Trump enjoys casting himself as a rogue in the traditional political scene, and this most recent attempt to reach the average American voter is relatively skillful: He could actually overcome the handicap of his wealth by expressing his willingness to part with some of it. "Personally, this plan would cost me hundreds of millions of dollars, but in all honesty, it's worth it," Trump told CNN. Not surprisingly, Pat Buchanan is calling Trump's plan "serious wacko stuff"; financial analysts are already up in arms over the effects such a tax could have on the stock market by effectively scaring investors out of the country and tying up wealth in government bank accounts.
Its dubious financial mechanics aside, will the Donald's tax plan win him any new voters? Don't count on it. "Trump thinks his voter base is made up of average working guys, and he thinks this proposal will play well with this demographic," says TIME political analyst Margaret Carlson. "The problem is, most of the these average guys think they're going to be Donald Trump someday, and with that in mind, they don't want a punishing tax levied on the wealthy. As long as the American dream is alive, this country will favor a progressive tax."