Best Gamblers in the World: Top 10 Richest & Most Famous

Written by: Ashley Grasse , Specialist in Casino, Games, and Trends
7 minute read
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Are the greatest gamblers of all time simply the ones that won the most, or are they the ones with unbelievable stories and colorful pasts? I’m going to take a look at some of the world’s most famous gamblers. You may recognize a few names, and others may surprise you.

Whether they amassed millions or gambled their possessions away, they certainly made names for themselves. Let’s take a peek into their lives.

Most Famous Gamblers in History

For thousands of years, people have enjoyed betting. Let’s explore the lives of the most famous gamblers in history, some of whom might also be considered infamous.

King Henry the VIII

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During his rule in the 1500s, King Henry’s gambling addiction earned him the nickname “England’s Number 1 Gambler.” He played a number of games, including dice, checkers, and Bragg, which is thought to be an early version of poker.

Apparently, he wasn’t very good at it. In the span of two years, he lost £3,250, which converts to $3,473,156.32 today.

He even gambled away the beloved St. Paul’s church bells on a single dice roll. When that didn’t go over too well, he had the winner of the game and recipient of the bells hanged for treason.

James Butler (Wild Bill) Hickok

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James Wild Bill Hickok was a frontierman, gunslinger, actor, and gambler in the late 1800s.

His short life was filled with perils that earned him his nickname, such as multiple duels and the time he nearly died fighting off a bear with a dagger. But it wouldn’t be a mauling that killed Wild Bill.

In 1876, Hickok was murdered while playing poker in a Deadwood saloon in Dakota Territory. An incensed fellow player from the previous day walked in and shot him in the back of the head.

The cards he was holding, two black aces and two black eights, became known as the Dead Man’s Hand.

Archie Karas

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Archie Karas is a Greek-American gambler with the longest and largest winning streak on record.

After leaving Greece and landing in Oregon, Archie became a skilled pool shark and poker player, eventually building up and then losing his whole bankroll.

In 1992, he drove to Las Vegas with $50 to his name, bent on turning his luck around.

Karas played pool with stakes reaching $40,000 a game and took his now $1.2 million winnings and turned it into $3 million playing poker.

In three months, his bankroll was up to $7 million. At the end of his three-year streak, he had amassed a fortune of $40 million.

Phil Ivey

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Phil Ivey is known as one of the best poker players in the world. He’s won ten World Series of Poker bracelets, a World Poker Tour Title, and was inducted into the Poker Hall of Fame.

His love for poker began as a teenager in his hometown of Brunswick, New Jersey, where he would play against his co-workers and use a fake ID to get into games in Atlantic City.

At 38, he’s the youngest player ever to win ten bracelets and also the fastest to achieve that accomplishment in just 14 years.

Edward Thorp

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Edward Thorp mastered the art of card counting. That’s because he was the person who invented it.

This math professor from California applied his skills to develop a way to beat the house in blackjack. He then tested his theory at several casinos, winning $11,000 in one weekend

In 1966, he published his strategy in the best-selling book Beat the Dealer. It became a blackjack bible to players everywhere and changed how casinos ran tables.

In other words, he’s the reason the deck gets shuffled after every hand.

The Richest Gamblers in the World

Were the players below incredibly smart or phenomenally foolish? Either way, they did what it took to become some of the richest gamblers in the world.

Bill Benter

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Bill Benter is a professional gambler and talented mathematician whose interests ranged from card counting to horse racing.

After getting banned from all Vegas strip casinos for being too good at blackjack, he partnered with Alan Woods, a fellow card counter and horse racing enthusiast. Together, they moved to Hong Kong in 1984 to conquer the horse race betting industry there.

With Benter’s arithmetical prowess and Woods’s racing experience, they developed software that could predict the winners of a race with surprising accuracy. He amassed tens of millions of dollars yearly with his model and is worth $1 billion today.

Anthony Bloom

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Anthony Bloom is an English sports bettor and poker player who also owns the professional football club Brighton and Hove Albion.

He studied mathematics at the University of Manchester and was always passionate about poker. He finished second in the Poker Million IX tournament and has won an estimated $4 million in poker games over the years.

He even earned himself a nickname, The Lizard, for his cold, calculated approach to playing. Bloom now runs a private sports betting syndicate called Starlizard. Between sports betting and poker, he is now worth $1.6 billion.

Zeljko Ranogajec

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Zeljko is an Australian professional gambler worth $610 million with a focus on blackjack and horse race betting.

He’s well-known for his advantage style of gambling, which helped him take a couple of hundred dollars and turn it into several million at blackjack tables.

After being banned from Australian and American casinos for card counting, he turned to horse racing. His success is partly due to the rebates and discounts he negotiated with betting pool operators.

His wagers alone reportedly account for 8-10% of the bookmaker TabCorp’s $10 billion yearly revenue.

Alan Woods

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Alan Woods’s story is very similar to Bill Benter’s in that they both started as mathematicians and made good money counting cards in blackjack.

Australian-born Woods ended up in Las Vegas playing blackjack full-time. When he retired from the game in 1982, he turned his focus to horse racing in Hong Kong, where the pool of horses was much smaller.

That’s when he crossed paths with Bill Benter. Their development of the software that could predict horse race winners certainly contributed to his wealth, although they dissolved their partnership in 1987.

Woods went on to become an extremely successful horse race bettor in his own right, worth $500 million.

Billy Walters

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Billy Walters is one of the most prosperous sports bettors of all time, having only had a losing season once in his 39 years of gambling. He went from living without running water in Kentucky as a child to being incredibly wealthy later in life.

Walters started gambling at nine years old and hit success in his 30s. In 1986, he and a partner put up $2 million and played roulette for 38 hours, walking away with $3.8 million.

When he began sports betting, he used computer analysis to determine his picks and had a winning streak that spanned three decades. He’s now worth $200 million.

My Favorite Gambling Success Story

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Some of the best tales from the casino are about average folks winning huge jackpots. My favorite gambling success story is about Elmer Sherwin. “It’s never too late to try” is the perfect adage for this two-time jackpot winner.

In 1989, at the age of 76, Sherwin won $4.6 million on the Megabucks slot machine in the Mirage in Las Vegas. He shared his winnings with loved ones and traveled to his heart’s content.

But that’s not where the story ends. Sixteen years later, at 92, Sherwin won again on the same slot game at the Cannery Casino and Hotel, taking home $21 million.

He’s the only person to win two Megabucks jackpots in their lifetime. He donated much of his second winnings to the Hurricane Katrina relief effort and enjoyed providing for his family until his passing at the age of 93.

Top Gamblers in the World: From Kings to Poker Champions

The stories of the best gamblers of all time, from medieval kings and gunslingers to modern poker tournament champions, captivate us with their remarkable lives, wins, and occasional missteps. Whether it’s tales of rising from nothing to riches or the adventures of gambling renegades, these iconic figures of the bet leave an unforgettable legacy in the gambling world.

So, after reading through these stories, who do you think deserves the title of the greatest gambler of all time: the ones who rose from rags to riches or the daring gambling rogues with questionable ethics?

Ashley Grasse

Ashley Grasse Specialist in Casino, Games, and Trends

Ashley Grasse is a research writer and online casino expert who dissects sites and games in detail to provide accurate, unbiased reviews. She's a gambling theory enthusiast, an expert on information accuracy that makes difficult concepts easy to understand, and a lover of the outdoors.

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