Top 12 Famous Casino Players for Real Money

Like any popular industry, gambling has its own heroes and villains. We aren’t going to support or condemn these adventurers in our article. We will just share the stories of ordinary people, who became ‘soldiers of fortune’ and chose a dangerous, but exciting life of the real-money casino players. These are experts who dedicated their time and effort to beating casinos. And, you know, they were pretty successful at their time!

Meet Professional Gamblers!

The following list includes only 12 names, but of course, there are a lot of other professional players as well. The thing is that it’s virtually impossible to unveil all bios. Thus, we will focus on the brightest ones.

1. Charles Wells

Charles Wells

Born in 1841 in the family of a British poet, Charles Wells grew up in France and worked at the shipyards. This famous gambler started his career as a professional cheater, when he launched his railway project in Pas-de-Calais. He raised funds for the project and disappeared with investors’ money.

Charles Wells was famous for his games in the Monte Carlo Casino in the 1890s. When playing, the gambler utilized Martingale and D’Alembert schemes, but people say that his winnings are the result of good fortune only. Some state that Wells won 23 out of 30 roulette spins and got a few million francs, which means he broke the casino bank.

At the end of 1892, he was arrested in Le Havre and was later extradited to his homeland, where he was convicted and sentenced to 8 years in prison. The prosecution concerned Wells’ fraudulent patent scheme. He sold his ‘valuable invention’ to a number of investors for an enormous amount of money at that time — 5,000 francs.

Fame: He won around 2 million francs in 1891 because of pure luck, was arrested several times and lost all his winnings.

2. Nick Dandolos

Nick Dandolos

Known as Nick the Greek, Dandolos (1883-1966) was born in a rich family. After he turned 18, his parents sent him to the United States with an allowance of $150 a week. Using these funds, Nick began his gambling career betting on horse races in Montreal. And only a few years later he moved to Chicago and started playing poker, dice, and roulette, thus growing his capital.

Dandolos is associated with a big five-month poker tournament where he was playing against Johnny Moss. Unfortunately, it wasn’t successful for Dandolos as he lost from $2 to $4 million to his opponent. Nick the Greek gambled a lot in various casinos, bet on horse races but ended up with empty pockets. It’s said that aged Dandolos was seen in gambling houses playing poker for tiny hands up to $5.

Fame: He won and lost $500 million approximately, and was included in the Poker Hall of Fame in 1979.

3. Titanic Thompson

Titanic Thompson

Alvin Clarence Thomas (1893-1974) is one of the most unusual gamblers in history. He bet on horse races, cards, dice, and other traditional casino games. Titanic Thompson, who got his nickname because he “sinks everybody”, once bet that he could send a golf ball 500 yards and won thanks to driving it onto a frozen lake. Thompson was an expert at finding a million ways to earn money, including gambling lectures to soldiers during WWI. The man participated in large poker tournaments and even arranged gambling trips with his son.

Fame: He bet on everything from cards to races and won almost always. He was also honored in the first WSOP in 1970.

4. Edward Thorp

Being called the father of card counting, Edward O. Thorp (born 1932) is a mathematics professor, top manager, and famous blackjack player. By observing and simulating millions of blackjack games on the university computer, Thorp invented his own counting system and won thousands of dollars in American casinos each weekend with his mates – Claude Shannon and Betty Shannon.

In 1962, the gambler published his book with the exact information about the counting technique he used but nobody could duplicate Thorp’s success so far. Ed is 86 years old now, but he still attends the annual Blackjack Ball (and even this year’s one, which was held in February), where he is treated as a hero player. He has shifted to the investment market and now earns a pretty penny on annual returns.

Fame: He invented the card counting technique for blackjack. Thorp earned thousands per weekend via gambling, but ultimately quit it and switched to hedge fund investing.

5. Akio Kashiwagi

Akio Kashiwagi

The Warrior or Akio Kashiwagi (1938-1992) was a famous Japanese real-estate agent and investor. He liked to play baccarat betting from $100,000 to $200,000 per hand. Kashiwagi could earn up to $6 million per one game, but also lost as much as $10 million.

The biggest mystery about the Warrior is his death. Kashiwagi was stabbed with a samurai sword and his body was left near Mount Fuji. This crime is still under investigation. It’s also said that Kashiwagi owed $4 million to various American casinos.

Fame: He was a well-known Japanese high roller and baccarat player, betting hundreds of thousands per hand.

6. Alan Woods

Alan Woods

The pioneer of quantitative gambling, Alan Woods (1945-2008) was born in New South Wales. He studied mathematics at the University of New England where he began playing poker and betting on horse races. Despite Woods didn’t finish his education, he utilized math skills in blackjack card counting and was pretty successful.

In 1982, Woods put an end to his professional blackjack gambling career. Then, he decided to bet on horse races instead of counting cards. With Bob Moore and Bill Benter (#10 in our list), the gambler developed a predictive computer system which generated $100,000 during the first season of horse races in 1987. Wood’s net worth in 2008 was around $480 million.

Fame: He created his own predictive system for horse racing, and earned millions of dollars with it.

7. Billy Walters

The unique story of Billy Walters (born 1946) shows that everything is possible. He made his first bet in the age of 9 and lost it. By 25, he had lost over $50,000 and the house! In 1986, Walters and his partner noticed a statistical flaw of a roulette wheel in one of the casinos in Atlantic City and were successful to earn $3.8 million in 36 hours. Later, Walters joined the group of sports gamblers who utilized software to predict outcomes. He bet on basketball and football matches with insane $50-$60 million wins per year. In 2017, Walters was imprisoned and fined because of insider trading.

Fame: He lost nearly everything, but then found exploits in casino systems and started his 30-year winning streak.

8. Gonzalo Garcia-Pelayo

The man who outplayed roulette wheels without cheating, Gonzalo Garcia-Pelayo (born 1947), started his career as a film producer in Spain. Once, he decided to play roulette and check the idea of biased machines. According to his vision, some numbers at a roulette wheel are picked more often than others due to micro-imperfections in its construction. Garcia-Pelayo analyzed thousands of roulette results and bet on the best numbers. He won around $1.5 million in Spain. The catch is that everything was fair in his actions!

Fame: He studied the flaws of roulette wheels for a few years, and earned millions thanks to his knowledge.

9. Archie Karas

The man who enjoyed the longest documented winning streak, Archie Karas (born 1950), started his impressive gambling career from a $2 million loss in Los Angeles. He then moved to Las Vegas with $50 of his own money, and $10,000 of the loaned funds. From 1992 to 1995, Karas outplayed famous poker players with the total win of $17 million, won $1.2 million at a 9-ball pool, and continued winning in nearly all games imaginable. He ended up with $40 million in his pockets but lost everything in 1995.

Fame: He has the biggest winning streak in the history of gambling with $40 million earnings in three years.

10. Bill Benter

This American gambler is still successful in playing casino games. Bill Benter (born 1957) got a physics degree in 1977, and was always aware of his unique math talents. He played blackjack in Las Vegas where he counted cards successfully thanks to Edward Thorp’s (#4 in our list) book. Benter was banned from all local casinos within a span of seven years.

Later, the gambler met Alan Woods (#6 in our list), partnered with him, and developed a software program to forecast horse races’ outcomes. Thanks to this tool, Benter has built his fortune which is nearly $1 billion now. Benter is a famous philanthropist, visiting professor, and the leader of his own charity foundation.

Fame: He created a forecasting system for horse betting and won nearly $1 billion with it. He also donates thousands of dollars to charity and political organizations.

11. Don Johnson

Here’s another man who can beat casinos for large sums. Don Johnson (born 1962) was invited to play high-stake blackjack during the crisis of 2008. He accepted offers but asked for a few changes to increase casino odds and reduce the house edge. Casinos agreed. As a result, Don Johnson won around $15.1 million in Atlantic City casinos, including $6 million in Tropicana and $5 million in Borgata. Nearly all houses that invited Johnson to play in 2008 have banned him after these insane winnings.

Fame: He appeared almost from nowhere, and earned more than $15 million during a six-month marathon of high-stake blackjack playing in Atlantic City.

12. Phil Ivey

Well, meet the king. Born in 1977, Phil Ivey is one of the youngest poker professionals. He began mastering his skills in the 1990s in New Jersey and then rushed in the world of professional poker. In the 2000s, Ivey won 7 WSOP bracelets including three awards in 2002! He now holds 10 bracelets plus one World Poker Tour title being the youngest player in the Poker Hall of Fame. Ivey has more than $26 million live tournament winnings. In addition, he plays online poker and earns a few million annually.

Fame: He has 10 WSOP bracelets, 1 World Poker Tour title, $26+ million live winnings, and a place in the Poker Hall of Fame.

The Importance of Responsible Gambling

As you can see, a lot of famous gamblers ended up with nothing in their pockets. It’s the nature of gambling. You can win millions, but you can still fail because of bad luck. Various strategies, approaches, and even cheats can’t guarantee regular wins because there’s always an element of randomness. Some of our heroes know when it’s better to stop and dedicate yourself to other activities such as philanthropy. Others refuse to take a break so they end up with huge debts. Even if you aren’t a professional player, you should learn from these examples.

Remember about responsible gambling. Be sure that you bet only the amount that you can afford to lose. Set time and money limits. Talk to your relatives and friends if you feel uncomfortable with gambling. Consider this activity as a hobby, recreation or work but never let yourself lose control. Play safe!