Not to digress too far, but it really is possible to make big bucks and pay near-zero taxes. This is why Warren Buffett supports a minimum tax on the wealthy, requiring people above a certain level to pay at least a 30% tax no matter how many deductions they have. Even Mitt Romney talked about limiting the total deductions that could be claimed.
http://www.nytimes.com/2012/11/26/opinion/buffett-a-minimum-tax-for-the-wealthy.html?_r=0
http://www.nytimes.com/2012/11/13/u...like-a-romney-idea-to-cap-tax-deductions.html
If Trump was smarter, he'd appeal to his base -- and maybe a lot of other people -- by releasing his taxes and saying "Lookee here, I'm one of the richest guys in the world, and I'm paying zero taxes, and it's all legal. That's how screwed up our system is, and if you elect me I'll change it, and I know how."