Vision Workbook 1 · PAGE 1 Investor Contact: This report is for informational purposes only. It should be read in conjunction with documents filed by Alleghany Corporation

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Investor Contact: This report is for informational purposes only. It should be read in conjunction with documents filed by Alleghany CorporationDale James with the U.S. Securities and Exchange Commission, including the company's Annual Reports on Form 10-K andPhone: (212) 508-8116 Quarterly Reports on Form 10-Q.

(Unaudited)

Twelve Months EndedDecember 31, 2019

Alleghany

ALLEGHANY CORPORATION AND SUBSIDIARIESFINANCIAL SUPPLEMENT

andThree Months Ended

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Forward-Looking Statements

• 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.

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 1995. Forward-lookingstatements 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 othercomparable 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 madeby, 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 expectationsand 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 theseforward-looking statements to differ, possibly materially, from that currently contemplated include:

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 inpolitical, 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, whichmay 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, orthe “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 reviseany forward-looking statements to reflect subsequent circumstances or events.

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PageI. FINANCIAL SUMMARY

10 Year Financial Summary 5Historical Growth in Book Value per Share 6Consolidated Financial Highlights 7Subsidiary Capital Allocation 8Consolidated Statements of Earnings 9

II. UNDERWRITING RESULTS & EARNINGS BY SEGMENT Premiums Written 10Consolidated Underwriting Results - Current Quarter 11Consolidated Underwriting Results - Prior Year Quarter 12Consolidated Underwriting Results - Current Year to Date 13Consolidated Underwriting Results - Prior Year to Date 14

III. BALANCE SHEET DETAILSCondensed Consolidating Balance Sheets 15Consolidated Total Investment Portfolio 16Debt Securities Portfolio Credit Quality 17Net Investment Income 18Financial Statement Portfolio Return 19Annualized Investment Book Yield 20Loss and Loss Adjustment Expenses (LAE) 21Capital Structure and Leverage Ratios 22

IV. Alleghany CapitalNoninsurance Revenue 23Results - Quarter to Date 24Results - Year to Date 25Condensed Consolidating Balance Sheets 26Condensed Consolidating Statements of Cash Flows 27

V. OTHERBasic and Diluted Earnings per Share Information 28Adjusted Earnings Reconciliation 29Return on Average Stockholders' Equity 30Book Value per Share 31Consolidated Changes in Stockholders' Equity 32Catastrophe Exposure 33Share Repurchase Detail 34Non-GAAP Financial Measures 35

ALLEGHANY CORPORATION AND SUBSIDIARIESFINANCIAL SUPPLEMENT TABLE OF CONTENTS

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Presentation

Definitions

• "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;

• “PCT” are to our wholly-owned subsidiary Precision Cutting Technologies, Inc. and its subsidiaries;

• "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.

ALLEGHANY CORPORATION AND SUBSIDIARIESBASIS OF 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 forshare, per share, percentage and ratio information.

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 thecontext otherwise requires. In addition, unless the context otherwise requires, references to,

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2010 2011 2012 2013 2014 2015 2016 2017 2018 2019

Book value per common share(2) 325.31$ 342.12$ 379.13$ 412.96$ 465.51$ 486.02$ 515.24$ 553.20$ 527.75$ 611.00$ Percent increase (decrease) 10.4% 5.2% 10.8% 8.9% 12.7% 4.4% 6.0% 7.4% (4.6%) 15.8%

Net invested assets per share 512.53$ 539.38$ 1,016.56$ 1,055.08$ 1,099.10$ 1,086.48$ 1,118.02$ 1,179.57$ 1,158.91$ 1,275.34$ Percent increase (decrease) 6.2% 5.2% 88.5% 3.8% 4.2% (1.1%) 2.9% 5.5% (1.8%) 10.0%

Invested assets and cash 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$ 20,070.9$ Net loss and loss adjustment

expense reserves 1,481.3 1,481.2 10,933.9 10,650.4 10,307.8 9,629.9 9,851.0 10,221.2 10,392.9 10,344.5 All debt and preferred stock 298.9 299.0 1,806.1 1,800.9 1,795.3 1,419.4 1,476.5 1,484.9 1,669.0 1,751.1 Common Stockholders' Equity

("CSE") attributable to Alleghany stockholders(2) 2,908.9 2,925.7 6,403.8 6,923.8 7,473.4 7,554.7 7,939.9 8,514.1 7,692.7 8,776.7

Common shares outstanding 8.94 8.55 16.89 16.77 16.05 15.54 15.41 15.39 14.58 14.36

Net premiums written 736.2$ 774.7$ 3,723.9$ 4,287.4$ 4,497.5$ 4,489.2$ 5,091.8$ 4,965.9$ 5,048.4$ 5,751.7$ Change in unearned premiums 31.9 (27.1) 9.1 (48.2) (86.9) (258.9) (116.0) (10.9) (72.2) (273.6) Net premiums earned 768.1$ 747.6$ 3,733.0$ 4,239.2$ 4,410.6$ 4,230.3$ 4,975.8$ 4,955.0$ 4,976.2$ 5,478.1$

Underwriting profit (loss) 130.9$ 49.5$ 220.3$ 420.7$ 494.8$ 466.6$ 401.3$ (316.4)$ (161.5)$ 33.0$

Net investment income 125.0 108.9 313.0 465.7 459.9 438.8 438.5 451.0 500.5 550.2 Net realized capital gains(3)

net of other than temporary impairment losses 85.0 123.5 155.0 188.1 210.8 80.0 18.0 90.3 (233.5) 683.5

Total investment results 210.0$ 232.4$ 468.0$ 653.8$ 670.7$ 518.8$ 456.5$ 541.3$ 267.0$ 1,233.7$

Net earnings attributable to Alleghany stockholders 198.5 143.3 702.2 628.4 679.2 560.3 456.9 90.1 39.5 857.8

Special dividend(2) - - - - - - - - (154.0) - Other changes in CSE (7.2) (126.5) 2,775.9 (108.4) (129.6) (479.0) (71.7) 484.1 (706.9) 226.2 Increase (decrease) in CSE 191.3$ 16.8$ 3,478.1$ 520.0$ 549.6$ 81.3$ 385.2$ 574.2$ (821.4)$ 1,084.0$

Combined Ratio 83.0% 93.4% 94.1% 90.1% 88.8% 89.0% 91.9% 106.4% 103.2% 99.4%

(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, 2018.(3) Includes changes in fair value of equity securities commencing in 2018. 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, 2019 for additional information regarding the adoption of certain new investment accounting guidance.

ALLEGHANY CORPORATION AND SUBSIDIARIES10 YEAR FINANCIAL SUMMARY(1)

(in millions, except per share data)

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Annual Growth: Book

Annual Y Stock BVPS vs Y Stock Value PerYear 1Q 2Q 3Q 4Q BVPS Price S&P 500 S&P 500 Price Share20012002 0.9% 0.9% (3.3%) 1.7% 0.2% (5.9%) (22.1%) 22.3% 148.52$ 162.75$ 0.91 x2003 0.1% 3.8% 1.3% 6.4% 11.9% 27.9% 28.7% (16.7%) 189.90 182.18 1.04 x2004 3.2% 3.7% (1.3%) 6.0% 12.0% 30.8% 10.9% 1.1% 248.33 204.08 1.22 x2005 2.3% 0.6% (1.9%) 3.2% 4.3% 1.6% 4.9% (0.6%) 252.18 212.80 1.19 x2006 5.4% 2.3% 2.8% 3.6% 14.8% 30.6% 15.8% (1.0%) 329.32 244.25 1.35 x2007 3.7% 3.8% 3.9% 2.9% 15.2% 12.8% 5.5% 9.7% 371.39 281.36 1.32 x2008 1.5% 2.1% (6.7%) (1.8%) (5.0%) (28.4%) (37.0%) 32.0% 265.74 267.37 0.99 x2009 (0.3%) 2.7% 5.2% 2.4% 10.3% (0.2%) 26.5% (16.2%) 265.28 294.79 0.90 x2010 2.3% (0.2%) 3.9% 4.0% 10.4% 13.2% 15.1% (4.7%) 300.36 325.31 0.92 x2011 5.1% (0.3%) (4.0%) 4.5% 5.2% (5.0%) 2.1% 3.1% 285.29 342.12 0.83 x2012 6.8% 1.6% 4.8% (2.5%) 10.8% 17.6% 16.0% (5.2%) 335.42 379.13 0.88 x2013 4.1% (1.8%) 3.4% 3.1% 8.9% 19.2% 32.4% (23.5%) 399.96 412.96 0.97 x2014 4.4% 4.8% 1.0% 2.1% 12.7% 15.9% 13.7% (1.0%) 463.50 465.51 1.00 x2015 2.4% 0.3% (0.5%) 2.1% 4.4% 3.1% 1.4% 3.0% 477.93 486.02 0.98 x2016 3.6% 1.9% 2.4% (1.9%) 6.0% 27.2% 12.0% (6.0%) 608.12 515.24 1.18 x2017 3.0% 3.1% (2.7%) 3.9% 7.4% (2.0%) 21.8% (14.4%) 596.09 553.20 1.08 x2018 0.3% (1) 2.8% 2.8% (8.4%) (2.8%) (1) 6.3% (1) (4.4%) 1.6% 623.32 527.75 1.18 x2019 8.0% 5.6% 1.8% (0.3%) 15.8% 28.3% 31.5% (15.7%) 799.57 611.00 1.31 x

Compound Annual Growth Rates (through December 31, 2019): 5 Year 6.0% (1) 11.9% 11.7%10 Year 7.8% (1) 11.8% 13.5%Since December 31, 2001 7.8% (1) 9.5% 8.1%

(1) Adjusted to reflect a $10 per share special dividend payment on March 15, 2018.

to-BookRatio

Growth in Book Value Per Share As of Year-End

ALLEGHANY CORPORATION AND SUBSIDIARIESHISTORICAL GROWTH IN BOOK VALUE PER SHARE

Price-

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As of As ofDecember 31, 2019 December 31, 2018 Change

HIGHLIGHTS Invested assets and cash 20,070.9$ 18,561.9$ 8.1%Total assets 26,931.6 25,344.9 6.3%Total stockholders' equity attributable to Alleghany stockholders 8,776.7 7,692.7 14.1%

Book value per share ("BVPS") 611.00$ 527.75$ 15.8%BVPS excluding accumulated other comprehensive income 599.07 541.60 10.6%

2019 2018 Change 2019 2018 Change

Gross premiums written 1,727.9$ 1,488.9$ 16.1% 6,656.4$ 5,895.6$ 12.9%Net premiums written 1,505.7 1,280.1 17.6% 5,751.7 5,048.4 13.9%Net premiums earned 1,434.9 1,306.0 9.9% 5,478.1 4,976.2 10.1%Net investment income 136.6 122.8 11.2% 550.2 500.5 9.9%Net earnings attributable to Alleghany stockholders 31.7 (712.1) n/m 857.8 39.5 2071.6%Adjusted earnings (losses) (84.4) (64.1) n/m 344.6 242.9 41.9%

PER SHARE Weighted average common shares outstanding:AND SHARE DATA Basic 14,384,186 14,743,777 (2.4%) 14,431,892 15,062,567 (4.2%)

Diluted 14,427,908 14,743,777 (2.1%) 14,443,476 15,062,567 (4.1%)

Earnings per share attributable to Alleghany stockholders:Basic 2.20$ (48.30)$ n/m 59.44$ 2.62$ 2168.6%Diluted 1.98 (48.30) n/m 59.39 2.62 2166.8%

Adjusted earnings (losses) per share data:Basic (5.87) (4.35) n/m 23.82 16.13 47.7%Diluted (6.09) (4.35) n/m 23.77 16.13 47.4%

FINANCIAL RATIOS Annualized return on average stockholders' equity 1.4% (35.0%) 10.4% 0.5%Annualized adjusted earnings return on average stockholders' equity (3.8%) (3.1%) 4.2% 3.0%

Loss and loss adjustment expense ratio 82.9% 88.4% (5.5) 67.3% 70.7% (3.4) Expense ratio 31.0% 30.7% 0.3 32.1% 32.5% (0.4) Combined ratio 113.9% 119.1% (5.2) 99.4% 103.2% (3.8)

For the Twelve Months EndedDecember 31,

For the Three Months EndedDecember 31,

ALLEGHANY CORPORATION AND SUBSIDIARIESCONSOLIDATED FINANCIAL HIGHLIGHTS

($ in millions, except share and per share data)

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Carrying %Value Allocation

Consolidated:Stockholder's equity attributable to Alleghany stockholders 8,776.7$ 89.8%Alleghany Parent debt(1) 994.2 10.2%

Total capital 9,770.9$ 100.0%

(Re)insurance subsidiaries stockholder's equity:TransRe 5,243.3$ 53.7%RSUI 1,873.8 19.2%CapSpecialty 394.7 4.0%AIHL Re 21.0 0.2%

7,532.8$ 77.1%Alleghany Capital subsidiaries stockholder's equity:W&W|AFCO Steel 255.2$ 2.6%Jazwares 235.1 2.4%Concord 108.5 1.1%PCT 105.3 1.1%Wilbert (45% investment; not consolidated) 81.6 0.9%Kentucky Trailer 81.2 0.8%IPS 67.0 0.7%

933.9$ 9.6%Other:Marketable securities and cash at Alleghany parent and AIHL 1,233.3$ 12.6%SORC 86.7 0.9%Alleghany Properties 24.1 0.2%Other items, net(2) (39.9) -0.4%

1,304.2$ 13.3%

-

(1) Excludes TransRe senior notes that mature in 2039 and debt at Alleghany Capital. (2) Primarily deferred compensation and deferred taxes, as well as Alleghany Capital parent.

December 31, 2019

ALLEGHANY CORPORATION AND SUBSIDIARIESSUBSIDIARY CAPITAL ALLOCATION

($ in millions)

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For the Twelve Months Ended December 31, 2019 September 30, 2019 June 30, 2019 March 31, 2019 December 31, 2018 December 31, 2019 December 31, 2018

RevenuesNet premiums earned 1,434.9$ 1,390.0$ 1,356.0$ 1,297.3$ 1,306.0$ 5,478.1$ 4,976.2$ Net investment income 136.6 147.8 142.7 123.0 122.8 550.2 500.5 Change in the fair value of equity securities 190.4 (16.7) 143.7 392.4 (741.8) 709.7 (229.0) Net realized capital gains (27.3) 3.9 12.4 4.4 (70.4) (6.5) (3.2) Other than temporary impairment losses (6.1) (3.6) - (10.0) (0.8) (19.7) (1.3) Noninsurance revenue 572.3 638.5 603.9 514.1 611.3 2,328.8 1,644.0

Total revenues 2,300.8 2,159.9 2,258.7 2,321.2 1,227.1 9,040.6 6,887.2

Costs and ExpensesNet loss and loss adjustment expenses incurred 1,189.4 907.7 796.8 792.5 1,153.9 3,686.4 3,520.4 Commissions, brokerage and other underwriting expenses 444.8 449.5 444.3 420.1 401.3 1,758.7 1,617.3 Other operating expenses 562.1 617.3 581.5 502.4 555.9 2,263.3 1,579.3 Corporate administration 7.2 22.3 26.0 19.4 (25.3) 74.8 15.9 Amortization of intangible assets 10.0 8.1 8.8 6.9 7.3 33.8 24.0 Interest expense 25.6 25.7 25.1 23.5 24.7 100.0 90.7

Total costs and expenses 2,239.1 2,030.6 1,882.5 1,764.8 2,117.8 7,917.0 6,847.6

Earnings (losses) before income taxes 61.7 129.3 376.2 556.4 (890.7) 1,123.6 39.6 Income taxes 25.5 28.0 71.3 108.5 (186.3) 233.4 (15.0) Net earnings (losses) 36.2 101.3 304.9 447.9 (704.4) 890.2 54.6

Net earnings (losses) attributable to noncontrolling interests 4.5 10.9 9.4 7.7 7.7 32.4 15.1 Net earnings (losses) attributable to Alleghany stockholders 31.7$ 90.4$ 295.5$ 440.2$ (712.1)$ 857.8$ 39.5$

Basic earnings (losses) per share attributable to Alleghany stockholders 2.20$ 6.27$ 20.46$ 30.40$ (48.30)$ 59.44$ 2.62$ Diluted earnings (losses) per share attributable to Alleghany stockholders 1.98 6.27 20.46 30.39 (48.30) 59.39 2.62

Basic adjusted earnings (losses) per share (5.87)$ 7.61$ 12.40$ 9.67$ (4.35)$ 23.82$ 16.13$ Diluted adjusted earnings (losses) per share (6.09) 7.61 12.40 9.66 (4.35) 23.77 16.13

SUPPLEMENTAL INFORMATIONPremiums written:

Gross premiums written 1,727.9$ 1,651.1$ 1,670.8$ 1,606.6$ 1,488.9$ 6,656.4$ 5,895.6$ Net premiums written 1,505.7 1,413.9 1,446.5 1,385.7 1,280.1 5,751.7 5,048.4

Net loss and loss adjustment expenses incurred:Current year 1,221.2 966.6 853.4 829.9 1,270.1 3,871.1 3,849.4$ Prior years (31.8) (58.9) (56.6) (37.4) (116.2) (184.7) (329.0)

1,189.4$ 907.7$ 796.8$ 792.5$ 1,153.9$ 3,686.4$ 3,520.4$

Loss and loss adjustment expense ratio 82.9% 65.3% 58.8% 61.1% 88.4% 67.3% 70.7%Expense ratio 31.0% 32.3% 32.8% 32.4% 30.7% 32.1% 32.5%Combined ratio 113.9% 97.6% 91.6% 93.5% 119.1% 99.4% 103.2%

For the Three Months Ended

ALLEGHANY CORPORATION AND SUBSIDIARIESCONSOLIDATED STATEMENTS OF EARNINGS

($ in millions, except per share data)

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2019 2018 Change % Change 2019 2018 Change % ChangeReinsurance segment:

Property 447.7$ 339.0$ 108.7$ 32.1% 367.7$ 257.3$ 110.4$ 42.9%Casualty & other 812.4 787.3 25.1 3.2% 795.2 752.9 42.3 5.6%

Total Reinsurance 1,260.1 1,126.3 133.8 11.9% 1,162.9 1,010.2 152.7 15.1%

Insurance segment:

RSUI 375.5 287.8 87.7 30.5% 250.2 193.5 56.7 29.3%CapSpecialty 99.6 81.7 17.9 21.9% 92.6 76.4 16.2 21.2%

Total Insurance 475.1 369.5 105.6 28.6% 342.8 269.9 72.9 27.0%

Intercompany elimination (7.3) (6.9) (0.4) 5.8% - - -

Total premiums written 1,727.9$ 1,488.9$ 239.0$ 16.1% 1,505.7$ 1,280.1$ 225.6$ 17.6%

2019 2018 Change % Change 2019 2018 Change % Change

Reinsurance segment:

Property 1,700.3$ 1,532.7$ 167.6$ 10.9% 1,328.8$ 1,169.4$ 159.4$ 13.6%Casualty & other 3,245.4 2,918.3 327.1 11.2% 3,166.2 2,799.7 366.5 13.1%

Total Reinsurance 4,945.7 4,451.0 494.7 11.1% 4,495.0 3,969.1 525.9 13.2%

Insurance segment:

RSUI 1,366.6 1,142.0 224.6 19.7% 912.0 773.3 138.7 17.9%CapSpecialty 371.8 328.8 43.0 13.1% 344.7 306.0 38.7 12.6%

Total Insurance 1,738.4 1,470.8 267.6 18.2% 1,256.7 1,079.3 177.4 16.4%

Intercompany elimination (27.7) (26.2) (1.5) 5.7% - - -

Total premiums written 6,656.4$ 5,895.6$ 760.8$ 12.9% 5,751.7$ 5,048.4$ 703.3$ 13.9%

Gross Premiums Written Net Premiums Written

($ in millions)

ALLEGHANY CORPORATION AND SUBSIDIARIESPREMIUMS WRITTEN

For the Twelve Months Ended December 31,

For The Three Months Ended December 31,Gross Premiums Written Net Premiums Written

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Reinsurance SegmentCasualty & Cap Alleghany Total Corporate

Property other Total RSUI Specialty Total Subtotal Capital(1) Segments Activities(2) Consolidated

Gross premiums written 447.7$ 812.4$ 1,260.1$ 375.5$ 99.6$ 475.1$ 1,735.2$ -$ 1,735.2$ (7.3)$ 1,727.9$ Net premiums written 367.7 795.2 1,162.9 250.2 92.6 342.8 1,505.7 - 1,505.7 - 1,505.7

Net premiums earned 341.0$ 784.4$ 1,125.4$ 220.4$ 89.1$ 309.5$ 1,434.9$ -$ 1,434.9$ -$ 1,434.9$

Net loss and loss adjustment expenses:Current year (ex-catastrophes) 193.2 569.7 762.9 118.8 55.3 174.1 937.0 - 937.0 - 937.0 Current year catastrophes 221.6 2.7 224.3 59.2 0.7 59.9 284.2 - 284.2 - 284.2 Prior years 4.0 (59.0) (55.0) (0.1) 23.3 23.2 (31.8) - (31.8) - (31.8)

418.8 513.4 932.2 177.9 79.3 257.2 1,189.4 - 1,189.4 - 1,189.4 Commissions, brokerage and other

underwriting expenses 108.4 247.6 356.0 52.0 36.8 88.8 444.8 - 444.8 - 444.8

Underwriting (loss) profit (186.2)$ 23.4$ (162.8) (9.5)$ (27.0)$ (36.5) (199.3) - (199.3) - (199.3)

Net investment income 88.8 43.0 131.8 2.9 134.7 1.9 136.6 Change in the fair value of equity securities 111.7 78.3 190.0 - 190.0 0.4 190.4 Net realized capital gains 16.6 (31.0) (14.4) 0.7 (13.7) (13.6) (27.3) Other than temporary impairment losses (5.9) (0.2) (6.1) - (6.1) - (6.1) Noninsurance revenue 6.1 1.4 7.5 562.6 570.1 2.2 572.3 Other operating expenses 10.1 4.6 14.7 541.0 555.7 6.4 562.1 Corporate administration - (0.3) (0.3) - (0.3) 7.5 7.2 Amortization of intangible assets - 0.3 0.3 9.7 10.0 - 10.0 Interest expense 6.8 - 6.8 5.9 12.7 12.9 25.6 Earnings (losses) before income taxes 37.6$ 50.4$ 88.0$ 9.6$ 97.6$ (35.9)$ 61.7$

Ratios:Net loss and loss adjustment expenses:

Current year (ex-catastrophes) 56.7% 72.6% 67.8% 53.8% 62.1% 56.2% 65.3%Current year catastrophe losses 65.0% 0.3% 19.9% 26.9% 0.7% 19.4% 19.8%Prior years 1.2% (7.5%) (4.9%) 0.0% 26.3% 7.5% (2.2%)

122.9% 65.4% 82.8% 80.7% 89.1% 83.1% 82.9%Expense 31.8% 31.6% 31.6% 23.6% 41.3% 28.7% 31.0%

Combined 154.7% 97.0% 114.4% 104.3% 130.4% 111.8% 113.9%

(1) Excludes certain minor, legacy investments that were previously reflected in Alleghany Capital in 2018 and prior periods.(2) Includes Alleghany Properties, SORC and activities at the Alleghany parent company. Also includes certain minor, legacy investments that were previously reflected in Alleghany Capital in 2018 and prior periods.

Insurance SegmentFor the Three Months Ended December 31, 2019

ALLEGHANY CORPORATION AND SUBSIDIARIESCONSOLIDATED UNDERWRITING RESULTS - CURRENT QUARTER

($ in millions)

PAGE 12



Gross premiums written 339.0$ 787.3$ 1,126.3$ 287.8$ 81.7$ 369.5$ 1,495.8$ -$ 1,495.8$ (6.9)$ 1,488.9$ Net premiums written 257.3 752.9 1,010.2 193.5 76.4 269.9 1,280.1 - 1,280.1 - 1,280.1

Net premiums earned 283.6$ 752.5$ 1,036.1$ 191.0$ 78.9$ 269.9$ 1,306.0$ -$ 1,306.0$ -$ 1,306.0$

Net loss and loss adjustment expenses:Current year (ex-catastrophes) 171.2 554.3 725.5 99.6 43.5 143.1 868.6 - 868.6 - 868.6 Current year catastrophes 286.0 18.3 304.3 96.2 1.0 97.2 401.5 - 401.5 - 401.5 Prior years (27.1) (75.3) (102.4) (14.2) 0.4 (13.8) (116.2) - (116.2) - (116.2)

430.1 497.3 927.4 181.6 44.9 226.5 1,153.9 - 1,153.9 - 1,153.9 Commissions, brokerage and other

underwriting expenses 83.7 233.9 317.6 51.8 31.9 83.7 401.3 - 401.3 - 401.3

Underwriting (loss) profit (230.2)$ 21.3$ (208.9) (42.4)$ 2.1$ (40.3) (249.2) - (249.2) - (249.2)

Net investment income 84.0 34.8 118.8 1.1 119.9 2.9 122.8 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 4.7 0.8 5.5 595.2 600.7 10.6 611.3 Other operating expenses 5.4 (6.2) (0.8) 548.6 547.8 8.1 555.9 Corporate administration - (3.6) (3.6) - (3.6) (21.7) (25.3) Amortization of intangible assets (0.3) 0.2 (0.1) 7.4 7.3 - 7.3 Interest expense 6.8 - 6.8 4.3 11.1 13.6 24.7 Earnings (losses) before income taxes (503.9)$ (350.3)$ (854.2)$ 36.4$ (817.8)$ (72.9)$ (890.7)$


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%


For the Three Months Ended December 31, 2018

ALLEGHANY CORPORATION AND SUBSIDIARIESCONSOLIDATED UNDERWRITING RESULTS - PRIOR YEAR QUARTER

($ in millions)

Insurance Segment

PAGE 13



Gross premiums written 1,700.3$ 3,245.4$ 4,945.7$ 1,366.6$ 371.8$ 1,738.4$ 6,684.1$ -$ 6,684.1$ (27.7)$ 6,656.4$ Net premiums written 1,328.8 3,166.2 4,495.0 912.0 344.7 1,256.7 5,751.7 - 5,751.7 - 5,751.7

Net premiums earned 1,280.1$ 3,046.9$ 4,327.0$ 824.2$ 326.9$ 1,151.1$ 5,478.1$ -$ 5,478.1$ -$ 5,478.1$

Net loss and loss adjustment expenses:Current year (ex-catastrophes) 695.6 2,160.7 2,856.3 425.2 189.9 615.1 3,471.4 - 3,471.4 - 3,471.4 Current year catastrophes 293.2 7.4 300.6 96.0 3.1 99.1 399.7 - 399.7 - 399.7 Prior years (46.2) (149.6) (195.8) (17.5) 28.6 11.1 (184.7) - (184.7) - (184.7)

942.6 2,018.5 2,961.1 503.7 221.6 725.3 3,686.4 - 3,686.4 - 3,686.4 Commissions, brokerage and other

underwriting expenses 424.2 982.6 1,406.8 219.2 132.7 351.9 1,758.7 - 1,758.7 - 1,758.7

Underwriting profit (loss) (86.7)$ 45.8$ (40.9) 101.3$ (27.4)$ 73.9 33.0 - 33.0 - 33.0

Net investment income 371.9 161.3 533.2 6.3 539.5 10.7 550.2 Change in the fair value of equity securities 386.1 319.7 705.8 - 705.8 3.9 709.7 Net realized capital gains 41.3 (35.3) 6.0 1.0 7.0 (13.5) (6.5) Other than temporary impairment losses (19.1) (0.6) (19.7) - (19.7) - (19.7) Noninsurance revenue 21.9 5.1 27.0 2,289.3 2,316.3 12.5 2,328.8 Other operating expenses 57.8 45.3 103.1 2,132.9 2,236.0 27.3 2,263.3 Corporate administration - 4.1 4.1 - 4.1 70.7 74.8 Amortization of intangible assets (0.1) 1.4 1.3 32.5 33.8 - 33.8 Interest expense 27.1 - 27.1 20.1 47.2 52.8 100.0 Earnings (losses) before income taxes 676.4$ 473.3$ 1,149.7$ 111.1$ 1,260.8$ (137.2)$ 1,123.6$


Current year (ex-catastrophes) 54.3% 70.9% 66.0% 51.6% 58.2% 53.4% 63.4%Current year catastrophe losses 22.9% 0.2% 6.9% 11.6% 0.9% 8.6% 7.3%Prior years (3.6%) (4.9%) (4.5%) (2.1%) 8.7% 1.0% (3.4%)

73.6% 66.2% 68.4% 61.1% 67.8% 63.0% 67.3%Expense 33.1% 32.2% 32.5% 26.6% 40.6% 30.6% 32.1%

Combined 106.7% 98.4% 100.9% 87.7% 108.4% 93.6% 99.4%


Insurance SegmentFor the Twelve Months Ended December 31, 2019

ALLEGHANY CORPORATION AND SUBSIDIARIESCONSOLIDATED UNDERWRITING RESULTS - CURRENT YEAR TO DATE

($ in millions)

PAGE 14



Gross premiums written 1,532.7$ 2,918.3$ 4,451.0$ 1,142.0$ 328.8$ 1,470.8$ 5,921.8$ -$ 5,921.8$ (26.2)$ 5,895.6$ Net premiums written 1,169.4 2,799.7 3,969.1 773.3 306.0 1,079.3 5,048.4 - 5,048.4 - 5,048.4

Net premiums earned 1,177.3$ 2,761.7$ 3,939.0$ 747.3$ 289.9$ 1,037.2$ 4,976.2$ -$ 4,976.2$ -$ 4,976.2$

Net loss and loss adjustment expenses:Current year (ex-catastrophes) 670.9 1,964.4 2,635.3 395.0 161.4 556.4 3,191.7 - 3,191.7 - 3,191.7 Current year catastrophes 481.8 18.3 500.1 154.9 2.7 157.6 657.7 - 657.7 - 657.7 Prior years (84.9) (181.2) (266.1) (58.7) (4.2) (62.9) (329.0) - (329.0) - (329.0)

1,067.8 1,801.5 2,869.3 491.2 159.9 651.1 3,520.4 - 3,520.4 - 3,520.4 Commissions, brokerage and other

underwriting expenses 384.9 897.4 1,282.3 211.9 123.1 335.0 1,617.3 - 1,617.3 - 1,617.3

Underwriting (loss) profit (275.4)$ 62.8$ (212.6) 44.2$ 6.9$ 51.1 (161.5) - (161.5) - (161.5)

Net investment income 327.0 153.9 480.9 4.8 485.7 14.8 500.5 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) 49.9 31.6 0.9 32.5 (35.7) (3.2) Other than temporary impairment losses (0.9) (0.4) (1.3) - (1.3) - (1.3) Noninsurance revenue 18.9 3.1 22.0 1,574.6 1,596.6 47.4 1,644.0 Other operating expenses 44.4 15.4 59.8 1,485.6 1,545.4 33.9 1,579.3 Corporate administration - (1.7) (1.7) - (1.7) 17.6 15.9 Amortization of intangible assets (2.3) 1.9 (0.4) 24.4 24.0 - 24.0 Interest expense 27.1 - 27.1 10.5 37.6 53.1 90.7 Earnings (losses) before income taxes (59.3)$ 162.0$ 102.7$ 59.8$ 162.5$ (122.9)$ 39.6$


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%


Insurance SegmentFor the Twelve Months Ended December 31, 2018

ALLEGHANY CORPORATION AND SUBSIDIARIESCONSOLIDATED UNDERWRITING RESULTS - PRIOR YEAR TO DATE

($ in millions)

PAGE 15

Reinsurance Insurance Alleghany Corporate Reinsurance Insurance Alleghany CorporateSegment(1) Segment(1) Capital Activities(2) Consolidated Segment Segment Capital Activities(2) Consolidated

AssetsInvestments:

Securities at fair value: Equity securities 1,537.6$ 963.8$ -$ 4.1$ 2,505.5$ 1,823.2$ 1,685.5$ -$ 64.1$ 3,572.8$ Debt securities 10,216.4 3,812.8 - 182.5 14,211.7 9,217.5 2,606.4 - 0.1 11,824.0 Short-term investments 280.7 498.2 - 135.9 914.8 131.2 458.2 - 304.4 893.8

12,034.7 5,274.8 - 322.5 17,632.0 11,171.9 4,750.1 - 368.6 16,290.6 Commercial mortgage loans 480.3 205.9 - - 686.2 473.6 203.0 - (0.1) 676.5 Other invested assets 325.2 84.0 82.7 81.7 573.6 394.0 82.2 77.3 2.5 556.0

Total investments(3) 12,840.2 5,564.7 82.7 404.2 18,891.8 12,039.5 5,035.3 77.3 371.0 17,523.1 Cash(3) 963.7 77.1 136.4 1.9 1,179.1 928.4 69.7 38.0 2.7 1,038.8 Reinsurance recoverables 946.8 801.0 - (65.8) 1,682.0 1,001.0 987.1 - (66.8) 1,921.3 Goodwill 8.8 49.0 465.2 - 523.0 8.8 49.0 397.3 - 455.1 Intangible assets, net of amortization 78.2 65.4 542.4 - 686.0 74.3 68.6 410.3 (0.1) 553.1 All other assets 2,320.5 673.4 821.6 154.2 3,969.7 2,450.9 491.9 791.1 119.6 3,853.5

Total assets 17,158.2$ 7,230.6$ 2,048.3$ 494.5$ 26,931.6$ 16,502.9$ 6,701.6$ 1,714.0$ 426.4$ 25,344.9$

Liabilities and Stockholders' EquityLoss and loss adjustment expenses 9,323.8$ 2,670.3$ -$ (65.7)$ 11,928.4$ 9,442.2$ 2,874.9$ -$ (66.8)$ 12,250.3$ Unearned premiums 1,668.1 910.1 - (12.0) 2,566.2 1,523.9 754.2 - (11.0) 2,267.1 Senior Notes and other debt 389.8 - 400.3 961.0 1,751.1 390.7 - 284.5 993.8 1,669.0 All other liabilities 533.2 477.2 542.3 151.7 1,704.4 422.6 376.1 398.1 99.2 1,296.0

Total liabilities 11,914.9 4,057.6 942.6 1,035.0 17,950.1 11,779.4 4,005.2 682.6 1,015.2 17,482.4

Redeemable noncontrolling interests ("RNCI") - - 204.8 - 204.8 - - 169.8 - 169.8

Total stockholders' equity attributable to Alleghanystockholders 5,243.3 3,173.0 900.9 (540.5) 8,776.7 4,723.5 2,696.4 861.6 (588.8) 7,692.7 Total liabilities, RNCI and stockholders' equity 17,158.2$ 7,230.6$ 2,048.3$ 494.5$ 26,931.6$ 16,502.9$ 6,701.6$ 1,714.0$ 426.4$ 25,344.9$

(1) Annualized pre-tax return on average equity for the reinsurance and insurance segments was: 13.6% and 16.1%, respectively, for the twelve months ended December 31, 2019.(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, 2019, includes $1,283.3 million of marketable securities and cash at our unrestricted holding companies, comprised of $312.6 million at the Alleghany parent (included in Corporate Activities), $920.7 million

at AIHL (included in the Insurance Segment), and $50.0 million at the TransRe holding company (included in the Reinsurance Segment). (4) Debt for Alleghany Capital includes certain intercompany debt. Debt for Corporate Activities includes the elimination of such debt in consolidation.(5) Insurance segment stockholders' equity as of December 31, 2019 includes $1,873.8 million related to RSUI, $394.7 million related to CapSpecialty and $21.0 million related to AIHL Re, with the remaining

stockholders' equity relating to the AIHL holding company and Roundwood. As of December 31, 2018, insurance segment stockholders' equity included $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.

December 31, 2019 December 31, 2018

ALLEGHANY CORPORATION AND SUBSIDIARIESCONDENSED CONSOLIDATING BALANCE SHEETS

($ in millions)

(5) (4)

(4) (4)

PAGE 16

CARRYING VALUEEquity securities 2,505.5$ 13.3% 2,092.3$ 11.1% 2,292.8$ 12.2% 2,523.1$ 13.8% 3,572.8$ 20.4%

Debt securities 14,211.7 75.2% 14,488.3 76.8% 14,129.6 75.4% 13,279.7 72.5% 11,824.0 67.5%

Short-term investments 914.8 4.8% 968.5 5.1% 1,054.8 5.6% 1,272.4 6.9% 893.8 5.1%

Commercial mortgage loans 686.2 3.6% 706.0 3.7% 691.4 3.7% 676.5 3.7% 676.5 3.9%

Other invested assets 573.6 3.1% 610.2 3.3% 579.0 3.1% 563.5 3.1% 556.0 3.1%

Total 18,891.8$ 100.0% 18,865.3$ 100.0% 18,747.6$ 100.0% 18,315.2$ 100.0% 17,523.1$ 100.0%

INVESTMENT ALLOCATION BY CARRYING VALUEEquity securities:

Common stock 2,501.4$ 13.2% 2,088.2$ 11.1% 2,288.7$ 12.2% 2,518.5$ 13.8% 3,567.4$ 20.4%

Preferred stock 4.1 0.0% 4.1 0.0% 4.1 0.0% 4.6 0.0% 5.4 0.0%

2,505.5 13.3% 2,092.3 11.1% 2,292.8 12.2% 2,523.1 13.8% 3,572.8 20.4%

Debt securities:U.S. Government obligations 1,215.0 6.4% 1,288.2 6.8% 1,256.5 6.7% 1,182.9 6.5% 1,022.4 5.8%

Municipal bonds 2,307.9 12.2% 2,348.7 12.4% 2,448.3 13.1% 2,469.7 13.5% 2,214.7 12.6%

Foreign government obligations 690.7 3.7% 756.9 4.0% 783.4 4.2% 779.7 4.3% 947.9 5.4%

U.S. corporate bonds 3,359.0 17.8% 3,326.0 17.6% 3,090.4 16.5% 2,750.0 15.0% 2,385.3 13.6%

Foreign corporate bonds 1,377.4 7.3% 1,454.1 7.7% 1,437.1 7.7% 1,421.7 7.8% 1,353.3 7.7%

Mortgage and asset-backed securities:Residential mortgage-backed securities ("RMBS") 1,840.4 9.7% 1,935.7 10.3% 1,915.9 10.2% 1,976.6 10.8% 1,387.9 7.9%

Commercial mortgage-backed securities ("CMBS") 871.7 4.6% 821.5 4.4% 788.4 4.2% 588.8 3.2% 533.3 3.0%

Other asset-backed securities 2,549.6 13.5% 2,557.2 13.6% 2,409.6 12.9% 2,110.3 11.5% 1,979.2 11.3%

14,211.7 75.2% 14,488.3 76.8% 14,129.6 75.4% 13,279.7 72.5% 11,824.0 67.5%

Short-term investments 914.8 4.8% 968.5 5.1% 1,054.8 5.6% 1,272.4 6.9% 893.8 5.1%

Commercial mortgage loans 686.2 3.6% 706.0 3.7% 691.4 3.7% 676.5 3.7% 676.5 3.9%

Other invested assets:Equity method investments 163.3 0.9% 176.7 0.9% 176.2 0.9% 175.6 1.0% 168.9 1.0%

Partnership investments 409.3 2.2% 399.9 2.1% 392.6 2.1% 377.1 2.1% 372.2 2.1%

Other 1.0 0.1% 33.6 0.3% 10.2 0.1% 10.8 0.0% 14.9 0.0%

573.6 3.1% 610.2 3.3% 579.0 3.1% 563.5 3.1% 556.0 3.1%

Total 18,891.8$ 100.0% 18,865.3$ 100.0% 18,747.6$ 100.0% 18,315.2$ 100.0% 17,523.1$ 100.0%

RATINGS(1) OF DEBT SECURITIES PORTFOLIO, BY CARRYING VALUEAAA/Aaa 2,284.5$ 16.1% 2,338.6$ 16.1% 2,225.6$ 15.8% 1,977.1$ 14.9% 1,860.2$ 15.7%

AA/Aa 5,901.5 41.5% 6,117.6 42.3% 6,145.4 43.4% 5,941.9 44.7% 5,048.3 42.7%

A 3,422.9 24.1% 3,426.3 23.6% 3,214.5 22.8% 2,823.1 21.3% 2,477.1 20.9%

BBB/Baa 2,094.2 14.7% 2,101.2 14.5% 2,050.9 14.5% 2,058.5 15.5% 1,921.8 16.3%

BB / Ba 89.3 0.7% 94.1 0.6% 80.7 0.6% 115.8 0.9% 167.8 1.5%

B 246.6 1.7% 226.4 1.6% 223.7 1.6% 200.5 1.5% 205.3 1.7%

CCC 24.4 0.2% 29.2 0.2% 33.4 0.2% 30.9 0.2% 34.7 0.3%

CC - 0.0% - 0.0% 0.4 0.0% - 0.0% 0.4 0.0%

Below CC 2.0 0.0% 2.1 0.0% 2.2 0.0% 2.6 0.0% 3.3 0.0%

Not rated 146.3 1.0% 152.8 1.1% 152.8 1.1% 129.3 1.0% 105.1 0.9%

14,211.7$ 100.0% 14,488.3$ 100.0% 14,129.6$ 100.0% 13,279.7$ 100.0% 11,824.0$ 100.0%

Duration of debt securities portfolio 4.2 years 4.2 years 4.2 years 4.2 years 4.2 years

Average credit quality(2) 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.

June 30, 2019December 31, 2019 September 30, 2019 December 31, 2018March 31, 2019

ALLEGHANY CORPORATION AND SUBSIDIARIESCONSOLIDATED TOTAL INVESTMENT PORTFOLIO

($ in millions)

PAGE 17

BelowBBB / Baa

AAA / Aaa AA / Aa A BBB / Baa or Not-Rated Total

U.S. Government obligations -$ 1,215.0$ -$ -$ -$ 1,215.0$ Municipal bonds 182.5 1,542.6 508.0 73.8 1.0 2,307.9 Foreign government obligations 430.8 164.8 94.0 1.1 - 690.7 U.S. corporate bonds 11.1 143.4 1,496.5 1,338.9 369.1 3,359.0 Foreign corporate bonds 266.2 128.9 599.5 337.7 45.1 1,377.4 Mortgage and asset-backed securities:

RMBS 1.9 1,832.7 - 0.5 5.3 1,840.4 CMBS 280.5 408.5 182.1 0.6 - 871.7 Other asset-backed securities 1,111.5 465.6 542.8 341.6 88.1 2,549.6

Total debt securities 2,284.5$ 5,901.5$ 3,422.9$ 2,094.2$ 508.6$ 14,211.7$

Percentage of debt securities 16.1% 41.5% 24.1% 14.7% 3.6% 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.

As of December 31, 2019

ALLEGHANY CORPORATION AND SUBSIDIARIESDEBT SECURITIES PORTFOLIO CREDIT QUALITY(1)

($ in millions)

PAGE 18

2019 2018

Interest income 123.0$ 107.6$ Dividends 9.0 23.7

Total interest income and dividends 132.0 131.3

Pillar Capital Holdings Limited and related funds 3.4 (7.7) Limited partnership interests in certain subsidiaries of Ares Management, L.P. - - Other investment results 8.1 5.3

Total investment income 143.5 128.9

Investment expenses (6.9) (6.1)

Net investment income 136.6$ 122.8$

Net investment income - after tax(1) 111.3$ 102.2$

December 31,2019 2018

Interest income 499.5$ 420.8$ Dividends 37.9 78.5

Total interest income and dividends 537.4 499.3

Pillar Capital Holdings Limited and related funds 15.0 (6.5) Limited partnership interests in certain subsidiaries of Ares Management, L.P. - 20.2 Other investment results 26.7 19.0

Total investment income 579.1 532.0

Investment expenses (28.9) (31.5)

Net investment income 550.2$ 500.5$

Net investment income - after tax(1) 449.2$ 416.9$

(1) Reflects income tax at a 21.0% statutory rate, except for tax-exempt interest income and dividends subject to dividend-received deductions.

Twelve Months Ended

Three Months Ended

($ in millions)

ALLEGHANY CORPORATION AND SUBSIDIARIESNET INVESTMENT INCOME

December 31,

PAGE 19

For the Twelve Months EndedDecember 31, 2019 September 30, 2019 June 30, 2019 March 31, 2019 December 31, 2018 December 31, 2019 December 31, 2018

Investment income and realized gains(1):Net investment income 136.6$ 147.8$ 142.7$ 123.0$ 122.8$ 550.2$ 500.5$ Change in the fair value of equity securities 190.4 (16.7) 143.7 392.4 (741.8) 709.7 (229.0) Net realized capital gains: Debt securities 18.9$ 9.7$ 12.4$ 4.4$ (35.5)$ 45.5$ (23.4)$ Other (46.2) (5.8) - - (34.9) (52.0) 20.2

(27.3) 3.9 12.4 4.4 (70.4) (6.5) (3.2) Other than temporary impairment losses: Debt securities (6.1)$ (3.6)$ -$ (10.0)$ (0.8)$ (19.7)$ (1.3)$ Other - - - - - - -

(6.1) (3.6) - (10.0) (0.8) (19.7) (1.3) 293.6 131.4 298.8 509.8 (690.2) 1,233.7 267.0

Opening net unrealized gains (losses) on debt securities(1) 476.0$ 372.7$ 166.2$ (71.9)$ (108.6)$ (71.9)$ 184.6$ Closing net unrealized gains (losses) on debt securities(1) 413.1 476.0 372.7 166.2 (71.9) 413.1 (71.9) Increase (decrease) in net unrealized gains on debt securities(1) (62.9)$ 103.3$ 206.5$ 238.1$ 36.7$ 485.0$ (256.5)$

Net investment income, realized gains and unrealized gains(1) 230.7$ 234.7$ 505.3$ 747.9$ (653.5)$ 1,718.7$ 10.5$

Opening aggregate invested assets 18,865.3$ 18,747.6$ 18,315.2$ 17,523.1$ 19,042.7$ 17,523.1$ 18,800.7$ Closing aggregate invested assets 18,891.8 18,865.3 18,747.6 18,315.2 17,523.1 18,891.8 17,523.1

Average invested assets, at carrying value(2) 18,878.6$ 18,806.5$ 18,531.4$ 17,919.2$ 18,282.9$ 18,207.5$ 18,161.9$

Financial statement portfolio return(1)(2) 1.2% 1.2% 2.7% 4.2% (3.6%) 9.3% 0.1%Annualized financial statement portfolio return(1) 4.9% 5.0% 10.9% 16.7% (14.3%)

(1) Before income taxes.(2) For the year-to-date periods, represents the sum of each quarterly return.


ALLEGHANY CORPORATION AND SUBSIDIARIESFINANCIAL STATEMENT PORTFOLIO RETURN

($ in millions)

PAGE 20

For the Twelve Months EndedDecember 31, 2019 September 30, 2019 June 30, 2019 March 31, 2019 December 31, 2018 December 31, 2019 December 31, 2018 S

Net investment income 136.6$ 147.8$ 142.7$ 123.0$ 122.8$ 550.2$ 500.5$

Opening invested assets:Debt securities portfolio, at amortized cost 14,012.3$ 13,756.9$ 13,113.5$ 11,895.9$ 12,179.8$ 11,895.9$ 12,536.8$ Equity securities portfolio, at cost 1,399.1 1,471.1 1,789.1 2,904.5 3,655.2 2,904.5 3,170.7 Short-term investments, at fair value(1) 968.5 1,054.8 1,272.4 893.8 690.6 893.8 578.1 Commercial mortgage loans(2) 706.0 691.4 676.5 676.5 695.9 676.5 658.4 Other invested assets, at carrying value(2) 610.2 579.0 563.5 556.0 556.4 556.0 743.3

17,696.1 17,553.2 17,415.0 16,926.7 17,777.9 16,926.7 17,687.3

Ending invested assets:Debt securities portfolio, at amortized cost 13,798.6$ 14,012.3$ 13,756.9$ 13,113.5$ 11,895.9$ 13,798.6$ 11,895.9$ Equity securities portfolio, at cost 1,625.3 1,399.1 1,471.1 1,789.1 2,904.5 1,625.3 2,904.5 Short-term investments, at fair value(1) 914.8 968.5 1,054.8 1,272.4 893.8 914.8 893.8 Commercial mortgage loans(2) 686.2 706.0 691.4 676.5 676.5 686.2 676.5 Other invested assets, at carrying value(2) 573.6 610.2 579.0 563.5 556.0 573.6 556.0

17,598.5 17,696.1 17,553.2 17,415.0 16,926.7 17,598.5 16,926.7 Average invested assets 17,647.3$ 17,624.7$ 17,484.1$ 17,170.9$ 17,352.3$ 17,262.6$ 17,307.0$

Investment book yield(3) 0.8% 0.8% 0.8% 0.7% 0.7% 3.1% 2.8%

Annualized investment book yield 3.1% 3.4% 3.3% 2.9% 2.8%

(1) Fair value approximates amortized cost.(2) For commercial mortgage loans, values reflect cost. For other invested assets, carrying value reflects the equity method of accounting for certain private equity and partnerships, and to a lesser extent, fair value or cost for certain other investments. (3) For the year-to-date periods, represents the sum of each quarterly yield.

ALLEGHANY CORPORATION AND SUBSIDIARIESANNUALIZED INVESTMENT BOOK YIELD

($ in millions)


PAGE 21

For the Twelve Months ended December 31, 2019 2018

Reserves, beginning of period 12,250.3$ 11,871.3$ Less: reinsurance recoverables(1) 1,857.4 1,650.1 Net reserves, beginning of period 10,392.9 10,221.2

Other adjustments (2.3) 0.9

Incurred loss and LAE, net of reinsurance, related to:Current year 3,871.1 3,849.4 Prior years (184.7) (329.0)

Total incurred loss and LAE, net of reinsurance 3,686.4 3,520.4

Paid loss and LAE, net of reinsurance, related to:(2)

Current year 884.6 838.9 Prior years 2,839.9 2,419.0

Total paid loss and LAE, net of reinsurance 3,724.5 3,257.9

Foreign currency exchange rate effect (8.0) (91.7)

Net reserves, end of period 10,344.5 10,392.9 Plus: reinsurance recoverables(1) 1,583.9 1,857.4 Reserves, end of period 11,928.4$ 12,250.3$

(1) Reinsurance recoverables in this table include only ceded loss and LAE reserves. (2) Includes paid loss and LAE, net of reinsurance, related to commutations.

ALLEGHANY CORPORATION AND SUBSIDIARIESLOSS AND LOSS ADJUSTMENT EXPENSES (LAE)

($ in millions)

PAGE 22

December 31, 2019 September 30, 2019 June 30, 2019 March 31, 2019 December 31, 2018

Capital StructureSenior Notes 1,384.1$ 1,384.0$ 1,384.1$ 1,384.0$ 1,384.5$ Other debt (excluding intercompany debt) 367.0 311.3 330.6 292.4 284.5 Senior Notes and other debt 1,751.1$ 1,695.3$ 1,714.7$ 1,676.4$ 1,669.0$

Redeemable noncontrolling interests 204.8 180.9 175.6 175.7 169.8 Stockholders' equity attributable to Alleghany

stockholders 8,776.7 8,828.7 8,685.9 8,236.5 7,692.7 Total capitalization 10,732.6$ 10,704.9$ 10,576.2$ 10,088.6$ 9,531.5$

Leverage RatiosDebt to total capitalization 16.3% 15.8% 16.2% 16.6% 17.5%

Net premiums written (trailing 12 months) 5,751.7$ 5,526.2$ 5,351.4$ 5,180.7$ 5,048.4$ Net premiums written (trailing 12 months) to stockholders' equity 0.66 x 0.63 x 0.62 x 0.63 x 0.66 x

Invested assets and cash 20,070.9$ 19,762.7$ 19,572.4$ 19,093.3$ 18,561.9$ Total investments and cash to stockholders' equity 2.29 x 2.24 x 2.25 x 2.32 x 2.41 x

Reserve for loss and loss adjustment expenses 11,928.4$ 11,634.0$ 11,631.8$ 11,855.1$ 12,250.3$ Deduct: reinsurance recoverable on ceded losses (1,583.9) (1,509.7) (1,557.1) (1,642.8) (1,857.4) Net reserve for loss and loss adjustment expenses 10,344.5 10,124.3 10,074.7 10,212.3 10,392.9

Net reserve for loss and loss adjustment expenses to stockholders' equity 1.18 x 1.15 x 1.16 x 1.24 x 1.35 x

ALLEGHANY CORPORATION AND SUBSIDIARIESCAPITAL STRUCTURE AND LEVERAGE RATIOS

($ in millions)

PAGE 23

2019 2018 Change % Change 2019 2018 Change % Change

Industrial:(2)

PCT 14.3$ 12.3$ 2.0$ 16.3% 39.3$ 34.5$ 4.8$ 13.9% Kentucky Trailer 59.6 46.5 13.1 28.2% 240.6 181.7 58.9 32.4% W&W|AFCO Steel 166.4 266.6 (100.2) -37.6% 825.7 700.9 124.8 17.8%

240.3 325.4 (85.1) -26.2% 1,105.6 917.1 188.5 20.6%Non-industrial: IPS 169.8 124.2 45.6 36.7% 646.5 378.0 268.5 71.0% Jazwares(3) 103.7 110.3 (6.6) -6.0% 351.2 244.4 106.8 43.7% Concord(4) 49.1 35.1 14.0 - 186.0 35.1 150.9 -

322.6 269.6 53.0 19.7% 1,183.7 657.5 526.2 80.0%

Corporate & other (0.3) 0.2 (0.5) -250.0% - - - 0.0%

Total 562.6$ 595.2$ (32.6)$ -5.5% 2,289.3$ 1,574.6$ 714.7$ 45.4%

(1) Classified as "noninsurance revenue" on Alleghany's consolidated statement of earnings.(2) Excludes Wilbert; Wilbert is accounted for under the equity method of accounting. (3) Typically, the first half of the year is a seasonal low for the sale of toys, and the second half of the year is a seasonal high for the sale of toys.(4) The results of Concord have been included in Alleghany’s consolidated results beginning with its acquisition by Alleghany Capital on October 1, 2018.

Three Months EndedDecember 31,

Twelve Months EndedDecember 31,

ALLEGHANY CORPORATION AND SUBSIDIARIESALLEGHANY CAPITAL NONINSURANCE REVENUE(1)

($ in millions)

PAGE 24

Non- Corp. & Non- Corp. &Industrial industrial other(2) Total(2) Industrial industrial other(2) Total(2)

Noninsurance revenue(3) 240.3$ 322.6$ (0.3)$ 562.6$ 325.4$ 269.6$ 0.2$ 595.2$ Net investment income 2.4 0.1 0.4 2.9 1.1 - - 1.1 Net realized capital gains 0.6 0.1 - 0.7 0.6 (0.2) - 0.4 Total revenues 243.3 322.8 0.1 566.2 327.1 269.4 0.2 596.7

Other operating expenses(3) 237.8 300.2 3.0 541.0 310.6 236.9 1.1 548.6 Amortization of intangible assets 3.2 6.5 - 9.7 3.1 4.3 - 7.4 Interest expense 2.4 3.5 - 5.9 2.9 1.2 0.2 4.3 Earnings (losses) before income taxes (0.1)$ 12.6$ (2.9)$ 9.6$ 10.5$ 27.0$ (1.1)$ 36.4$

Earnings (losses) before income taxes (0.1)$ 12.6$ (2.9)$ 9.6$ 10.5$ 27.0$ (1.1)$ 36.4$ Less: net realized capital gains (0.6) (0.1) - (0.7) (0.6) 0.2 - (0.4) Add: amortization of intangible assets 3.2 6.5 - 9.7 3.1 4.3 - 7.4 Adjusted earnings (losses) before income taxes(4) 2.5$ 19.0$ (2.9)$ 18.6$ 13.0$ 31.5$ (1.1)$ 43.4$

(1) The Alleghany Capital segment consists of: (i) industrial operations conducted through PCT, Kentucky Trailer, W&W|AFCO Steel and a 45% equity interest in Wilbert Funeral Services, Inc. ("Wilbert"); (ii) non-industrial operations conducted through IPS, Jazwares and Concord, beginning October 1, 2018; and (iii) corporate operations at the Alleghany Capital level.(2) Excludes certain minor, legacy investments that were previously reflected in Alleghany Capital in 2018 and prior periods.(3) 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, 2019 and 2018, other operating expenses also included $1.1 million and $4.5 million, respectively, of finders' fees, legal and accounting costs and other transaction-related expenses.(4) Refer to "Non-GAAP Financial Measures" on page 35 of the Financial Supplement.


Equity, beginning of period 536.1$ 410.7$ (45.3)$ 901.5$ 447.9$ 321.1$ 67.9$ 836.9$ Earnings (losses) before income taxes (0.1) 12.6 (2.9) 9.6 10.5 27.0 (1.1) 36.4 Income taxes(7) (2.1) (1.5) (2.8) (6.4) (0.8) (0.8) (4.4) (6.0) Net earnings attributable to noncontrolling interests(8) 1.4 (5.9) - (4.5) (1.5) (6.2) - (7.7) Capital contributions (returns of capital) and other(9) (12.0) (5.3) 18.0 0.7 6.4 102.2 (106.6) 2.0 Equity, end of period 523.3$ 410.6$ (33.0)$ 900.9$ 462.5$ 443.3$ (44.2)$ 861.6$

(5) Represents stockholders' equity attributable to Alleghany.

(6) Excludes certain minor, legacy investments that were previously reflected in Alleghany Capital in 2018 and prior periods.

(7) 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 2019 was $0.2 million and ($2.6) million, respectively, and for the fourth quarter of 2018 was

($2.8) million and ($5.7) million, respectively.

(8) During the fourth quarter of 2019, noncontrolling interests outstanding were approximately as follows: Kentucky Trailer-23%; W&W|AFCO Steel-20%; IPS-15%; Jazwares-25%; and Concord-15%.

(9) For the fourth quarter of 2018, capital contributions primarily reflect funding provided by Alleghany to Alleghany Capital for the acquisition of Concord.

ALLEGHANY CORPORATION AND SUBSIDIARIESALLEGHANY CAPITAL RESULTS - QUARTER TO DATE(1)


($ in millions)

2019 2018

For the Three Months Ended December 31,


ALLEGHANY CAPITAL EQUITY(5)

($ in millions)

PAGE 25


Noninsurance revenue(3) 1,105.6$ 1,183.7$ -$ 2,289.3$ 917.1$ 657.5$ -$ 1,574.6$ Net investment income 6.1 (0.2) 0.4 6.3 4.7 0.1 - 4.8 Net realized capital gains 1.3 (0.3) - 1.0 1.2 (0.3) - 0.9 Total revenues 1,113.0 1,183.2 0.4 2,296.6 923.0 657.3 - 1,580.3

Other operating expenses(3) 1,038.0 1,076.4 18.5 2,132.9 880.8 595.0 9.8 1,485.6 Amortization of intangible assets 12.5 20.0 - 32.5 9.8 14.6 - 24.4 Interest expense 11.6 8.1 0.4 20.1 7.4 2.9 0.2 10.5 Earnings (losses) before income taxes 50.9$ 78.7$ (18.5)$ 111.1$ 25.0$ 44.8$ (10.0)$ 59.8$

Earnings (losses) before income taxes 50.9$ 78.7$ (18.5)$ 111.1$ 25.0$ 44.8$ (10.0)$ 59.8$ Less: net realized capital gains (1.3) 0.3 - (1.0) (1.2) 0.3 - (0.9) Add: amortization of intangible assets 12.5 20.0 - 32.5 9.8 14.6 - 24.4 Adjusted earnings (losses) before income taxes(4) 62.1$ 99.0$ (18.5)$ 142.6$ 33.6$ 59.7$ (10.0)$ 83.3$

(1) The Alleghany Capital segment consists of: (i) industrial operations conducted through PCT, Kentucky Trailer, W&W|AFCO Steel and a 45% equity interest in Wilbert; (ii) non- industrial operations conducted through IPS, Jazwares and Concord, beginning October 1, 2018; and (iii) corporate operations at the Alleghany Capital level.(2) Excludes certain minor, legacy investments that were previously reflected in Alleghany Capital in 2018 and prior periods.(3) 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, 2019 and 2018, other operating expenses also included $4.1 million and $7.7 million, respectively, of finders' fees, legal and accounting costs and other transaction-related expenses.(4) Refer to "Non-GAAP Financial Measures" on page 35 of the Financial Supplement.


Equity, beginning of period 462.5$ 443.3$ (44.2)$ 861.6$ 363.6$ 331.3$ (7.7)$ 687.2$ Earnings (losses) before income taxes 50.9 78.7 (18.5) 111.1 25.0 44.8 (10.0) 59.8 Income taxes(7) (2.8) (4.0) (18.0) (24.8) (1.7) (2.2) (6.7) (10.6) Net earnings attributable to noncontrolling interests(8) (7.7) (24.7) - (32.4) (3.2) (11.9) - (15.1) Capital contributions (returns of capital) and other(9) 20.4 (82.7) 47.7 (14.6) 78.8 81.3 (19.8) 140.3 Equity, end of period 523.3$ 410.6$ (33.0)$ 900.9$ 462.5$ 443.3$ (44.2)$ 861.6$

(5) Represents stockholders' equity attributable to Alleghany.

(6) Excludes certain minor, legacy investments with a carrying value of $17.7 million as of December 31, 2018, that were previously reflected in Alleghany Capital in 2018 and prior periods.

(7) 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 2019 was ($10.5) million and ($16.5) million, respectively, and for the full year 2018 was ($5.3) million and ($9.4)

million, respectively.

(8) During the 2019, noncontrolling interests outstanding were approximately as follows: Kentucky Trailer-23%; W&W|AFCO Steel-20%; IPS-15%; and Concord-15%. In connection with an acquisition on

October 1, 2019, the noncontrolling interests of Jazwares were increased from approximately 23 percent to approximately 25 percent. Prior to April 1, 2019, the noncontrolling interests of PCT were

approximately 11 percent. All noncontrolling interest holders of PCT have exercised their repurchase options and sold their ownership interests to PCT effective April 1, 2019.

(9) For 2019, capital contributions primarily reflect funding provided by Alleghany Capital to PCT for the acquisition of a consumable cutting tool manufacturer.

For 2018, capital contributions primarily reflect funding provided by Alleghany to Alleghany Capital for the acquisition of Concord and funding provided by Alleghany Capital for the acquisition of

Hirschfeld Holdings, LP by W&W|AFCO Steel.

For the Twelve Months Ended December 31, 2019

ALLEGHANY CORPORATION AND SUBSIDIARIESALLEGHANY CAPITAL RESULTS - YEAR TO DATE(1)

($ in millions)


2019 2018

ALLEGHANY CAPITAL EQUITY(5)

($ in millions)

For the Twelve Months Ended December 31, 2018

PAGE 26

Non- Corp. & Non- Corp. &Industrial Industrial other Consolidated Industrial Industrial other Consolidated

AssetsCash 41.3$ 58.0$ 37.1$ 136.4$ 11.3$ 23.2$ 3.5$ 38.0$ Other invested assets 81.6 (1) 1.1 - 82.7 76.0 (1) 1.8 (0.5) 77.3 Property and equipment at cost, net 124.0 20.3 - 144.3 121.8 16.5 - 138.3 Goodwill 170.3 297.7 (2.8) 465.2 151.7 248.4 (2.8) 397.3 Intangible assets, net of amortization 185.1 357.3 - 542.4 152.2 258.1 - 410.3 All other assets(2) 393.9 298.3 (14.9) 677.3 379.2 272.1 1.5 652.8

Total assets 996.2$ 1,032.7$ 19.4$ 2,048.3$ 892.2$ 820.1$ 1.7$ 1,714.0$

Liabilities and Stockholders' EquityDebt 149.3$ 251.0$ -$ 400.3$ 186.4$ 98.1$ -$ 284.5$ All other liabilities(3) 253.8 236.1 52.4 542.3 176.9 175.3 45.9 398.1

Total liabilities 403.1 487.1 52.4 942.6 363.3 273.4 45.9 682.6

Redeemable noncontrolling interests ("RNCI") 69.8 135.0 - 204.8 66.4 103.4 - 169.8

Total stockholders' equity attributable to Alleghanystockholders 523.3 410.6 (33.0) 900.9 462.5 443.3 (44.2) 861.6 Total liabilities, RNCI and stockholders' equity 996.2$ 1,032.7$ 19.4$ 2,048.3$ 892.2$ 820.1$ 1.7$ 1,714.0$

(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.

December 31, 2019 December 31, 2018

ALLEGHANY CORPORATION AND SUBSIDIARIESALLEGHANY CAPITAL CONDENSED CONSOLIDATING BALANCE SHEETS

($ in millions)

PAGE 27


Non- Corp. & Non- Corp. &Industrial Industrial other Consolidated Industrial Industrial other Consolidated

Cash flows from operating activitiesNet earnings (losses)(1) 48.1$ 74.7$ (36.5)$ 86.3$ 23.3$ 42.6$ (18.4)$ 47.5$ Adjustments to reconcile net earnings (losses) to net cash provided by (used in) operating activities: Depreciation and amortization 29.1 27.0 - 56.1 24.3 20.2 - 44.5 Net realized capital (gains) (1.3) 0.3 - (1.0) (1.2) 0.3 - (0.9) Change in assets and liabilities 58.6 42.9 20.8 122.3 (75.9) (48.9) 10.0 (114.8) Net adjustments 86.4 70.2 20.8 177.4 (52.8) (28.4) 10.0 (71.2) Net cash provided by (used in) operating activities 134.5 144.9 (15.7) 263.7 (29.5) 14.2 (8.4) (23.7)

Cash flows from investing activitiesNet (increase) decrease in short-term investments - - - - - - - - (Purchases) sales of property and equipment (11.7) (8.0) - (19.7) (6.1) (7.2) - (13.3) Purchases of affiliates and subsidiaries, net of cash acquired (66.5) (150.7) - (217.2) (153.1) (9.8) (68.6) (231.5) Other, net - 0.3 - 0.3 (0.5) (0.4) 9.3 8.4 Net cash provided by (used in) investing activities (78.2) (158.4) - (236.6) (159.7) (17.4) (59.3) (236.4)

Cash flows from financing activitiesIncrease (decrease) in debt (37.1) 152.1 - 115.0 77.7 26.7 - 104.4 Capital contributions (returns of capital) 10.8 (103.8) 49.3 (43.7) 101.6 (20.0) 75.3 156.9 Other, net - - - - 7.7 0.7 (19.2) (10.8) Net cash provided by (used in) financing activities (26.3) 48.3 49.3 71.3 187.0 7.4 56.1 250.5

Net increase (decrease) in cash 30.0 34.8 33.6 98.4 (2.2) 4.2 (11.6) (9.6) Cash at beginning of period 11.3 23.2 3.5 38.0 13.5 19.0 15.1 47.6 Cash at end of period 41.3$ 58.0$ 37.1$ 136.4$ 11.3$ 23.2$ 3.5$ 38.0$

Supplemental disclosure of cash flow informationCash paid during the period for:Interest paid 11.5$ 6.1$ -$ 17.6$ 6.8$ 2.2$ -$ 9.0$ Income taxes paid (refunds received)(1) 1.2 0.9 4.3 6.4 0.2 1.7 (0.2) 1.7

(1) Federal income taxes for most Alleghany Capital subsidiaries are incurred and presented at the Alleghany Capital level.

2019 2018

ALLEGHANY CORPORATION & SUBSIDIARIESALLEGHANY CAPITAL CONDENSED CONSOLIDATING STATEMENTS OF CASH FLOWS

($ in millions)

PAGE 28


Net earnings (losses) attributable to Alleghany stockholders 31.7$ 90.4$ 295.5$ 440.2$ (712.1)$ 857.8$ 39.5$ Effect of dilutive securities (3.2) - - - - - - Income (loss) available to common stockholders for

diluted earnings per share 28.5$ 90.4$ 295.5$ 440.2$ (712.1)$ 857.8$ 39.5$

Weighted average common shares outstanding applicable to basic earnings per share 14,384,186 14,422,581 14,439,545 14,481,255 14,743,777 14,431,892 15,062,567

Effect of dilutive securities 43,722 - - 3,981 - 11,584 - Adjusted weighted average common shares

outstanding applicable to diluted earnings per share 14,427,908 14,422,581 14,439,545 14,485,236 14,743,777 14,443,476 15,062,567

Basic earnings (losses) per share attributable to Alleghany stockholders 2.20$ 6.27$ 20.46$ 30.40$ (48.30)$ 59.44$ 2.62$

Diluted earnings (losses) per share attributable to Alleghany stockholders 1.98 6.27 20.46 30.39 (48.30) 59.39 2.62

ALLEGHANY CORPORATION AND SUBSIDIARIESBASIC AND DILUTED EARNINGS PER SHARE INFORMATION



PAGE 29

For the Twelve Months EndedDecember 31, 2019 September 30, 2019 June 30, 2019 March 31, 2019 December 31, 2018 December 31, 2019 December 31, 2018

Net earnings (losses) attributable to Alleghany stockholders 31.7$ 90.4$ 295.5$ 440.2$ (712.1)$ 857.8$ 39.5$

Adjustments to net earnings:Change in the fair value of equity securities 190.4 (16.7) 143.7 392.4 (741.8) 709.7 (229.0) Net realized capital gains (27.3) 3.9 12.4 4.4 (70.4) (6.5) (3.2) Other than temporary impairment losses (6.1) (3.6) - (10.0) (0.8) (19.7) (1.3) Amortization of intangible assets (10.0) (8.1) (8.8) (6.9) (7.3) (33.8) (24.0) Income tax effect of adjustments (30.9) 5.1 (30.9) (79.8) 172.3 (136.5) 54.1

116.1 (19.4) 116.4 300.1 (648.0) 513.2 (203.4)

Adjusted earnings (loss) (84.4)$ 109.8$ 179.1$ 140.1$ (64.1)$ 344.6$ 242.9$

Weighted average common shares outstanding:Basic 14,384,186 14,422,581 14,439,545 14,481,255 14,743,777 14,431,892 15,062,567 Diluted 14,427,908 14,422,581 14,439,545 14,485,236 14,743,777 14,443,476 15,062,567

Earnings (losses) per share attributable to Alleghany stockholders:Basic 2.20$ 6.27$ 20.46$ 30.40$ (48.30)$ 59.44$ 2.62$ Diluted(1) 1.98 6.27 20.46 30.39 (48.30) 59.39 2.62

Adjusted earnings (losses) per share data:Basic(2) (5.87)$ 7.61$ 12.40$ 9.67$ (4.35)$ 23.82$ 16.13$ Diluted(1)(2) (6.09) 7.61 12.40 9.66 (4.35) 23.77 16.13

(1) The numerators for calculating diluted earnings per share and operating earnings per share may be further reduced for the effect of dilutive securities. (2) For adjusted earnings per share on a year-to-date basis: basic is calculated as the sum of individual quarters, and adjusted is calculated as basic less any dilution under GAAP.

ALLEGHANY CORPORATION AND SUBSIDIARIESADJUSTED EARNINGS RECONCILIATION

($ in millions, except share and per share amounts)


PAGE 30


Opening stockholders' equity attributable to Alleghany stockholders 8,828.7$ 8,685.9$ 8,236.5$ 7,692.7$ 8,595.1$ 7,692.7$ 8,514.1$

Closing stockholders' equity attributable to Alleghany stockholders 8,776.7 8,828.7 8,685.9 8,236.5 7,692.7 8,776.7$ 7,692.7$

Average stockholders' equity 8,802.7$ 8,757.3$ 8,461.2$ 7,964.6$ 8,143.9$ 8,234.7$ 8,103.4$

Net earnings (losses) attributable to Alleghany stockholders 31.7$ 90.4$ 295.5$ 440.2$ (712.1)$ 857.8$ 39.5$

Return on average stockholders' equity 0.4% 1.0% 3.5% 5.5% -8.7% 10.4% 0.5%

Annualized return on average stockholders' equity 1.4% 4.1% 14.0% 22.1% -35.0%

Adjusted earnings (loss) (84.4)$ 109.8$ 179.1$ 140.1$ (64.1)$ 344.6$ 242.9$

Adjusted return on average stockholders' equity -1.0% 1.3% 2.1% 1.8% -0.8% 4.2% 3.0%

Annualized adjusted return on averagestockholders' equity -3.8% 5.0% 8.5% 7.0% -3.1%


ALLEGHANY CORPORATION AND SUBSIDIARIESRETURN ON AVERAGE STOCKHOLDERS' EQUITY - CONSECUTIVE QUARTERS

($ in millions)

PAGE 31

December 31, 2019 September 30, 2019 June 30, 2019 March 31, 2019 December 31, 2018

Total stockholders' equity attributable to Alleghany stockholders ("Equity") 8,776.7$ 8,828.7$ 8,685.9$ 8,236.5$ 7,692.7$

Shares outstanding 14,364,628 14,405,508 14,430,862 14,447,737 14,576,509

Book value per share 611.00$ 612.87$ 601.90$ 570.09$ 527.75$

Quarter-over-quarter growth (0.3%) 1.8% 5.6% 8.0% (8.4%)

Accumulated other comprehensive income (loss)("AOCI") 171.3$ 223.3$ 152.0$ (14.2)$ (202.0)$

Equity excluding AOCI 8,605.4$ 8,605.4$ 8,533.9$ 8,250.7$ 7,894.7$

Book value per share excluding AOCI 599.07$ 597.37$ 591.36$ 571.07$ 541.60$

Quarter-over-quarter growth 0.3% 1.0% 3.6% 5.4% (8.3%)

ALLEGHANY CORPORATION AND SUBSIDIARIESBOOK VALUE PER SHARE


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Total Stock- Total Stock-holders' Equity Redeemable holders' Equity Redeemable

Attributable to Noncontrolling attributable to noncontrollingAlleghany Interest Alleghany Interest

Balance as of the beginning of the period 8,828.7$ 180.9$ 7,692.7$ 169.8$

Add (deduct):

Net earnings 31.7 4.5 857.8 32.4

Other comprehensive income, net of tax:Change in unrealized gains: debt securities portfolio (49.4) - 382.6 - Change in unrealized currency translation adjustment 11.0 - 2.9 - Retirement plans (13.6) - (12.2) -

Comprehensive income, net of tax (20.3) 4.5 1,231.1 32.4

Treasury stock repurchase (32.0) - (144.4) -

Other 0.3 19.4 (2.7) 2.6

Balance as of the end of the period 8,776.7$ 204.8$ 8,776.7$ 204.8$

ALLEGHANY CORPORATION AND SUBSIDIARIESCONSOLIDATED CHANGES IN STOCKHOLDERS' EQUITY

($ in millions)

For the Three Months Ended December 31, 2019 December 31, 2019

For the Twelve Months Ended

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Gross Loss Net Loss Gross Loss Net Loss(before tax) (after tax) (before tax) (after tax)

($ in billions)

U.S., Wind 2.1$ 0.7$ 2.7$ 0.8$

Florida, Wind 1.4$ 0.6$ 1.9$ 0.7$ California, Earthquake 1.1 0.5 2.0 0.7 Gulf Coast, Wind 0.9 0.5 1.6 0.6 Northeast U.S., Wind 0.9 0.4 1.7 0.7 Japan, Earthquake 0.6 0.2 0.9 0.3 Europe, Wind 0.5 0.2 0.7 0.3 Japan, Wind 0.5 0.2 0.5 0.2

ALLEGHANY CORPORATION AND SUBSIDIARIESCATASTROPHE EXPOSURE

Natural or man-made catastrophe events may expose our reinsurance and insurance subsidiaries to underwriting losses across multiple lines of business and, in any given year, could have a material adverse effecton our financial condition, results of operations, cash flows and liquidity. Further, the potential for accumulated losses from multiple events, and uncertainty as to the frequency and severity of such events, presentunique challenges for managing risk. Our reinsurance and insurance subsidiaries take certain measures to mitigate the impact of catastrophe events including considering catastrophe risks in their underwriting andpricing decisions, purchasing reinsurance, monitoring and modeling accumulated exposures, and managing exposure in key geographic zones and product lines that are prone to catastrophe events.

We set and monitor subsidiary and group-level limits to single zone exposures as well as to aggregate exposures from multiple events within any one year and at multiple points along the loss distribution curve. Forexample, we seek to limit the after-tax impact of all natural catastrophes occurring in any given year, net of related estimated pre-overhead underwriting profit, to 15 percent of Alleghany’s stockholders’ equity at the250-year return period (having a likelihood of being exceeded in any single year of 0.4 percent). Our loss estimates for zonal and aggregate catastrophe exposures are updated and reviewed against tolerances aspart of our oversight processes on a quarterly basis. Risk tolerances are subject to change based on our view of the risk-return characteristics of business being underwritten.

We assess the probability of occurrence and severity of catastrophe events through the use of industry recognized models and other techniques. Where appropriate, we supplement these models with our ownassessment of exposures which, in our view, may not be appropriately captured by these models. There is no single standard methodology or set of industry standard assumptions to project possible losses relatedto catastrophe exposures and the form and quality of the data obtained, including data obtained from insureds and ceding companies, and used in these models are not uniformly compatible with the datarequirements of all models. Therefore, the use of different methodologies and assumptions could materially change the projected losses. Finally, these modeled losses may not be comparable with estimates madeby other companies. Although the analytical tools used to estimate catastrophe exposure are useful in both pricing and monitoring catastrophe risk, the estimates derived by use of these techniques are inherently uncertain and do notreflect our maximum exposures to these events and it is highly likely that our losses will vary, perhaps materially, from these estimates. Although the models are frequently updated, these projections arenevertheless inherently imprecise. It is highly likely that our losses will vary, perhaps materially, from these estimates.

Potential catastrophe losses are typically expressed in terms of the probable maximum loss, or “PML.” PMLs may be expressed as Occurrence Exceedance Probability, or “OEP,” which reflect losses that may occur in any single event due to the defined peril in the indicated region, or as Aggregate Exceedance Probability, or “AEP,” which reflect losses from multiple events that may occur in any given year. The following is an overview of such modeled OEP PMLs from property, engineering, marine and energy exposures and the associated natural perils that we deem most significant based upon contracts in force at January 1, 2020 for TransRe and December 1, 2019 for RSUI. Modeled results also reflect losses arising from certain of our invested assets that have specific catastrophe exposures. The estimated amount of these modeled losses are presented for both a 100-year return period (having a likelihood of being exceeded in any single year of 1.0 percent) and a 250-year return period (having a likelihood of being exceeded in any single year of 0.4 percent). These modeled losses are presented in two ways: (i) gross catastrophe losses; and (ii) after-tax net catastrophe costs (that is, gross losses, net of reinsurance, net reinstatement premiums and taxes). The reduction for reinsurance assumes that all reinsurers fulfill their obligations in accordance with contract terms. Given the uncertainty of the frequency, severity and location of catastrophe events, we may experience losses significantly larger than the estimated PMLs in any given year defined peril in the indicated region. These modeled losses are estimated based upon contracts in force at January 1, 2020 for TransRe and December 1, 2019 for RSUI. In addition to the single zone PMLs, we have added a “U.S. wind” PML to our disclosures which reflects our occurrence PML for the entire U.S. Modeled results also reflect losses arising from certain of our invested assets that have specific catastrophe exposures. In any given year, we may experience losses from multiple events and may also experience events that impact multiple geographies, and therefore, we may experience losses significantly larger than the OEP PMLs shown in any given year.

100 Year Return Period 250 Year Return Period

“Florida, Wind” and "Northeast U.S., Wind" have the highest modeled after-tax net catastrophe costs for a 100 and 250-year return period single zone occurrence, respectively. These costs would representapproximately 7 percent and 8 percent, respectively, of stockholders’ equity attributable to Alleghany as of December 31, 2019, compared with approximately 6 percent and 8 percent, respectively, for the highestmodeled after-tax net catastrophe costs for a 100 and 250-year return period single zone occurrenceas of December 31, 2018. There is much uncertainty and imprecision in the compilation of these estimates.Moreover, the makeup of our in-force business is constantly changing as new business is added and existing contracts terminate or expire, including contracts for reinsurance coverage purchased by us. In addition,there could be possible scenarios that are not captured in our analysis. Additionally, other risks, such as an outbreak of a pandemic disease, a major terrorist event, the bankruptcy of a major company or a marineand/or aviation disaster, could also have a material adverse effect on our business and operating results. As a result, there can be no assurance that we will not experience after-tax net catastrophe costs fromindividual and / or multiple events that will exceed these estimates by a material amount. There also can be no assurance that we will not experience catastrophe events more frequently than the modeledprobabilities would suggest.

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ApproximateTotal Number of Dollar Value of

Shares Repurchased Shares That May Total Cost Total Number as Part of Publicly Yet Be Repurchased of Shares

of Shares Average Price Announced Plans Under the Plans or RepurchasedPeriod Repurchased Paid per Share or Programs* Programs (in millions)* (in millions)

January 1 to January 31, 2019 101,814 618.72$ 101,814 208.5$ 63.0$ February 1 to February 28, 2019 16,176 639.62 16,176 198.2 10.4 March 1 to March 31, 2019 11,577 617.19 11,577 191.0 7.1

Quarter ended March 31, 2019 129,567 621.19 129,567 80.5$

April 1 to April 30, 2019 6,417 620.07 6,417 187.0$ 4.0$ May 1 to May 31, 2019 6,644 675.49 6,644 182.5 4.5 June 1 to June 30, 2019 6,185 678.84 6,185 178.3 4.2

Quarter ended June 30, 2019 19,246 658.09 19,246 12.7$

July 1 to July 31, 2019 675 683.37 675 177.9$ 0.5$ August 1 to August 31, 2019 11,859 745.58 11,859 169.0 8.8 September 1 to September 30, 2019 12,864 776.72 12,864 659.1 10.0

Quarter ended September 30, 2019 25,398 759.70 25,398 19.3$

October 1 to October 31, 2019 14,843 774.10$ 14,843 647.6$ 11.5$ November 1 to November 30, 2019 12,799 780.83 12,799 637.6 10.0 December 1 to December 31, 2019 13,238 792.53 13,238 627.1 10.5

Quarter ended December 31, 2019 40,880 782.17 40,880 32.0$

Twelve months ended December 31, 2019 215,091 671.44$ 215,091 144.4$

Quarter ended March 31, 2018** 35,072 606.40$ 35,072 341.9$ 21.3$ Quarter ended June 30, 2018 368,551 582.92 368,551 527.1 214.8 Quarter ended September 30, 2018 76,299 602.24 76,299 481.1 46.0 Quarter ended December 31, 2018 342,927 611.15 342,927 271.5 209.5

Year ended December 31, 2018** 822,849 597.48 822,849 271.5 491.6$

* In November 2015, the Alleghany Board of Directors authorized the repurchase of additional shares of common stock, at such times and at prices as management determines to be advisable, up to an aggregate of $400.0 million. In June 2018, the Alleghany Board of Directors authorized, upon the completion of the previously announced program, the repurchase of additionalshares of common stock, at such times and at prices as management determines to be advisable, up to an aggregate of $400.0 million. In September 2019, the Alleghany Board of Directorsauthorized, upon the completion of the previously announced program, the repurchase of additional shares of common stock, at such times and at prices as management determines to be advisable, up to an aggregate of $500.0 million.

** On March 15, 2018, Alleghany paid a $154.0 million ($10 per share) special dividend.

ALLEGHANY CORPORATION AND SUBSIDIARIESSHARE REPURCHASE DETAIL

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UNDERWRITING PROFIT

ADJUSTED EARNINGS (AND ADJUSTED EARNINGS PER SHARE)

ADJUSTED EARNINGS BEFORE INCOME TAXES

ANNUALIZED INVESTMENT BOOK YIELD

BOOK VALUE PER SHARE EXCLUDING ACCUMULATED OTHER COMPREHENSIVE INCOME ("BVPS x-AOCI")

BVPS x-AOCI is calculated by dividing: (i) stockholders' equity attributable to Alleghany stockholders less AOCI, all as determined in accordance with GAAP, by (ii) sharesoutstanding. Alleghany uses BVPS x-AOCI as a supplement to BVPS, the most comparable GAAP financial measure, in order to better disclose its per share performance byexcluding the effects of AOCI, which includes changes in interest rates and credit spreads on its debt securities portfolio, among others. A reconciliation of BVPS to BVPS x-AOCIis presented within "Book Value Per Share" on page 31 of the Financial Supplement.

ALLEGHANY CORPORATION AND SUBSIDIARIESNON-GAAP FINANCIAL MEASURES

Adjusted earnings before income taxes represents noninsurance revenue and net investment income less other operating expenses and interest expense, and does not include: (i)amortization of intangible assets; (ii) change in the fair value of equity securities; (iii) net realized capital gains; (iv) OTTI losses; and (v) income taxes. Because adjusted earningsbefore income taxes excludes income taxes, change in the fair value of equity securities, net realized capital gains, OTTI losses and amortization of intangible assets, it provides anindication of economic performance that is not affected by investment activity, levels of effective tax rates or levels of amortization resulting from acquisition accounting. Alleghanyuses adjusted earnings before income taxes as a supplement to earnings before income taxes, the most comparable GAAP financial measure, to evaluate the performance ofcertain of its noninsurance operating subsidiaries and investments. A reconciliation of adjusted earnings before income taxes to earnings before income taxes is presented onpages 24 and 25 of the Financial Supplement.

Throughout this Financial Supplement, Alleghany's results of operations are presented in the way that Alleghany believes will be the most meaningful and useful to investors,analysts, rating agencies and others who use financial information in evaluating Alleghany's performance. This Financial Supplement includes various "non-GAAP financialmeasures" under U.S. Securities and Exchange Commission rules and regulations. These non-GAAP financial measures are not meant to be considered in isolation or as asubstitute for measures of operating performance prepared in accordance with accounting principles generally accepted in the United States of America, or "GAAP." When suchmeasures are disclosed, reconciliations to the most comparable GAAP measure are provided.

Underwriting profit represents net premiums earned less net loss and LAE and commissions, brokerage and other underwriting expenses, all as determined in accordance withGAAP, and does not include net investment income, change in the fair value of equity securities, net realized capital gains, other than temporary impairment, or "OTTI," losses,noninsurance revenue, other operating expenses, corporate administration, amortization of intangible assets and interest expense. Alleghany uses underwriting profit as asupplement to earnings before income taxes, the most comparable GAAP financial measure, to evaluate the performance of its reinsurance and insurance segments and believesthat underwriting profit provides useful additional information to investors because it highlights net earnings attributable to Alleghany's reinsurance and insurance segment'sunderwriting performance. Earnings before income taxes may show a profit despite an underlying underwriting loss, and when underwriting losses persist over extended periods, areinsurance 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 presentedwithin "Consolidated Underwriting Results" on pages 11 through 14 of the Financial Supplement.

Adjusted earnings and adjusted earnings per share exclude (on an after-tax basis): amortization of intangible assets; net realized capital gains; OTTI losses; and change in the fairvalue of equity securities, all as determined in accordance with GAAP. Alleghany uses adjusted earnings and adjusted earnings per share as a supplement to net earningsattributable to Alleghany stockholders and earnings per share, respectively, the most comparable GAAP financial measures, to provide useful additional information to investors byhighlighting net earnings and earnings per share attributable to its performance exclusive of change in the fair value of equity securities, realized capital gains or losses,impairments and amortization of intangible assets. A reconciliation of adjusted earnings and adjusted earnings per share to net earnings attributable to Alleghany stockholders andearnings per share, respectively, is presented within "Adjusted Earnings Reconciliation" on page 29 of the Financial Supplement.

Annualized investment book yield is calculated by dividing net investment income by average aggregate invested assets at book value. In calculating annualized investment bookyield, net investment income for the period, determined in accordance with GAAP, is multiplied by the number of such periods in a calendar year in order to arrive at annualized netinvestment income. Alleghany utilizes and presents annualized investment book yield in order to better disclose the performance of its investments.

Documents

Vision Workbook 1 · PAGE 1 Investor Contact: This report is for informational purposes only. It should be read in conjunction with documents filed by Alleghany Corporation