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"A fool and his money are soon parted" is once again proven true.
I hate saying it but this fool is still winning. Everyone else is losing.
Or maybe everything in life has nuance and can't be simply boiled down to "winning" and "losing".
Trump is not only mega rich, but he's also the head of an actual cult of personality. Those are feathers in his cap no doubt. On the other hand, not only has he lost multiple elections, he's a twice impeached criminal with 91 very serious charges (and counting) against him and a pile of hard evidence to back it all up. The odds of him spending what few remaining years he has left behind bars are non-zero, and no matter what happens he will incur massive financial costs one way or another.
In an alternate reality he could have sat out 2016 and spent the last decade of his life golfing and stuffing his fat fucking face, and he would have still been rich enough to live however he wanted. But instead he has put the world's biggest magnifying glass up his own corrupt asshole, and it's all not looking so great.
Trump is actually very bad with money, historically. His father was the clever businessman, and Trump apparently squandered his inheritance. His partially public tax returns reveal as much. He’s lost absolute fortunes. He couldn’t even get a casino in Atlantic City to stay afloat. I’m pretty sure that everything about his public image is a lie.
I’m pretty sure the Atlantic City bankruptcy was intentional, and was the result of a money laundering scheme. His high rise condos are the same thing but easier to manage (because he is not that smart and has alienated most of his more intelligent co-conspirators at this point in his life.)