The Most Famous High Rollers and Their Amazing Casino Stories

At a casino, an average player will get complimentary drinks for spending a bit more money than usual, but he’ll hardly be able to build the casino’s profits. That’s what high rollers do. With their budgets often exceeding $1 million, they are the perfect customers for a gambling venue. And this is why high roller casinos will do just about anything to get them to play. With so much money involved, their gambling sessions are often fascinating and exciting. Here are some of the best casino stories involving casino whales from all over the world.

1. Akio Kashiwagi

The Japanese real estate tycoon, often linked to the Yakuza, was one of the most famous high rollers. Also known as “The Warrior,” Kashiwagi would routinely spend $200,000 in a single game of baccarat.

In the early 1990s, he first visited Atlantic City to play at one of Donald Trump’s casinos. It took him two nights to win around $6 million, but his experience didn’t have a happy ending. Trump made a deal with the Japanese casino whale to return and gamble $12 million. The condition was to either double that money or lose everything. After losing $10 million, he called it a day and return to Japan.

Kashiwagi amassed around $15 million in gambling debts. However, he failed to repay them, as he was killed in 1992, stabbed 150 times with a samurai sword. To this day, his killer hasn’t been brought to justice.

2. Phil Ivey

A poker professional, Ivey is considered to be one of the best poker players in the world. But he also likes to spend money on other casino games. He particularly liked craps and spent $500,000 traveling to five different casinos in five different cities just to see how lucky he is.

In 2012, Ivey won nearly $11 million while playing baccarat at a casino in London. That was just a couple of months after he won $9.6 million in Atlantic City. However, the Crockfords casino refused to pay him his winnings, accusing the poker pro of using a technique that predicted which card would be dealt. A lawsuit ensued. In 2017, Ivey lost the legal battle over his winnings.

3. Terrance Watanabe

The rich heir to his father’s company, the millionaire from Nebraska, loved to spend vast sums of money, quickly becoming a favorite customer for many casinos around the world. Especially as he wasn’t quite at gambling.

According to available sources, from 2003 to 2007, Watanabe gambled away around $220 million. He lost a staggering $127 million in one year alone. During that period, he lived in high roller suites at various casinos, including Caesar’s Palace, Rio, and Wynn. He lost $5 million on a regular basis but eventually got banned from most casinos due to his drunken behavior and huge debts.

4. Don Johnson

Johnson is a true gambling hero to many people out there. He became famous in 2011 after winning $15 million in three of the leading Atlantic Casinos. He did it fair and square by exploiting the casino policy of attracting high rollers. And here’s how.

High rollers have the privilege of negotiating the terms of the games they play. They often receive discounts on losses. Johnson negotiated not only a big discount but also blackjack rules, which made the game fifty-fifty. Essentially, he was spending the house’s money to beat the house. Eventually, he was barred from playing, but he got a hell of a story to tell.

5. Archie Karas

One of the famous casino high rollers of all time, Karas managed to turn $50 into $40 million. Originally from Greece, he came to the United States on a cruise ship, learned how to play poker, and wrote history. It didn’t take him long to build his reputation in Los Angeles, winning $2 million and then losing it in only a couple of years.

In 1992 he arrived in Las Vegas with only $50 in his pocket. He came to experience the high roller gambling stories many can only dream about. And he did it. In the next two years, Karas went on “The Run,” not losing a single round during that period. He played all kinds of games – poker, blackjack pool, craps – and won every single time, earning around $40 million.

Unfortunately, all good things come to an end, and in the years after “The Run,” he lost everything. In 2013, he was caught cheating and permanently banned from all casinos in Nevada.

6. Kerry Packer

The Australian media magnate Kerry Packer was known as the founder of World Series Cricket. But he’ll also be remembered as one of the biggest high rollers in history. Such status comes with many exciting stories, and here’s one of them.

His casino visits during the 1980s and 1990s were legendary. One time in London, he visited a casino and played £15 million of four roulette tables. In the end, he lost everything! On one occasion, he reportedly won $20 million at the MGM Grand in Las Vegas while betting $250,00 per hand. The story says he tipped the casino staff $1 million.

During a poker game against a Texas oil tycoon at a Las Vegas Casino, Pecker’s opponent yelled, “I’m worth $60 million”. The Australian took out a coin and asked, “heads or tails?”

7. Adnan Kashoggi

Apart from being an infamous arms dealer, Adnan Kashoggi was also a passionate gambler. The wealthy Saudi became one of the richest men during the 1980s but was accused of money laundering with Imelda Marcos and taking part in the Iran-Contra affair.

During the 1980s and 1990s, Kashoggi loved spending large amounts of money at casinos in Las Vegas and London. He particularly enjoyed betting on baccarat. Kashoggi even threw parties in casinos and spent hundreds of thousands of dollars on escorts every year. However, his fortunes started to decline in the 1990s, and soon he was unable to repay his debts. He owed more than £3 million to the Ritz in London but repaid only a part of it – twelve years later.

8. Charles Barkley

Former NBA star Charles Barkley was unstoppable on the court but was equally unstoppable at the casino tables. He has been open about his relationship with gambling, often talking about his wins and losses.

Up until 2013, Barkley regularly visited casinos at Las Vegas, with only one goal – to win $1 million. He refused to leave until he either won or lost a million and especially liked to play blackjack. The basketball legend was also known for playing at regular tables, alongside customers gambling $10 a hand.

9. Kamel Nacif Borge

Kamel Nacif Borge is yet another shady figure who became a gambling legend. Known as “The Denim King,” the controversial businessman was often suspected of drug trade and corruption.

He also rightfully earned the status of one of the biggest casino whales in the history of Las Vegas. Nacif often visited Vegas, where he spent from $1 million to $5 million on baccarat. Although he would often refuse to pay his debts, he was still invited back. He was close with casino owners that one of them paid $2 million to bail Nacif out of jail.

10. The Sultan of Brunei

Brunei may be one of the smallest counties in the world, but its ruler is one of the wealthiest people alive. With his net worth exceeding $20 billion, the Sultan is also one of the most prominent casino whales. He keeps his activities secretive, while he particularly enjoys traveling to Las Vegas, London, and Macao, where he regularly spends $1 million a night.

Some of his family members are among the biggest high rollers. The Sultan’s ex-wife often visited London casinos, where she would spend millions of pounds. Princ Jefri, the Sultan’s brother, is also an avid gambler.

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