Taking lots of high risks with other people’s money (the equivalent of heads I win, tails you lose) is one of the definitions of being a bad businessman.

Why? Sounds like a very profitable business to be in. And it takes a rare talent to be able to accomplish that with other people's money in debt. It's very common to do it in equity, that's basically the entire Silicon Valley financial system, but most people can't get banks to take the other side of that deal.

Trump's business isn't - and wasn't - in running casinos. It's in running a development company. And these deals turned out great for that business. He was able to take over the Taj with Other People's Money and get a billion dollars to put into it. All upside for him, no downside. The bet turned against him when interest rates skyrocketed and the Taj went into BK, but he was able to cut a deal where the banks only took half the equity interest to restructure the debt. So he still had the massive upside on his potential, just a bit less - and still was in the deal. Then he was able to set up a public offering for a new entity to take out everyone's interest in the property at close to par (about $900 million) - meaning he made out like a bandit on his equity, and kept a lucrative stream of income for his brand name on the hotel. That new entity then went bankrupt, but again not any problem for Trump's actual businesses.

Trump's actual business - running a development company - performed amazingly through all this. He was enormously successful at that. It's the nature of real estate development, which is in some ways like poker. Some deals will succeed, some will fail - and the key is to make sure you lose less on the deals that fail than you win on the deals that work. Some developers like to operate in the area where none of their deals fail, but none of them are massive home runs (low variance). Others work in the high-risk/high reward area (high variance), and their most important skill is making sure that when their deals fail, they're not the ones holding most of the losses.

I expect that's why Trump keeps pointing out - correctly! - that he never went bankrupt. Some of his SPE's did - but that's why you have SPE's in the first place! So that they go bankrupt, and not you!