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What you said doesn’t make any sense. Either it wasn’t $40 a share when he sold it like you said in this comment or it was $40 a share like you said in the previous comment.
I guarantee you his contract looks like something like this, “If you meet X performance metric, the company will buy N amount of shares (maximum 2000) back at the maximum/average stock price within Y days and sell you back the amount of shares sold (maximum 2000) for Z dollars.”