[PPT] - Alleghany Investor Presentation August 2020 Our Management PowerPoint Presentation

SLIDE 1

Alleghany

Investor Presentation August 2020

SLIDE 2 2

“Conservatism dominates our management philosophy. We shun investment fads and fashions in favor of acquiring relatively few interests in basic financial, industrial and

ther enterprises that offer the

potential to deliver long-term value to our investors”

Own high-quality underwriting franchises

― Underwrite for profit ― Grow premiums only when market allows for profitable growth ― Consistently maintain appropriately prudent loss reserves

Invest for total return when risk/reward is

attractive

Acquire quality businesses at reasonable prices

― Provide resources, support and oversight to help them grow revenues, profits and returns

Maintain a conservative financial and operating

risk profile

Hold significant unrestricted liquidity for

potential opportunities (and downturns)

Our Management Approach

Philosophy Strategy 1 2 3 5 4

SLIDE 3

I. COVID-19 Update & Outlook

SLIDE 4 4

2020 Overview & Outlook

COVID-19 is a ‘Catastrophe in Progress’. Outcome remains highly uncertain
Re/Insurance:
$288 million reserved for COVID-19 losses (TransRe: $268 million / RSUI: $20 million;

primarily IBNR)

Event cancellation, property / business interruption are most significant components
Market conditions and leading indicators continue to improve at an accelerating pace
Alleghany Capital:
Alleghany Capital companies’ 2Q revenues and earnings impacted by sharp declines in

economic activity and project site closures and delays, but overall impacts appear manageable

Improving momentum entering 2H 2020
Investments/Financial:
Investment portfolio defensively positioned; lower than average allocation to risk assets
Continuing pressure on net investment income given low yield environment
Ample liquidity with over $1.2 bn cash and marketable securities at holding company

SLIDE 5 5

COVID-19 Pandemic: Year-to-Date Losses by Business Line

$288 million of Pandemic related losses (primarily IBNR) comprised as follows:

($ in millions)

TransRe RSUI Total Commentary Event Cancellation $ 111 $ 111

Estimated remaining event limits, net of provisions, of

approximately $25 million for 1H 2020, ~$35 million for 2H 2020 and ~$70 million in 2021 Property 68 $ 20 88

TransRe: Primarily related to non-North American

property contracts / treaties

RSUI: Large majority of policies include explicit

pathogen exclusions; provision follows detailed claims review and primarily relates to small number of U.S. property policies with low layer or sub-limited coverage grant as well as a provision for legal expenses Accident & Health 38 38

One specific cover
Higher overall loss ratio selections

Guaranty 31 31

Higher loss ratio selections for trade credit, surety and

mortgage business Other 20 20

Includes specifically impacted miscellaneous treaties or

coverages Total $ 268 $ 20 $ 288

SLIDE 6

II. Performance Highlights – 1st Half 2020

SLIDE 7 7

Summary of 1H 2020 Results

(1) Attributable to Alleghany stockholders. (2) Net earnings attributable to Alleghany stockholders excluding (on an after-tax basis) change in the fair value of equity securities, net realized gains, change in allowance for credit losses on available for sale securities and amortization of intangible assets. (3) Accumulated other comprehensive income. (4) Includes cumulative effect of adoption of new accounting pronouncements and other.

Income Statement

1H 2020 Change vs. 1H 2019 Net Premiums Written $3,012- 6%-- Net Investment Income 231- (13)% Underwriting Result (64) N/M Combined Ratio 102.3% (10) pts- Net Losses(1) $(184) N/M Adjusted Earnings(2) 86 (73)%

($ in millions)

Strong net premium written growth, driven

by both Reinsurance (+4%) and Insurance (+17%)

Decline in net investment income due to

lower (re)investment yields, as well as lower dividend and partnership income

Underwriting result and adjusted earnings

impacted by $288mm of estimated pre-tax COVID-19 losses (See slide 5)

Underlying results strong; combined ratio

ex-COVID-19 of 92.2%

1H 2020 impacted by pre-tax impairment

charges of $74 million relating to write- downs of Stranded Oil oil field assets

Book value per share adjusted for March

2020 special dividend declined by 0.8% during the first half of 2020

Excluding the impact of movements in

AOCI and the special dividend, declined by 2.2% during 1H 2020

Commentary

1H 2020 Changes in Equity

Q4 ‘19 Stockholders’ Equity $8,777--- Net Losses (184)-- Change in AOCI(3) 121--- Special Dividend (215)-- Share Repurchases (44)-- Other(4) 2)-- Q2 ‘20 Stockholders’ Equity $8,456---

SLIDE 8 8

Alleghany Quarterly and Year to Date Consolidated Performance

(1) Attributable to Alleghany stockholders. (2) Adjusted for $15/share dividend paid in March 2020.

Net Premiums Written Net Investment Income Adjusted Earnings(1) BVPS Growth(2)

($ in millions)

$1,478 $1,447 Q2 '20 Q2 '19 $3,012 $2,832 1H '20 1H '19 102.3% 92.5% 1H '20 1H '19 102.8% 91.6% Q2 '20 Q2 '19

Combined Ratio Net Earnings(1)

$119 $143 Q2 '20 Q2 '19 $231 $266 1H '20 1H '19 $12 $179 Q2 '20 Q2 '19 $86 $319 1H '20 1H '19 $177 $296 Q2 '20 Q2 '19 $(184) $736 1H '20 1H '19 7.6% 5.6% Q2 '20 Q2 '19 (0.8%) 14.1% 1H '20 1H '19

+2% +6%

17%
13%
93%
73%
40%

N/M

Ex. AOCI:

2.2% 3.6% (2.2)% 9.4%

SLIDE 9 9

Underwriting Performance – 1H 2020

Reinsurance Insurance

Total Re/Insurance Property Casualty & Other Total RSUI Cap Specialty Total Loss ratio 80.2% 72.0% 74.4% 66.2% 60.5% 64.8% 72.3% Expense ratio 31.1% 30.3% 30.5% 23.5% 41.3% 28.1% 30.0% Combined ratio 111.3% 102.3% 104.9% 89.7% 101.8% 92.9% 102.3% Catastrophe activity & prior year development: Current year catastrophe losses 32.1% 5.1% 13.1% 12.1% 0.8% 9.2% 12.2% Net (favorable) adverse development in prior year loss reserves (9.2%) (3.2%) (4.9%) 3.2% 0.1% 2.4% (3.3%) Combined ratio excluding catastrophe losses and prior year development 88.4% 100.4% 96.7% 74.4% 100.9% 81.3% 93.4%

Strong Underlying Performance Offset by Significant Catastrophe (COVID-19) Activity

SLIDE 10 10

Consolidated: Alleghany Capital Subsidiaries: Stockholders' Equity $ 8,456 87.7% Jazwares $ 287 3.0% Parent Company Debt(1) 1,190 12.3% W&W|AFCO Steel 255 2.6% Total Capital $ 9,646 100.0% Wilbert(2) 146 1.5% Precision Cutting Technologies 127 1.3% Shares outstanding (mm)

14.31

Concord 108 1.1% BVPS $ 590.85 Kentucky Trailer 80 0.8% BVPS ex. AOCI 570.45 IPS 66 0.7% Market Capitalization

$ 7,474

Total Alleghany Capital $ 1,067 11.1% Re/insurance: Other: TransRe $ 5,154 53.4% Parent cash and marketable securities(3) $ 1,197 12.4% RSUI 1,746 18.1% Stranded Oil 26 0.3% CapSpecialty 399 4.1% Alleghany Properties 24 0.2% AIHL Re 24 0.2% Other items, net(4) 9 0.1% Total Re/insurance $ 7,323 75.9% Total Other $ 1,256 13.0%

Capital Allocation as of June 30, 2020

Note: All subsidiaries are majority owned unless otherwise stated. Market data as of July 31, 2020. (1) Excludes $350 million par value senior notes at TransRe that mature in 2039 as well as $439 million of debt (excluding intercompany debt) at Alleghany Capital. (2) On April 1, 2020, Alleghany Capital acquired an additional approximately 55% of Wilbert it did not previously own, bringing its equity interest to approximately 100%. As of that date, Wilbert is accounted for on a fully-consolidated basis. Prior to April 1, 2020, Alleghany had a 45% equity investment accounted for using equity method. (3) Parent cash and marketable securities exclude $45 million of cash at the TransRe holding company, which is included in TransRe capital. (4) Primarily Alleghany parent deferred compensation and taxes, as well as ACC parent. amounts in millions, except book value per share

SLIDE 11

III. Re/Insurance Operations

SLIDE 12 12

Cumulative Results Over H

lding Period

Subsidiary / Acquisition Date Cash & Investments Stockholders’ Equity Years Held Ne t Premiums Written Underwriting Profits (Losses) Combined Ratio Ne t Dividends IRR

$13,991 2.7x $5,154 8 $31,427 $907 97.1% $1,732 8.8% 3,946 2.3x 1,746 17 12,571 1,824 84.8 1,324 11.3 925 2.3x 399 18 3,692 (58) 101.6 130 5.0

Total (Re)insurance

$18,894(1) 2.6x 7,323(1)

($ in millions)

Current (Re)insurance Operations

Note: As of June 30, 2020. (1) Includes AIHL Re.

March 6, 2012 July 1, 2003 January 1, 2002

SLIDE 13 13

Consolidated Underwriting Results for Past 10 Years

Note: Underwriting profit is a non-GAAP financial measure. Refer to the appendix for further information.

Underwriting Profit Combined Ratio

2010-to-Date Underwriting Profits of $1.7 B and Combined Ratio of ~95.9%

$131 $50 $220 $421 $495 $467 $401 ($316) ($162) $33 ($64) '10 '11 '12 '13 '14 '15 '16 '17 '18 '19 1H '20 Pre-

TransRe

83.0% 93.4% 94.1% 90.1% 88.8%89.0% 91.9% 106.4% 103.2% 99.4% 102.3% 95.9%

'10 '11 '12 '13 '14 '15 '16 '17 '18 '19 1H '20 Pre- TransRe Catastrophe Losses ($mm):

31 74 470 15 1 95 62 226 818 65 8 400 346

Ex. C

atastrophe C

mbined Ratio (%):

79.0 83.5 81.5 86.5 86.6 87.5 87.4 89.9 90.0 92.1 90.1 ($ in millions)

SLIDE 14 14

TransRe – Structural Competitive Advantages

History of Prudently Navigating Market Conditions and Opportunities

Diversified,

global reinsurer with casualty & specialty expertise

Long-standing client and intermediary

relationships  70% proportional business  Leads or co-leads more than half

f its book
Strong balance sheet and infrastructure
Leveraging market position with third

party capital  Generates recurring fee income

TransRe has returned net dividends of

$1,732 million since acquisition and repaid $667 million in senior notes

Net Premiums Written(1)

(LTM 1H 2020)

Net premiums written up 3.5%
Underwriting loss of $109mm
Combined ratio of 104.9%; ex. COVID-19

combined ratio of 92.7%

1H 2020 Highlights

$3.9 billion(1)

(1) Excludes a certain large whole account quota share treaty which contributed $673 million to LTM 1H 2020 net premiums written.

Business Overview

Personal Auto / Motor 12% Traditional Casualty 18% Professional Liability 17% Non- Catastrophe Property 21% Catastrophe Property 7% A&H 8% Guaranty 7% Marine & Energy 4% Aviation 2% Engineering 1% Other Specialty 3% Property 28% Casualty 47% Specialty 25%

SLIDE 15 15 3.6% 10.4% 11.3% 1.9% 8.4% 12.4% 5.3% 6.8% 7.3% 3.4% 2.8% 9.4% 3.3% 3.9% 7.6% 2018 2019 YTD 2020

Total Currently Estimated Rate Change(1) (%)

Traditional Casualty Professional Liability Non-Catastrophe Property Catastrophe Property Other

TransRe – Positive Estimated Renewal Rate Momentum

Note: Based on data received from cedents as of July 1, 2020. Data excludes a certain large whole account quota share treaty. (1) Estimated primary rate changes plus reinsurance rate changes on XOL treaties for the respective treaty year for all renewal treaties globally. Pro rata treaty rate change data based on intermittently provided data from cedents and therefore reflected here with an estimated 6-month lag. (2) Includes personal auto and various specialty lines.

All Lines: 4% All Lines: 9% All Lines: 6%

Significantly higher renewal rates in certain peak catastrophe zones (e.g. Japan & Florida)

(2)

SLIDE 16 16

RSUI – Taking Advantage of Improving E&S Market

Continued New Business and Rate Momentum with Double Digit Renewal Rate Increases on Multiple Lines

Underwriting Profit

Cumulative Underwriting Profit: $1.8 billion

(Cumulative data for 2H 2003 – 1H 2020 period)

30 years dedicated exclusively to

wholesale specialty insurance market

Proven ability to generate underwriting

profit and grow book value through cycles

Highly experienced underwriters
Nimble and reacts quickly to
pportunities
Proprietary, in-house developed

technology, models and analytical tools

Diversified profitable portfolio

Business Overview

Net premiums written up 22%
Combined ratio of 89.7%; 4.7 point

improvement in expense ratio

Underwriting profit of $48mm

1H 2020 Highlights

D&O Liability 7%

Professional Liability 20% General Liability 7% Umbrella / Excess 14% Property 51%

Alternative Structures 1%

SLIDE 17 17

1%

25% 26% 38%

4%

3% 7% 13%

1%
1%

4%

1%

5% 6% 14% 28% 0% 10% 17% 10% 2017 2018 2019 1H 2020

New Business Submissions (Units)

RSUI – Continued Acceleration in Rate Increases

Note: Data is quarterly rate and new business submission increases over prior-year quarter.

1% 2% 3% 13% 3% 4% 6% 15%

1%
1%

3% 4% 2% 5% 8% 14%

3%

5% 9% 14% 2017 2018 2019 1H 2020

Renewal Rate Change (%)

SLIDE 18 18

CapSpecialty – Repositioning for Greater Efficiency & Overall Profitability

Meaningful Progress Towards Its Goal of Becoming A Preferred Specialty Insurer for Small and Mid-Sized Businesses

Gross Premiums Written

$382 million

(LTM Q2 2020)

Well-diversified specialty company
Niche product focus for small and mid-

size businesses

Recognized experts in select classes
Select distribution
Current focus on profitable growth,

expense management & technology

ptimization

Business Overview

Net premiums written up 4%
Combined ratio of 101.8%
8+% rate improvement on renewal book

1H 2020 Highlights

Traditional Property & Casualty 24% Healthcare 24% Specialty Casualty 19% Professional Liability 19% Surety 14%

SLIDE 19

IV. Investments & Alleghany Capital

SLIDE 20 20

Investments Are a Significant Part of Our Earnings Power

(1) Excludes Alleghany Capital. (2) Includes net investment income, net realized gains (losses), net of changes in allowance for credit losses on available for sale securities, change in fair value of equities and change in net unrealized gains (losses) on debt securities.

Portfolio Allocation Investment Leverage(1) Investment Results Pre-Tax

Avg. Credit

Quality of Debt Securities: AA-

Total: $20.3 billion

Portfolio Allocation

Debt Securities 74% Equity Securities 7% Cash & Short-term 14% Commercial Mortgage Loans 3% Other Invested Assets 2% 2.73x 2.59x 2.55x 2.56x 2.72x 2.55x 2.72x

2014 2015 2016 2017 2018 2019 1H '20 5.3% 1.0% 2.6% 7.1% 0.1% 9.3% 0.6% 2.5% 2.5% 2.5% 2.5% 2.8% 3.1% 2.6% 2014 2015 2016 2017 2018 2019 1H 2020

Annualized financial statement return on average invested assets Annualized investment book yield

(2)

SLIDE 21 21

Investment Return Components (Pre-Tax)

$460 $439 $439 $45 1 $5 01 $550 $231 $211 $80 $18 $90 ($5 ) ($26) ($40) $25 ($185 ) $28 $636 ($229) $710 ($281) $307 ($15 8) ($20) $129 ($25 7) $485 $141 $1,002 $176 $465 $1,306 $10 $1,719 $52 2014 2015 2016 2017 2018 2019 1H 2020 Change in unrealized gains (losses) - fixed income Change in fair value - equitites Net realized gains (losses), net of change in allowance for credit losses Net investment income ($ in millions)

SLIDE 22 22

Illustrative Impact of Declining Interest Rates

(1) Fixed income invested assets as of June 30, 2020 and comprised of debt securities, short-term investments and commercial mortgage loans. (2) Combined ratio points based on LTM net premiums earned of $6 billion. ($ millions, unless otherwise stated)

Reinvestment risk applies to approximately 15% of invested assets each year
Floating rate securities comprise less than 10% of portfolio
Illustration assumes no growth in premiums earned and invested float

Annual Impact Fixed income invested assets(1) $ 16,755 % Reinvested annually 15% Amount reinvested or at lower yield $ 2,513 ∆ Average reinvestment rate (1%) Annual decline in net investment income (NII) (25) Equivalent CoR points(2) 0.4

Low yields are putting pressure on overall re/insurance profitability Improved underwriting results are necessary to compensate

SLIDE 23 23

$25 $43 $64 $93 $161 $86 $19 $33 $50 $83 $143 $74 2015 2016 2017 2018 2019 LTM Q2 '20

Corporate Activity & Deal Expenses Non-Industrial Industrial Adjusted EBT (Net of Corp. Activity & Deal Expenses)

Alleghany Capital - Earnings Growth History

($ millions) (1) Adjusted earnings before income taxes (“Adjusted EBT”), a non-GAAP measure, represents noninsurance revenue less all operating expenses, and does not include: (i) amortization of intangible assets; (ii) change in the fair value of equity securities; (iii) net realized capital gains; (iv) change in allowance for credit losses on available for sale securities; and (v) income taxes. Excludes certain minor, legacy investments that were previously reflected in Alleghany Capital in 2018 and prior periods. (2) Adjusted EBT excluding ACC corporate activity and deal expenses. (3) ACC Share of Adjusted EBT calculated based on weighted average ownership percentages and includes corporate activity and deal expenses.

Adjusted Earnings Before Tax(1) – 100% Basis

“Although COVID-19 significantly impacted activity and earnings in the first half of 2020, Alleghany Capital’s businesses are well positioned with improving momentum going into the second half of 2020”

ACC Share of A dj. EBT(3)

$16 $25 $38 $66 $112 $59

Diversified Portfolio of High-Performing Businesses Help Mitigate Individual Business Seasonality

(2) (2) (2) (2) (2) (2)

SLIDE 24 24 Company / Acquired Reven ue(1) / % Owned 20 20 Update 2 012 $39 100%

Revenue up 25

% in 1H driven by recent acquisitions

Decline in consumable p

arts businesses due to temporary customer facility closures, p articularly in the aerospace segment

2 013 $241 77%

Revenue down 15% in 1H impacted by lower production and revenue recognition related to

temporary facility closures and employee absenteeism in certain states due to COVID-19

Recent increased global demand for mobile imaging and healthcare solutions relating to COVID-19

2 017 $826 80%

Revenue down 22%

in 1H due to customer driven design delays at t wo large projects (now resolved) and COVID-19-related construction site closures reducing erector m anhours

Strong new project wi

ns driven by infrastructure and technology sectors, leading to significant increase in backlog since year-end 2019 and this time l ast year 2 017 $179 100%

Alleghany acquired remaining 55% on April 1,

2020

Strong 1H

with increased demand from funeral home and cemetery customers, but e arnings impacted by one-time fair value charges related to acquisition accounting

Critical provider of necessary services during COVID-19 p

andemic 2 015 $646 85 %

Revenue negatively impacted by customer site closures due to COVID-19
Project pipeline increased significantly in 2Q, with m

any opportunities related to potential C OVID- 19 vaccines and treatments

Increased global interest in biopharmaceutical R&D and production c

apacity

2 016 $351 76%

1H

revenue negatively impacted by product shipment delays from Asia and store closures globally related to COVID-19. Revenue also declined Y OY given tough comparison to initial l aunch of the Fortnite license in the first h alf of 2019, wh ich occurred at a typically slow period in the toy industry

Completed acquisition of Kelly Toys, a leading producer of plush toys on April 1, 2020
Positive recent order trends and point of s

ale data, but p ace of global retail reopenings and related consumer spending activity remain a question

M

arket share g ains with key retailers and licensors 2 018 $186 85 %

Revenue impacted by sharp drop in hotel occupancy, wh

ich troughed in M arch and h as increased consistent with industry trends through 2Q

Highly variable cost model allows for profitability, even with unprecedented drop in global hotel
ccupancy

(1) 2019. Non-insurance revenues are on 100% basis in $millions. (2) 45% stake acquired in 2017. On April 1, 2020, Alleghany Capital acquired an additional approximately 55%, bringing its equity interest to approximately 100%. Wilbert revenue is presented for informational purposes as it was not consolidated in 2019. (3) 30% stake acquired in 2014, majority stake acquired in 2016.

Alleghany Capital – Business Updates

Industrial Non-Industrial

(2) (3)

SLIDE 25

II. Macroeconomic & Industry Backdrop

SLIDE 26 26

1) E&S market opportunity is significant; RSUI is well positioned

Significant competitors

retrenching

Changing view of certain risks

(e.g., wildfires, commercial auto, capital constraints, volatility aversion)

Limits compression

2) Reinsurance market firming

Property market clearly firming
Accelerated opportunity in

casualty lines with rate increases above claim trends 3) Strong backlogs and order books at Alleghany Capital 1) Coronavirus pandemic & related global economic downturn

COVID-19 related potential losses;

regulatory / judicial risk associated with business interruption

Rising credit risk

2) Low interest rates 3) Political uncertainty 4) Global geopolitical and economic uncertainty 5) Increasing loss costs / social inflation / nuclear verdicts in casualty lines

Key Macroeconomic & Industry Themes

Opportunities Challenges 1 2 3 1 2 3 4 5

SLIDE 27 27 (7.7)% 1.6% (7.9)% 2.3%

(10 .1)% 3.2% (5.2)% 1.0 % 11.1% (12)% (10)% (8)% (6)% (4)% (2)% 0% 2% 4% 6% 8% 10% 12% 14% 1998 2000 2002 2004 2006 2008 2010 2012 2014 2016 2018 2020E World United States European Union East Asia & Pacific U.S. Unemployment

Pandemic-Driven Global Recession; Spike in Unemployment

Source: World Bank. GDP growth (annual %) based on constant local currency and U.S. dollars for aggregates. (1) U.S. unemployment rate as of June 30, 2020.

Significant Uncertainty Around The Macro-Economic Impact of a Prolonged Pandemic

(1)

Real GDP Growth & U.S. Unemployment (YOY)

SLIDE 28 28 30 .7x 24.8x 30. 5x 0.0x 5.0x 10.0x 15.0x 20.0x 25.0x

30.0x 35.0x 2009 2011 2013 2015 2017 2019 Shiller P/E - S&P 500

Persistent Low Interest Rates; High Asset Prices

Source: Bloomberg. Market data as of July 31, 2020. (1) Based on average inflation-adjusted earnings from the previous 10 years, known as the Cyclically Adjusted PE Ratio (CAPE Ratio).

Treasury Yields & Credit Spreads Is the S&P 500 Overpriced?

0. 55% 1. 46% 0.0% 0.5% 1.0% 1.5% 2.0% 2.5% 3.0% 3.5% 4.0% 2010 2012 2014 2016 2018 2020

Yield / Spread

UST 10Y BBB Credit Spreads

Jan 2018 - Jul 2020

(20%) (10%) 0% 10% 20% 30% 2014 2015 2016 2017 2018 2019 Quarterly Earnings Growth

13.44%

(1)

SLIDE 29 29

Key Alleghany Takeaways

 Leading franchise across global reinsurance and specialty insurance  Long-term focus with track record of disciplined underwriting and risk

management through insurance and investment cycles

 Conservative financial profile and strong capitalization  Holding company conservatively capitalized with significant liquidity allowing

us to manage through the downturn, support subsidiaries and respond to

pportunities

 Diversified and conservative investment portfolio; demonstrated investment

capability and performance

 Alleghany Capital has achieved critical mass. Despite current pressures, we

expect improved earnings contribution and double-digit return on equity over the long-term

SLIDE 30 30

Delivering Consistent BVPS Growth Over Cycles

(1) Excludes the impact of a $10.00 per share special dividend payment on March 15, 2018. (2) Includes special dividend on $10 paid in 2018 and assumes proceeds are reinvested in Alleghany book value.

Book Val ue Annual Rolling Annualized Averag e(2) Year Per Share * Growth in BVPS Three-Year Four-Year Five-Year Seven

Year

Ten-Year 1999 $ 122.27 2000 141.0 3 15.3% 2001 162.36 15.1% 2002 162.75 0.2% 10.0% 2003 182.18 11.9% 8.9% 10.5% 2004 204.08 12.0% 7.9% 9.7% 10.8% 2005 212.80 4.3% 9.3% 7.0% 8.6% 2006 244.25 14.8% 10.3% 10.7% 8.5% 10.4% 2007 281.36 15.2% 11.3% 11.5% 11.6% 10.4% 2008 267.37 (5.0%) 7.9% 7.0% 8.0% 7.4% 2009 294.79 10.3% 6.5% 8.5% 7.6% 8.9% 9.2% 2010 325.31 10.4% 5.0% 7.4% 8.9% 8.6% 8.7% 2011 342.12 5.2% 8.6% 5.0% 7.0% 7.7% 7.7% 2012 379.13 10.8% 8.7% 9.1% 6.1% 8.6% 8.8% 2013 412.96 8.9% 8.3% 8.8% 9.1% 7.8% 8.5% 2014 465 .51 12.7% 10.8% 9.4% 9.6% 7.5% 8.6% 2015 48 6.02 4.4% 8.6% 9.2% 8.4% 8.9% 8.6% 2016 515.24 6.0% 7.7% 8.0% 8.5% 8.3% 7.8% 2017 553.20 7.4% 5.9% 7.6% 7.9% 7.9% 7.0% 2018 527.75 (4.6%)(1) 3.4% 3.7% 5.4% 6.7% 7.2% 2019 611.00 15.8% 6.5% 6.4% 6.0% 7.3% 7.8% Averag e 8.6% 8.1% 8.2% 8.2% 8.3% 8.2%

SLIDE 31

Appendix I. Company Overview

SLIDE 32 32

A History of Investing in Successful Companies

Alleghany holding

co mpany f

rmed
Nickel Plate,

Chesapeake & Ohio, Erie and Pere Marquette Railroads (merged into Penn Central in 1968)

1929 1946 1949 1968 1974 1985 2003 1986 1995 2002 20 12 2007 1991 1993 20 13 20 20

Investors Diversified Services (“IDS”) (sold to American Express in 1984) New York Central Railroad (merged into Penn Central in 1968) MSL Industries Jones Motor Company Chicago Title (spun off in 1998/1999) Shelby Insurance (sold in 1991) Underwriters Reinsurance Company (sold to Swiss Re in 2000) World Minerals (sold in 2005) Darwin Underwriters established (IPO in 2006 and sold in 2008) PacificComp (sold to CopperPoint in 2017) Alleghany Ca pital Corporation Ro undwood (formerly Alleghany Capital Partners) Alleghany Asset Management (sold to ABN Amro in 2001)

20 14 20 15 20 17 20 18

Legacy Alleghany Current Alleghany / Logo

2008

SLIDE 33 33

Over 90 years as a public company (NYSE: Y)

$8.5 billion in book value
$7.5 billion equity market capitalization
$20.3 billion in total cash & investments
Baa1 senior debt rating from Moody’s
BBB+ senior debt rating from Standard & Poor’s
a- senior debt rating from A.M. Best

Alleghany Today

Notes: Financial data as of June 30, 2020 unless otherwise indicated. Gross premiums are LTM June 30, 2020. Market data as of July 31, 2020. (1) Best’s Review March 2019 – Top 50 Global Reinsurers; ranking based on unaffiliated gross premiums written in 2018. (2) A.M. Best U.S. Surplus Lines – Segment Review, September 2019.

Reinsurance Insurance Investments

Alleghany Capital Co rporation TransRe RSUI CapSpecialty

GAAP equity of $5.2

billion

Gross premiums

wr itten of $5 .0 billion

Top 15

global reinsurer(1)

GAAP equity of $1.7

billion

Gross premiums wr

itten

f $1.5 billion
10th largest U.S. e

xcess & surplus lines group(2)

GAAP equity of $0.

4 billion

Gross premiums wr

itten

f $0.

4 billion

Focuses on niche

specialty commercial lines Asset Management

$18.4 billion fixed

income

$1.4 billion equity

portfolio

$0.

4 billion other invested assets Subsidiaries & Investments

SLIDE 34 34 52% 53% 62% 58% 39% 26%

2015 2016 2017 2018 2019 Q2 '20

Modest Financial Leverage and Conservative Risk Profile

(1) Reflects net occurrence PML (after-tax) in a 1-in-250 year event (having a likelihood of being exceeded in any single year of 0.4 percent) for largest single zone peril (e.g. Northeast U.S. Wind for Q2 ‘20). (2) Risk assets are defined as high yield bonds, below investment grade collateralized loan obligations and bank loans, publicly traded equity securities, private equity and partnership interests.

Debt to Capital Holding Company Liquidity Peak Zone PML / Shareholder Equity(1) Risk Assets / Shareholders’ Equity(2)

(millions)

15.8% 15.6% 14.7% 17.5% 16.3% 18.9% 2015 2016 2017 2018 2019 Q2 '20

Other Debt (ACC) Senior Notes

$821 $1,047 $1,383 $1,122 $1,283 $1,242 2015 2016 2017 2018 2019 Q2 '20 10% 7% 8% 8% 8% 7% 2015 2016 2017 2018 2019 Q2 '20

SLIDE 35 35

Non-GAAP Financial Measures

This document may contain non-GAAP financial measures. Reconciliations of these non-GAAP financial measures to the most direct comparable GAAP measures and related information are provided in our financial supplement and Form 10- K and 10-Q filings, which are available on our website at www.alleghany.com, and below. Adjusted Earnings Before Income Taxes 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) change in allowance for credit losses on available for sale securities; and (v) income taxes. Because adjusted earnings before income taxes excludes income taxes, change in the fair value of equity securities, net realized capital gains, credit losses for available for sale securities and amortization of intangible assets, it provides an indication of economic performance that is not affected by investment activity, levels of effective tax rates or levels of amortization resulting from acquisition accounting. Alleghany uses adjusted earnings before income taxes as a supplement to earnings before income taxes, the most comparable GAAP financial measure, to evaluate the performance of certain of its noninsurance operating subsidiaries and investments. A reconciliation of adjusted earnings before income taxes to earnings before income taxes is presented on page 29 of the Financial Supplement. Underwriting Profit Underwriting profit represents net premiums earned less net loss and LAE and commissions, brokerage and other underwriting expenses, all as determined in accordance with GAAP, and does not include net investment income, change in the fair value of equity securities, net realized capital gains, credit losses for available for sale securities, noninsurance revenue, other operating expenses, corporate administration, amortization of intangible assets and interest expense. Alleghany uses underwriting profit as a supplement to earnings before income taxes, the most comparable GAAP financial measure, to evaluate the performance of its reinsurance and insurance segments and believes that underwriting profit provides useful additional information to investors because it highlights net earnings attributable to Alleghany's reinsurance and insurance segment's underwriting performance. Earnings before income taxes may show a profit despite an underlying underwriting loss, and when underwriting losses persist over extended periods, a reinsurance or an insurance company's ability to continue as an ongoing concern may be at risk. A reconciliation of underwriting profit to earnings before income taxes is presented within "Consolidated Underwriting Results" on pages 11-14 of the Financial Supplement.