGHTS Total investments and cash $ 18,561.9 $ 19,639.1 (5.5%) Total assets 25, ,384.3 (0.2%) Total stockholders' equity attributable to Alleghany stockholders 7, ,514.1 (9.6%) Book value per share $ $ (4.6%) Book value per share including dividends (2.8%) For the Three Months Ended December 31, For the Twelve Months Ended December 31, Change Change Gross premiums written $ 1,488.9 $ 1, % $ 5,895.6 $ 5, % Net premiums written 1, , % 5, , % Net premiums earned 1, , % 4, , % Net investment income (5.0%) % Net earnings (losses) attributable to Alleghany stockholders (712.1) NM (56.2%) Operating earnings (losses) (64.1) NM % PER SHARE Weighted average common shares outstanding: AND SHARE DATA Basic 14,743,777 15,391,388 (4.2%) 15,062,567 15,410,034 (2.3%) Diluted 14,743,777 15,391,388 (4.2%) 15,062,567 15,410,034 (2.3%) Earnings (losses) per share attributable to Alleghany stockholders: Basic $ (48.30) $ 9.96 NM $ 2.62 $ 5.85 (55.2%) Diluted (48.30) 9.96 NM (55.2%) Operating earnings (losses) per share data: Basic $ (4.35) NM $ $ % Diluted (4.35) NM % FINANCIAL RATIOS Annualized return on average stockholders' equity (35.0%) 7.3% 0.5% 1.1% Annualized operating income return on average stockholders' equity (3.1%) 7.5% 3.0% 0.5% Loss and loss adjustment expense ratio 88.4% 55.0% % 73.1% (2.4) Expense ratio 30.7% 34.1% (3.4) 32.5% 33.3% (0.8) Combined ratio 119.1% 89.1% % 106.4% (3.2) PAGE 7

8 CONSOLIDATED STATEMENTS OF EARNINGS - CONSECUTIVE QUARTERS ($ in millions, except per share data) For the Three Months Ended December 31, 2018 September 30, 2018 June 30, 2018 March 31, 2018 December 31, 2017 September 30, 2017 June 30, 2017 March 31, 2017 December 31, 2016 Revenues Net premiums earned $ 1,306.0 $ 1,225.4 $ 1,237.0 $ 1,207.8 $ 1,262.1 $ 1,239.7 $ 1,243.9 $ 1,209.2 $ 1,239.2 Net investment income Change in the fair value of equity securities (741.8) (42.5) Net realized capital gains (70.4) (54.0) Other than temporary impairment losses (0.8) - - (0.5) (3.8) (6.1) (3.8) (3.2) (7.0) Noninsurance revenue Total revenues 1, , , , , , , , ,455.3 Costs and Expenses Net loss and loss adjustment expenses incurred 1, , Commissions, brokerage and other underwriting expenses Other operating expenses Corporate administration (25.3) (4.7) Amortization of intangible assets Interest expense Total costs and expenses 2, , , , , , , , ,360.5 Earnings (losses) before income taxes (890.7) (522.3) Income taxes (186.3) (212.3) Net earnings (losses) (704.4) (310.0) Net earnings (losses) attributable to noncontrolling interest (0.4) Net earnings (losses) attributable to Alleghany stockholders $ (712.1) $ $ $ $ $ (314.2) $ $ $ 69.5 Basic earnings (losses) per share attributable to Alleghany stockholders $ (48.30) $ $ $ $ 9.96 $ (20.38) $ 6.60 $ 9.68 $ 4.51 Diluted earnings (losses) per share attributable to Alleghany stockholders (48.30) (20.90) Basic operating earnings (losses) per share $ (4.35) $ (1.07) $ 9.78 $ $ $ (21.27) $ 6.56 $ 7.46 $ 7.27 Diluted operating earnings (losses) per share (4.35) (1.07) (21.79) SUPPLEMENTAL INFORMATION Premiums written: Gross premiums written $ 1,488.9 $ 1,475.3 $ 1,472.7 $ 1,458.7 $ 1,354.2 $ 1,471.8 $ 1,450.0 $ 1,420.8 $ 1,360.4 Net premiums written 1, , , , , , , , ,198.6 Net loss and loss adjustment expenses incurred: Current year 1, , , Prior years (116.2) (75.0) (52.2) (85.7) (125.6) (61.5) (63.6) (47.7) (106.3) $ 1,153.9 $ $ $ $ $ 1,491.9 $ $ $ Loss and loss adjustment expense ratio 88.4% 78.2% 59.7% 55.5% 55.0% 120.3% 59.1% 57.8% 57.9% Expense ratio 30.7% 33.3% 32.5% 33.6% 34.1% 32.1% 33.3% 33.8% 33.8% Combined ratio 119.1% 111.5% 92.2% 89.1% 89.1% 152.4% 92.4% 91.6% 91.7% PAGE 8

9 CONSOLIDATED STATEMENTS OF EARNINGS - YEAR TO DATE ($ in millions, except per share data) For the Twelve Months Ended December 31, Revenues U/W Net premiums earned $ 4,976.2 $ 4,955.0 Net investment income Change in the fair value of equity securities (229.0) - Net realized capital gains (3.2) Other than temporary impairment losses (1.3) (16.9) Noninsurance revenue 1, Total revenues 6, , Costs and Expenses Net loss and loss adjustment expenses incurred 3, ,620.2 Commissions, brokerage and other underwriting expenses 1, ,651.2 Other operating expenses 1, Corporate administration Amortization of intangible assets Interest expense Total costs and expenses 6, ,387.9 Earnings before income taxes Income taxes (15.0) (63.8) Net earnings Net earnings attributable to noncontrolling interest Net earnings attributable to Alleghany stockholders $ 39.5 $ 90.1 Basic earnings per share attributable to Alleghany stockholders $ 2.62 $ 5.85 Diluted earnings per share attributable to Alleghany stockholders SUPPLEMENTAL INFORMATION Premiums written: Gross premiums written $ 5,895.6 $ 5,696.9 Net premiums written 5, ,965.9 Net loss and loss adjustment expenses incurred: Current year 3, ,918.8 Prior years (329.0) (298.6) $ 3,520.4 $ 3,620.2 Loss and loss adjustment expense ratio 70.7% 73.1% Expense ratio 32.5% 33.3% Combined ratio 103.2% 106.4% PAGE 9

10 PREMIUMS WRITTEN Reinsurance segment: For the Three Months Ended December 31, Gross Premiums Written Net Premiums Written Change % Change Change % Change Property $ $ $ (28.8) (7.8%) $ $ $ (44.4) (14.7%) Casualty & other % % Total Reinsurance 1, % 1, % Insurance segment: RSUI % % CapSpecialty % % PacificComp (38.3) (100.0%) (37.3) (100.0%) Total Insurance (8.5) (2.2%) (6.1) (2.2%) Intercompany elimination (6.9) (6.7) (0.2) 3.0% % Total premiums written $ 1,488.9 $ 1,354.2 $ % $ 1,280.1 $ 1,179.4 $ % Reinsurance segment: For the Twelve Months Ended December 31, Gross Premiums Written Net Premiums Written Change % Change Change % Change Property $ 1,532.7 $ 1,557.8 $ (25.1) (1.6%) $ 1,169.4 $ 1,233.1 $ (63.7) (5.2%) Casualty & other 2, , % 2, , % Total Reinsurance 4, , % 3, , % Insurance segment: RSUI 1, , % % CapSpecialty % % PacificComp (162.6) (100.0%) (160.2) (100.0%) Total Insurance 1, ,509.6 (38.8) (2.6%) 1, ,155.8 (76.5) (6.6%) Intercompany elimination (26.2) (23.3) (2.9) 12.4% Total premiums written $ 5,895.6 $ 5,696.9 $ % $ 5,048.4 $ 4,965.9 $ % PAGE 10

11 CONSOLIDATED UNDERWRITING RESULTS - CURRENT QUARTER For the Three Months Ended December 31, 2018 Reinsurance Segment Casualty & Insurance Segment Cap Alleghany Total Corporate Property other Total RSUI Specialty Total Subtotal Capital Segments Activities* Consolidated Gross premiums written $ $ $ 1,126.3 $ $ 81.7 $ $ 1,495.8 $ - $ 1,495.8 $ (6.9) $ 1,488.9 Net premiums written , , , ,280.1 Net premiums earned $ $ $ 1,036.1 $ $ 78.9 $ $ 1,306.0 $ - $ 1,306.0 $ - $ 1,306.0 Net loss and loss adjustment expenses: Current year (ex-catastrophes) Current year catastrophe losses Prior years (27.1) (75.3) (102.4) (14.2) 0.4 (13.8) (116.2) - (116.2) - (116.2) , , ,153.9 Commissions, brokerage and other underwriting expenses Underwriting (loss) profit $ (230.2) $ 21.3 (208.9) $ (42.4) $ 2.1 (40.3) (249.2) - (249.2) - (249.2) Net investment income (0.6) Change in the fair value of equity securities (339.3) (351.6) (690.9) - (690.9) (50.9) (741.8) Net realized capital gains (32.0) (3.3) (35.3) 0.4 (34.9) (35.5) (70.4) Other than temporary impairment losses (0.5) (0.3) (0.8) - (0.8) - (0.8) Noninsurance revenue Other operating expenses 5.4 (6.2) (0.8) Corporate administration - (3.6) (3.6) - (3.6) (21.7) (25.3) Amortization of intangible assets (0.3) 0.2 (0.1) Interest expense Earnings (losses) before income taxes $ (503.9) $ (350.3) $ (854.2) $ 34.7 $ (819.5) $ (71.2) $ (890.7) Ratios: Net loss and loss adjustment expenses: Current year (ex-catastrophes) 60.4% 73.7% 70.0% 52.1% 55.1% 53.0% 66.5% Current year catastrophe losses 100.8% 2.4% 29.4% 50.4% 1.3% 36.0% 30.7% Prior years (9.6%) (10.0%) (9.9%) (7.4%) 0.6% (5.1%) (8.8%) 151.6% 66.1% 89.5% 95.1% 57.0% 83.9% 88.4% Expense 29.5% 31.1% 30.6% 27.1% 40.4% 31.0% 30.7% Combined 181.1% 97.2% 120.1% 122.2% 97.4% 114.9% 119.1% * The primary components of corporate activities are Alleghany Properties, SORC and activities at the Alleghany parent company. PAGE 11

12 CONSOLIDATED UNDERWRITING RESULTS - PRIOR YEAR QUARTER For the Three Months Ended December 31, 2017 Reinsurance Segment Insurance Segment Casualty & Cap Pacific Alleghany Total Corporate Property other Total RSUI Specialty Comp Total Subtotal Capital Segments Activities* Consolidated Gross premiums written $ $ $ $ $ 77.0 $ 38.3 $ $ 1,360.9 $ - $ 1,360.9 $ (6.7) $ 1,354.2 Net premiums written , , ,179.4 Net premiums earned $ $ $ $ $ 68.6 $ 40.1 $ $ 1,262.1 $ - $ 1,262.1 $ - $ 1,262.1 Net loss and loss adjustment expenses: Current year (ex-catastrophes) Current year catastrophe losses 10.3 (5.2) Prior years (32.0) (76.8) (108.8) (15.9) (0.3) (0.6) (16.8) (125.6) - (125.6) - (125.6) Commissions, brokerage and other underwriting expenses Underwriting (loss) profit $ 38.6 $ $ 40.7 $ 1.1 $ (0.3) Net investment income Change in the fair value of equity securities Net realized capital gains (6.8) 1.7 (5.1) (11.6) 5.4 Other than temporary impairment losses (3.7) (0.1) (3.8) - (3.8) - (3.8) Noninsurance revenue 5.1 (0.1) Other operating expenses Corporate administration Amortization of intangible assets (1.0) 0.8 (0.2) Interest expense Earnings (losses) before income taxes $ $ 67.5 $ $ 32.3 $ $ (44.2) $ Ratios: Net loss and loss adjustment expenses: 0.0% Current year (ex-catastrophes) 62.8% 67.3% 65.8% 56.0% 55.1% 75.5% 58.5% 64.0% Current year catastrophe losses 3.3% (0.8%) 0.5% 2.5% 0.9% 0.0% 1.8% 0.8% Prior years (10.2%) (11.8%) (11.1%) (8.8%) (0.4%) (1.5%) (5.9%) (9.8%) 55.9% 54.7% 55.2% 49.7% 55.6% 74.0% 54.4% 55.0% Expense 31.8% 36.5% 35.0% 27.9% 42.8% 26.6% 31.3% 34.1% Combined 87.7% 91.2% 90.2% 77.6% 98.4% 100.6% 85.7% 89.1% * The primary components of corporate activities are Alleghany Properties, SORC and activities at the Alleghany parent company. PAGE 12

13 CONSOLIDATED UNDERWRITING RESULTS - CURRENT YEAR TO DATE For the Twelve Months Ended December 31, 2018 Reinsurance Segment Casualty & Insurance Segment Cap Alleghany Total Corporate Property other Total RSUI Specialty Total Subtotal Capital Segments Activities* Consolidated Gross premiums written $ 1,532.7 $ 2,918.3 $ 4,451.0 $ 1,142.0 $ $ 1,470.8 $ 5,921.8 $ - $ 5,921.8 $ (26.2) $ 5,895.6 Net premiums written 1, , , , , , ,048.4 Net premiums earned $ 1,177.3 $ 2,761.7 $ 3,939.0 $ $ $ 1,037.2 $ 4,976.2 $ - $ 4,976.2 $ - $ 4,976.2 Net loss and loss adjustment expenses: Current year (ex-catastrophes) , , , , ,191.7 Current year catastrophe losses Prior years (84.9) (181.2) (266.1) (58.7) (4.2) (62.9) (329.0) - (329.0) - (329.0) 1, , , , , ,520.4 Commissions, brokerage and other underwriting expenses , , , ,617.3 Underwriting (loss) profit $ (275.4) $ 62.8 (212.6) $ 44.2 $ (161.5) - (161.5) - (161.5) Net investment income Change in the fair value of equity securities (104.2) (80.0) (184.2) - (184.2) (44.8) (229.0) Net realized capital gains (18.3) (35.7) (3.2) Other than temporary impairment losses (0.9) (0.4) (1.3) - (1.3) - (1.3) Noninsurance revenue , , ,644.0 Other operating expenses , , ,579.3 Corporate administration - (1.7) (1.7) - (1.7) Amortization of intangible assets (2.3) 1.9 (0.4) Interest expense Earnings (losses) before income taxes $ (59.3) $ $ $ 58.1 $ $ (121.2) $ 39.6 Ratios: Net loss and loss adjustment expenses: Current year (ex-catastrophes) 57.0% 71.1% 66.9% 52.9% 55.7% 53.6% 64.1% Current year catastrophe losses 40.9% 0.7% 12.7% 20.7% 0.9% 15.3% 13.2% Prior years (7.2%) (6.6%) (6.8%) (7.9%) (1.4%) (6.1%) (6.6%) 90.7% 65.2% 72.8% 65.7% 55.2% 62.8% 70.7% Expense 32.7% 32.5% 32.6% 28.4% 42.5% 32.3% 32.5% Combined 123.4% 97.7% 105.4% 94.1% 97.7% 95.1% 103.2% * The primary components of corporate activities are Alleghany Properties, SORC and activities at the Alleghany parent company. PAGE 13

14 CONSOLIDATED UNDERWRITING RESULTS - PRIOR YEAR TO DATE For the Twelve Months Ended December 31, 2017 Reinsurance Segment Insurance Segment Casualty & Cap Pacific Alleghany Total Corporate Property other Total RSUI Specialty Comp Total Subtotal Capital Segments Activities* Consolidated Gross premiums written $ 1,557.8 $ 2,652.8 $ 4,210.6 $ 1,056.8 $ $ $ 1,509.6 $ 5,720.2 $ - $ 5,720.2 $ (23.3) $ 5,696.9 Net premiums written 1, , , , , , ,965.9 Net premiums earned $ 1,181.9 $ 2,626.8 $ 3,808.7 $ $ $ $ 1,146.3 $ 4,955.0 $ - $ 4,955.0 $ - $ 4,955.0 Net loss and loss adjustment expenses: Current year (ex-catastrophes) , , , , ,100.7 Current year catastrophe losses Prior years (94.5) (155.0) (249.5) (43.2) (3.4) (2.5) (49.1) (298.6) - (298.6) - (298.6) 1, , , , , ,620.2 Commissions, brokerage and other underwriting expenses , , , ,651.2 Underwriting (loss) profit $ (281.6) $ 18.2 (263.4) $ (57.1) $ 4.3 $ (0.2) (53.0) (316.4) - (316.4) - (316.4) Net investment income Change in the fair value of equity securities Net realized capital gains (1.5) Other than temporary impairment losses (15.8) (1.1) (16.9) - (16.9) - (16.9) Noninsurance revenue Other operating expenses Corporate administration Amortization of intangible assets (4.6) 3.1 (1.5) Interest expense 27.0 (0.1) Earnings (losses) before income taxes $ (19.1) $ $ 92.6 $ 52.8 $ $ (108.7) $ 36.7 Ratios: Net loss and loss adjustment expenses: Current year (ex-catastrophes) 55.7% 68.3% 64.3% 52.8% 54.7% 75.4% 56.4% 62.6% Current year catastrophe losses 43.7% 2.5% 15.3% 32.2% 1.8% 0.0% 20.7% 16.5% Prior years (8.0%) (5.8%) (6.5%) (6.0%) (1.4%) (1.5%) (4.3%) (6.0%) 91.4% 65.0% 73.1% 79.0% 55.1% 73.9% 72.8% 73.1% Expense 32.4% 34.4% 33.8% 28.9% 43.2% 26.2% 31.8% 33.3% Combined 123.8% 99.4% 106.9% 107.9% 98.3% 100.1% 104.6% 106.4% * The primary components of corporate activities are Alleghany Properties, SORC and activities at the Alleghany parent company. PAGE 14

15 ALLEGHANY CAPITAL RESULTS - QUARTER TO DATE (1) For the Three Months Ended December 31, Non- Corp. & Non- Corp. & Industrial industrial other Total Industrial industrial other Total Noninsurance revenue (2) $ $ $ 0.2 $ $ $ $ 0.3 $ Net investment income (1.7) (0.6) (0.1) 0.6 Net realized capital gains 0.6 (0.2) Total revenues (1.5) Other operating expenses (2) Amortization of intangible assets Interest expense (0.1) 1.0 Earnings (losses) before income taxes $ 10.5 $ 27.0 $ (2.8) $ 34.7 $ 4.9 $ 9.7 $ 17.7 $ 32.3 Operating earnings (losses) before income taxes (3) $ 13.0 $ 31.5 $ (2.8) $ 41.7 $ 5.9 $ 13.0 $ (3.2) $ 15.7 Add: net realized capital gains 0.6 (0.2) Less: amortization of intangible assets (3.1) (4.3) - (7.4) (1.9) (3.6) - (5.5) Earnings (losses) before income taxes $ 10.5 $ 27.0 $ (2.8) $ 34.7 $ 4.9 $ 9.7 $ 17.7 $ 32.3 (1) The Alleghany Capital segment consists of: (i) industrial operations conducted through Bourn & Koch, Kentucky Trailer, W&W AFCO Steel beginning April 28, 2017, and a 45 percent equity interest in Wilbert Funeral Services, Inc. ("Wilbert"), beginning August 1, 2017; (ii) non-industrial operations conducted through IPS, Jazwares and Concord, beginning October 1, 2018; and (iii) corporate operations at the Alleghany Capital level. (2) For industrial and non-industrial operations: (i) noninsurance revenue consists of the sale of manufactured goods and services; and (ii) other operating expenses consist of the cost of goods and services sold and selling, general and administrative expenses. For the three months ended December 31, 2018 and 2017, other operating expenses also included $4.5 million and $0.3 million, respectively, of finders' fees, legal and accounting costs and other transaction-related expenses. (3) Refer to "Non-GAAP Financial Measures" on page 34 of the Financial Supplement. ALLEGHANY CAPITAL EQUITY (4) For the Three Months Ended December 31, 2018 For the Three Months Ended December 31, 2017 Non- Corp. & Non- Corp. & Industrial industrial other Total Industrial industrial other Total Equity, beginning of period $ $ $ 86.8 $ $ $ $ (9.0) $ Earnings (losses) before income taxes (2.8) Income taxes (5) (0.8) (0.8) (4.4) (6.0) 1.9 (0.2) (7.2) (5.5) Net earnings attributable to noncontrolling interest (6) (1.5) (6.2) - (7.7) (0.9) (4.2) - (5.1) Capital contributions (returns of capital) and other (7) (106.1) 2.5 (1.2) (8.2) Equity, end of period $ $ $ (26.5) $ $ $ $ 11.2 $ (4) Represents stockholders' equity attributable to Alleghany. (5) Federal income taxes for most Alleghany Capital subsidiaries are incurred at the Alleghany Capital corporate level. Estimated federal income tax (expense) benefit incurred at the Alleghany Capital corporate level attributable to industrial and non-industrial operations for the fourth quarter of 2018 were ($2.6) million and ($5.7) million, respectively, and for the fourth quarter of 2017 were $0.8 million and ($3.4) million, respectively. (6) During the fourth quarter of 2018, noncontrolling interests outstanding were approximately as follows: Bourn & Koch-11%; Kentucky Trailer-23%; W&W AFCO Steel-20%; IPS-15%; Jazwares-23%; and Concord-15% (7) For the fourth quarter of 2018, primarily reflects funding provided by Alleghany to Alleghany Capital for the acquisition of Concord. PAGE 15

16 ALLEGHANY CAPITAL RESULTS - YEAR TO DATE (1) For the Twelve Months Ended December 31, Non- Corp. & Non- Corp. & Industrial industrial other Total Industrial industrial other Total Noninsurance revenue (2) $ $ $ - $ 1,574.6 $ $ $ 0.8 $ Net investment income (1.7) Net realized capital gains 1.2 (0.3) Total revenues (1.7) 1, Other operating expenses (2) , Amortization of intangible assets Interest expense Earnings (losses) before income taxes $ 25.0 $ 44.8 $ (11.7) $ 58.1 $ 14.6 $ 30.6 $ 7.6 $ 52.8 Operating earnings (losses) before income taxes (3) $ 33.6 $ 59.7 $ (11.7) $ 81.6 $ 17.9 $ 46.1 $ (13.3) $ 50.7 Add: net realized capital gains 1.2 (0.3) Less: amortization of intangible assets (9.8) (14.6) - (24.4) (4.8) (16.1) - (20.9) Earnings (losses) before income taxes $ 25.0 $ 44.8 $ (11.7) $ 58.1 $ 14.6 $ 30.6 $ 7.6 $ 52.8 (1) The Alleghany Capital segment consists of: (i) industrial operations conducted through Bourn & Koch, Kentucky Trailer, W&W AFCO Steel, beginning April 28, 2017, and a 45 percent equity interest in Wilbert, beginning August 1, 2017; (ii) non-industrial operations conducted through IPS, Jazwares and Concord, beginning October 1, 2018; and (iii) corporate operations at the Alleghany Capital level. (2) For industrial and non-industrial operations: (i) noninsurance revenue consists of the sale of manufactured goods and services; and (ii) other operating expenses consist of the cost of goods and services sold, and selling, general and administrative expenses. For the twelve months ended December 31, 2018 and 2017, other operating expenses also included $7.7 million and $7.2 million, respectively, of finders' fees, legal and accounting costs and other transaction-related expenses. (3) Refer to "Non-GAAP Financial Measures" on page 34 of the Financial Supplement. ALLEGHANY CAPITAL EQUITY (4) For the Twelve Months Ended December 31, 2018 For the Twelve Months Ended December 31, 2017 Non- Corp. & Non- Corp. & Industrial industrial other Total Industrial industrial other Total Equity, beginning of period $ $ $ 11.2 $ $ $ $ (12.1) $ Earnings (losses) before income taxes (11.7) Income taxes (5) (1.7) (2.2) (6.7) (10.6) 1.1 (0.3) (10.8) (10.0) Net earnings attributable to noncontrolling interest (6) (3.2) (11.9) - (15.1) (2.3) (8.1) - (10.4) Capital contributions (returns of capital) and other (7) (19.3) (21.6) Equity, end of period $ $ $ (26.5) $ $ $ $ 11.2 $ (4) Represents stockholders' equity attributable to Alleghany. (5) Federal income taxes for most Alleghany Capital subsidiaries are incurred at the Alleghany Capital corporate level. Estimated federal income tax (expense) benefit incurred at the Alleghany Capital corporate level attributable to industrial and non-industrial operations for the full year of 2018 were ($5.3) million and ($9.4) million, respectively, and for the full year 2017 were ($2.4) million and ($10.7) million, respectively. (6) During 2018, noncontrolling interests outstanding were approximately as follows: Bourn & Koch-11%; Kentucky Trailer-21%; W&W AFCO Steel-20%; IPS-15%; Jazwares-23% and Concord-15%. (7) For 2018, primarily reflects funding provided by Alleghany Capital to W&W AFCO Steel for the acquisition of Hirschfeld and funding provided by Alleghany to Alleghany Capital for the acquisition of Concord. For 2017, primarily reflects funding provided by Alleghany Capital for the acquisition of W&W AFCO Steel and the investment in Wilbert. PAGE 16

17 CONDENSED CONSOLIDATING BALANCE SHEETS December 31, 2018 December 31, 2017 Reinsurance Insurance Alleghany Corporate Reinsurance Insurance Alleghany Corporate Segment (1) Segment (1) Capital Activities (2) Consolidated Segment Segment Capital Activities (2) Consolidated Assets Investments: Securities at fair value: Equity securities $ 1,823.2 $ 1,685.5 $ - $ 64.1 $ 3,572.8 $ 1,844.4 $ 1,816.7 $ - $ $ 4,099.5 Debt securities 9, , , , , ,721.4 Short-term investments , , , , , ,399.0 Commercial mortgage loans (0.1) Other invested assets (15.2) (7.4) Total investments (3) 12, , , , , ,800.7 Cash (3) , Reinsurance recoverables 1, (66.8) 1, (67.8) 1,746.5 Goodwill Intangible assets, net of amortization (0.1) (0.1) All other assets 2, , , ,204.8 Total assets $ 16,502.9 $ 6,701.6 $ 1,731.7 $ $ 25,344.9 $ 16,713.5 $ 6,892.0 $ 1,139.0 $ $ 25,384.3 Liabilities and Stockholders' Equity Loss and loss adjustment expenses $ 9,442.2 $ 2,874.9 $ - $ (66.8) $ 12,250.3 $ 9,128.0 $ 2,811.1 $ - $ (67.8) $ 11,871.3 Unearned premiums 1, (11.0) 2, , (10.3) 2,182.3 Senior Notes and other debt , ,484.9 All other liabilities , ,225.2 Total liabilities 11, , , , , , , ,763.7 Redeemable noncontrolling interest ("RNCI") Total stockholders' equity attributable to Alleghany stockholders 4,723.5 (4) (4) 2, (606.5) 7, , , (397.0) 8,514.1 Total liabilities, RNCI and stockholders' equity $ 16,502.9 $ 6,701.6 $ 1,731.7 $ $ 25,344.9 $ 16,713.5 $ 6,892.0 $ 1,139.0 $ $ 25,384.3 (1) Annualized pre-tax return on average equity for the reinsurance and insurance segments was: -1.2% and 5.7%, respectively, for the twelve months ended December 31, (2) The primary components of corporate activities are Alleghany Properties, SORC and activities at the Alleghany parent company. Also includes consolidation and elimination entries, including those that exist between the reinsurance and insurance segments. (3) As of December 31, 2018, includes $1,122.3 million of marketable securities and cash at our unrestricted holding companies, comprised of $352.1 million at the Alleghany parent (included in Corporate Activities), $714.4 million at AIHL (included in the Insurance Segment), and $55.8 million at the TransRe holding company (included in the Reinsurance Segment). (4) Insurance segment stockholders' equity as of December 31, 2018 includes $1,633.1 million related to RSUI, $366.9 million related to CapSpecialty and $17.0 million related to AIHL Re, with the remaining stockholders' equity relating to the AIHL holding company and Roundwood. As of December 31, 2017, insurance segment stockholders' equity included $1,700.9 million related to RSUI, $367.7 million related to CapSpecialty and $14.8 million related to AIHL Re, with the remaining stockholders' equity relating to the AIHL holding company and Roundwood. PAGE 17

18 ALLEGHANY CAPITAL CONDENSED CONSOLIDATING BALANCE SHEETS December 31, 2018 December 31, 2017 Non- Corp. & Non- Corp. & Industrial Industrial other Consolidated Industrial Industrial other Consolidated Assets Cash $ 11.3 $ 23.2 $ 3.5 $ 38.0 $ 13.5 $ 19.0 $ 15.1 $ 47.6 Other invested assets 76.0 (1) (1) Property and equipment at cost, net Goodwill (2.8) (2.9) Intangible assets, net of amortization All other assets (2) Total assets $ $ $ 19.4 $ 1,731.7 $ $ $ 39.6 $ 1,139.0 Liabilities and Stockholders' Equity Debt $ $ 98.1 $ - $ $ 63.4 $ 37.6 $ - $ All other liabilities (3) Total liabilities Redeemable noncontrolling interest ("RNCI") Total stockholders' equity attributable to Alleghany stockholders (26.5) Total liabilities, RNCI and stockholders' equity $ $ $ 19.4 $ 1,731.7 $ $ $ 39.6 $ 1,139.0 (1) Represents Alleghany Capital's investment in Wilbert. (2) Primarily represents accounts receivable, costs on uncompleted contracts in excess of billings, inventory and other current assets. (3) Primarily represents accounts payable, billings on uncompleted contracts in excess of costs, accrued expenses and other current liabilities. PAGE 18

19 CONSOLIDATED TOTAL INVESTMENT PORTFOLIO December 31, 2018 September 30, 2018 June 30, 2018 March 31, 2018 December 31, 2017 September 30, 2017 June 30, 2017 March 31, 2017 December 31, 2016 CARRYING VALUE Equity securities $ 3, % $ 5, % $ 4, % $ 4, % $ 4, % $ 3, % $ 3, % $ 2, % $ 3, % Debt securities 11, % 12, % 12, % 12, % 12, % 13, % 13, % 13, % 12, % Short-term investments % % % % % % % 1, % % Commercial mortgage loans % % % % % % % % % Other invested assets % % % % % % % % % Total $ 17, % $ 19, % $ 18, % $ 18, % $ 18, % $ 18, % $ 18, % $ 18, % $ 18, % INVESTMENT ALLOCATION BY CARRYING VALUE Equity securities: Common stock $ 3, % $ 5, % $ 4, % $ 4, % $ 4, % $ 3, % $ 3, % $ 2, % $ 3, % Preferred stock % % % % % % % % - 0.0% 3, % 5, % 4, % 4, % 4, % 3, % 3, % 2, % 3, % Debt securities: U.S. Government obligations 1, % 1, % % 1, % % 1, % 1, % 1, % 1, % Municipal bonds 2, % 2, % 2, % 3, % 3, % 4, % 4, % 4, % 4, % Foreign government obligations % % % % 1, % 1, % 1, % 1, % 1, % U.S. corporate bonds 2, % 2, % 2, % 2, % 2, % 2, % 2, % 2, % 2, % Foreign corporate bonds 1, % 1, % 1, % 1, % 1, % 1, % 1, % 1, % 1, % Mortgage and asset-backed securities: Residential mortgage-backed securities ("RMBS") 1, % 1, % 1, % 1, % % % 1, % % 1, % Commercial mortgage-backed securities ("CMBS") % % % % % % % % % Other asset-backed securities 1, % 2, % 1, % 1, % 1, % 1, % 1, % 1, % 1, % 11, % 12, % 12, % 12, % 12, % 13, % 13, % 13, % 12, % Short-term investments % % % % % % % 1, % % Commercial mortgage loans % % % % % % % % % Other invested assets: Equity method investments % % % % % % % % % Partnership investments % % % % % % % % % Other % % % % % % % % % % % % % % % % % % Total $ 17, % $ 19, % $ 18, % $ 18, % $ 18, % $ 18, % $ 18, % $ 18, % $ 18, % RATINGS (1) OF DEBT SECURITIES PORTFOLIO, BY CARRYING VALUE AAA/Aaa $ 1, % $ 2, % $ 1, % $ 1, % $ 1, % $ 2, % $ 2, % $ 2, % $ 2, % AA/Aa 5, % 5, % 5, % 5, % 5, % 5, % 5, % 5, % 5, % A 2, % 2, % 2, % 2, % 2, % 2, % 2, % 2, % 2, % BBB/Baa 1, % 1, % 1, % 1, % 1, % 1, % 1, % 1, % 1, % BB / Ba % % % % % % % % % B % % % % % % % % % CCC % % % % % % % % % CC % % % % % % % % % Below CC % % % % % % % % % Not rated % % % % % % % % % $ 11, % $ 12, % $ 12, % $ 12, % $ 12, % $ 13, % $ 13, % $ 13, % $ 12, % Duration of debt securities portfolio 4.2 years 4.3 years 4.3 years 4.4 years 4.4 years 4.5 years 4.5 years 4.5 years 4.5 years Average credit quality (2) AA- AA- AA- AA- AA- AA- AA- AA- AA- (1) The debt securities portfolio credit quality is measured using the lowest rating of the Standard & Poor's Ratings Services, Moody's Investors Service, Inc. or Fitch Ratings, Inc. (2) The average debt securities portfolio credit quality is measured by weighting each individual security's rating, which uses the lowest ratings of the Standard & Poor's Ratings Services, Moody's Investors Service Inc. or Fitch Ratings Inc. PAGE 19

20 DEBT SECURITIES PORTFOLIO CREDIT QUALITY (1) December 31, 2018 Below BBB / Baa AAA / Aaa AA / Aa A BBB / Baa or Not-Rated Total U.S. Government obligations $ - $ 1,022.4 $ - $ - $ - $ 1,022.4 Municipal bonds , ,214.7 Foreign government obligations U.S. corporate bonds ,385.3 Foreign corporate bonds ,353.3 Mortgage and asset-backed securities: RMBS , ,387.9 CMBS Other asset-backed securities ,979.2 Total debt securities $ 1,860.2 $ 5,048.3 $ 2,477.1 $ 1,921.8 $ $ 11,824.0 Percentage of debt securities 15.7% 42.7% 20.9% 16.3% 4.4% 100.0% (1) The debt securities portfolio credit quality is measured using the lowest rating of the Standard & Poor's Ratings Services, Moody's Investors Service, Inc. or Fitch Ratings, Inc. PAGE 20

21 NET INVESTMENT INCOME Three Months Ended December 31, Interest income $ $ Dividends Total interest income and dividends Pillar Capital Holdings Limited and related funds (7.7) 1.2 Limited partnership interests in certain subsidiaries of Ares Management, L.P Other investment results Total investment income Investment expenses (6.1) (7.9) Net investment income $ $ Net investment income - after tax (1) $ $ 91.7 Twelve Months Ended December 31, Interest income $ $ Dividends Total interest income and dividends Pillar Capital Holdings Limited and related funds (6.5) (1.7) Limited partnership interests in certain subsidiaries of Ares Management, L.P Other investment results Total investment income Investment expenses (31.5) (28.1) Net investment income $ $ Net investment income - after tax (1) $ $ (1) Reflects income tax at a 21.0% and 35.0% statutory rate for 2018 and 2017, respectively, except for tax-exempt interest income and dividends subject to dividend-received deductions. PAGE 21