So you think you’re pretty good at gambling, but are you good enough to deserve a spot in the Hall of Fame? Keeping in mind, of course, that the greatest gamblers of all time achieve winning streaks that are almost beyond belief. We’re talking about Phil Ivey, Chris Moneymaker, and a few of the other names you’ve likely already heard. But just how good are the best of all time, and do they really deserve such high praise? Let’s take a closer look at the greatest gamblers of all time.
Richard Nixon
Wait a second, Richard Nixon? Yes, the president with the sketchy career is on the list of the greatest gamblers of all time. Hear us out and we’ll explain. Did you know that Nixon actually partly funded his initial political campaigns with Poker winnings? Yes, we’re serious, look it up. While in the military Nixon was an avid Poker player, winning so much money that he used it to fund his political career. We’re not suggesting he was a gambling genius like some others on this list, but he did eventually get the job of president. So if becoming president is a good metric for success, he was clearly one of the best players in the world.
Doyle Brunson
Doyle Brunson retired in 2018 and passed away in 2023, but still stands as an idol to professional gamblers everywhere. He won a grand total of 10 World Series Of Poker (WSOP) bracelets, making him among the best pro Poker players in the world. He also wrote a well-known Poker strategy book. If you want insight into how he was so good, pick up Super/System at a bookstore near you.
Another interesting fact about Brunson is that, bizarrely, some claim that he is partly responsible for the invention of the Texas Hold’Em style of playing Poker. Looking into it, there are indeed some sources that claim he is the inventor of the game. Either way, he does have many Poker hands named after him, which is good enough to be seen as a legend.
The MIT Blackjack Team
We were torn about putting the infamous MIT Blackjack team on this list, given that these pro players were, in fact, very deliberately cheating. However, if we’re talking about successful gambling it’s hard to deny that the team did very well, even if not working entirely within the law. If you’re unfamiliar with the team, they hit casinos as a team and used frowned-on card counting techniques to rake in millions. What’s most interesting is that it was a group of college professors that got the whole scam rolling.
Obviously no longer active, it’s hard to deny that the MIT Blackjack Team found major success with gambling, even if they eventually had to face the law.
Don Johnson
No, not the actor, we’re talking about the Blackjack player that famously won 15 million over the course of 2 years in Atlantic City. While the MIT Blackjack Team won their millions illegally, Johnson won his cash with skill alone. He won so much, in fact, that Atlantic City casinos were hesitant about letting him back in. How did he do it? By playing like a pro.
Johnson is famous for insisting that he will only ever play Blackjack games where the house has an edge of just 0.26%. So next time you’re hitting up Blackjack at Casino Grand Bay do a little research on the house edge of each game. In case you didn’t know, some Blackjack games have a lower house edge than others.
Chris Moneymaker
Chris Moneymaker is best known for dramatically changing the gambling landscape. In 2003 he won entry into the WSOP via the internet, an impressive achievement at the time. That he then went on to win the WSOP is the stuff of legends. Following his win online Poker sites saw a flood of interest, giving way to an era now known as the Poker boom. Tens of thousands of amateur online gamblers suddenly understood it was possible to be pro, even if currently playing in online tournaments.
Chris Moneymaker has a book rightly titled ‘How An Amateur Poker Player Turned $40 into $2.5 Million At The World Series Of Poker.’ You might want to check the book out if you’re likewise an amateur player.
Billy Walters
If you know anything about the greatest gamblers in history you’ve heard of Billy Walters. Though, it’s not Poker or Blackjack that he’s a pro at, it’s sports betting. Walters is known to win consistently at sports betting, doing so for close to 30 years now. This winning streak more than proves that he is relying on far more than just luck. Yes, it seems like he truly understands sports betting in a deep, profound way.
Most interesting is that Walters grew up poor, only the forge a path to being a millionaire by sheer willpower alone. He got a little help along the way, of course, but it is Walter’s determination that took him to the top. Walters still gambles to this very day, known for sending runners to do his betting for him. Why? Because many sportsbooks won’t accept his million-dollar bets, knowing that the chances are he’ll walk away a winner.
Edward Thorp
Last on our list is a true legend of gambling, though is another that we were hesitant to put on this list. Thorp is the man that, in the 60s, literally wrote the book on card counting. Hence, the MIT Blackjack Team wouldn’t have success if Thorp hadn’t written his book.
To be fair, when Thorp wrote his book the idea of card counting was fresh and not thought of as illegal yet. So, technically, he didn’t feel he was doing anything wrong. Either way, casinos did eventually start kicking him out, so he made most of his money selling his book rather than robbing local casinos. You likely already know his book, Beat The Dealer, and if you haven’t already read it don’t hesitate to take a look. We’re not suggesting you start counting cards, but do believe there is a great deal to learn from the book as far as Blackjack strategy in general goes.
