found this while browsing this thread, very interesting take.Here's a good read on his bankruptcies. Without doing a real deep dive into this, most of them are casino's/hotels during the recession in the 1990's. It's odd to me you think he's not a good businessman. He's a billionaire, you don't get rich from making more bad decisions than good decisions. When you dabble in real estate there's a lot of loopholes...I use them too. Our tax system has many gray areas in it, many loopholes, if you don't use them while staying within the law, you are a fool.
i prefer to think that some people know how to get money, but are too oldfashioned, i remember how many people lost their money when COVID 19 was a thing. Many people had land based casinos, and they did not liked digital ones, so in the end every guy who moved to a digital casino using sth like nowplix platform (or any other thing) earned money, and every guy (most of them, not every tbh) who tried to get money on offline casino lost some.
Also, I totally agree with your point about the tax system. Most of the people I know who refused to use the gray areas or legal loopholes ended up giving up completely. Honestly, in today’s world, only fools try to stay 100% clean while managing money. The system rewards those who understand how to use it.