10 of the Most Successful Gamblers in History

Famous Gamblers Billy Walters, Richard Nixon, Doyle Brunson, Money Flying
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.

Beat The Dealer Book by Edward ThorpHe 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.

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But he’s not just a famous sports bettor. Walters also owns multiple businesses, including car dealerships, a golf course, and a car rental franchise.

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.”

Pro Poker Player Chris Moneymaker, Moneymaker Autobiography Book

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

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

MIT Blackjack Card Counting Team, Money Spread Out
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.

They recruited new players with flyers they posted at colleges throughout the United States, but they were selective about who they admitted to the team.

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.

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The number of people who’ve actually won the Main Event at the World Series of Poker is breathtakingly small, by the way.

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.

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 Giving Speech, Poker Cards Spread OutRichard 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.

In the United States, becoming president is probably the pinnacle of success.

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.

It wasn’t the best poker strategy book I’ve ever read, just the first, and I still credit it with giving me a fundamental understanding of starting hands in Texas hold’em and the different types of players.

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.