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.

For example, when Trump says he is worth $10 billion, which causes his critics to say he is worth far less (but still billions) he is making all of us “think past the sale.” The sale he wants to make is “Remember that Donald Trump is a successful business person managing a vast empire mostly of his own making.” The exact amount of his wealth is irrelevant.

When a car salesperson trained in persuasion asks if you prefer the red Honda Civic or the Blue one, that is a trick called making you “think past the sale” and the idea is to make you engage on the question of color as if you have already decided to buy the car. That is Persuasion 101 and I have seen no one in the media point it out when Trump does it.

The $10 billion estimate Trump uses for his own net worth is also an “anchor” in your mind. That’s another classic negotiation/persuasion method. I remember the $10 billion estimate because it is big and round and a bit outrageous. And he keeps repeating it because repetition is persuasion too.

I don’t remember the smaller estimates of Trump’s wealth that critics provided. But I certainly remember the $10 billion estimate from Trump himself. Thanks to this disparity in my memory, my mind automatically floats toward Trump’s anchor of $10 billion being my reality. That is classic persuasion. And I would be amazed if any of this is an accident. Remember, Trump literally wrote the book on this stuff.

From Scott Adams (yes, of Dilbert fame) on the clown genius Donald Trump and how he's quite cleverly using verbal jiu-jitsu to turn his critics' attacks to his favor. A Republican card of Trump and Mark Cuban would be like something out of a satire novel and cause the media to swallow itself. Adams think it would win the election.

James Surowiecki on Trump and why he's won over working-class Republican voters:

Working-class voters face stagnant wages and diminished job prospects, and a 2014 poll found that seventy-four per cent of them think “the U.S. economic system generally favors the wealthy.” Why on earth would they support a billionaire?

Part of the answer is Trump’s nativist and populist rhetoric. But his wealth is giving him a boost, too. The Democratic pollster Stanley Greenberg, who’s published reams of work on white working-class attitudes, told me, “There is no bigger problem for these voters than the corruption of the political system. They think big companies are buying influence, while average people are blocked out.” Trump’s riches allow him to portray himself as someone who can’t be bought, and his competitors as slaves to their donors. (Ross Perot pioneered this tactic during the 1992 campaign.) “I don’t give a shit about lobbyists,” Trump proclaimed at an event in May. And his willingness to talk about issues that other candidates are shying away from, like immigration and trade, reinforces the message that money makes him free.

Trump has also succeeded in presenting himself as a self-made man, who has flourished thanks to deal-making savvy. In fact, Trump was born into money, and his first great real-estate success—the transformation of New York’s Commodore Hotel into the Grand Hyatt—was enabled by a tax abatement worth hundreds of millions of dollars. Yet many voters see Trump as someone who embodies the American dream of making your own fortune. And that dream remains surprisingly potent: in a 2011 Pew survey, hard work and personal drive (not luck or family connections) were the factors respondents cited most frequently to explain why people got ahead. Even Trump’s unabashed revelling in his wealth works to his benefit, since it makes him seem like an ordinary guy who can’t get over how cool it is to be rich.