Top 10 Famous Gamblers in History

Some of the biggest gamblers in history are people who have changed games in some way, negatively or positively. The Top 10 Famous Gamblers in History are high-stakes gamblers with big fortunes to play with, some of whom have lost big as well. As Gambling is a negative expectation activity for 99% of participants, only gamble with money you can afford to lose. Use online gambling site or casino tools for responsible gambling and seek Gamblers Anonymous help if you start to gamble adversely and negatively affect your life in some way.

Throughout the guide we shall explore the various strategies used by the famous gamblers to succeed at their games, their greatest successes and their failures. We will also cover many of the terms and concepts used in the gambling industry, and explain them so that you can clearly see the difference between a professional poker player, and a casino gambler.

The Most Famous Gamblers of All Time

For a person to be considered the best gambler of all time, there are a few criteria that must be met:

• The gambler must be innovative, which means they need to be able to come up with different ways to play games of chance in order to gain an advantage.
• The gambler must also be very resilient, meaning they have to be able to bounce back from a long losing streak.
• Finally, the gambler must be well known, so that people can see their success and try to follow in their footsteps.

Below is a list of the top 10 most famous gamblers of all time, which includes several of the best professional poker players in the world as well as a few other famous gamblers from around the globe.

Edward Thorp

The famous gambler behind the book and movie, ‘Beat the Dealer’. He developed the first ever mathematically proven card counting system for Blackjack, known as the Hi-Lo system. The famous book, ‘Beat the Dealer’ outlines his strategy in full detail. His following book, ‘Beat the Market’ outlines his mathematical approach to stock market and option trading. In the book, Thorp a renowned mathematician and author, and a hedge-fund manager, a legendary advantage player (AP) who has made most of his estimated net worth from the world of Quant finance. His innovative ideas have led to casinos all over the world to play with multi-deck of shoes and even to change the rules of the game such as to cut the cards earlier.

Billy Walters

The High-Roller Sports Gambler with Hundreds of Millions in the Bank. Billy Walters is an American gambler of unusual standing. In his three decades of gambling he has managed to earn an enormous sum and remains the only high-stakes gambler in the history of the game with hundreds of millions in his bank account. His success, however, is deeply intertwined with that of his giant syndicate of rich gamblers to whom he introduces the lines where he sees value. His ingenuity and business acumen as the chairman of Stockponys.com have created the most successful financial assessment tool to compare odds from around the globe using his mastery of ‘Closing Line Value’ and information asymmetry to take on the bookmakers of the world and thus has earned himself the status of a gaming icon. However, he has been indicted for insider trading in the financial markets and sentenced to 5 years in prison but was released when he appealed. As before, his enormous ingenuity in making hundreds of millions in the world’s biggest gaming arena has not damaged his reputation. He is the sort of figure that inspires huge admiration for his tremendous ability to thrive in both the high-stakes world of gaming as well as the treacherous waters of the world of finance.

Phil Ivey

The ‘Tiger Woods of poker’ is one of the world’s greatest all-round gamblers. A highly skilled naturally gifted player who has dominated many poker games including being one of the best Gin Rummy players of all time and has won multiple World Series of Poker (WSOP) bracelets and several World Poker Tour (WPT) events including the 2002 WPT Bellagio Freeroll. As well as being a professional poker player Ivey is a high-stakes gambler and has been involved in two notable cases of edge-sorting in casinos around baccarat games, one at the Borgata in Atlantic City and the other at the Crockfords in London. Ivey and his business associate, Cheung Yin Sun, had won millions of dollars at the Borgata baccarat tables using edge-sorting and were due to be paid but the Borgata refused to pay them stating that Ivey had been using an illegal method to gain an advantage and therefore was not entitled to his winnings. Ivey claimed that he had simply found an obvious casino weakness and was using it to make money but the Borgata and Crockfords both stated that edge-sorting was against the terms of play of chemin de fer and therefore Ivey and Sun were not entitled to the money they had won.

Archie Karas

Archie Karas was born in 1950 as Anargyros Nicholas Karabourniotis. He was a Greek-American gambler best known for his phenomenal winning streak nicknamed ‘The Run’ in the early 1990s. Archie transformed a $50 loaned by a friend into a staggering $40 million within three years from 1992. The Run was so named because during his time as a gambler Archie played a variety of games including Poker, Pool and Aggressive Craps betting in huge amounts in high-stakes environment. In particular Craps, a negative-expectation game in the long run, was where Archie put all his money on Pass Line and odds bet. Archie lost his entire fortune in late 1995 and his life thereafter was marked by tragic decline. Archie was found dead in his apartment in Los Angeles on 7th of September 2024.

Amarillo Slim

Amarillo Slim (Thomas Austin Preston Jr.) was the very first professional gambler. He was a poker icon and brought poker into the open air of public entertainment. Slim would play poker in and out of Casinos and Poker Rooms all across the country. He has won many tournaments including the 1972 WSOP Main Event and won many WSOP bracelets in poker tournaments. The famous gambler would challenge anyone to any bet. He always managed to come out on top. It was said that famous individuals such as Frank Sinatra and even famous athletes like Muhammad Ali couldn’t beat Amarillo Slim in a game of cards or any other wagers. He was a gambler’s gambler. He made many TV appearances, including on late night talk shows. He’s the first poker celebrity and paved the way for all modern poker players.

Stu Ungar

Stu Ungar was the best all around poker player in history. His ability to read the people he played against and to remember the cards that had been previously discarded were a couple of his strengths. His greatest strength of all however was at the game of gin rummy, in which he was said to be the greatest gin rummy player of all time. His ability to win large pots of money at hold’em would come through his ability to read his opponents and pull off an incredible bluff. Ungar was a three time winner of the WSOP main event. He won his first two in 1980 and 1981. He came back from years of drug abuse to win the third in 1997. Although Ungar won a fortune playing poker he died a poor man. This was due in large part to his drug abuse and his inability to control his gambling. He would often spend all in hoping to hit a big hand and would play hands that he knew he was the under dog in. The man had great skill at the tables but was brought down by personal problems outside of poker.

Chris Moneymaker

Chris Moneymaker was an accountant before he went on to become a poker sensation and change the face of the industry. The amateur played in a $39 online satellite to win his seat to the 2003 $10,000 World Series of Poker Main Event and went on to defeat some of the world’s best players to claim the championship and a multi-million-dollar payday. Moneymaker’s incredible run of form has been credited for triggering the ‘poker boom’ after his story captured the hearts and imaginations of millions of around the world. Online poker rooms experienced huge increases in traffic as people tried their luck at becoming the next big thing at the tables and a new generation of poker players flocked to live tournaments in the hope of emulating Moneymaker’s success.

Tony Bloom

Tony Bloom is a name that is known throughout the world of sports betting. Known by his poker alias ‘The Lizard’ and by many as the owner of the Brighton & Hove Albion soccer team, he is the mastermind behind one of the world’s largest sports betting syndicates. Based in the UK, Tony and his team of experts utilize a host of complex quantitative models, pouring over vast amounts of data from all corners of the globe in order to pinpoint where the odds are being ‘mispriced’. And when they find it, they make a pretty penny from it. We never find out how much that pretty penny is, but we do know that a large portion of his winnings have been used to bankroll the Brighton & Hove Albion soccer team to the prestigious Premier League. As one of the few modern gamblers to have made a name for himself and amassed a small fortune, Tony is a true legend in the world of gambling.

Doyle Brunson

Doyle Brunson, affectionately known to fans worldwide as “Texas Dolly”, is arguably the greatest Poker player of all time. A true legend from the early days of Poker, Doyle Brunson traveled up and down the American South playing in many of the underground Poker Games that existed at the time. In addition to his success playing Poker tournaments, he won a record 10 WSOP Bracelets, including back to back Main Events in 1976 and 1977 with the very same hand of 10-2. It was after Doyle Brunson retired from full time Poker that he went on to write one of the first ever in-depth strategy books on the game, Super/System. The book revealed many of the Poker strategies that were used by the game’s top players at the time to the reader, increasing the skill level of the overall game of Poker. Sadly, Texas Dolly passed away in 2023 but his legacy will live on forever.

Kerry Packer

Kerry Packer was a media mogul from Australia and is widely recognized as the largest ‘whale’ ever to have played in casinos around the world. The amount of money he had at his disposal was legendary and his playing was feared by all the major casinos. He would often play for six-figure sums per hand in baccarat and blackjack, losing tens of millions of dollars in just a few days, only to come back and win it all back. He was also famous for his large tips to the casino staff, sometimes buying them cars and even paying off their mortgages.

What makes a gambler become legendary?

A gambler becomes legendary not simply by winning large amounts of money, but by leaving a lasting impact on gambling culture, strategy, or the industry itself. The most memorable figures in gambling history are often those who changed the way games were played, developed innovative winning methods, or inspired future generations of players.

One of the best-known examples is Edward Thorp, whose pioneering work on card counting transformed blackjack strategy and demonstrated that skill and mathematics could influence outcomes in certain casino games. Figures like Thorp became legendary not only because of their success, but because they fundamentally changed how players approached gambling.

A gambler can also achieve legendary status through influence and recognition within the wider gambling community. Some earn their place through remarkable achievements, while others become famous for helping popularize a game or attract new audiences. Chris Moneymaker, for example, is widely credited with helping spark the poker boom after his victory in the 2003 World Series of Poker, inspiring millions of players to take an interest in both online and live poker.

Ultimately, gambling legends are remembered for more than their winnings. Their innovations, achievements, and contributions to the industry often have a lasting effect that continues to shape gambling long after their biggest victories have passed.

Differences between poker pros and casino gamblers

The main difference between poker professionals and casino gamblers is that poker pros rely on skill, strategy, and long-term decision-making, while most casino gamblers participate in games that are primarily based on chance and are played against the house.

Professional poker players compete against other players rather than the casino itself. In most poker games, the casino earns revenue by collecting a small rake from each pot, regardless of who wins. To achieve consistent long-term results, poker professionals must develop strong strategic skills, understand poker theory, manage risk effectively, and maintain disciplined bankroll management to withstand inevitable losing periods.

Casino gamblers, on the other hand, typically play house-banked games such as roulette, craps, or slot machines. These games are designed with a built-in house edge, meaning the casino holds a statistical advantage over time. While some highly skilled Advantage Players use techniques such as card counting or other legal advantage-play strategies to improve their odds in specific games, casinos often monitor these activities closely and may restrict or limit players who consistently demonstrate an edge.

The biggest gambling wins in history

Archie Karas’ famous “Run” would probably be the largest documented amount of money won by a gambler playing against the house at casino games, coming in at around 40 million dollars. However, this was achieved over a period of three years and he has said himself he hasn’t played in years. The biggest single event payout would be from a progressive slot machine, these big payouts can occur at any time for very lucky individuals, with most paying out around the $20 million mark.

There are some legendary gamblers that have made a lot of money, some of the biggest sports bettors in history, poker players and some of the world’s largest quantitative syndicates. These people can have turnover of billions of dollars but it is spread over thousands of bets over the course of decades. In reality, they are more like high frequency trading firms than casino gamblers.

Frequently Asked Questions

Who is the greatest gambler of all time?

Archie Karas is famously said to be the greatest gambler in history. Not only did he amass a huge fortune within a short space of time, but he managed to achieve all of this whilst playing at casinos around the world. The legendary mathematician and gambler Edward Thorp is also said to be the greatest gambler in history. Although he makes his fortune from playing a variety of games, it is his incredible mathematical ability that sets him apart from the rest. 

Which gambler won the most money in history?

The world’s richest gambler is a difficult subject to tackle, as the majority of large cash games and private sports betting syndicates are kept extremely under wraps. Although billionaire Kerry Packer wagered millions of dollars in high-stakes casino games of baccarat and blackjack, he had also gone on some of the largest losing streaks in casino history. While there are some individuals, such as Edward Thorp and Tony Bloom, who have become rich through poker combined with legitimate quantitative investing, or by running their own proprietary sports betting syndicates, or even owning various businesses to earn very high returns on their invested capital, the vast majority of their wealth was not earned playing against the negative expectation of casino table games.

What games do famous gamblers usually play?

There are many famous gamblers, each with their own specialty of game or style.

• First and foremost are the mathematicians and advantage players, who use complex systems to beat games at a high rate of return. The most famous of these is probably Edward Thorp, who developed the first effective system for counting cards in blackjack. Today, there are many other games on which to apply these strategies, such as Baccarat, roulette, and others.
• Then there are the high-rollers of the casino, the so-called “whales” who bet enormous sums in the hopes of huge returns. Famous casino gamblers such as Kerry Packer like to bet large sums of money on Baccarat and/or blackjack, games in which there is the greatest potential for winning a huge amount of money.
• There are also the master sports bettors, who use in-depth statistics and other data to generate a high level of return on their wagers. Famous sports bettors like Billy Walters and Tony Bloom have made huge fortunes by betting on sports.
• And then there are the poker players. Poker has many variations, each with its own skill level and potential for return. The poker players that are best known are those that have made a fortune playing Texas Hold’em, a variation in which there are huge skill differentials between players. Famous poker players such as Doyle Brunson and Stu Ungar made a fortune by exploiting these skill differentials.

See also: How to Become a Professional Gambler: A Comprehensive Guide