The story of Akio Kashiwagi, drawn from Trump’s memoirs and news accounts from the day, offers a revealing window into Trump’s instincts. It shows that Trump isn’t just a one-time casino owner—he’s also a gambler, prone to impulsive, even reckless action. In The Art of the Comeback, published in 1997, Trump explains that until he met Kashiwagi, he saw himself as an investor who dealt only in facts and reason. But his duel with the great whale in action made him realize “that I had become a gambler, something I never thought I was.”

Perhaps just as important, when gambling failed him, Trump didn't quit: He doubled down. But he did it shrewdly, summoning a RAND Corporation mathematician to devise a plan that would maximize his chance of fleecing his Japanese guest.

And it worked. Kind of. In Trump’s recollection, which he shared for this story, his showdown with Kashiwagi was another one of his many great wins. Just don’t look too hard at the ledger.

A bizarre and nutty tale of the time Donald Trump hired a RAND Corp mathematician to try to win back money a Japanese gambler took from one of his hotels in a hot night of Baccarat.

Before reading the piece, I thought perhaps they had changed the rules of the game somehow to raise the house edge. But no, they just changed the terms under which Kahiwagi to play, counting on the house edge to manifest over the long run.

Behind the trademark bluster, however, Trump grew more calculated. Having looked in the mirror and seen a gambler, he reverted to careful strategy. Trump consulted Jess Marcum, a mathematical probabilities expert who co-founded the Rand Corporation—a government-affiliated think tank then better known for modeling nuclear war with the Soviet Union—on how to maximize his odds in a second showdown with Kashiwagi. Marcum knew the only way to compensate for the house’s very slight baccarat advantage, of just over one percent, was to keep the game going for as long as possible. Time was on Trump’s side.

So Marcum and an Atlantic City casino insider named Al Glasgow prepared a report for Trump proposing a “freeze out” agreement. Under the deal, Kashiwagi would bring $12 million to the table and play until he had either doubled it—or lost everything. Even with huge bets, that would take a long time. Marcum simulated the match in detailed hand written notes. Kashiwagi might surge ahead early, he estimated, but after 75 hours at the table – far longer than he had stayed the first time - his chances of winning would fall to 15 percent. The key was to prevent a repeat of Kashiwagi’s first visit, when he had walked out while ahead.

Kashiwagi, presumably fuzzier on the probabilities, agreed to the terms. There was no legal way to hold him to such a deal but Trump felt the men were honor-bound. “Gamblers are honorable, in their own way—at least about gambling,” he later wrote.

The peculiar thing about Trump is that, as offended as I am but so many of the things he says, I'm not convinced he actually believes half the things he spews with such gusto. Yes, he's a politician, and they're always churning out rhetoric for reasons of positioning, but Trump exceeds even other politicians in his commitment to artifice.

Because of that, when he says something I disagree with, I'm more offended by the casual way he tosses around such damaging ideas than the ideas themselves, and when he says something I agree with—which is, admittedly, rare—I don't give him much credit.

He needs no exaggeration to be rendered a caricature, because he has done it himself, both figuratively and literally, like one of those figures in Pinocchio who becomes the physical embodiment of its own hubris. If you were a cartoonist on assignment to lampoon him, you could just snap a photo and collect a full day's pay.