Can you imagine how many gamblers have won and lost money throughout history? We're not just talking about hundreds or even thousands of people. Hundreds of millions of people, probably even billions, have gambled something to try to win.
Almost all of these gamblers have failed. With so many to choose from, making a list of the 10 most successful gamblers in history might sound like a herculean task.
As it turns out, there are fewer success stories than you might think. Here are my picks for the 10 most successful gamblers in history.
1 – Edward Thorp
Edward Thorp is a math professor who literally wrote the book on card counting. Beat the Dealer was the first book about card counting that mathematically demonstrated that you could beat the house edge in blackjack by tracking the ratio of high cards to low cards left in the deck.
Barney Curley is both a professional gambler and a trainer and hails from Northern Ireland. He has a reputation for being one of racing's most colourful characters. Despite watching his father run up massive gambling debts he still decided to take up the same 'career' himself. Jan 23, 2021 Becoming a professional gambler isn't that difficult, however, joining the ranks of the most famous gamblers of all times is quite the feat. So, what does it take?Well that depends on your game, your drive, and just how much you are willing to risk.
He personally used his card counting techniques in Lake Tahoe, Las Vegas, and Reno, starting with a bankroll of $10,000 provided by his friend Manny Kimmel. Their first weekend at the tables, they won $11,000.
Thorp was also one of the first card counters to use disguises to prevent casinos from backing him off.
Keep in mind that he developed these card counting techniques in 1966, when a computer less powerful than your cell phone took up an entire room in a university somewhere. There were no personal computers to rely on.
He's also known to have won at baccarat, backgammon, and roulette, using various other advantage techniques, some of which are now illegal.
2 – Billy Walters
Most people think of Billy Walters as the most successful sports bettor in the history of sports betting in all the popular Las Vegas casinos. He's been winning sports bets consistently for 30+ years, which is certainly enough of a winning streak that it can't be accounted for by a 'lucky streak.'
His has a true rags-to-riches story, too. He grew up poor in Kentucky, and he was (more or less) orphaned before he was two years old. His grandmother had to raise him, as his father died and his mother ran off.
Not everything about his story is rosy, though. He was also convicted of insider trading and is serving five years in prison.
3 – Phil Ivey
When you've won 10 World Series of Poker bracelets, like Phil Ivey has, you can start to stake your claim at being the best poker player in the world. According to the Wikipedia page about Ivey, multiple sources have called him the best.
I don't even have the time to list all of his poker tournament wins. There are just too many of them.
More interesting to my readers, probably, is the tale of how Phil Ivey got involved in an edge sorting scheme to make money. In 2012, Ivey won over $11 million playing baccarat in London.
But Crockfords, the casino where he was playing, refused to pay him because they caught him using an advantage play technique called 'edge sorting.' The casino called it cheating, but Ivey claims that he was just making intelligent use of an imperfection in the playing cards in use.
Ivey had a similar experience with the Borgata, too. Litigation ensued. The courts ruled in favor of the casinos, agreeing that edge sorting constitutes cheating.
Who knows what Ivey will get into next?
4 – Chris Moneymaker
You gotta love someone with the last name of Moneymaker who goes on to win the Main Event in the World Series of Poker, which is what Chris Moneymaker did in 2003. It was a huge cultural event, because he won his entry into the WSOP on the internet. This resulted in a huge influx of players to online poker sites during the so-called 'poker boom.'
You can read more about Chris Moneymaker in his autobiography, Moneymaker: How an Amateur Poker Player Turned $40 into $2.5 Million at the World Series of Poker.
One interesting note about the title of his autobiography, though. Moneymaker actually bought into the satellite tournament for $86, not $40. He just misremembered the details.
Moneymaker still plays poker and has continued to rack up winnings. He's won over $3.5 million in his career, which includes the $2.5 million from his win at the WSOP.
5 – Don Johnson
Famous Professional Gamblers Photos
Please don't confuse this Don Johnson with the actor, who I love, but who isn't a gambler (at least as far as I know).
The Don Johnson I'm referring to here is a businessman and a gambler who won over $15 million playing blackjack, and he did it WITHOUT using the counting cards technique in blackjack.
His run against the three Atlantic City casinos in 2011 and 2012 is historic now. It's important to note that even though he wasn't counting cards, Johnson was thinking like an advantage player. He insisted on blackjack rules that gave the house a small edge of only 0.26%.
He then negotiated a loss rebate deal with the casino that turned that small edge for the casino into an edge for the player. His losses were limited, which means that he didn't risk much money compared to his potential win. Such a move is called a 'positive expectation bet.'
It would be hard to duplicate Johnson's success, as casinos are probably more sophisticated now, thanks to his large win.
6 – The MIT Blackjack Team
While I'm on the subject of blackjack, let's include this group of students from MIT who counted cards as a team and took the casinos for millions. The MIT Blackjack Team isn't a new organization either. They've been winning money from the casinos since 1979.
Prospective teammates had to pass a test, then they were thoroughly trained. Before being allowed to play with the team's money, they had to demonstrate perfect play for the management of the team.
Besides traditional card counting techniques, the MIT Blackjack Team uses shuffle tracking and ace tracking techniques. It's estimated that the techniques used by the team give them an edge over the casino in the 2% to 4% range.
They did not, however, invent the concept of team play in blackjack. Ken Uston is known for starting one of the first blackjack teams.
They even made a movie about the MIT Blackjack Team. It's called 21 and stars Kevin Spacey. It's an extremely loose adaptation of actual events, though.
7 – Doyle Brunson
Texas Dolly, which is Doyle Brunson's nickname, retired in 2018, but his poker exploits are legendary. I've read that he invented Texas hold'em, although I don't believe that's actually true. He's won the World Series of Poker twice, and he's written multiple poker books, the most famous being Super/System.
Like Phil Ivey, who's profiled earlier on this page, Brunson has a total of 10 WSOP bracelets.
Brunson is a member of a club that only includes four people.
If you've never read it, Super/System is definitely worth checking out, even though much of the language is dated.
Most Famous Gambler
8 – Stanford Wong
You'd be hard-pressed to find a better book about getting an edge at blackjack than Wong's tome, Professional Blackjack. He owns his own publishing company, Pi Yee Press, and he's a well-known gambling expert. Wong isn't his real name, though, his real name is John Ferguson. He uses a pseudonym to stay one step ahead of casino security.
His last name has become a verb in the advantage play community. 'Wonging' is when you count cards as an observer and don't place a bet until you have an edge over the casino because of the count. It's easy to understand why someone whose very name has become a verb used to describe a gambling technique would make a list of most successful gamblers in history.
9 – Richard Nixon
But Crockfords, the casino where he was playing, refused to pay him because they caught him using an advantage play technique called 'edge sorting.' The casino called it cheating, but Ivey claims that he was just making intelligent use of an imperfection in the playing cards in use.
Ivey had a similar experience with the Borgata, too. Litigation ensued. The courts ruled in favor of the casinos, agreeing that edge sorting constitutes cheating.
Who knows what Ivey will get into next?
4 – Chris Moneymaker
You gotta love someone with the last name of Moneymaker who goes on to win the Main Event in the World Series of Poker, which is what Chris Moneymaker did in 2003. It was a huge cultural event, because he won his entry into the WSOP on the internet. This resulted in a huge influx of players to online poker sites during the so-called 'poker boom.'
You can read more about Chris Moneymaker in his autobiography, Moneymaker: How an Amateur Poker Player Turned $40 into $2.5 Million at the World Series of Poker.
One interesting note about the title of his autobiography, though. Moneymaker actually bought into the satellite tournament for $86, not $40. He just misremembered the details.
Moneymaker still plays poker and has continued to rack up winnings. He's won over $3.5 million in his career, which includes the $2.5 million from his win at the WSOP.
5 – Don Johnson
Famous Professional Gamblers Photos
Please don't confuse this Don Johnson with the actor, who I love, but who isn't a gambler (at least as far as I know).
The Don Johnson I'm referring to here is a businessman and a gambler who won over $15 million playing blackjack, and he did it WITHOUT using the counting cards technique in blackjack.
His run against the three Atlantic City casinos in 2011 and 2012 is historic now. It's important to note that even though he wasn't counting cards, Johnson was thinking like an advantage player. He insisted on blackjack rules that gave the house a small edge of only 0.26%.
He then negotiated a loss rebate deal with the casino that turned that small edge for the casino into an edge for the player. His losses were limited, which means that he didn't risk much money compared to his potential win. Such a move is called a 'positive expectation bet.'
It would be hard to duplicate Johnson's success, as casinos are probably more sophisticated now, thanks to his large win.
6 – The MIT Blackjack Team
While I'm on the subject of blackjack, let's include this group of students from MIT who counted cards as a team and took the casinos for millions. The MIT Blackjack Team isn't a new organization either. They've been winning money from the casinos since 1979.
Prospective teammates had to pass a test, then they were thoroughly trained. Before being allowed to play with the team's money, they had to demonstrate perfect play for the management of the team.
Besides traditional card counting techniques, the MIT Blackjack Team uses shuffle tracking and ace tracking techniques. It's estimated that the techniques used by the team give them an edge over the casino in the 2% to 4% range.
They did not, however, invent the concept of team play in blackjack. Ken Uston is known for starting one of the first blackjack teams.
They even made a movie about the MIT Blackjack Team. It's called 21 and stars Kevin Spacey. It's an extremely loose adaptation of actual events, though.
7 – Doyle Brunson
Texas Dolly, which is Doyle Brunson's nickname, retired in 2018, but his poker exploits are legendary. I've read that he invented Texas hold'em, although I don't believe that's actually true. He's won the World Series of Poker twice, and he's written multiple poker books, the most famous being Super/System.
Like Phil Ivey, who's profiled earlier on this page, Brunson has a total of 10 WSOP bracelets.
Brunson is a member of a club that only includes four people.
If you've never read it, Super/System is definitely worth checking out, even though much of the language is dated.
Most Famous Gambler
8 – Stanford Wong
You'd be hard-pressed to find a better book about getting an edge at blackjack than Wong's tome, Professional Blackjack. He owns his own publishing company, Pi Yee Press, and he's a well-known gambling expert. Wong isn't his real name, though, his real name is John Ferguson. He uses a pseudonym to stay one step ahead of casino security.
His last name has become a verb in the advantage play community. 'Wonging' is when you count cards as an observer and don't place a bet until you have an edge over the casino because of the count. It's easy to understand why someone whose very name has become a verb used to describe a gambling technique would make a list of most successful gamblers in history.
9 – Richard Nixon
Richard Nixon was (obviously) a highly-flawed individual, but it's hard to imagine leaving him off a list of most successful gamblers.
Even though he never won the World Series of Poker or any major poker tournaments, he's a huge success story because he used his poker winnings to fund his political campaigns. Bet at home casino.
In the United States, becoming president is probably the pinnacle of success.
Famous Professional Gamblers Women
10 – Phil Hellmuth
My favorite poker player is Phil Hellmuth who has won 15 WSOP bracelets. His nickname is 'the Poker Brat.' The first poker strategy book I ever read, in fact, was called Play Poker Like the Pros.
He's also made several instructional poker videos.
My favorite thing about watching Hellmuth play is how emotional he gets. I read somewhere that he claims that he externalizes those emotions so they don't come out in play. In other words, it only looks like he's on tilt.
Conclusion
That's my list of the 10 most successful gamblers in history, but you might have some gamblers you like better for your own reasons. If that's the case, please feel free to pony up a name or two for consideration in the comments below.
With the Supreme Court ending a federal ban on sports betting, the floodgates have opened for some, or all, of the 50 states to legalize wagers on athletic events. With this brave new world of gaming, we'll see extra focus on players, officials, spreads, lines and money, all as leagues, law enforcement and sports books try to ensure that sports gambling stays incorruptible. Good luck with that: Ever since professional sports were created, players have been betting on games and gamblers have been finding ways to infiltrate the games to shift the odds in their favor. Here are 11 of the biggest scandals in sports gambling history.
1. The Black Sox (1919 World Series): 'Never before in the history of America's biggest baseball spectacle has a pennant-winning club received such a disastrous drubbing in an opening game.' So wrote The New York Times after the Chicago White Sox were defeated 9-1 in Game 1 of the 1919 World Series, unaware that said drubbing was the result of eight players who had agreed to help throw the Series for gamblers.
The degree to which each player helped has been a debate for almost a century. Joe Jackson, banned for life along with seven teammates, hit .375 with a .956 OPS over the eight games and didn't make an error. 'How do you explain that?' Kevin Costner correctly asks in Field of Dreams. (Jackson admitted taking money.) Others, like pitcher Eddie Cicotte and Chick Gandil (allegedly the on-field mastermind) took a noticeable dive.
It turns out that the Sox throwing the Series was the worst-kept secret in baseball. Even before Game 1, the baseball world was atwitter with word that the fix was in but the commissioner's office was apparently content to look the other way. It was until a separate case one year later that the word about 1919 got out. None of the Black Sox were found guilty in court (a rumor suggests that owner Charlie Comiskey and kingpin Arnold Rothstein helped disappear some key paperwork) but were banned from baseball for life.
2. CCNY point shaving (1950): In 1951, 32 college basketball players from seven schools around the country were caught up in a mafia-run point shaving scheme that hit four New York schools and three out-of-state teams, including Kentucky. It was a major blow for college basketball, especially considering that the bulk of the accused players had been on CCNY's 1950 team, which became the first (and only) team to ever win the NCAA and NIT tournaments. The scandal decimated the team — which rivaled the Yankees and the Dodgers for New York sports supremacy at the time — and effectively ended the school's affiliation with big-time athletics. Despite an insistence from a holier-than-thou Adolph Rupp that his boys weren't involved in such nefarious schemes, Kentucky was banned for a full season as well.
3. Pete Rose: The all-time hit king was banned for life in 1989 for betting on games, something he adamently denied for 15 years. He finally admitted to betting while managing the Reds, but insisted he never bet on baseball while he was a player. Never! A few years later, that was proven to be another lie — evidence showed that Rose bet about once a day in 1987, typically for around $2,000. Though he frequently bet on his Reds, Rose vows he never bet against his own team and, despite his flexibility with the truth, this claim seems legit. No evidence has ever come out to suggest otherwise and, to be honest, it doesn't really fit with what we know about the man.
4. Paul Hornung and Alex Karras: Before Pete Rose, there was Paul Hornung and Alex Karras. The former was an NFL MVP who set a league scoring record in 1960 that stood for 46 years (and is still the second-highest total in history). The latter was a first-team All-Pro defensive lineman. Despite their success (or maybe because of it), Hornung and Karras routinely bet up to $500 on NFL games while associating with known gamblers. Both men were contrite (Rose should have taken note of that in 1989) and, in issuing his indefinite suspension, Rozelle took care to mention that neither player bet on or against their own teams. The suspension was dropped after a full season. Hornung was later elected to the Hall of Fame and Karras starred on the 1980s sitcom Webster.
5. BC Goodfellas: The most notorious real-life gangster portrayed in Goodfellas didn't go down for the Lufthansa heist, whacking Billy Batts, robbery, murders or aiding and abetting Joe Pesci being called a clown. Jimmy Burke (played by Robert DeNiro in Martin Scorsese's mob masterpiece) went to jail because Henry Hill (Ray Liotta) ratted, almost off-handedly, about a point shaving scandal involving the Boston College basketball team. Hill had been arrested on various drug counts and, in his interviews, casually mentioned the BC story. Once it became clear that the Feds were interested in this to help bring down members of the Lucchese family (remember, Al Capone went down for tax evasion), Hill asked for immunity and ratted on his friends. Flamingo casino reviews. It had been a successful partnership, for a little. After a rocky start, the syndicate began winning money on Boston College, by betting the Eagles to win games but lose against the spread or fail to cover a big spread in a game they wouldn't have won anyway.
6. John 'Hot Rod' Williams: Before he became a beloved NBA veteran, John 'Hot Rod' Williams faced jail time over a 1985 point shaving scandal at Tulane that ended up shuttering the basketball program for four seasons. With a healthy mix of money, cocaine and 1980s-era bravado, five players were accused of shaving points in two games, all for a shared pot of $17,000. Williams twice went to trial – the first was declared a mistrial and the second ended with his acquittal on five counts. He went on to play 13 years in the NBA.
7. Rick Tocchet: The story of Tocchet, an NHL All-Star and Stanley Cup champion, was sordid enough. He pled guilty to involvement with a $2 million gambling ring that took bets from the rich and famous. But Tocchet's tale took an unexpected turn when the name of Janet Gretzky, wife of the Great One, appeared in the books.
8. Art Schlichter:The fourth pick of the 1982 draft accrued nearly $1 million in gambling debts by the end of his first year in the NFL, by betting various sports including, allegedly, 10 NFL games. (Like Hornung and Karras, Schlichter was never accused of betting on his own team or using his position to influence his wagers.) Schlichter was reinstated in 1984, was out of the league by 1985, never won an NFL game and has spent the last 30 years in and out of jail. His latest offense — a scan selling phony tickets to sporting events — sent him to prison for a decade.
9. Joe Namath: After Super Bowl III, Namath, a playboy bachelor, was the biggest thing in American sports. He decided to capitalize on it by opening a night club named, cleverly, Bachelor III. Mark Kriegel wrote in his biography Namath: ' regulars included con men, fences, bookmakers and of course made men — exactly the kind of guys you'd expect to find in a hot East Side joint.'
Commissioner Pete Rozelle told Namath to sell his interest in the club because of its reputation but, rather than sell, Namath retired instead. He changed his tune one month later after a meeting with Rozelle. On his way out of the commissioner's apartment, after agreeing to cut ties with his club, Namath was approached by Rozelle's 11-year-old daughter. 'Mr. Namath, I just want you to know that everyone in the Rozelle family doesn't hate you.'
10. Tim Donaghy: In 2007, an FBI investigation revealed that Tim Donaghy, a longtime NBA referee, had bet on NBA games and fed information to other gamblers after falling into debt. The scandal was both a huge story and quickly faded from the public consciousness, almost like sports fans want to delude themselves into thinking that everything is always on the up and up.
11. Northwestern: Dewey Williams and a teammate were given a brief prison sentence for their role in fixing games during the 1995 season. Why gamblers didn't trust Northwestern basketball players to simply lose games on their own, as per usual, is the enduring mystery of this tale.
