0000950123-10-087495 Sample Contracts

ALLEGHANY CORPORATION $300,000,000 5.625% Senior Notes due 2020 UNDERWRITING AGREEMENT
Underwriting Agreement • September 20th, 2010 • 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 $300,000,000 aggregate principal amount of its 5.625% Senior Notes due 2020 (the “Securities”). The Securities will be issued pursuant to an Indenture to be 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 to be dated as of September 20, 2010 (the “First Supplemental Indenture” and together with the Base Indenture, the “Indenture”). This is to confirm the agreement concerning the purchase of the Securities from the Company by the Underwriters.

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

This FIRST SUPPLEMENTAL INDENTURE, dated as of September 20, 2010 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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