Against All Odds: The Gambling Whale Who Lost to Donald Trump and Was Killed With a Japanese Sword

  • Akio Kashiwagi was a high-roller gambler who played baccarat at the Trump Plaza
  • He was stabbed 150 times by a Japanese sword, with some linking it to the Yakuza
  • The famous whale died owing as much as $4m to Donald Trump-owned casinos
Samurai sword
Akio Kashiwagi was a high-rolling gambler who played baccarat at casinos and was killed with a Japanese sword. [Image:]

Mysterious death

The gambling world is full of mysterious, terrifying, and wonderful stories, from bizarre bad beats to hair-raising heists, murders, and even ghosts. But when it comes to mysteries involving high-rollers, the tale of Akio Kashiwagi – who was killed by a Japanese sword – springs to mind.

the hallmarks of the Japanese criminal organization known as the Yakuza

Considered one of the world’s top five gamblers, Kashiwagi’s murder was never solved. Found dead in his kitchen at the age of 54, he was stabbed as many as 150 times. However, according to reports, his death had the hallmarks of the Japanese criminal organization known as the Yakuza.

Known for his high-rolling antics, Kashiwagi would wager as much as $10m in a single gambling session. His game of choice was baccarat, a fast-paced card game similar to blackjack.

Setting the scene

Although we know he was the son of a carpenter and the middle child of ten siblings, the life of Kashiwagi is murky. Outside of his high-rolling activities, Kashiwagi was said to have lived a normal life. He worked as a farmhand and then later as a tour guide at Mt. Fuji.

The story goes that later on in life Kashiwagi became a Tokyo real estate investor, bringing in revenue of $15m a year. Yet, at the same time, he’s thought to have claimed income of around $100m per year and owned assets amounting to $1bn, including a palatial Tokyo home where he had a private chef who cooked him marinated monkey meat.

He was also married to a popular geisha six years his senior and they had three children together. Before his death, he enjoyed samurai dramas and traditional Japanese furniture, and rumors circulated that he had ties to the Yakuza.

Beating Trump

Donald J. Trump, then a budding casino mogul in Atlantic City, met Kashiwagi in 1990. Trump first heard about Kashiwagi from the late Sir James Goldsmith, a European financier and casino owner, after Kashiwagi won $20m at Goldsmith’s Diamond Beach Casino in Australia.

Trump was warned against inviting Kashiwagi to Atlantic City, as it was deemed too risky. However, he went against that advice, hoping that Kashiwagi’s high-roller status would give him the publicity he needed to boost Trump Plaza as the place to be.

bet no less than $167,000 on each hand and gambled for 14-hour stretches

Piles of $5,000 chips were waiting for Kashiwagi upon his arrival at the reserved table in Trump’s casino. Trump may have believed Kashiwagi could push the casino’s image up, but the Japanese businessman ended up costing him highly. According to reports, Kashiwagi bet no less than $167,000 on each hand and gambled for 14-hour stretches.

While casino games tend to have an in-built advantage to the house, with baccarat that edge is relatively narrow for the dealer. After two days of playing, Kashiwagi announced that he was heading back to Tokyo with millions of Trump’s dollars in his pocket. Reports vary on the exact amount, but this is thought to have ranged from $6m to $9m.

The story made the headlines across the globe as it was believed Kashiwagi nearly bankrupted Trump:

A costly return

Unsatisfied with the loss he took the first time around, Trump wanted Kashiwagi back, but this time he wanted to ensure that the baccarat gambler played for longer. Under a “freeze out” agreement that Trump proposed, Kashiwagi would bring $12m to the table and play until he had either doubled it or lost everything.

The key to this new agreement was to avoid a repeat of last time by keeping Kashiwagi playing for as long as possible. After 75 hours, his chances of beating the house would fall to 15%.

It wasn’t long before Trump found himself down $15m to Kashiwagi, making him consider ending the game early. However, based on the probability that Kashiwagi would eventually lose, Trump was asked to wait. The gambling went on for five more days. On the sixth day, Trump finally made money back from Kashiwagi: $10m.

Several stories have come to light as to what happened next. One is that when Trump made his $10m, he called the game off, which Kashiwagi agreed to even though he was not pleased. The other is that Kashiwagi claimed Trump violated the agreement by calling the game off before he had lost his full $12m. Either way, it is evident that Kashiwagi left Atlantic City owing Trump money.

Death theories

Gaining popularity from his adventures in Atlantic City, Kashiwagi was met with media attention upon his return to Japan. One year after his battle with Trump, the story goes that Kashiwagi ran away from television cameras, tripped over a curb, and broke his ankle. The high roller then retreated into his home and wasn’t seen again until his stabbed body was discovered in his kitchen.

Although his killer(s) were never found, there has been speculation over his death and the manner in which he died.

Kashiwagi placed himself in the crosshairs of the Yakuza by losing such a vast sum

The most popular story is that Kashiwagi had connections with the Yakuza. Many believe he was able to gamble with such large quantities of cash because of his association with the organized crime group. Perhaps Kashiwagi placed himself in the crosshairs of the Yakuza by losing such a vast sum to Trump.

Another, perhaps more outlandish theory, is that Trump had Kashiwagi killed because he refused to pay his outstanding debt. It is thought that he still owed $4m to the Trump Plaza Hotel and Casino upon his death. Gaming executives have confirmed his debts to casinos in Nevada and Atlantic City totaled nearly $9m.

Whatever the reason behind his untimely death, Kashiwagi will always be known as one of the world’s most prolific gamblers.

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