Alleghany : 2022 Second Quarter Financial Supplement

Alleghany

ALLEGHANY CORPORATION FINANCIAL SUPPLEMENT

Three Months Ended

and

Six Months Ended

June 30, 2022

(Unaudited)

Investor Contact:	This report is for informational purposes only. It should be read in conjunction with documents filed by Alleghany Corporation
Dale James	with the U.S. Securities and Exchange Commission, including the company's Annual Reports on Form 10-K and
Phone: [phone]	Quarterly Reports on Form 10-Q.

Forward-Looking Statements

Certain statements contained in this Financial Supplement may be deemed to be "forward-looking statements" within the meaning of the Private Securities Litigation Reform Act of 1995. Forward-looking statements may be identified by the use of words such as "may," "will," "expect," "project," "estimate," "anticipate," "plan," "believe," "potential," "should" or the negative versions of those words or other comparable words. Forward-looking statements do not relate solely to historical or current facts, rather they are based on management's expectations as well as certain assumptions and estimates made by, and information available to, management at the time. These statements are not guarantees of future performance. These forward-looking statements are based upon Alleghany's current expectations and are subject to a number of uncertainties and risks that could significantly affect current plans, anticipated actions and Alleghany's future financial condition and results. Factors that could cause these forward-looking statements to differ, possibly materially, from that currently contemplated include:

• significant weather-related or other natural or man-made catastrophes and disasters;
• the effects of outbreaks of pandemics or contagious diseases, including the length and severity of the recent worldwide coronavirus pandemic, known as COVID-19, including its impact on our business;
• 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 at Alleghany or its 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;
• difficult and volatile conditions in the global economy;
• the failure to complete the merger with Berkshire Hathaway Inc. on the terms and timeline currently contemplated or at all;
• risks related to the conduct of our business while the merger with Berkshire Hathaway Inc. is pending; and
• risks related to uncertainties related to the consummation of the merger with Berkshire Hathaway Inc.

Additional risks and uncertainties include general economic and political conditions, including the effects of a prolonged U.S. or global economic downturn or recession; changes in costs; variations in political, economic or other factors; risks relating to conducting operations in a competitive environment; effects of acquisition and disposition activities, inflation rates, or recessionary or expansive trends; changes in interest rates; extended labor disruptions, civil unrest, or other external factors over which we have no control; changes in our plans, strategies, objectives, expectations, or intentions, which may happen at any time at our discretion; and other factors discussed in Alleghany's most recent Annual Report on Form 10-K and subsequent filings with the Securities and Exchange Commission, or the "SEC." All forward-looking statements speak only as of the date they are made and are based on information available at that time. Alleghany does not undertake any obligation to update or revise any forward- looking statements to reflect subsequent circumstances or events.

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ALLEGHANY CORPORATION

BASIS OF PRESENTATION

Presentation

All financial information contained herein is unaudited. Certain amounts may not reconcile exactly due to rounding differences. Unless otherwise noted, all data is in millions of U.S. dollars, except for share, per share, percentage and ratio information.

Definitions

References in this financial supplement (the "Financial Supplement") to the "Company," "Alleghany," "Alleghany Corporation", "we," "us," and "our" refer to Alleghany Corporation and its consolidated subsidiaries unless the context otherwise requires. In addition, unless the context otherwise requires, references to,

• "TransRe" are to our wholly-owned reinsurance holding company subsidiary Transatlantic Holdings, Inc. and its subsidiaries;
• "AIHL" are to our wholly-owned insurance holding company subsidiary Alleghany Insurance Holdings LLC;
• "RSUI" are to our wholly-owned subsidiary RSUI Group, Inc. and its subsidiaries;
• "CapSpecialty" are to our wholly-owned subsidiary CapSpecialty, Inc. and its subsidiaries;
• "AIHL Re" are to our wholly-owned subsidiary AIHL Re LLC;
• "Roundwood" are to our wholly-owned subsidiary Roundwood Asset Management LLC;
• "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;
• "Wilbert" are to our majority-owned subsidiary Wilbert Funeral Services, Inc. and its subsidiaries;
• "Piedmont" are to our wholly-owned subsidiary Piedmont Manufacturing Group, LLC and its subsidiaries; and
• "Alleghany Properties" are to our wholly-owned subsidiary Alleghany Properties Holdings LLC and its subsidiaries.

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		ALLEGHANY CORPORATION
		FINANCIAL SUPPLEMENT
		TABLE OF CONTENTS
I.	FINANCIAL SUMMARY	Page
	10 Year Financial Summary	6
	Historical Growth in Book Value per Share	7
	Consolidated Financial Highlights	8
	Capital Allocation by Subsidiary	9
	Consolidated Statements of Earnings	10
	Earnings by Segment	11 - 12
	Share Repurchase Detail	13
II.	UNDERWRITING RESULTS
	Premiums Written	15
	Consolidated Underwriting Results	16 - 19
	Catastrophe Exposure	20
III.	ALLEGHANY CAPITAL
	Product and Service Revenues	22
	Results	23
	Equity	24
	Condensed Consolidating Balance Sheets	25
	Condensed Consolidating Statements of Cash Flows	26
IV.	BALANCE SHEET AND INVESTMENT ITEMS
	Condensed Consolidating Balance Sheets	28
	Consolidated Total Investment Portfolio	29
	Debt Securities Portfolio Credit Quality	30
	Net Investment Income	31
	Loss and Loss Adjustment Expenses (LAE)	32
	Capital Structure and Leverage Ratios	33
V.	RECONCILIATIONS
	Basic and Diluted Earnings per Share Information	35
	Adjusted Earnings Reconciliation	36 - 37
	Return on Average Stockholders' Equity	38
	Book Value per Share	39
	Consolidated Changes in Stockholders' Equity	40
	Financial Statement Portfolio Return	41
	Annualized Investment Book Yield	42
	Non-GAAP Financial Measures	43

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Financial Summary

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