Yakuza costs Donald Trump $4 million

How Donald Trump lost $4 million to the sharp end of a Samurai Sword.

By Joe Audritt

In 1992 Casino high roller, Akio Kashiwagi, was brutally slaughtered in his home while owing millions of dollars in gambling debts. Kashiwagi was stabbed 150 times with what was believed to be a Samurai sword – the hallmark of infamous Japanese criminal gang, the feared Yakuza.

Before his untimely death, Kashiwagi, a Japanese property tycoon, was courted by Donald Trump after meeting him at a party in Tokyo the night before Mike Tyson’s heavyweight boxing bout with Buster Douglas.

Trump, who had recently moved into the Atlantic City casino business, was in need of more income for his casinos to turn a profit – and so he went whale fishing (a high roller who bets large sums of money and is offered extended credit.)

akio-kashiwagiOriginally from a modest background working as a farmhand, Kashiwagi, moved into the Japanese property market and boasted earning $100 million a year with asserts of $1 billion. He lived in a mansion near Mt. Fuji known as the ‘Kashiwagi Castle’ and employed a chef who would serve him marinated monkey meat.

Kashiwagi was also a degenerate gambler who had built a reputation all over the world for his high stakes baccarat binges. Playing for days on end Kashiwahi would play up to $200,000 a hand.

This was just the type of income Trump had been looking for and, after offering him a penthouse suit, greeted Kashiwagi at the Trump Plaza casino with a signed copy of Trump’s book The Art of the Deal as a gift.

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A baccarat table had been roped off for Kashiwagi’s private use with $5,000 chips neatly stacked on top awaiting play. Trump arranged for the Japanese property mogul to be well catered for with tea, hot towels, a private bathroom and a Japanese chef brought in specially.


Trump then left Kashiwagi to play while he went off to tell the press how exciting all this was: “Have you ever seen action like this? This guy is great, the best in the world. The best.”

In reality Trump was sweating the action. He had been warned by his top casino executive not to invite the notorious Kashiwagi who was known as the ‘Warrior’ on the high stakes gambling circuit. The Warrior had been responsible for almost bankrupting Goldsmith’s Diamond Beach casino in Australia after winning $20 million.

Within half an hour of his arrival at the table Kashiwagi was up $1 million. Reflecting on the event later Trump admitted: “From the very first hand, Kashiwagi started beating the hell out of us.”

Instead of being the pragmatic business man he had always believed himself to be Trump realised he had become a gambler himself. “What the hell am I doing? I asked myself. Cash flow is way down and I’m playing with a guy who could win $40 or $50 million in a matter of days.”

While Trump bragged to the press, Kashiwagi built stacks of chips a foot high on the table until he ran out of space and then built stacks on the floor. Trump later reflected on his lack of logic in inviting Kashiwagi to play $250,000 against him 70 times an hour for hours on end.

Spooked by the media attention he was getting, Kashiwagi left for Tokyo after only two days of what was expected to be several days of high stakes action.

He took $6 million of winnings with him.

Looking to recoup his loss Trump immediately looked to host Kashiwagi once more – this time with a plan. Trump had employed Jess Marcon, a mathematical probabilities expert with a photographic memory to coach him in a new strategy for his rematch with Kashiwagi. Marcon advised Trump that his odds of cleaning up Kashiwagi increased the longer Kashiwagi played.

Trump and Kashiwagi made a gentleman’s agreement that Kashiwagi would return and play with a winner-take-all stipulation in place. The game would not end until Kashiwagi either won $12 million or lost $12 million.

This time Trump was visibly nervous as Kashiwagi sat at the table and with good reason. Trump fell behind $9 million on top of the $6 million Kashiwagi had previously won when Trump considered stopping the game. He was advised against it and told to trust the odds.

The odds where on his side and Kashiwagi eventually went on a losing streak dropping $10 million to Trump after six days of play.

The game was then called to a halt. Trump claimed that Kashiwagi had agreed to stop play. Kashiwagi, however, contested that Trump had reneged on the $12 million winner-take-all deal. A furious Kashiwagi left the Trump Plaza announcing via an aide that he intended to burn the autographed copy of Art of the Deal he had been given by Trump.

Kashiwagi left again for Tokyo leaving behind a $4 million debt with the Trump Plaza casino. He apparently returned to a frenzied media anxious to hear of his bust up with Donald Trump and subsequently went into hiding.

In Art of the Comeback Trump wrote: “[Kashiwagi] was never seen again until his body was found hacked to pieces by a Samurai sword.”

Kashiwagi’s debt to the Trump Plaza casino was never collected.

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