Good point Ed. Plus, he has a huge Alternative Minimum Tax obligation based on the excess of the Fair Market Value over his cost. That FMV is established at exercise and if the stock drops to $5 per share it's tough cookies. You still owe the tax on the big number. I would bet that his tax obligation will exceed his $250,000 cost. It can quickly wipe you out, as one poster explained to me about 6 months ago.
I'm not an accountant, so my apologies if the facts aren't straight.