Y Alleghany Corp

On February 23, 2022, Alleghany Corporation (the “Company”) entered into an employment agreement (the “Employment Agreement”) with Joseph P. Brandon, the President and Chief Executive Officer of the Company, effective as of December 31, 2021, the date Mr. Brandon assumed the role of Chief Executive Officer of the Company.

Pursuant to the Employment Agreement, Mr. Brandon will receive (i) an initial annual base salary of $1,050,000 (increased from $940,000), (ii) a target annual cash bonus equal to 200% of base salary, (iii) an annual long-term incentive award with a grant date market value equal to 300% of base salary, and (iv) a matching performance share award in respect of up to $7.5 million of shares of Company common stock purchased by Mr. Brandon between October 1, 2021 and September 30, 2022. Mr. Brandon will also be eligible to participate in the Company’s Deferred Compensation Plan and any other benefit plans made available to other senior executives of the Company.

The Employment Agreement provides that, upon a termination of Mr. Brandon’s employment by the Company without “Cause” (as defined in the Employment Agreement), other than due to his death or “Total Disability” (as defined in the Employment Agreement), Mr. Brandon would be entitled to salary continuation until the aggregate gross amount of such payments is $1,050,000, subject to his (i) execution of a general release of claims in favor of the Company and its affiliates, and (ii) continued compliance with the terms of all confidentiality, non-compete, non-solicit, invention assignment, non-disparagement and similar obligations to the Company and its affiliates. In addition, if Mr. Brandon’s employment is terminated as a result of “Retirement” (as defined in the Employment Agreement) or due to his death or Total Disability, he will be entitled to pro-rata vesting of his outstanding long-term incentive awards, provided that, solely in the case of the matching performance share award (described herein), such termination occurs on or after December 31, 2024.

On February 23, 2022, the Compensation Committee of the Board of Directors approved the Company’s entry into a performance share matching award agreement, in the form attached to the Employment Agreement (the “Award Agreement”), pursuant to which Mr. Brandon will be granted a matching performance share for each share of Company common stock purchased by Mr. Brandon between October 1, 2021 and September 30, 2022, up to a maximum of $7.5 million, including, for such purpose, any amounts credited to his deferred account under the Company’s Deferred Compensation Plan as of April 1, 2022 that he elects to notionally invest in the Company’s common stock. Additional performance shares will be credited to Mr. Brandon upon payments of dividends by the Company on its common stock.

The performance shares will be earned based on the Company’s “Adjusted Book Value Per Common Share” (as defined in the Award Agreement) achievement during the five year period commencing January 1, 2022 and ending December 31, 2026

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(the “Performance Period”). 200% of the target performance shares will be earned for Adjusted Book Value Per Common Share achievement of 10% or more, 100% will be earned for Adjusted Book Value Per Common Share achievement of 7%, 50% will be earned for Adjusted Book Value Per Common Share achievement of 4% and 0% will be earned for Adjusted Book Value Per Common Share achievement of less than 4%, with straight-line interpolation used to calculate the earned amount if achievement is between the percentages above.

To earn the performance shares, Mr. Brandon is required to remain in continued employment through the end of the Performance Period, except that, if his employment is terminated on or after December 31, 2024 (i) by the Company without Cause, or (ii) due to his death, Total Disability or Retirement, Mr. Brandon will be entitled to pro-rata vesting of his matching performance shares based on the Company’s “Adjusted Book Value Per Common Share” achievement during the performance period as of the December 31^st immediately preceding his termination date or, if his employment terminates on December 31^st, as of such date.

Mr. Brandon must maintain unencumbered beneficial ownership of the purchased shares on which matching performance shares are granted throughout the five-year Performance Period in order to receive the full amount of matching performance shares. Mr. Brandon has also committed to not sell or transfer shares of Alleghany common stock he owned as of date of grant of the performance shares during the Performance Period, unless consented to by the Compensation Committee.

The foregoing descriptions of the Employment Agreement and the Award Agreement are qualified in their entirety by the full text of the Employment Agreement and the Award Agreement, which are incorporated herein by reference. The Employment Agreement (which includes the Award Agreement as an exhibit thereto) is attached hereto as Exhibit 10.1.

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