It did sound like Trump used some sketchy techniques to avoid paying taxes, such as stiffing people on loans (if the NYT article is correct).
I think a lot of the hype around people paying more taxes than rich people in a given year is an anti-pattern though. There are obviously some people doing sketchy or illegal things to avoid paying tax, and I personally think the law should be enforced on them. It's perfectly reasonable for a rich person to pay zero in taxes though, and if you think about how money works, then you would actually expect rich people to pay tax less often. They already have a bunch of money in their personal bank account, so they don't need to acquire any new income in order to live comfortably, so it makes sense that they would keep all their new assets in business assets or deferred assets or whatever. And then if they need to convert their business asset into spendable money, like Bezos wanting to buy a $1B yacht or something absurd, then he would need to sell Amazon stock which would be taxed as income. It seems like most people don't realize that stock in a company isn't money or a spendable asset. For it to count as money, you have to actually sell it to someone, which reduces your ownership and ability to control your company. Companies would be different if their founders could not maintain large ownership and control. We'd end up with a lot of companies that are distributed across many people, and that are excruciatingly slow, non-innovative, and dumb, just like governments are. There is a place for government, but using the government style for innovative products would make the world move 10 times slower.
I don't really comment in politics much, sorry for the wall of text lol.