Trump isn't as wealthy as people make him out to be. He has made some very bad investments.
Uh...in like 1992. He's rich as anything and was even then. When you own as much real estate in NYC as he does, you're automatically top .5% EASILY.
Try top 0.01%. But he isn't as fabulously wealthy as he is often claimed to be, just high-profile. And even recently he's had a lot of setbacks (the loss of Riverside South in 2005, the recent failure of the Trump SoHo Hotel, etc.), more than your average real estate mogul. He takes huge risks and gets burned a lot.