famous high roller casino players

People play online casino games for different reasons. For some it’s a pastime, for some it’s a hobby, and most players just stick to relatively small stakes. But there are gamblers out there who turned it into a life-long passion. Just like with any activity, gambling has a history and its own legends. Players who changed the scene forever with ingenuity, bravery, or just plain luck.

In this article, we’ll take a look at some of the greatest gamblers of all time. Live dealer casinos are greatly inspired by the traditions of gambling, so there’s a lot we can learn by studying these.

Archie Karas

We’re starting this list strong with Anargyros Nicholas Karabourniotis, better known as Archie Karas. In a tale worthy of a feature film, Karas went on a record-breaking winning streak lasting from 1992 to 1995. This event went into Las Vegas legend known simply as The Run – arguably the longest gambling winning streak in recorded history.

The story is pretty much every gambler’s dream scenario. Karas went to Vegas with $50, borrowed a $10,000 bankroll, and turned it into $40 million. Poker, Dice, Baccarat – no gambling game was outside Archie’s scope. His streak led him to clean out some of the top poker players of the time. Some of the greatest gamblers in Vegas refused to play him simply due to the outrageous sums he was putting up as stakes. Apparently, the famed Binion’s Horseshoe casino ran out of $5,000 chips, which was the biggest chip available back then.

So what did Archie Karas do with his newfound wealth? What every true gambler would – lost it all in 3 months. It’s truly one of the greatest stories of the ups and downs of gambling.

Akio Kashiwagi

Speaking of stories begging for a Hollywood script – how about a mysterious Japanese gambler known as ‘The Warrior?’ A real estate investor with supposed underworld connections, Kashiwagi had a famous showdown with former US President Donald Trump which saw millions exchange hands. It all sounds too dramatic to be real, but Kashiwagi was approached by Trump in the early 90s. The idea was to attract high-rollers to his burgeoning casino businesses in Atlantic City.

Akio soon arrived in Atlantic City and started his high-rolling streak with hundreds of thousands up in a game of Baccarat. The publicity stunt went as well as Trump could have hoped for, but there was one problem.  Despite the house edge, the high-rolling guest kept winning. After the first night, he cleaned the house for over $4 million.

In a long and epic struggle, Trump hired mathematicians and government-funded think tanks to figure out how he kept losing. He managed to prolong the game over multiple visits of Kashiwagi to Atlantic City and finally came out on top. The media attention surrounding the showdown was enormous – but that didn’t stop Trump Plaza from going under just 2 years later. And Kashiwagi was found hacked to pieces by a samurai sword in his Tokyo home.

Didn’t we say this was prime movie script material?

Don Johnson

Let’s fast forward a few years and look at the man who changed blackjack and reportedly brought the Atlantic City casino industry to its knees.

A bit of context first. After the 2008 financial crisis, the casino industry was hit as hard as every other part of the world. Casinos found it hard to rely on quarter-stake slot machines for profits – especially the huge establishments of Vegas and Atlantic City. They were desperate for high-rollers. Johnson used this to negotiate slight changes in blackjack rules to get the house edge as low as possible. These include dealers having to stand on soft 17, six decks, re-splitting aces, and more. As you may already know, these changes continue to echo even through live online blackjack games.

The result? In fleeced three separate casinos out of $15.1 million in a matter of days. Tales are told to this day of Don winning $800,000 in a single hand during a 12-hour marathon at the Tropicana casino. Apparently, this was great publicity, and casinos were virtually fighting over where he will play. They were all hoping his luck would eventually run out – which it never did.

Johnson eventually went down into history as one of the greatest blackjack players of all time. If anything, he taught us that you need to be careful about which blackjack tables you should play at. A slight rule variation can end up earning you quite a bit.

Charles De Ville Wells

This time, we’ll take a longer look back at a legend who quite literally had songs written about him. A short disclaimer, though – this particular gambling legend was a proven fraudster. As such, his winning record should be taken with a grain of salt.

Wells was a British man who essentially tricked people into bankrolling his roulette spree in 1891. Convincing them that the money was actually a business investment, he used it to play roulette across the French Riviera. His shadily-funded spree was quite successful, though. Reportedly, he won upwards of a million francs within days, which translates to roughly $13 million in today’s money.

In a particularly song-worthy sitting, he won over 100,000 francs at a roulette table in Monte Carlo. Such an amount exceeded the day’s payout reserve, leading to the casino closing the table. This moment was remembered as Wells “breaking the bank at Monte Carlo.” The event has since been immortalized in a popular British music-hall song.

How did he manage to win roulette so convincingly? Well, there’s still wild speculation about what exactly happened. Wells himself claimed that he developed an “infallible system”. However, his reputation as a fraudster and knowing how roulette works make this unlikely. Some claim he co-operated with casinos as a publicity stunt, some claim he cheated. Just as likely, however, is that he was simply incredibly lucky.