Well, he would buy a building or a hotel say for $250 mil, get a mortgage for $300 mil to 'fix it all up'- pocket a nice chunk for himself and take the leftover money to buy something else- a classic pyramid scheme...
When the real estate market took a turn for the worse (in 1990) he was left with a dozen places that were worth a lot less than he owed, and he couldn't pay back the mortgages...brutal- and his fathers fortune bailed him out more than once...However he was pretty darned clever how he got out of it all- way too boring a finance story but there were a couple of excellent books written about it- he is no dummy- especially when he can use other peoples money!! You wouldn't believe how little of all the "TRUMP" properties he actually owns- very few...He develops them and manages them, but he's a front man with other people putting up the money, most of them are not actually his !! 
When the real estate market took a turn for the worse (in 1990) he was left with a dozen places that were worth a lot less than he owed, and he couldn't pay back the mortgages...brutal- and his fathers fortune bailed him out more than once...However he was pretty darned clever how he got out of it all- way too boring a finance story but there were a couple of excellent books written about it- he is no dummy- especially when he can use other peoples money!! You wouldn't believe how little of all the "TRUMP" properties he actually owns- very few...He develops them and manages them, but he's a front man with other people putting up the money, most of them are not actually his !! 





At least Donald tried to offer some answers, good or bad, instead of just taking sides...