Trump has never actually been wealthy. Any money he has made has been offset by larger losses and debts. He bankrupted a casino for fucks sake.
Trump is not successful. He is where he is now because he is the useful idiot and is being funded by putin, saudi princes, etc.
Trump is the equivalent of the people you see driving a maserati or a lexus that spend all of their money looking rich while living in a run down trailer or apartment that needs raized.