First, from the beginning, Trump's Taj Mahal casino in Atlantic City was not his idea or his project. The Taj Mahal was originally owned and developed by James Crosby of Resorts International.
Next, before the Taj Mahal was finished, Mr. Crosby apparently died on the operating table in a hospital. After a bidding war between Trump and Merv Griffith, Trump ended up owning the unfinished casino. If Trump didn't come in at the last minute, lots of jobs would have been lost in the first place. At least that's what I think how Trump saw the Taj Mahal. Nevertheless, Trump did learn a big lesson on insulating himself on his business bets and America needs a leader that has already learned from his/her mistakes. Learning from your mistakes means you have to be humble enough to admit the mistake in the first place.
Second, The Plaza Hotel, Trump's 2nd Bankruptcy, was already in financial distress before Trump entered the picture and took over. If Trump didn't come in and invest in the Plaza Hotel, lots of employees, union or not, would have been fired anyway.
The other two bankruptcies appear to be another chapter in the same casinos and hotel businesses there were distressed from before. And none of those bankruptcies were personal bankruptcies.
To make money in real estate, you have to buy low (i.e., blight/distressed/crime-ridden/empty lot), and sell high. Buying High and Selling High? Wow, that's very hard to do and if that happens, then a real estate crash or bubble is about to happen.
Trump knows this, and you have to take chances in "risky" properties to make money. Taking chances in safe bets(e.g., expensive, well-run properties) means making zero or paying too much.
Hence, Trump takes risks in distressed properties which means you win some, you lose some.
Trump knows this and you have to take chances in "risky" properties to make money. Taking chances in safe bets(e.g. expensive, well-run properties) means making zero or paying too much.se already distressed properties, Trump wouldn't have declared bankruptcy as he wouldn't have taken on a well-known risk, to begin with. However, all those casino and hotel employees would have been fired.