X0306 4 2020-05-11 0000775368 ALLEGHANY CORP /DE Y 0001361747 Kirby Jefferson C/O ALLEGHANY CORPORATION 1411 BROADWAY, 34TH FLOOR NEW YORK NY 10018 1 0 0 0 Common Stock 2020-05-11 4 A 0 280 A 95890 D Common Stock 159097 I Held by trusts w. reporting person as co-trustee and beneficiary Common Stock 23707 I Held by trust w. reporting person as co-trustee and beneficiaries as reporting person's descendants Common Stock 24886 I Held by trusts w. reporting person as sole trustee and beneficiaries as reporting person's children Common Stock 27586 I Held by trust w. reporting person as sole trustee and beneficiary Common Stock 19 I Held by reporting person's spouse Common Stock 364 I Held by reporting person's children sharing the same household Grant of 280 shares of restricted stock for no cash consideration under the Alleghany Corporation 2015 Directors' Stock Plan, reflecting such number of restricted stock shares equal to $150,000 (as determined by the Board of Directors in accordance with the plan) divided by the average of the closing sales prices of the common stock on the 30 consecutive trading days preceding the grant date as reported by the NYSE. Under the Alleghany Corporation 2005 Directors' Stock Plan, when the registrant pays a cash dividend on its common stock, each director holding restricted stock units ("RSUs") awarded under such plan(s) is credited with a corresponding dividend on his or her RSUs in the form of additional RSUs. As a result, this reflects 24 RSUs received as dividends in connection with a special cash dividend of $15.00 per share of common stock paid on March 16, 2020. /s/ Stela Burghart, Attorney-in-Fact 2020-05-11