The Most Famous Gamblers of All Time

The Top 10 Most Famous Gamblers in History

Gambling has been enjoyed by players worldwide for countess years. And there is no shortage of gamblers that have become famous (or in some cases infamous) throughout history. We have collated the most famous of all gamblers for your perusal. Here is our top 10 list of the most famous gamblers of all time:

You will no doubt recognise many of the names on our list – they are famous after all. Yet perhaps there are some that you are not familiar with. In the following sections, we will explore each of these famed gamblers in more detail. Find out what made these gamblers stand out from the crowd to be considered the most famous gamblers in history.

1. Archie Karas – The Biggest Winning Run in Casino History

Archie Karas is considered by many as one of the best gamblers in history. He is famous for the longest and largest documented casino gambling winning streak in history, known as The Run. Karas arrived in Las Vegas in December 1992 with just $50. By the beginning of 1995, he won more than $40 million. The high stakes gambler went on to lose it all the following year.

Karas was born on the Greek island of Cephalonia in 1950 and ran away from home at the age of 15. He made his way to the USA, where he undertook jobs in bars to pay his way. He boosted his money by playing pool, before moving on to LA’s poker rooms. Karas built a bankroll of more than $2 million playing high stakes poker, but then lost all but $50.

The American-Greek gambler headed to Las Vegas, where he had the greatest winning run in the history of casino gambling. He boosted his $50 bankroll with a $10,000 loan from an old poker friend. He swiftly won enough at the poker tables to repay his debt. His winning streak continued playing both poker and craps at Binion’s Horseshoe Casino.

Within two years, Karas won a massive $40 million, making him one of the most famous gamblers on the Las Vegas casino circuit. Still, all good things must come to an end, and Archie Karas’s legendary winning run ended in 1995. Over the following year, he went on to lose his $40 million playing high stakes poker, craps, and baccarat.

2. Nick Dandolos – Inspiration Behind the World Series of Poker

Another Greek to make it onto our list of most famous gamblers in history is Nick “The Greek” Dandalos. Born to a wealthy family, Nick moved to the United States when he was 18, where he lived off an allowance from his parents. He soon moved from Chicago to Montreal, where he started to make a name for himself gambling on horse races.

After he won more than $500,000 gambling on the horses, Nick returned to Chicago, where he lost all his winnings playing dice and card games. Still, Dandalos went on to improve his casino gaming skills and went on to make a name for himself playing poker.

From January to May 1949, Dandalos went head-to-head against legendary poker player Johnny Moss. The pair played every known poker variant in games set up by Horseshoe Casino owner, Benny Binion. This became a major tourist attraction, as many flocked to see the pair compete. This game is widely acknowledged as the inspiration for the World Series of Poker.

What makes Nick Dandalos stand out as one of the most famous gamblers in history is that he repeatedly went from rags to riches, winning and losing money gambling. It has been estimated that Nick the Greek won and lost over $500 million on gambling during his lifetime.

3. Phil Ivey – The Youngest 10-Time WSOP Winner

Phil Ivey is among the most famous professional gamblers of all time. He has earned a reputation as one of the world’s best poker players. Ivey started playing poker professionally at the age of 20, although he had been playing against his grandfather since he was just eight years old. As a teenager, he used to play poker in the casinos of Atlantic City using a fake ID, which earned him the nickname “No Home Gerome”.

In 2000, Phil Ivey won his first WSOP bracelet. He went on to become the youngest poker player to win ten WSOP bracelets, aged just 38. As well as his WSOP achievements, Ivey has also played at the final table of the World Poker Tour nine times. He won the title in 2008, along with a prize of $1,596,100.

Ivey has amassed total live earnings of over $30 million to date. He also achieved success playing poker at online gambling sites, with his estimated online poker winnings exceeding $19 million. Ivey’s wins also make him one of the richest gamblers in the world to date.

Phil Ivey has also become famous through edge sorting scandals. In August 2012, Ivey won £7.3 million playing baccarat at Crockfords Casino in London. However, the casino refused to pay the winnings due to his use of edge sorting. Following lengthy legal proceedings, the UK courts sided with the casino, ruling that the edge sorting technique amounted to cheating. Ivey lost a similar case against the Borgata Casino in Atlantic City, who recouped winnings made by Ivey using edge sorting at their casino in 2014.

4. Doyle Brunson – Legendary Poker Pro

Doyle Brunson is a legendary professional poker player from the United States. He had a career that spanned 50 years before announcing his retirement in 2018. Referred to as the most influential figure in the world of poker, he was the first-ever player to win $1 million in poker tournaments.

Brunson won 10 WSOP bracelets in total, a feat only matched by Phil Ivey and Johnny Chan. Texas Dolly won the WSOP main event in 1976 and 1977, making him one of only four players to win multiple times. He was also the first player to win both a World Poker Tour title and the WSOP Main Event.

I’m a gambler. I’ll always be one. I couldn’t be anything else. So, my life will always be full of wins and losses. I wouldn’t have it any other way. It’s exciting. There’s never been a dull moment in my life. – Doyle Brunson, Poker Pro

As well as making a name as a professional poker player, Brunson has also written several books on the topic. Super/System was released in 1978 and is considered as one of the most authoritative books to be written about poker. A sequel was released in 2004. Doyle also wrote Poker Wisdom of a Champion which was published in 1984 and re-released with the title According to Doyle in 2003.

Doyle put his poker expertise to good use as a consultant on the poker movie, Lucky You. He coached lead stars, Eric Bana and Robert Duvall, teaching them how to play poker like a pro. Brunson also made a cameo appearance in the movie. He also appeared in the 2007 poker movie, The Grand.

5. Kerry Packer – Biggest Gambling Loss in Britain

Kerry Packer was an Australian media tycoon and one of the wealthiest and most influential Australians of his time. Packer famously founded World Series Cricket. Yet as an avid gambler, he also became well known for his large gambling wins and losses, including the biggest reported gambling loss in British history.

In 1999, Packer experienced a three-week-long run of bad luck at London casinos. He reportedly lost around A$28 million playing high stakes casino games, a record loss in Britain. Around the same time, he also spent around £15 million playing high stakes roulette at a major London casino. Casino operators confirmed that Packer lost it all.

Packer frequently visited not only London casinos but Las Vegas casinos too. He reportedly won A$33 million at the MGM Grand Casino in Las Vegas. Playing at UK casinos also rewarded him with as much as A$7 million in winnings each year. Packer’s gambling was not limited to casino games, and he was also renowned for his large wins and losses betting on horse racing.

6. Wild Bill Hickok – Died Playing Poker in the Old West

Next on our list of famous gamblers is one of the most famous Old West gamblers in history. Wild Bill Hickock was a folk hero of the American Old West. He was known as a lawman, soldier, gunfighter and gambler. Hickok was one of the best-known poker players of the era. He was among the first players to be admitted into the Poker Hall of Fame in 1979.

Legend has it that Wild Bill was shot dead in 1876 while playing poker. Hickok was playing poker at Nuttal & Mann’s Saloon in Deadwood, Dakota Territory and was sat with his back to the door. A disgruntled gambler, Jack McCall, put a bullet through the back of Bill’s head, killing him instantly.

While various accounts of the story have been given, it is believed that McCall lost heavily playing poker, and had been insulted when Hickok gave him money to pay for breakfast. At the time of his death, Wild Bill was holding a hand containing two pairs; black aces and eights. This hand has since become known as the dead man’s hand.

7. Phil Hellmuth – Pro Poker Player with an Attitude

Phil Helmuth is yet another professional poker player to make it onto our list of most famous gamblers of all time. Hellmuth has won a record 15 WSOP bracelets, more than any other poker player. He also holds the record for the most WSOP cashes and the most WSOP final tables. He also won the Main Event of the 1989 World Series of Poker.

It is not just his success at playing poker that makes Hellmuth a famous gambler. He is renowned as an extremely emotional player that is prone to temper tantrums. This earned him the nickname of the Poker Brat. He is also notorious for arriving late at the poker table.

Hellmuth’s celebrity profile has been boosted through several instructional poker videos. He also released his book Play Poker Like the Pros in 2003 and went on to release another two books over the following two years. Hellmuth continues to play poker professionally, and to date, has amassed total live earnings of over $24 million.

8. Billy Walters – Prolific Vegas Sports Gambler

Billy Walters is one of the most famous sports gamblers ever. He is also the most successful of all Las Vegas sports bettors, with a winning streak that extended over 30 years. Walters started gambling at the age of 9, betting (and losing) his paper round earnings on the 1955 World Series.

Walters’ bad luck continued as he gambled, and he reportedly lost $50,000 gambling by the time he reached 22. Yet, during his late 30’s, his luck significantly improved. He reportedly won $3.8 million at the Atlantic Club Casino Hotel in Atlantic City, by betting strategically on a biased roulette wheel.

Yet it is sports betting that makes Billy Walters one of the most famous gamblers in history. For over 30 years, Walters bet on various sports, including basketball, college football and NFL. He used computer analysis to predict the most likely outcome of major sporting competitions. His biggest wins included $3.5 million on the Super Bowl XLIV and $2.2 million on a college football game.

Walters’ success drew the attention of Las Vegas bookmakers. He frequently used runners to place bets so that the bookies would not know who was behind the wager. Walters stopped all gambling aside from sports betting in 1987 and returned to his business empire. He went on to be found guilty of insider trading in April 2017 and sentenced to five years in jail.

9. Bill Benter – One of the Richest Gamblers Ever

Bill Benter is one of the richest gamblers of all time. As a maths professor, Benter put his mathematical skills into practice playing blackjack at Las Vegas casinos in the 1970s. Honing the card counting skills described in Edward O. Thorp’s book, Beat the Dealer, Benter became a successful professional gambler at the blackjack tables. However, his success led to a ban from all Las Vegas Strip casinos within seven years.

Benter decided to put his mathematical skills to good use to excel in other forms of gambling. He partnered with Alan Woods, an expert horse racing gambler and went on to develop one of the most successful analysis computer software programs in horse racing betting. Benter moved to Hong Kong where he continually improved the software to get the edge over the Hong Kong horse racing market.

By analysing and incorporating no fewer than sixteen variables, Benter was able to bet on the outcome of horse racing events accurately. It is estimated that he can bring home $5 – $10 million in horse racing bets in a single day. Bill Benter makes an estimated $100 million annually betting with his advanced software formula.

10. Edward O. Thorp – The Creator of Card Counting

No list of the most famous gamblers of all time would be complete without Edward O. Thorp. The mathematics professor was specialised in the field of probability. He developed a program for calculating probability in blackjack, which led to the introduction of card counting. Thorp has rightly earned the nickname of the Grandfather of Card Counting.

Thorp originally tried out his card counting theory at casinos in Reno, Las Vegas, and Taho. He hit the blackjack tables, with a $10,000 bankroll, funded by Manny Kimmel. Kimmel was a professional and wealthy gambler who had heard about Thorp’s card counting theory. Thorp’s experiment proved successful, and he won $11,000 in a single weekend.

Thorp notoriously used disguises, such as a false beard and wrap-around glasses to conceal his appearance when playing at Las Vegas casinos. His card counting strategy quickly spread throughout the gambling community, making Thorp a celebrity among blackjack players. With such interest in his blackjack strategy, Thorp published a book in 1962, titled Beat the Dealer, to share his ideas with a wider community. His book is considered to be the original guide to card counting.

Frequently Asked Questions About Famous Gamblers

We have reached the end of our list of top 10 famous gamblers. Yet that is not all we have to offer you. For your convenience, we have collated the most common questions about the topic. Check it out for more useful info. We also recommend checking out our online gambling blog, for even more interesting reads.