Trump's whole financial history is fairly amusing, as far as I can see. The bottom line is that he is actually not very successful, given what he started with. The ultimate put-down was a guy who noted that he inherited a fair amount of real estate, in the form of buildings with tenants. Calculating what Trump would currently be worth if he did nothing much more than sit back and collect rent, effectively, the answer came out to be <drum roll> about the same as what he is worth now. Dynamic performance, yes?