Hard to say he lost that much money. It could all have been tax shelters or financial gymnastics. At one time trump was fired as a customer by Deutsche Bank because he owed them $40 million he had failed to pay. He ingratiated himself with the private banking department of Deutsche Bank and got them to loan him $50 million. He used $40 million of the money to pay back the real estate department the money he owed them. He was able to repay the private banking department after he recovered from a bankruptcy or two. He was back in business with Deutsche bank. That is what I mean by financial gymnastics. None of that would show in his tax return. You would have to see the books. Personally I doubt he lost that much but he did take a bath financially in Atlantic City. How big a bath I have no idea. Probably nowhere near a billion. All business people engage in legal financial gymnastics. Without it, one would be non-competitive. I've always thought business was fun except for the money part of it. You need to take what the press tells you about his finances with a big grain of salt. The reporters aren't business people.