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Featuring straightforward rules and a low house edge, Blackjack is one of the easiest casino games to get started with. But the nature of Blackjack also makes it one of the most difficult games to master.

Despite this, some players have won significant amounts by getting an edge over the house in Blackjack. Here is a comprehensive list of the most successful Blackjack players in history.

Don Johnson

Hailing from Salem, Oregon, Don Johnson is one of the most successful players in Blackjack history. Interestingly, Johnson didn’t always imagine himself as a professional blackjack player. As a teenager, he wanted to become a professional jockey. But his dreams got shattered when he grew taller than the maximum height limit for jockeys. However, he stayed close to the horse racing industry by taking up the job of a racetrack manager.

It was in the early 2000s when Johnson learned the game of Blackjack and started playing it on a regular basis. His first significant Blackjack win came in the year 2010 when he grabbed $220,000 by beating the Trump Taj Mahal in a Blackjack game. Shortly after this, Johnson was invited by Atlantic City casinos to play Blackjack at high stake tables.

Johnson accepted the offers but negotiated some tweaks to the standard Blackjack rules so that he could have a better edge. This led to him winning over $15.1 million in just a span of six months – $4 million from Caesars, $5 million from Borgata and over $6 million from Tropicana.

James Grosjean

James Grosjean is another highly regarded professional player in the Blackjack community. James first got introduced to the game of Blackjack when he was studying Economics at the University of Chicago. Since then, he has had several successful runs at both land-based gambling venues and online casino sites. 

Additionally, he has authored two best-selling casino gambling books – Beyond Counting and Exhibits CAA: Beyond Counting. In both books, readers can find a mathematical analysis of betting systems for Blackjack Switch and other casino games. Also, the books are filled with several strategies that James developed for advantage play.

Bill Benter

Born in 1957 in Pittsburg, United States, Bill Benter is one of the most successful casino players in the world today. With a knack for mathematics from an early age, Benter moved on to study physics at one of the most prestigious research universities in the US. However, his life took a U-turn when he came across the popular Beat the Dealer book by Edward Thorp.

Soon after, Benter joined a Las Vegas Blackjack card counting team that was started by Alan Woods. Here, he earned over $80,000 per year for a while. But after discovering that they were using the card counting system to play Blackjack games, Benter and his group were banned by the Vegas casinos. This eventually led to Bill trying his luck at horse race betting and developing one of the most popular analysis software for horse racing.

MIT Blackjack team

If you’ve played land-based or live Blackjack before, then you’d probably be aware of the MIT Blackjack team. Consisting of students from the Massachusetts Institute of Technology and other leading universities in the US, the group made fortunes by counting cards and using other complex betting systems. This was done at Blackjack tables worldwide.

Led by Bill Kaplan, the team had numerous successful Blackjack runs throughout the 1970s and 1980s. The winning spree of the Blackjack team has also inspired several books, with the most popular of them being Bringing Down the House by Ben Mezrich. What’s more, the story of the MIT team has been beautifully adapted in the film “21” by Kevin Spacey.

Kerry Packer

An Australian media tycoon and proprietor, the name Kerry Packer is akin to some of the most successful players in Blackjack history. Throughout his casino gambling journey, Kerry experienced a number of significant wins and losses. He then proceeded on to win over $33 million playing Blackjack at the MGM Grand Casino in Las Vegas.

Owing to his love for Infinite Blackjack and casino gambling in general, London’s Ritz Hotel had an exclusive room for Packer. Here, he would wager a minimum of $10,000 on each Blackjack hand. Interestingly, Packer wasn’t as successful at Baccarat as he was at the Blackjack tables. In fact, he is known to have lost more than $27 million in less than a year at high-stake Baccarat tables.

Ken Uston

Born in 1935 in New York, US, Ken Uston is another highly successful player in Blackjack history. In the gambling world of the mid-20th century, Ken was widely known for his top-notch card-counting skills. Using his knowledge of advantage play, Ken developed the reputation of an infamous card counter.

During his early days as a Blackjack player, he won significant amounts by counting cards and wagering on Blackjack side bets. But his advantage play led to him getting banned by several land-based gambling venues. Besides gambling, Uston was interested in computing and has written numerous best-selling books on video games and personal computers. Uston left the world at the early age of 52.

Bryce Carlson

As with several other Blackjack pros on our list, Bryce Carlson got introduced to the game of Blackjack in the 1970s. Because of his knack for exchanging Blackjack tips with other skilled players, Carlson took no time to become a professional player.

Bryce is also a highly respected writer in this field. His book, Blackjack for Blood, details comprehensive strategies to get an edge in the game. What’s more, Carlson is also the creator behind the Omega II Blackjack machine.