0001193125-20-145113 Sample Contracts

ALLEGHANY CORPORATION $500,000,000 3.625% Senior Notes due 2030 UNDERWRITING AGREEMENT May 13, 2020
Underwriting Agreement • May 18th, 2020 • Alleghany Corp /De • Fire, marine & casualty insurance • New York

Alleghany Corporation, a Delaware corporation (the “Company”), proposes to issue and sell to the several underwriters (the “Underwriters”) named in Schedule 1 attached to this agreement (this “Agreement”) acting severally and not jointly, the respective amounts set forth in such Schedule 1 of $500,000,000 aggregate principal amount of its 3.625% Senior Notes due 2030 (the “Securities”). The Securities will be issued pursuant to an Indenture, dated as of September 20, 2010 (the “Base Indenture”), between the Company and The Bank of New York Mellon, as trustee (the “Trustee), as supplemented by a first supplemental indenture dated as of September 20, 2010 (the “First Supplemental Indenture”), a second supplemental indenture dated as of June 26, 2012 (the “Second Supplemental Indenture”), a third supplemental indenture dated as of September 9, 2014 (the “Third Supplemental Indenture”), and a fourth supplemental indenture to be dated May 18, 2020 (the “Fourth Supplemental Indenture” and to

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ALLEGHANY CORPORATION as Issuer AND THE BANK OF NEW YORK MELLON as Trustee FOURTH SUPPLEMENTAL INDENTURE Dated as of May 18, 2020 Supplement to Indenture dated as of September 20, 2010
Fourth Supplemental Indenture • May 18th, 2020 • Alleghany Corp /De • Fire, marine & casualty insurance

This FOURTH SUPPLEMENTAL INDENTURE, dated as of May 18, 2020 is entered into by and between ALLEGHANY CORPORATION, a Delaware corporation, as issuer (the “Company”), and THE BANK OF NEW YORK MELLON, as Trustee under the Indenture (as hereinafter defined) (the “Trustee”).

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