The 10 Most Amazing High Roller Casino Stories

table stacked with chips

At casinos, regular people like us might get free drinks for gambling away our hard-earned money, but it is the high rollers who the casinos really count on to build their enormous profits. High rollers, who have budgets ranging from $100k to $1m, and especially the biggest casino whales, whose budgets can run into the tens of millions, are the real customers that casinos do just about everything to bring in the door. With that kind of money being thrown around, there are certainly some amazing high roller gambling stories; here are the 10 best.

Akio Kashiwagi

Akio Kashiwagi, a mysterious real estate tycoon from Japan who is said to have had ties to the Yakuza, was one of the biggest casino whales of them all. He earned himself the nickname, “The Warrior” and routinely bet $200k on a single hand of baccarat, which is among the most popular casino games for high rollers, in Atlantic City, Las Vegas, and Monte Carlo.

In early 1990, Kashiwagi was lured to Atlantic City by another real estate magnate, Donald Trump, to play at one of Donald Trump's three casinos there. By all accounts, in just two nights Kashiwagi won nearly $6m of Trump's money. But Donald would have the last laugh, as he made a deal with Kashiwagi to return and gamble $12m until he either doubled it or lost it all. After $10m in losses, he called it quits and headed back to Japan while still owing Trump money.

It is estimated that Kashiwagi owed as much as $15m in gambling debts to various casino owners, and this could be one of the reasons why, in 1992, he was found dead in his home, stabbed 150 times with a samurai sword. His killer has never been found. Talk about crazy casino whale stories – this one may be the craziest of all!

Phil Ivey

Poker pro Phil Ivey is known for being one of, if not the very best, poker player in the entire world. And while poker may be a game of skill, where it's better to be good than lucky, Ivey also likes to hit the casino floors with huge stacks of cash to see how lucky he is. An avid craps player, he has been known to fly to five different casinos in five different cities on mega “craps tours”, betting $100k on each roll of the dice.

Phil Ivey poker player

Phil Ivey is known for being a great poker player, but he also likes to shot the craps for large sums.

However, it seems that Ivey may have more than luck going for him at the tables. In 2012, he won around $11m in one stunning baccarat session at London's Crockfords casino. This came just a few months after he won $9.6m at the Borgata casino in Atlantic City. Crockfords, however, refused to pay, stating that Ivey was using a technique called 'edge sorting' to predict which cards would be dealt next. Ivey sued the casino for his winnings, and it has yet to be determined if Ivey cheated or if his win was one of history's great high roller stories.

Terrance Watanabe

Terrance Watanabe was a man who made his fortune as the heir to his father's party-supply import company. He is also the subject of one of our crazy casino stories. The Nebraska millionaire treated his money with the same lack of attention as his customers treated the cheap plastic trinkets he got rich selling. Terrance Watanabe became one of the most sought-after whales in the entire world not just because he loved gambling, but because he was terrible at it.

There is no way to know for certain, but it is estimated that Watanabe lost approximately $220m, most of his fortune, in casinos in a five-year stretch from 2003-2007, with him losing an astounding $127m in 2007 alone. For a time he basically lived in various casino high roller suites, his favorites being the Wynn, Rio, and Caesar's Palace. Watanabe was known to gamble drunk, play games with huge house edges like roulette or slots, and make idiotic decisions at the blackjack table. He routinely lost $5m a day, and ended up being barred from most casinos for his drunken behavior and inability to pay his debts.

Don Johnson

A real-life hero to many in the gambling world, Don Johnson became world-famous in 2011 for winning $15m from three of the top Atlantic City casinos in mere days. The best part about his amazing casino stories is that he wins completely legally, by using the casino's own desperation for bringing in high rollers against them, and thus creating one of the best high roller gambling stories ever.

While the average Joe has to play by the house rules, whales are offering them the chance to negotiate the terms of the games they play, such as the betting amounts and even the rules themselves. They also offer discounts on losses, so if a high roller losses $1m, he gets back $100k.

Don Johnson is known as the man who "broke atlantic city".

Don Johnson is known as the man who "broke Atlantic City".

When the Tropicana, Caesar's, and Borgata casinos came calling, Don Johnson knew the casino tricks used by casinos, did the math and negotiated blackjack rules which would basically make the game 50/50, and with a big loss discount, he was essentially playing the house's money. He won $15m in total before the casinos cut him off, and they won't be making the same mistake with Don Johnson anytime soon.

Archie Karas

Known as the man who turned $50 into $40 million, Archie Karas is one of the most famous high rolling casino winners of all time, which also makes his one of our best casino stories. Born Anargyros Karabourniotis, this poor Greek immigrant came to America while working on a cruise ship, discovered how to play poker, and never looked back. He soon became one of the most famous poker players in Los Angeles, winning and then losing, $2m in just a few years.

After his epic loss in 1992, he headed to Las Vegas with $50 is his pocket, hoping of living the high roller Vegas gambling stories so many other down-and-out gamblers dream about. Except Karas's dream actually came true. From 1992 to 1994, he went on what is now simply called “The Run”, nearly three straight years where Karas simply could not lose. No matter what he played – poker, blackjack, craps, pool – Karas won, amassing nearly $40m during his streak, often betting $100k a hand.

But all good things must come to an end, and Karas proceeded to lose his entire fortune in the years following “The Run”. His epic fall was punctuated by being caught cheating in 2013 and subsequently banned for life from all Nevada casinos.

Kerry Packer

The late Australian media tycoon Kerry Packer is remembered by many as the founder of World Series Cricket. But for those in the casino industry, he is remembered as one of the biggest whales who has ever lived. Of the many Kerry Packer gambling stories there are to tell, and we’ve got just the one.

In the 80s and 90s, Packer's casino visits became the stuff of legends. While many of the high roller gambling stories about him are undoubtedly exaggerations, some of these extraordinary tales must be true. He supposedly walked into a London casino one night, simultaneously played £15m on four separate roulette tables and lost every single penny. On the other end of the spectrum, he is reported to have won $20 million in a single night at the MGM Grand in Vegas, wandering from table to table betting $250k a hand. Legend has it that night he tipped the MGM staff $1m.

The late Kerry Packer is the founder of World Series Cricket, his son James is also the owner of several casinos.

Perhaps the best Kerry Packer story involves him playing poker against a Texas oil tycoon at the Stratosphere casino in Vegas. During a heated argument, the tycoon yelled, “I'm worth 60 million!” Packer replied by pulling a coin out of his pocket and simply asked, “heads or tails?”

Adnan Kashoggi

In casinos, a whale is a whale, and it doesn't matter how a player got his or her money, just that they are willing to gamble it away on the casino floor. Notorious Saudi arms dealer Adnan Kashoggi was one of the richest men in the world in the 80s, accused of participating in the Iran-Contra affair and money laundering with Imelda Marcos, and was one of the biggest whales that casinos had every seen.

In the 80s and 90s, Kashoggi took the casinos of London and Las Vegas by storm, betting huge sums of money, primarily on baccarat. He threw lavish parties in casinos and was known for his taste in prostitutes, reportedly spending half a million dollars on escorts a year. As his fortunes declined in the 90s, he because infamous among casinos for failing to pay his gambling debts. It is said that the refused to pay more than £3m in gambling debts to the Ritz in London, eventually repaying part of the debt a mere 12 years later.

Charles Barkley

Basketball legend Charles Barkley was a monster on the court, and an even bigger monster at the casino tables. Unlike many people who have struggled with gambling over the years, Barkley has been refreshingly open about his wins, losses, and great Las Vegas high roller stories, throughout his long gambling career.

Charles Barkley

Barkley, a former NBA star is known for his gambling love and gambling losses.

Before taking a break from gambling in 2013, Barkley would routinely visit Las Vegas and he had a single goal every time – win $1m. At first, he would come to town and refuse to leave until he had either won or lost a million at the blackjack tables. He says that in his later years he learned how to lose, and would often leave the casino after only losing $200k. Barkley has become famous in gambling circles as one of the few whales who doesn't play in a roped-off high rollers area. He often plays at the regular tables alongside people betting $10 a hand, and is known to be remarkably friendly and fun to play with.

Kamel Nacif Borge

Another shadowy figure who seems to blur the line between legitimate businessman and criminal is Kamel Nacif Borge, a Lebanese-Mexican known as “El Rey de la Mezclilla” - “The Denim King.” In addition to being a jeans-manufacturing entrepreneur, he is suspected of being involved in the Mexican drug trade and other corruption scandals.

What is not in doubt, however, is his status as one of the biggest whales in the history of Las Vegas. Nacif would routinely head to Vegas with anywhere from $1m to $5m to play with and bets as much as $200k per hand on baccarat. Although he has run afoul of Vegas casinos by refusing to pay his debts or throwing things across the casino floor when the cards aren't going his way, the huge amount of money Nacif brings in means that he continues to be invited back. He is so close with certain casinos, in fact, that Ted Binion is reported to have put up $2m to once bail Nacif out of jail.

The Sultan of Brunei

Although he is the head of one of the tiniest countries in the world, the current Sultan of Brunei is one of the richest people alive, with a net worth exceeding $20 billion. He is also considered to be one of the world's biggest, yet most secretive whales. While there are plenty of casino gambling stories about secret trips to Las Vegas, Macao, and London casinos where he routinely drops $1m a night, how much and how often the Sultan gambles remains on the biggest casino mysteries around.

There is no doubt, however, that his family are among the biggest high rollers out there. The Sultan's former wife, Mariam Aziz, often visited London casinos where she encouraged her female bodyguards to gamble, and is said to have lost £3m during one whirlwind weekend. The Sultan's brother, Prince Jefri is known to be an avid gambler and frequently stops at casinos while living a playboy lifestyle that even James Bond would be envious of.

 

Not quite high rollers but you can explore VegasMaster's readers casino stories here.

About The Author

As a member of the VegasMaster writing staff, I pride myself on delivering quality information about my favorite topic: the online gaming industry. In addition to playing a wide-variety of online casino games, I keep up on the latest iGaming news and trends. My passion for the industry has made me both an experienced player and researcher.

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