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Most rich people don't have cash on hand and don't want it.
I remember reading a story where a con man is talking about money. He tells his protege that if he wants to look like a rube he'll pull out a fat wad of hundreds. If he wants to look like a doctor or lawyer he'll use a premium credit card, but if he wants to look like a real high roller he'll come in with an assistant who handles the payments.
It's a little like physics. Different rules when you get to the quantum level.
I'll take it one step further, most rich people pay for big bills with debt whenever possible. That's because debt doesn't incur tax events. It's better to take out a 10 year loan for 1 billion dollars and pay it off by slowly selling of equity then it is to sell 1 billion in equity + the extra you'll need to pay off the tax man.
I'm sure some real accountants and lawyers could give us many more examples.
The difference with most "billionaires" is that the bank wants their business and wants to lend to them. Trump, not so much.
That's the point. He's not really a billionaire. He'd be even further from it if it wasn't for the grifting that has happened since he started his run.
Nobody had ever made money campaigning before. He didn't find a loophole, he wanted the ego boost but a confluence of factors meant he made money to cover his debts. That's all starting to crumble as the malfeasance that got him there has consequences. However he has yet to really feel them.
There's a Mafia scam called a 'bust out.'
The mob takes over a legit business, call it Joe's Diner. Joe starts ordering new equipment and tons of food. Joe's partners sell the new stuff and keep the cash, whle poor Joe is left with a mountain of debt. Eventually the diner goes broke.
I can see something like that happening here. I'm not a lawyer or an accountant, but I know that when you're playing with billions of dollars, it's easy to skip out with a few million here and there.