Donald J. Trump always held himself out as one of the richest people one could ever hope to meet; he had helicopters, a BIG plane, and a gaudy gold-colored penthouse in a building named after him. But in many ways – most people weren’t fooled. He appeared rich.

Oh, he was “rich” – he didn’t make a living as a writer. But he was a millionaire who spent like a billionaire.

Soon, according to Trump’s biographer and current financial interpreter, Trump’s need to post a bond to appeal his New York civil ruling will expense Trump as the unstable, haphazard business person that he’s always been.

Shock face. The guy who suggested that I.V. bleach may be a possible COVID cure has trouble with finances. Wonderfully, it won’t take anything exotic to demonstrate the issues, just checks that won’t clear but needed to keep his cases going:

According to Tim O’Brien, who goes back decades with Trump, noted in a Rewsweek‘report:

“Now, here we are in 2024, and he is about to get exposed. It is going to be a slow grind. I don’t think there’s going to be a lot of drama on Monday. But the process of opening the kimono and discovering indeed Donald Trump has no financial clothing, at least not the kind of financial clothing he claims he’s had, begins.”

Slow grind? That sounds even more appropriate than a sudden punch because it gives Trump more time to sit and agonize over what is happening while realizing that there’s nothing he can do about it.

According to O’Brien, banks figured out the one way to ensure that Trump would feel his obligations and be sure to pay them back. Instead of allowing Trump to use his businesses to guarantee loans, banks, and insurance companies required Trump to guarantee loans with his personal money – and, just like in politics, that changed the game.

He said, ‘You know, my father always said, ‘You never personally guarantee any loans.’ And I made a mistake. I personally guaranteed too much money in the early 1990s,” O’Brien recalled. “‘I didn’t think it would catch up with me. And it did. And I learned my lesson. I would never personally guarantee a loan after that.'”

His dad said that?

Well, my father always said, “Don’t spend money you don’t have. And don’t get a loan you can’t pay back,” and that largely fell on deaf ears, too – though not at the level Trump failed.

But now, with the need to put up cash for his appeals and – perhaps – start paying his liabilities, it does seem like it will be a slow grind, and one that leaves the MAGA emperor with no clothes.

But the “no clothes” will certainly fit.

Jason Miciak is an editor at large for Occupy Democrats who freelances for friends at Political Flare.