MONSTER Blackjack Wins Over the Years

Characterized as an elegant blend of luck and skill, blackjack has the potential to award some pretty delicious prizes to players. Unlike poker and other tournament-based games, the most significant wins at the blackjack table are likely not public knowledge. Unless someone catches it on camera or posts about it on the interwebs, most people won't ever hear about it.

There are also plenty of high rollers who would likely not want their casino habits shared for all to see. However, there are a few known instances of blackjack players taking away hefty sums from the tables. While we might not know about every huge win, here are a few of the ones we do know about — at least the details that are publicly available, anyway. 

Card Counting Kings and Queens 

Quite possibly the most significant blackjack winners ever are the notorious MIT blackjack team. Formed around 1979 by students from MIT, Harvard, and other prestigious institutions, the team had dozens of members over the years it operated. Using card counting and other acts of subterfuge, they managed to win millions of dollars from unsuspecting casinos.

Operating until the early 2000s, the blackjack team's total winnings remain a mystery. The exact amount they amassed is a secret known only to the team members themselves. Those who have dared to speak publicly about their success are cautious, refraining from revealing the actual sum for obvious reasons. Speculation suggests that the team's winnings could range from a staggering $5 million to a mind-boggling $100 million. 

While the exact figure remains unknown, the reluctance of former team members to share their earnings hints at a substantial amount. American author Ben Mezrich famously wrote a book called Bringing Down the House about the exploits of six members of the blackjack team and the millions they won. He used composite characters and different names, but swears by the story's authenticity. 

Eventually, Mezrich’s account was made into the 2008 film 21, starring Jim Sturgess, Kate Bosworth, and Laurence Fishburne. The book and the resulting movie have come under scrutiny since they were released though, with some of the events being contested by the real-life people involved.  

UFC Boss Conquers the Blackjack Tables 

Dana White is recognized as the face and boss of the UFC, one of the most successful fighting promotions in the world. A lesser-known aspect of the man is his skills at the blackjack table, which have seen him win upwards of $7 million after only a single night of playing. In interviews dating back several years, White has detailed how his success at the tables has seen him win some very generous prizes, often over $1 million.

White's blackjack success has its drawbacks though. His ability to play is severely restricted nowadays as casinos are wary of his high stakes wins. According to White, various venues have imposed play limits, capped his winnings, and taken other measures. In one instance, the Palms Casino even presented him with a UFC style belt, declaring him the Blackjack Champion and requesting he refrain from playing at the venue again.

There is even a video online of White receiving a call from a casino manager asking him not to return for a while. Allegations of card counting are nothing new, but White says he has never used the tactic, which is legal, to win. Casinos still welcome the UFC boss in, but not all of them offer him high stakes. In an August 2022 interview with GQ, White explained that casinos have not necessarily banned him, despite reports to the contrary; they just don't want him playing the high stakes he likes.

Media Mogul Takes a Casino to the Cleaners 

Australian media tycoon Kerry Packer was known for his vast business empire and sessions at the blackjack tables. He apparently won and lost a fortune playing blackjack over the years. Luckily the man was a billionaire because his play levels were truly eye watering if you can believe the rumours of his exploits. One story always does the rounds whenever the topic of the biggest blackjack wins comes up though, because he supposedly won tens of millions in only 40 minutes. 

Depending on the source and where you read about the story, sometime in the 1990s, Packer was playing at a casino somewhere in Las Vegas. Which casino and the exact date differ, as does the overall prize he won, which only adds to the mystique of the whole tale. As the story goes, over about 40 minutes and across eight tables, Packer won between 20 and 40 million dollars, playing $250,000 a hand. If true, he would likely have the record for the biggest win at the blackjack tables ever. The story has been retold so many times that it's hard to know the truth; it certainly makes a good story though. 

Don Johnson Changes the Game

His name isn't well known outside of the casino and horse racing industry, but Don Johnson is a very rare individual. He negotiated new rules for a casino game, blackjack, and then walked away with a small fortune of around $15 million. Sound ridiculous? It's not every day somebody can walk into a casino and tell them to change its games to suit them. Well, the truth is often stranger than fiction. 

Following the 2008 financial crisis, it was a grim time for businesses; consumers didn't have much disposable income. Even casinos felt the pinch, forcing them to get creative and offer modified versions of standard games to attract high rollers. In 2011 Johnson took up the offer and negotiated some terms for blackjack that you would never see in the modern era. He asked for six decks, a maximum table play amount of $100,000, and a 20% loss rebate that would reset every day, to name just a few of the stipulations.

According to Johnson, with his rules, the house edge was lowered to less than 1%. Generally, the house edge for blackjack is over 2%. Surprisingly, three casinos agreed to his terms and Johnson won some big prizes as a result. He took over $6 million playing blackjack one night at Atlantic City's Tropicana Casino. Johnson won another $5 million from the Borgata and at least $4 million or more from Caesars. 

At one point, Johnson says he won $800,000 in one hand, while another three hand sequence scored him $1.2 million. Eventually, after watching millions of prizes walk out the door, the casinos refused to offer these rules and reverted back to the standard set. It's unclear what happened next, but it appears Johnson stopped playing and quit while he was ahead.

The Holy Rollers Break the Bank 

Very similar to the MIT blackjack team, just a little lesser known, a team of keen evangelicals known as the 'Church Team', were counting cards in blackjack at casinos all around America from 2005 to 2011. Like the MIT team, the exact figure won by the Church Team isn't known, estimates reach well into the millions. According to former team members who have since shared their experiences, the syndicate had dozens of players and investors during their six year run. 

Authorities have described the Church Team as one of American history's most sophisticated card counting operations. The Simpsons even did an episode about them. Their story was told in its entirety during a documentary called Holy Rollers: The True Story of Card Counting Christians directed by former group member Bryan Storkel. The exact extent of their winnings will likely never be known, but it's probably a safe bet it was very lucrative for everyone involved.

Ben Affleck Says He is a Danger to Blackjack Tables 

Hollywood megastar Ben Affleck has been in some truly outstanding films, and some less than stellar ones. However, what you may not know is outside of the glitz and glamour; he is a keen casino game player. 
He actually won the 2004 California State Poker Championship, qualifying for the 2004 World Poker Tour final tournament. Along with Leonardo DiCaprio and Tobey Maguire, Affleck was also part of the now infamous high stakes game run by Molly Bloom and immortalized in the film Molly's Game. If you haven't seen the movie, and you like poker, after you finish reading this go watch it immediately, you won’t regret it. 

Aside from poker, Affleck is also a top-notch blackjack player. According to media reports and paparazzi who follow around actors like vultures, Affleck has won some truly staggering prizes while playing blackjack. In one instance back in 2014, he was asked to leave the high stakes room at the Hard Rock Hotel in Las Vegas and play a new game after a series of wins aroused suspicion he was counting cards. 

Depending on the source, Affleck reportedly walked away from the Hard Rock Hotel with between $800,000 and over $1 million. After the media storm, Affleck said he likes blackjack and has invested a lot of time to get good at the game, making him dangerous to blackjack tables everywhere. So if you are a blackjack table, be afraid, be very afraid, because Ben Affleck is apparently coming for you.

Blackjack Competitions Offer Some Big Prizes Too

In the early 2000s somebody had an idea to create a World Series of Blackjack, similar to the World Series of Poker. The series only lasted three sessions, but it awarded grand prizes of between $100,000 and $500,000. Other big blackjack tournaments around the world have offered prize pools of up to and over a million dollars as well. While these are relatively small in comparison to other high stakes wins, they are still nothing to scoff at.