Well, my opinion is anyone who inherited what amounts to around $100 million from their father, who absolutely was a demonstrably successful businessman, would be doing incredibly badly to be worse off than that - especially when their investment was in real estate in New York City. I'm sure he made some good moves, but I'm also sure if he started with a dollar in his pocket instead of $100 million he'd be running a used car dealership, not the president, all else being equal.
Trump's finances and statements remind me of Robert Maxwell: opaque and dubious.
If there were errors, I'm sure Trump would have found a way to "correct" this wackypedia page
https://en.wikipedia.org/wiki/Wealth_of_Donald_Trump#1980s_and_1990s containing
"...Former Forbes reporter Jonathan Greenberg said in 2018 that during the 1980s Trump had deceived him about his actual net worth and his share of the family assets in order to appear on the list. According to Greenberg, ... it took decades to unwind the elaborate farce Trump had enacted to project an image as one of the richest people in America. Nearly every assertion supporting that claim was untrue. ... In our first-ever list, in 1982, we included him at $100 million, but Trump was actually worth roughly $5 million ..."
and
"After several years on the Forbes List, Trump's financial losses in the 1980s caused him to be dropped from 1990 to 1995, and reportedly obliged him to borrow from his siblings' trusts in 1993."
Oops. Not what you would expect from a good business men, e.g. Bill and Dave, or Gates, or ....
This does have relevance to tariffs, I promise! I wonder if this is another case of rich people assuming they are rich because they are the "best people" (as in somehow superior to the rest of us folk). This is seen all the time, I think Musk is one of the most prominent examples right now. Musk was also born into wealth which gave him a significant advantage in early life. He has had some successes to say the least, but I wonder if it was mostly a case of being in the right place at the right time. He now believes he is the best man in the world to run platforms like X, tunnel under Los Angeles (earthquakes be damned) and that the Cybertruck is a good product. Is the president suffering a similar ill? His tariffs are "right" - he has always believed in them, way back to his first campaign in the 80's he promoted the idea of tarriffing other nations, and under his first presidency he got into a trade war and that didn't totally destroy everything. There's no evidence that the trade war benefited the US either, but "I've been right about so many other things in my real estate deals - this applies to being president too!" could be a factor here.
That applies in many walks of life, including fund managers (75% underperform the market, the others are just lucky), scientists (e.g. Linus Pauling and his DNA and Vitamin C theories).
If that's the case, it may take a serious deviation from the norm, or intervention by Congress or the Supreme Court, to stop these in the end - if he listens to either.
He has stuffed the supreme court with his appointees.
Given the power-grabs, overreach and assault it is currently under, it remains to be seen whether the much-vaunted US Constitution is worth the paper it is written on. Example power grab: congress is supposed to set foreign tariffs, but Trump claims the American's desire for fentanyl from China is a national emergency enabling
him to set tariffs on Norfolk Island and Gabon.