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This will ultimately be what does him in. He can play legal games for years with ease, but the moment he's forced to pony up actual hard cash his house of cards will collapse. Best case scenario for him right now is that he can dip into the GOP's finances to pay this fine, although if he does so that's opening up yet another can of worms that's likely to come back and bite him. No bank is going to loan him money, and his supporters collectively don't have enough cash to cover that fee even if he could convince them to send him even more money.
Any more judgements like this one and he's going to have to start seriously liquidating assets and with how leveraged most of them probably are even that's going to net him a lot less actual cash than it might seem like. There's a reason he grifts so hard and it's not because he's so amazingly successful.
What’s to stop him from just declaring bankruptcy to avoid all of this, aside from him losing face?
Because bankruptcy proceedings would effectively have to wait in the legal queue in this case
He cant
Watch him dip into GOP funds, croak, and leave the GOP holding the bag.
This is really the best part of all this.
Every dollar the GOP spends on Trump's legal issues (which in fairness they kinda have to do since they've now molded the entire party around that one person) is a dollar that they're not spending on his campaign, not spending on polling and research, not spending on skilled campaign managers and advisors, and especially not spending on downticket races.
We're still far enough out from November that I haven't bothered to read up on contested house and senate seats, or state government races that are predicted to possibly flip one way or the other, but a cash strapped Republican party will have less money to pump into those races as well.
We can only hope
I think he probably has more cash than you think. Selling one or more of his properties to flip the bill will be embarrassing, but there is no doubt he has the financial means to weather this storm.
I think he can cover all the judgements to date, but I don't think he'll be able to do so without selling multiple properties unless he can steal the money from the GOP. But selling any of his properties is going to hurt him badly. He's relying on the revenue from those properties to cover his expenses and the more of them he's forced to liquidate the more precarious his finances will be. A few more judgements against him in the hundreds of millions range like this one and even selling every last property he owns might not be enough.
You can't embarrass or shame Trump, he doesn't care, but if you force him to actually pay his bills? Now that, that will hurt him badly.
You may be right
Selling a large commercial asset is NOT what anyone wants to do right now. He would be selling at a loss and it would be a huge ego hit.
Additionally selling a large real estate property is exceptionally difficult to do in a short amount of time.
That's what makes it even sweeter, this is equivilant to main lineing a barrel of corn syrup. Fucking love it