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Nearly everybody gambles in some form or another, whether that be a lottery ticket, a prop bet with friends or playing casino games like blackjack and roulette at an online casino. Just as in any competitive forum, some players are more skilled than others. In the context of gambling, that success can lead to fame and great fortune. We’ve taken a look back through recent history and put together a list of the most successful gamblers of all-time. While their backgrounds and stories may vary, they all share one important factor in common: they win.

Amarillo Slim

American gambling legend, Amarillo Slim started by touring the country looking for poker games. He may have won the 1972 World Series of Poker but Amarillo Slim was better known for his famous proposition bets. He had a reputation for making sly and witty wagers that would ensure himself a win. It could have been at the poker table, race track, pool hall or even ping pong table; Amarillo Slim would have a clever proposition ready and waiting. Sadly, this legendary gambler passed away in 2012 at the age of 83. 

Edward Thorp

As a former math professor, Thorp is considered by many casino gamblers as the father of modern card counting. He wrote the card counting book ‘Beat the Dealer’ in 1962. This groundbreaking guide was the first book to clearly outline the mathematical formula needed for players to gain an edge over casinos in blackjack. Thorp put his card counting skills to the test when a friend bankrolled him with $10,000 and they walked away up $11,000 after their first weekend at the tables. Thorp was also known to have developed winning formulas for other popular casino games such as baccarat, backgammon and roulette. The man was a mathematical genius and clearly ahead of his time as a gambler.

Archie Karas

Any gambler who can take $50 and turn it into more than $40 million in just 3 years deserves a spot on this list. That incredible run enjoyed by Karas between the years of 1992 and 1995 is one of the longest winning streaks ever recorded and it quickly made a name for the Greek gambler. Karas came over to America at just 15-years-old and started making money gambling at the pool hall before moving on to poker and casino games. Although he’s won and lost many fortunes in his time, few gamblers will ever put together a winning streak as impressive as Archie Karas. 


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Billy Walters

When it comes to betting at casino sportsbooks, not many gamblers can equal the resume of Billy Walters. Raised by his grandmother in Kentucky with next to nothing, he started betting on baseball at a young age with money earned from his paper route. As Walters got older, his bet amounts quickly grew along with his success. Walters won consistently at sports betting for over 30 years and was eventually gambling millions of dollars on a weekly basis. Some of his wagers grew so large they had the power to shift the betting lines all on their own. As of 2014, his net worth was estimated at over $100 million. However, Walters was found guilty of insider trading in 2017 and served four years in prison before his sentence was commuted by former President Donald Trump.

Doyle Brunson

The game of poker is enjoyed by millions of players around the world and part of that has to do with Doyle Brunson. Nicknamed Texas Dolly, Brunson is a two-time winner of the World Series of Poker (1976, 1977) and has done as much as anyone to grow the popular card game. Now a member of the Poker Hall of Fame, Brunson was the first ever player to win $1 million in poker tournaments and enjoyed great success on the felt for decades. He also wrote some of the game’s most definitive books, one of those being his 1978 publication, ‘Super System’, which has since become the Poker bible for millions of gamblers. 

Bill Kaplan

You may not be familiar with his name, but Kaplan hit the mainstream when his story was turned into a Hollywood movie starring Kevin Spacey called ‘21’. Kaplan helped put together the famous MIT blackjack team; a group of young students who used shuffle tracking methods and card counting systems to beat the casinos. The team was able to gain an edge on the house and they won a lot of money as a result. While Kaplan’s team of talented blackjack players eventually disbanded, what they were able to accomplish at the tables will not soon be forgotten.


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