How One of the World’s Biggest Casino Whales Nearly Bankrupted Donald Trump

It reads like an Elmore Leonard story.

The blood-splattered Shoji; the discredited, bankrupt, former millionaire, stabbed as many as 150 times; probably with a katana; the iconic Samurai sword and Yakuza weapon of choice. No forced entry, no theft, scores of suspects. Still unsolved.

On January 3, 1992, the body of Akio Kashiwagi was found in the kitchen of his Fujiyoshida home, in the shadow of Mount Fuji. He was the son of a carpenter and born in poverty. He made his fortune in real estate and lost it all at the casino. He died, aged 54.

He was known as “The Warrior” or “Mr K”. His most famous adversary, in a crowded field, was the one and only Donald Trump.

Trump feted Kashiwagi; wooing him to play at his Atlantic City casinos. It didn’t end well for either party; a classic Trump manoeuvre.

Kashiwagi the Whale

To understand why Trump was so keen to seduce Kashiwagi, you need to understand the value of the whale.

Kashiwagi was a monster. In whale terms, he was Blue; one of the world’s top five gamblers; as big as they come.

Kashiwagi’s preferred game was James Bond’s favorite: baccarat. He would happily wager up to $250,000 per hand; playing up to 70 hands every hour.

He would play for up to 14 hours, non-stop; gambling in excess of $10 million in a session. He would either lose it all – or double up.

Trump was tipped off about Kashiwagi in 1990 by entrepreneur and businessman James Goldsmith; a shareholder in the casino group Aspinalls.

Kashiwagi had almost broken the bank at the Aspinall Room, in the Diamond Beach Hotel Casino, in Darwin.

He was flown to Australia and won $6.5 million. Two weeks later, he returned and won another $4 million.

Fortunately, for the club, he brought his friend Hideaki Watase who lost $4 million.

The owners, Goldsmith and John Aspinall, wanted to keep Kashiwagi playing. They invited him back for a third time.

Trump Gets Involved in the Action

He arrived at 6pm, played through the night, and left with nearly $17 million. The casino was broke. Saved only by cash injections from its investors.

But Kashiwagi wasn’t invulnerable. He had lost $6 million at Steve Wynn’s Mirage Casino in Las Vegas.

Kashiwagi was the uber-whale. Trump couldn’t resist courting him. To host a whale like Kashiwagi was a big deal.

It would help position the Trump casino franchise as a world-class brand; the destination for the gambling elite. It would also give Trump the thing he craves like nothing else: attention.

To seal the deal, Trump rolled out the red carpet of charm, with bucketloads of costly comps, including an $800,000 jade statue of Buddha, the finest luxury penthouse in the hotel, complete with grand piano, butler service, and a line of credit worth $6 million, to match the $6 million Kashiwagi brought with him.

When Kashiwagi landed in Atlantic City, on Trump’s private jet, he was accompanied by four bodyguards; employed to ensure his face was never captured on film.

Unlike Trump, Kashiwagi was an extraordinarily secretive man. Trump greeted him with a signed copy of his autobiography.

Baccarat Blues for Trump

Two days after his arrival, Kashiwagi finally played his first hand of baccarat. Within half an hour, he had won $1 million.

This whale was making waves and Trump was morphing into Captain Ahab.

“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,” fumed Trump, in his book ‘The Art of the Comeback‘.

By nightfall, Trump was down $4 million. He had spent the day watching Kashiwagi play $250,000 hands, at a rate of more than one a minute.

Trump said: “But this had nothing to do with logic or reason. I was merely sitting on the sidelines watching as one of the best gamblers in the world played against me for $250,000 per hand, seventy times an hour.”

Trump tried to make light of the situation, describing Kashiwagi as ‘the greatest gambler ever – the best in the world’.

After two days, the whale swam out of Atlantic City; reportedly irritated by gawkers, journalists, and an ever-increasing froth of publicity.

He left with anything from $6.2 million to $12 million of Trump’s money in his pocket. Trump was furious. He had expected Kashiwagi to stay for several days, not just two.

Trump Invites Kashiwagi Back for Round Two

To his credit, and the horror of his advisors, Trump doubled down.

Where other casino owners would have thrown in the towel, Trump employed mathematical probabilities expert Jess Marcum.

Marcum was a numbers genius and is credited with being the original inventor of card counting. (Read our card counting guide if you’d like to have a go yourself.)

Marcum told Trump that time was his ally. Get Kashiwagi back and keep him at the tables for as long as you can. Marcum calculated that after 75 hours, Kashiwagi’s chances of winning would drop to just 15%.

Eventually, the house always wins. That’s how baccarat odds work (and every other casino game).

In May 1990, three months after his win, Kashiwagi returned to the Trump Plaza for a serious baccarat bender.

Trump and Kashiwagi had agreed to a $12 million dollar deal. He would play until he had either doubled his money or lost it all.

But Trump ended the game after seven days. Kashiwagi had played 5,056 hands of baccarat, over a total of 70 hours. He was down $10 million when Trump decided to pull the plug.

Kashiwagi was furious. He claimed that Trump had betrayed the deal, stopping the game early.

The gifted signed copy of Trump’s new book was destined for the fire. “We are going to burn it soon,” said Kashiwagi.

Who Killed Akio Kashiwagi?

Kashiwagi almost had the last laugh. He had been playing with credit. He wrote a check that either bounced or was cancelled. No one really knows.

Trump’s lawyers threatened to sue. Trump was also struggling to get credit. All three of his Atlantic City casinos would be bankrupt by 1992.

Kashiwagi was murdered earlier that year. He never got to see Trump’s Atlantic City adventure come crashing down.

But his run-in with Trump was the beginning of the end. Although he paid Trump $6 million of the $10 million that he owed him, Trump was left out of pocket, still owed $4 million.

Of course, Trump framed it as a win.

“I loved our matches with him. He was a great player who loved big numbers. He made me a lot of money when money was very tight and the economy was crashing.”

In the end, Kashiwagi committed the gambler’s ultimate mistake: he chased a loss.

He travelled to Las Vegas and lost another $10 million. In Europe, he dropped an additional $5 million at the tables.

The big baccarat run was well and truly over.

At the same time, Kashiwagi’s business imploded. The Japanese asset price bubble had ruptured. Real estate values plummeted.

Kashiwagi now owned a portfolio of debt. He owed $131 million; more than the total value of his deflated property assets.

The whale went into hiding and was never seen alive again.

No one knows exactly who or why Kashiwagi was murdered. He was massively in debt and it is believed that he was ‘made an example of’.

Japanese police arrested two Yakuza operatives – a woman and a man – but they were both released, when the police couldn’t find a murder weapon.

The case remains unsolved and the statute of limitations for the murder expired in January 2015.

The moral of the story: never chase a loss and be very careful if you’re gambling with Donald Trump.