Blackjack’s Biggest Winners and How They Did it

From automatic shufflers to multi-deck shoes, Blackjack has undergone major changes since it was first played with a house-backed Dealer in Nevada in 1931. Most of these changes didn’t come into effect until the ‘60s, which is around the same time that Edward Thorp’s ground-breaking book Beat the Dealer was released. That publication put Blackjack, and more specifically card counting, on the map and it became a big target for advantage players everywhere. Millions of dollars have been handed over to card counters ever since, causing casinos to make changes to the game in order to increase house edge.

In this article, we’re showcasing six of the biggest and how to play Blackjack, check out our online Blackjack guide because you’re going to want to get started after reading about these remarkable accomplishments. We’ll start on the campus of Massachusetts Institute of Technology.


1. MIT Blackjack Team

In the early ‘80s, Harvard graduate Bill Kaplan backed and co-managed a group of MIT students who were using card counting techniques to beat casinos and generate a profit in Atlantic City. When Kaplan joined the syndicate, he made key changes to the way they were operating, combining team play with card counting in order to maximize profits, flipping the edge as great as 4%. The MIT would place a card counter at a table, who would signal the Big Player to enter the game when the shoe was rich in 10s; this way, they were able to evade detection for a long time.

Kaplan wasn’t the only investor. Over the years, external investors saw unreal returns on their stakes north of 300%, making it one of the most profitable Blackjack schemes in history. Kaplan was eventually banned from casinos, causing him to step back from the venture and return to his real estate business.


2. Kerry Packer Plays Eight Hands at Once

If you think about the biggest Blackjack winners ever, you likely think about Kerry Packer. When the billionaire Australian media tycoon would show up at any casino in Las Vegas or London, it was risky business for the establishment, as his wild spending sprees could bankrupt a casino just as easily as it could secure them a healthy financial future. He’d been known to play numerous Blackjack hands a round, sometimes betting $75,000, $250,000 and eventually $500,000 a hand, often winning and losing in the eight-figure range. Packer was a favourite among the service industry, as he was known for his tendency to pay off dealers’ and servers’ mortgages when they provided good service.


3. Shoeless Joe Wins $1.3 Million

When a gruff, homeless-looking man walked into Treasure Island Casino with no shoes on, not much was expected from his initial investment of $400—likely a Social Security check from the government. The man stationed himself at a Blackjack table and began playing, mostly following basic strategy, but also veering away wildly in unexpected ways. He started winning and kept winning, eventually reaching $1.3 million, at which point the casino began comping him and providing him with appropriate attire.

The man, who called himself Joe, continued to play as his luck ran dry. He allegedly played down his massive bankroll to $60,000—still not bad for a $400 investment.


4. Ken Uston

Hall of Fame Blackjack player, Ken Uston, had a mind for numbers. As a 16-year-old, he started attending Yale for Economics before doing his MBA at Harvard Business School. Uston was an avid poker player, and in a game, he met Al Francesco—the man credited for inventing Blackjack team play. Uston ended up joining Francesco’s Blackjack team where they combined team play with advanced strategy and card counting in order to amass $4.5 million in profit. Uston was eventually banned from casinos across the nation, and if he showed up on their premises, they’d immediately start to look for his undercover teams. If anyone knew how to win big at Blackjack using math to gain an edge, it was Ken Uston.


5. Don Johnson Has a Blackjack Year Worth $15 Million

Don Johnson, a former racetrack manager, didn’t meet his fortune riding on luck—he flipped the edge in his favour by negotiating player-friendly Blackjack rules with casinos. During the economic depression of 2008, many casinos were willing to take a cut in order to get high rollers back at their tables. Some of the changes that Johnson negotiated include getting to re-split Aces, having the Dealer stand on soft 17, and getting a 20% cash-back rebate on losses. With the changes, Johnson won a total of $1.2 million from three back-to-back hands, which contributed to the $15 million he won from Tropicana, Borgata and Caesars in 2011 during a six-month span.


6. Dana White Wins $2 Million in Three Months

In 2012, UFC promoter Dana White had his credit cut in half at Palms Casino in Las Vegas after experiencing a hot streak playing Blackjack. Frustrated with the decision, he boycotted the casino for almost two years until he was lured back with a gift of a $5,000 bottle of wine. When he returned to the Blackjack tables, he enjoyed another hot streak that stretched over two months. He was playing $25,000 a hand and winning, so his limit was decreased to $5,000, and then eventually, he was sent packing. White took $2 million from the casino in his second stint and tipped around $200,000 to dealers, who will certainly be sad to see him go.

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