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Most Famous Gamblers of All Time

Written by, Toni Maglovski

Updated March, 16, 2022

Gambling, for some people, isn’t just a game. The most famous gamblers have introduced new techniques in the gambling world and raised the bar for generations to come. 

But, how many of them have gone down in history, and how did they get there?

Let’s find out.

Top 10 Famous Gamblers

  • Edward Thorp
  • Billy Walters
  • Chris Moneymaker
  • Doyle Brunson
  • Richard Nixon
  • Phil Ivey
  • John Montagu
  • Phil Hellmuth
  • Archie Karas
  • Nick Dandolos (Nick the Greek)
  • Edward Thorp

At the top of the list of successful gamblers is Edward Thorp, an honourable member of the Blackjack Hall of Fame. 

He’s a maths professor, inventor, author, blackjack player, and pro gambler, known for being a strategic player who relies on theories and techniques.

Thorp wrote a book on card counting in 1966, titled “Beat the Dealer,” which is a guide on how to use maths to beat the house edge in blackjack by tracking the ratio of high cards to low cards in the deck. He used the IBM 704, a research tool that helped him explore the probabilities of winning in the game. 

Thanks to this card counting technique, he managed to win $11,000 on the first weekend of gambling with his friend Manny Kimmel. Their saga continued in Lake Tahoe, Reno, and Las Vegas. 

Thorp is also one of the first famous professional gamblers to successfully use camouflage in casinos to prevent backing off.

  • Billy Walters

Known as the most successful professional sports bettor in the history of America, Billy Walters had over thirty years long career in sports betting.

Walters dived into the world of betting when he was only 9 years old He made his first bet on the 1955 World Series using money he earned from his paper route.

He also bet on golf and eventually went on to eventually become a high-stakes gambler, winning a record amount of $3,800,000 playing roulette for 38 hours at the Atlantic Club Casino Hotel.

He also won  $175,000 after participating in the Super Bowl of Poker in 1986.

At one point, Walters claimed in an interview with “60 Minutes” that he never had a losing year.

Walters was later convicted for insider trading and was released from prison in 2020, after 5 years, to serve his sentence at home. Shortly after, he was pardoned by the outgoing president.

  • Chris Moneymaker

Moneymaker was chosen to play poker at the 2003 World Series of Poker in an online tournament. By winning the $2.3 million prize, he went from an unknown poker enthusiast to one of the most famous gamblers overnight.

He used the money to open his company MoneyMaker Gambling and travelled the globe as a professional gambler. Moneymaker also started working as a representative for Harrah’s Entertainment and Poker Stars.

But, his best contribution to the world of gambling is the Moneymaker effect. His victory at the tournament is believed to have inspired many to join the online poker community and he is partially credited for the poker boom that started in 2003.

How did he win? It’s unclear what technique he used to successfully win games, but Moneymaker has said that successful poker players have a good poker face and always make their opponent feel uncomfortable.

  • Doyle Brunson

Doyle Brunson, known as Texas Dolly and poker expert, played poker for more than fifty years and won the World Series of Poker twice.

Brunson started off as a basketball player but didn’t manage to fulfil his dream of joining the NBA due to a knee injury.

While he worked as a school principal, Brunson sometimes played illegal poker games in Fort Worth. He later moved to Las Vegas where he officially started his poker career. 

Brunson was a regular on the poker tables in Vegas and participated in the WSOP from the first tournament to his retirement.

The Texas Dolly made it in the history books because of his earnings. He is the first player to earn $1 million in poker tournaments and his net worth is estimated to be around $75 million.

Brunson also published “Super/System,” a poker textbook in which he revealed his techniques and shared tips, before his retirement. Although he admitted that this cost him money on the tables, he published another version of the same book in collaboration with several other well-known gamblers.

  • Richard Nixon

Some politicians like to gamble, and President Richard Nixon was no exception. 

Nixon learnt the art of poker in the Navy, tutored by James Stewart, and was a meticulous student. He made sure to learn the fundamentals of the game, before risking any of his money.

He liked the strategic part of the game and was good at bluffing and figuring out how to exploit other players’ flaws.

However, Nixon, unlike some of the gamblers on this list, wasn’t into high-stake games. He preferred small but regular earnings.

According to his biography, he even passed up an opportunity to meet Charles Lindbergh, American aviator, and author, because he was hosting a poker game. 

Nixon stopped playing when the war ended.

Believe it or not, poker helped Nixon get to the White House. He funded his political campaign with money he earned during a poker game. It is believed that he invested around $6000 from his poker earnings into his congressional run.

  • Phil Ivey

Phil Ivey is known as the Tiger Wood of poker and played poker every day for fourteen consecutive years.

He first started playing poker in New Jersey with his coworkers and was the first gambler to beat the famous poker player, Amarillo Slim at the World Series of Poker Main Event. In 2009, he outplayed 147 poker players to win his bracelet. 

Ivey ended up winning ten World Series of Poker bracelets and became the youngest poker player to do so at the age of 38.

It is estimated that he earned over $100 million from his poker winnings. But, he didn’t get there without professional gambling techniques. 

Ivey used a technique called edge-sorting while playing baccarat. It helped him recognise the good cards from their patterns and won $11 million. However, the Crockfords Casino found out caught him relying on the technique and refused to pay him. 

  • John Montagu

John Montagu was a famous nobleman, captain, and negotiator in the 18th century who accomplished a lot as the 4th Earl of Sandwich. He was also a conservative gambler and the inventor of the sandwich, at least according to him.

During his college years, he started horse betting and went on to play cards. It is believed that he often played for hours and that he always requested meat in between two slices of bread during his marathon gambling sessions. 

As a gambler, Montagu won and lost thousands of pounds daily, mostly by chasing his losses. Still, he once had a winning streak that allowed him to pay for Captain Cook’s journey, during which he discovered Australia and some surrounding islands.  Cook named the islands “The Sandwich Islands” in honour of Montagu.

Montagu spent his retirement days playing cards with anyone that agreed to a game.  .

  • Phill Hellmuth

Phill Hellmuth, also known as the Poker Brat, became the youngest player who won the Main Event of WSOP in 1989, at the age of 24. He earned an estimated $15,000,000 and was placed fourth on the WSOP All Time Money List.

Several years later, in 1993, he won three bracelets in one WSOP tournament and won memorable amounts of money in tournaments year after year.

Apart from playing poker, one of Hellmuth’s ambitions was to write a New York Times Best Seller, which he eventually accomplished. He wrote, “Play Poker Like the Pros” in which he explains different types of poker games – including Seven-Card Stud, Omaha, Texas Hold-em, and Razz – and elaborates on the proven techniques to defeat other players. 

Hellmuth is also featured in the movie “Shark Out of Water,” which deals with behavioural addiction and the not-so-well-known side of the poker game.

  • Archie Karas

Anargyros Karabourniotis, better known as Archie Karas or The Greek, is a poker star, professional casino gamber, pool shark, and high roller who holds the record for the longest winning streak in casino pro-gambling. This period called The Run lasted from 1992 to 1995, when Karas made $40 million out of $50. 

The Greek immigrant was unbeatable in many high-stakes games including roulette, baccarat, blackjack, and poker. He once managed to turn pocket change into $7 million.

He played against gambling legends including Stu Ungar, Chip Reese, Puggy Pearson, and Johnny Moss. Due to his high stakes, he had to transfer from cards to dice. He played craps and used the Martingale technique.

However, after only three months in the Sin City of Las Vegas, Karas lost his fortune and never went back to the old glory days.

In 2013 in San Diego he was arrested for card marking in blackjack and was sentenced to three years probation.

Karas is believed to have lost his last money on dice and baccarat.

  • Nick Dandolos (Nick the Greek)

Nick the Greek is one of the biggest legends of gambling in the world. He started with horse betting in Canada and built a career in dice and card games in the US.

Dandolos’ gambling career was a rollercoaster, due to which he is known as the man who went from rags to riches 75 times. There were times when he would win $6.5 million, just to lose it all the next day. 

When he moved permanently to Las Vegas, he continued to play independently although he had offers to play for mafia bosses and casino owners. 

Dandolos’ longest game session lasted for five months, during which he played many different poker games against Moss, and ended up losing $4 million.

Still, Nick left the Italian mafia boss, Frank Costello broke, which prompted the New York Times to declare him a poker king the very next day.

Dandolos lived a luxurious life but died pennilessly. It’s worth noting that a good portion of his poker-earned money was donated to various charities. 

Bottom Line

Gambling, especially online, is becoming more popular by the day. With competition becoming fiercer, it’s tougher to win games in the 21st century. This also means that many players are raising the stakes and will certainly be remembered as one of the most famous gamblers in the history of the world.

I always had an appetite for learning new things and random facts about almost everything, which is why when I got offered the job to work as a content writer at Don't Disappoint Me I took it without hesitation. Writing on a daily basis took my love for words and research to a whole new level, and made me realize that this is a career I would love to pursue. Although I spend most of my time researching my next piece, you can also find me on the football court, in the gym, or at home with a book in my hand.