It makes sense if the company had agreed to buy the shares off of him at market rates and then sell him stock back at a significant discount. Doing this would allow him to claim the money gained as capital gains rather than employment income, and it wouldn't count as insider trading if it was an arrangement made and timelines settled upon before the bullshit was planned.

It could be something like having his contract say that the company will buy back X shares when the share price hits $Y in value, for instance.

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."