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Not many people can afford to run an airliner on their inheritance, but what trump has managed to do is spend vast amounts of money his whole life and somehow not become personally bankrupt. Hopefully this will change soon.
That wasn't his money - it was loans/investments that he again, was able to procure because he lied about his worth.
I've seen some analysis that says he would be richer if he had just taken his inheritance and left it in the bank...