Leaving aside the horrific bombing aspect of the situation, it was an awful plan.
There would obviously be a paper trail of an odd, and probably large, short sale transaction. And he didn't think investigators would look into that and have some questions for him? And he happened to be staying at the hotel with the team?
To add to the stupidity, even with the bombing, the stock price didn't even fall. What in the world was this guy thinking? How he could have planned this whole thing out and think not only that it would work but that he'd also get away with it is unreal.
Fortunately his incompetence carried over into his ability to inflict massive damage.