Is Donald Trump setting himself up for one final bankruptcy?

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When the news broke last week that Donald Trump was suddenly trying to sell off the lease to his one truly profitable hotel, we pointed out that the only reason for Trump do this is if he’s so broke right now, he’s willing to give up future income just to score some cash right now.

When the news broke last night that Trump was making the humiliating move of changing his residency from New York to Florida, ostensibly for financial purposes, a pattern became clear. Trump is suddenly making moves that make him look terrible, and moves that will hurt him financially in the future, all for the sake of trying to survive in the short term. Not only is he clearly out of money, he’s past the point of caring about appearances or future prospects.

Even as we were wondering if Trump might be trying to raise cash to survive any upcoming asset forfeitures, Trump biographer David Cay Johnston put his finger on what might be the final piece of the puzzle. He tweeted on Thursday night that Florida law allows its residents to designate one property as homestead, and retain it during personal bankruptcy.

If that’s what is indeed going on here, it would be stunning. Yes, Donald Trump has had several corporate bankruptcies. But that’s always been just a way of shedding one of his poorly-run and money-losing properties at a time without having to pay his bills. Personal bankruptcy would be new territory for Trump. It’s something you only do if you’re out of cash, too deeply in debt to survive for long, and you have no hope of digging out.

It’s also not something you do if you’re President of the United States and you’re planning to run for reelection. Sure, Trump’s core support base wouldn’t care if he filed for personal bankruptcy and lost nearly all his properties during the 2020 election. But Trump didn’t get elected with his base alone, and can’t get reelected with his base alone. If he files personal bankruptcy, it’ll mean he’s giving up on 2020. That’s why it would be such a remarkable development if it’s what’s really happening here. But he’s on a path to lose badly in 2020 anyway, so if he’s flat broke, then bankruptcy would make sense.