I agree, if he was part of the amnesty, he was screwed.
However IF he had had enough balls to say ...
"look here's my taxes, you can see how I made my money. We have a tax issue, I follow the law like most Americans, but it's time to change the law and eliminate all these loopholes/credits so that you don't need a degree to figure out what the government is costing you."
If he had done that, and followed it with a real tax reform plan, I would have voted for him. He could have used his low rate and the loopholes he employs to launch that platform. He could have used it to bring americans together, instead of the "47%", because ALL Americans use tax loopholes/credits and we all understand how complicated the code is.