Top 10 Most Successful Gamblers in History

You cannot begin to imagine the number of gamblers that have won huge amounts of money, and the number that have lost similar amounts in the history of gambling. You will be surprised that this is not about hundreds of people or even thousands.

This involves millions of humans, and if properly counted, we may be looking at billions even. They have all gambled in one way or the other with the intention of winning.

Most of the names which appear on this list became famous from the physical tournaments they entered but there have been some equally impressive wins from players winning at bingo, casino games and poker tournaments over the internet. For the newest bingo sites, check out where you’ll find loads of bonuses, information and the latest sites to play.

The history is that the greater number of these gamblers failed. However, many have also succeeded. There are many names that will come up when you look at the number that succeeded, but we will be looking at the 10 most successful in the sector.

Though the success stories in gambling may be fewer than you may want to believe, we’ve succeeded in picking out the 10 most successful in the history of gambling.

1. Edward Thorp

He is a professor of mathematics and was the one that gave the world the first book on card counting. The name of the book is ‘Beat the Dealer’’ and in it, he made a mathematical demonstration of how the house edge could be beaten by the player in blackjack games.

This is achievable when the ratio of high cards to low cards remaining in the deck is tracked. With his card counting technique, this man went into Reno, Las Vegas, and Tahoe, and with a bankroll of about $10,000 from a loan given to him by his friend Manny Kimmel, he won $11,000 at the table after the weekend.

He came up with the idea of using disguises so the casinos won’t pick him out and back him off. He also enjoyed winnings at roulette, baccarat, and backgammon games with different strategies.

2. Billy Walters

Many people will name Billy the most successful in the history of sports betting. He was very popular in all the big name Las Vegas casinos, as he was consistently winning sports bets for more than 30 years running. The winning streak was so long that you can’t even calculate it, and you can’t equate it even with the biggest lucky streak.

He came from nothing to something. Growing up in Kentucky, he was a very poor kid, after becoming an orphan before the age of 2. He was raised by his grandmother after his mother took off following the death of his father.

It is also good to know that he was a respectable man with many means of livelihood, like car rentals, and car dealerships franchise, plus a golf course. So, he was not just idling around gambling. However, at some point, he was convicted of insider trading, so he is serving jail time.

3. Phil Ivey

Phil is that guy that many bettors would want to be like. He was so legendary that he won up to 10 World Series of poker bracelets. Many sources regard him as the best poker player in the world.

A look at his poker history reveals that he got involved in so many poker tournaments and came out victorious in many of them. Interestingly, in the bid to land more zeros, Phil engaged in an ‘edge-sorting’ scheme. This earned him $11 million in baccarat games in London. But he was not paid the money by Crockfords casino where he won it, because of the edge sorting.

They saw it as cheating, while he says he made smart use of a loophole in the playing cards, and there is nothing wrong with it. He also encountered the same thing in Borgata, and then took them to court. But the courts declared that the casinos were right.

4. Chris Moneymaker

When someone goes by such a last name and goes ahead to win a major event of the World Series of Poker, it will definitely catch your attention. Moneymaker won the title in 2013 in a very large cultural event and he came in through the WSOP. He bought the ticket to the event for $86 and went ahead to win $2.5 Million. He continued playing poker after that, and is estimated to have won up to $3.5 million in his career.

5. Don Johnson

He is a businessman and gambler, and not an actor. This is the man that landed $15 million winnings by playing blackjack. The good thing about him is that he did not have to count cards to win the money.

He had a very historic run against the three casinos in Atlantic City between 2011 and 2012, and while using the ‘advantage player thinking’ ability to execute games, he also prefers to play at blackjack tables with 0.26% or smaller house edge. He applied the “positive expectation bet,” with the casinos reducing the house edge and increasing the player’s edge, to reduce his losses. He won a lot with this.

6. MIT Blackjack Team

This was a card counting team. It involved a group of students from MIT, and they did their card counting as a unit and won millions at the casinos. This team has been in existence for a very long time, landing huge casino wins since 1979.

Tests are conducted for those who prefer to join after flyers about them are posted across the country, and successful candidates are trained before joining the team. They also employ the ‘ace tracking’ and ‘shuffle tracking’ techniques to complement the ‘card counting’ strategy. There is a movie about them named the ‘21 and Stars Kevin Spacey’.

7.  Doyle Brunson

He was nicknamed the ‘Texas dolly’ and went into retirement in 2018. He is a legendary poker player and many people say he is the inventor of the Texas Hold’em. He has achieved victory two times at the World Series of Poker, and many poker books have been written by him, with the Super/System as the most popular. He and only three other people have won the World Series of Poker’s main event.

8. Stanford Wong

Wong’s book ‘Tome; Professional Blackjack’ teaches the best way to have an edge over blackjack. He is the owner of a publishing firm Pi Yee Press, and he is a professional gambler. His birth name is John Ferguson and to avoid being picked by the casino security, he employs a pseudonym.

He has a term attached to his last name. The act of counting cards and not wagering until you’ve observed an edge over the casino is now referred to as ‘Wong’. So, you can now understand how successful he was in the field.

9. Richard Nixon

Nixon actually had a lot of flaws as a human being, but no one will say that he was not successful with his gambling life. He did not get to win the Poker World Series or other major tournaments. However, what he won playing poker was used to finance his political campaigns. He ended up becoming the president of the powerful United States.

10. Phil Hellmuth

Among all the mentioned gamblers, Phil the poker legend is the most successful. This man has won up to 15 WSOP bracelets. He was nicknamed the ‘poker brat’. He wrote ‘Play Poker like the Pros’ which is among the first and the most comprehensive poker books out there.

There are also many poker videos made by him. He is that player that invests all his emotions while playing. He says that those emotions are shown externally to prevent them from interfering internally.


You may prefer some other gamblers and their achievements. However, I feel that these are the best 10 in the history of gambling. But, you can also make your own list based on your criteria for measuring.

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