There was a lot weird about that deal, but you've highlighted the one thing that is pretty clearly not insider trading. Had the CEO bought a bunch of shares, t

There was a lot weird about that deal, but you've highlighted the one thing that is pretty clearly not insider trading. Had the CEO bought a bunch of shares, that would very possibly be insider trading, because he is (presumably) trading on information that doesn't belong to him, but belongs to the company, ie, the board. In the US, insider trading is a crime about misappropriation of information. But the board can do whatever they want. They can grant the CEO a large cash bonus, at any time, for any reason or no reason. And they can grant him a chunk of valuable options. And they can certainly do so because of a soon-to-be-announced deal, because again, they're the ones who "own" that information. Now, why the board might have thought that was a good idea, and to what extent the board was fulfilling their fiduciary duty to the stockholders is a separate question. Giving employees who do a good job a bonus is pretty routine, but on the other hand, just randomly giving the CEO an (effective) giant sack of cash is very much not routine, and there's a lot of practical reasons why companies do not usually do that. "It might violate insider trading laws" is, however, not one of them. :)