Playing with Fire Back when Donald Trump was just a budding
newcomer on the Atlantic City scene, a mysterious Japanese businessman with a penchant for high-stakes
gambling very nearly took The Donald for every penny he had.
The future US President invited well-known high-roller Akio Kashiwagi to gamble at Trump
Plaza, hoping that the Japanese whale might generate some much-needed dollar signs for
his new casino.
Trump failed to anticipate that Kashiwagi’s top-shelf gambling skills and seemingly bottomless
pocketbook had the potential to bankrupt his Atlantic City venture before it ever got off
the ground.
Trump was ever so close to going COMPLETELY bankrupt, not just business bankrupt!
The Gambler By the time Kashiwagi was garnering the attention
of Trump and his business associates, the Tokyo-based tycoon had already established
himself as one of the world’s premiere gamblers.
He was the son of a humble carpenter but amassed a gigantic fortune for himself off the back
of his savvy real estate investments.
In fact, around the time Trump began courting the business mogul to play at his casino,
Kashiwagi’s net worth was said to be upwards of a billion dollars.
He touted an annual income of $100 million.
He lived like royalty in Tokyo, residing in a palatial estate with his own private chef
on hand to cook whatever his heart desired.
Kashiwagi was an extremely secretive individual who kept out of the spotlight as much as possible.
His obsession with privacy and his aversion to photographs raised some eyebrows during
his rise to prominence in the ‘80s and ‘90s.
Some went so far as to question the legitimacy of Kashiwagi’s business endeavors.
Rumors began swirling that the billionaire had direct ties to the Yakuza, Japan’s network
of organized crime syndicates.
The waters surrounding Kashiwagi got even murkier when an independent assessment of
his real estate firm determined that it was only bringing in $15 million a year, not the
$100 million he claimed annually.
What exactly accounted for that extra $75 million in income?
Nobody knows for sure.
But one of the ways Kashiwagi commonly got his hands on some extra cash was by gambling.
He was, by all accounts, a “whale” of the gambling universe, a high-roller who wasn’t
afraid to reach deep inside his wallet when making bets at the card table.
He was known for making million-dollar wagers when playing baccarat, the blackjack-like
casino staple that happened to be his game of choice.
Trump Attention The stories of Kashiwagi’s big-money gambling
exploits were the stuff of legend.
It’s no wonder he caught the eye of Donald Trump, a man who seeks out publicity like
his life depends on it.
Trump first caught wind of the baccarat wizard when he won nearly $20 million on the floor
of the Diamond Beach casino in Australia.
His massive winnings almost put the late Sir James Goldsmith’s casino out of business.
Such is the danger of a billionaire willing to bet gobs of money on a game of chance.
However, gambling is inherently a two-sided coin.
Throwing millions of dollars around at a time can make you lots of money as quickly as it
can lose you lots of money.
For instance, at the Mirage casino in Las Vegas, Kashiwagi lost $6 million thanks to
some lousy baccarat luck.
For casino owners, a wealthy gambler’s misfortune can be a huge boon for business, especially
when that gambler intends to spend more and more money trying to dig themselves out of
their hole.
As the 1980s were coming to a close, Trump was still trying his luck on the Atlantic
City boardwalk.
He had aggressively pursued the casino business in the years leading up to his showdown with
Kashiwagi, opening up three Atlantic City hotel-casinos in total, including the Trump
Taj Mahal, which he branded “the eighth wonder of the world” in typical Trump fashion.
While Trump seemed tailor-made for the glitz and glam of the casino world, he quickly discovered
that the gambling industry was an unavoidable money pit.
It’s a competitive space that is particularly cash-intensive, and it, therefore, requires
a lot of money to stay afloat.
Getting a wealthy big shot like Kashiwagi to spend lots of money on his casino floor
could go a long way, helping Trump stand out under the bright lights of America’s Playground.
Trump Moves There was just one problem: Kashiwagi wanted
nothing to do with The Donald.
The loud-mouth American business magnate was the very antithesis of everything the quiet
Japanese gambler represented.
Kashiwagi was a tight-lipped man who avoided media attention like the plague.
He and Trump were like oil and water.
But Trump wasn’t going to take no for an answer.
In February of 1990, he took a flight to Tokyo.
He was there on business, promoting an upcoming fight between Mike Tyson and Buster Douglas,
but he used his trip to Japan as an opportunity to cozy up with Kashiwagi.
On the eve of the heavyweight bout, Trump threw a private party for friends and business
associates.
One of the bigwigs there that night was, of course, Kashiwagi.
Trump brought Tyson over for a picture with the gambler, but the camera-shy businessman
had no intention of saying cheese.
He covered his face and refused to take a photograph.
While their relationship didn’t start on the best of terms, Trump made sure Kashiwagi
knew that there was a penthouse in Trump Plaza with his name on it anytime he found himself
in Atlantic City.
Trump’s advisors told him that luring Kashiwagi could potentially end in disaster.
The man’s been known to bring casinos to the brink of bankruptcy, after all.
But Trump insisted that he knew what he was doing.
While the Japanese recluse couldn’t stand Trump’s bombastic personality, he also couldn’t
say no to a chance to take millions of dollars from the man at his own casino.
The Showdown A few days after the fight in Tokyo, Kashiwagi
made his way to Atlantic City, where he was greeted with a signed copy of Trump’s book,
The Art of the Deal, delivered by the author himself.
The gambler went up to his suite in the Trump Plaza hotel and didn’t come out for two
whole days.
When he finally emerged, there were towering stacks of $5,000 chips awaiting his arrival
on the casino floor.
The game was on.
His baccarat table was sectioned off behind event ropes so he wouldn’t be disturbed
as he played marathon sessions of his favorite card game.
He had a private bathroom, his own personal Japanese chef, and a squad of bodyguards at
his disposal as well.
From the start, Kashiwagi was doing what he did best, making big bets and winning big
hands.
Within 30 minutes, Trump was nursing a million-dollar loss from that private baccarat game alone.
Trump’s advisors had warned him that this might be a possibility.
They were proven right by the minute, while the billionaire’s risky gamble on Kashiwagi
looked like a bust.
Reporters from the Inquirer were standing by to document the whole PR charade.
When speaking to the press, Trump put on a smile, marveling at one of the greatest gamblers
in the world.
Behind closed doors, Trump was sweating bullets.
His casino was already low on cash, and Kashiwagi was fixing to take the little money he had
left in the vault.
As the showdown between Trump and Kashiwagi continued into the weekend, the gambler’s
luck came and went.
He had his fair share of cold streaks but always seemed to win it all back and then
some.
Then, suddenly, he decided it was time for him to leave.
The growing media circus that had surrounded his game of baccarat was a little more than
the reclusive Kashiwagi could handle.
He flew back to Tokyo, having won $6 million during his stay at Trump Plaza.
The Rematch Rather than gracefully admit defeat, a desperate
Trump decided to challenge the elusive Japanese billionaire to a rematch of sorts.
He decided to set some specific rules for Kashiwagi’s return, however.
Under Trump’s terms, the whale would bring $12 million of his own money to the table.
He would continue to play until he either doubled it or lost it all to the casino.
Trump and his advisors certainly did their homework when creating these stipulations.
The odds of Kashiwagi meeting the requirements they laid out in the agreement were not very
high at all.
Something like 15% if the gambler stayed at the table for longer than 75 hours.
Kashiwagi didn’t seem to pay these unfavorable statistics much mind, as he eventually consented
to Trump’s terms.
The rematch was set.
In May, the great Japanese gambler returned to Trump Plaza.
He had every intention of taking even more of Donald Trump’s money with him back to
Tokyo, while Trump had revenge on his mind.
Kashiwagi’s second go-around started off exactly like his first.
He opened with a scorching hot streak, and at one point, he had swiped another $9 million
from a now-panicked Trump, who considered stopping the game before his Japanese rival
literally put him out of business.
But Kashiwagi had not yet doubled his 12 million, so the game continued.
Trump’s close confidante Jess Marcum, who had helped come up with the framework of the
rematch, told him to remain patient.
Let the math play out.
It was highly unlikely that Kashiwagi was going to win their little game, even though
things looked bleak for Trump at the present moment.
As Kashiwagi vs. Trump part 2 continued, the gambler’s fortune began to turn as he suddenly
hit a nasty losing streak.
That streak lasted until Trump had successfully earned back all the money Kashiwagi had previously
won and then some.
After six days, Kashiwagi was 10 million in the hole.
Walking Away The terms of their agreement stated that he
had to keep playing until he doubled his original $12 million or lost it all.
As it currently stood, he had only lost 10 million, meaning he still had 2 million left
to play with.
However, having recouped his losses from February while tacking on an extra $4 million profit,
Trump called the game.
Trump claims in his memoirs that he had honored his agreement with Kashiwagi to the letter.
That’s not the way the gambler saw it, however.
He was enraged at Trump’s refusal to allow him to continue playing despite the fact that
he still had $2 million left from his original buy-in.
He stormed back to Tokyo, planning to toss his signed copy of Trump’s book where he
felt it belonged—in the fireplace.
Skipping Town The whale skipped town before his $6 million
check to Trump’s casino ever cleared.
It’s unclear whether the check bounced or Kashiwagi canceled it in a rage, but either
way, Trump never received the money he was owed.
Trump’s people made a stink in the media, threatening the Japanese mogul with lawsuits.
Kashiwagi’s team also took to the press to smear his hated rival.
They claimed Trump had offered the gambler a $5,000 shopping spree at Macy’s during
his stay in Atlantic City, but the credit card Trump gave him had been rejected at the
register.
It was a war of words between two petulant billionaires, but that’s all it ever came
to.
Kashiwagi, it seems, had bigger fish to fry in Tokyo.
He was found dead in his home in January of 1992.
The authorities determined the gambler was murdered, but his case was never solved.
Kashiwagi’s premature demise meant he never got to relish in his rival’s Atlantic City
downfall.
All three of Trump’s casinos eventually went bankrupt.
He had to admit defeat on the streets of Atlantic City, having never recovered the money Kashiwagi
owed him.
Trump went on to have plenty of other eventful chapters in his future, but none of them ever
got the billionaire shaking in his boots like the time he faced off against one of the greatest
gamblers the world has ever seen, very nearly losing it all.
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