Explain Like I'm Five

Trump has a lot of wealth on paper, but a lot of it is tied up in real estate, which isn't the easiest thing to turn into cash when you need it. And a lot is tied up in stock, but since he got caught fixing the books for the Trump Organization, he can't really use that as his personal piggybank without a lot of scrutiny. And Truth Social is worth over a billion on paper but will crash if he starts to sell any of his stock, which would cause a lot of new problems right now.

Meanwhile, he is burning through money at an insane rate. I mean historically, he's lost far more money than he's ever been worth. He's always had to have new businesses and schemes to cycle through as the old ones crumble. He basically never made a profit until the Apprentice, and that actually caused problems because he'd structured his operations around losing money, leaving other people holding the bag when things go completely south, writing off the loses for tax purposes, and, well, cooking the books.

But with hundreds of millions in judgements against him, on top of the hundred million plus in legal fees, he's in a bit of a bind. He already had to put a $175 million up for bond to appeal the judgment civil judgment against the Trump Organization. If he loses the appeal, he's out not just the $175 million, but the full $489 million judgement, plus about $115k a day in interest. Plus he's got the E Jean Carroll judgments and ongoing cases because he's a dumb bastard that can't stop himself from committing defamation every time he leaves a courthouse after losing a defamation case.

While he has been funneling money from his PAC to cover his legal bills that only goes so far, and as I understand it, he can't use that for actual judgements against him. If he loses the election, he may be fighting legal battles for years to come, that PAC money will likely dry up, and if he doesn't have the cash when the court demands it, he could see his assets seized and auctioned off. If he wins the election, he can do basically anything and we're all fucked.

So to simplify this a bit, imagine that he spent almost all his money on a lot of properties without getting a single monopoly, while his opponent has hotels on the dark blue and green properties. He keeps trying to survive the gauntlet and pass go to stay in the game, and maybe he can survive by mortgaging everything, but it's much easier for him if he has the cash to pay the bill.