Top 6 Biggest Blackjack Wins & How to Make Money Playing Blackjack

Blackjack is one of the most popular casino table games that's survived the test of time and is still played by millions today, alongside Baccarat and Poker. As the digital world continues to take over, many of these classic casino games have transitioned to be playable at online casinos like Rivalry.

Blackjack is known for its low house edge and simple rules, being one of the easiest casino games to pick up and play. This doesn't change at an online casino, with the added benefits of being played in the comfort of your own home and a higher Return-To-Player (RTP) rate of 99.28%.

In this article, we'll explore the biggest Blackjack wins ever recorded, ranging from sheer dumb luck to mastered mathematical strategies. These stories will showcase the incredible fortunes that are possible when playing Blackjack.

Could you be the next player in the Blackjack Hall of Fame? Read on for the biggest Blackjack wins of all time and learn how to win big when playing online at Rivalry.

Honorable Mention: Shoeless Joe - $1.5 million

The story of the mystery man, aka Shoeless Joe, is a near-perfect tale of rags to riches. He earned his notorious nickname by entering a casino barefoot back in 1995. He was reportedly made homeless after being kicked out by his wife, with nothing but a $300 security check to his name. Facing the streets and potential starvation, the stakes couldn't have been any higher for him.

Trying his luck, he managed to win $1.5 million from his $300 security check in a single day of playing Blackjack. However, those looking to make a bag through Blackjack following Shoeless Joe's example should think twice. His story shows why Blackjack strategy is so important — his game plan involved reckless doubling and splitting (which you should always try to avoid), which meant he also lost most of his winnings on the same day. Despite this, he's still down in the history books as one of the biggest wins in Blackjack.

#5: Dana White - $2 million

Dana White is a story of "what ifs." Aside from being an expert Blackjack player, he's also well-known as the president of the UFC and an American businessman used to being in the public eye, not always for good reason. In 2012, Palms Casino accused him of card counting after he racked up considerable winnings and banned him.

White was eventually allowed back at Palms Casino, thanks to the new casino manager in 2014. Over a few months, White accumulated around $2 million through playing Blackjack. However, the casino first made him lower his bets from $25K to $5K before capping his wins at $2 million to finally end his winning streak.

Imagine the casino manager hadn't instated White's win cap; he would likely have been much higher on this list. That hasn't stopped White from still enjoying a Blackjack game, though. He's known for splashing the cash at any casino that will have him but has never reached a winning streak like the one in 2014.

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#4: Ken Uston - $4.5 million

Ken Uston, otherwise known as the King of Blackjack Strategy, invented the genius idea of teaming up together to play Blackjack. Alongside mastering Blackjack strategy and the statistics behind this classic card game, he's also been credited with inventing famed card counting techniques. Thanks to Uston, many casinos have adopted multi-hand Blackjack and use several card deck shoes to negate card counting.

In the '70s and '80s, Uston led his Blackjack team to victory at several casinos, where they wagered as much as $12K per hand, raking millions in profit returns. It's estimated that Uston and his Blackjack squad gathered around $4.5 million, marking their names in the history books for years to come.

#3: Don Johnson - $15.1 million

As the millionaire CEO of Heritage Development, Don Johnson played Blackjack games for fun with no issues dipping into his substantial bankroll to place large bets. Although he had luck and wealth on his side, Johnson is also known for his impressive mathematical blackjack strategy and card counting abilities.

Johnson's win didn't happen at the same table. It was instead accrued over several months, starting in December 2010. He followed Blackjack best practices, like sticking to the most favorable house rules and taking every opportunity to split a high hand into four. His calm and calculated playing style led to his enviable Blackjack wins.

Johnson's Blackjack success was so widely known that it led to the 2014 Netflix documentary titled; "The Player: Secrets of a Vegas Whale." This program deep dives into the life of a notorious gambler, providing an insider's look at how he beat the odds and walked away with millions.

#2: Kerry Packer - $40 million

Kerry Packer went balls to the wall to win $40 million at the Las Vegas MGM Grand Casino. His gameplay strategy was wild, playing eight hands simultaneously on the same table. He maintained a default stake of $250K in each round.

After less than an hour at the Blackjack table, he walked away with a jaw-dropping $40 million. His dealer even got a nice $1 million tip. While he isn't the most skillful Blackjack player, he proves that having a juicy bankroll can also be a winning strategy. His extravagant play style eventually resulted in him getting a lifetime casino ban.

#1: The MIT Blackjack Team - $50 - 100 million

The MIT Blackjack Team was a collective of students from MIT, Harvard, and other educational institutions. They used advanced mathematical strategies like card counting to beat casinos nationwide, headed by Bill Kaplan.

With around 80 members in their ranks, the MIT Blackjack Team visited various casinos in the 80s and 90s, even going as far as to wear disguises to avoid suspicion and recognition. They would have one player acting as a "spotter" to card count and alert the "big bettor" when to approach the tables with high-value cards left in the deck.

During their prime, it's estimated that the MIT Blackjack Team earned anything between 50 to 100 million with their escapades. Their triumph and unrivaled strategies inspired the iconic film "21," based on the New York Times bestselling novel by Ben Mezrich, "Bringing Down The House."

Many people took the movie and novel as gospel and incorporated the MIT Blackjack Team strategies into their gameplay. As a result, casinos have had to evolve their Blackjack game to make the MIT Blackjack team's strategies ineffective in many Blackjack tables today.

How to Win Big Playing Blackjack

These incredible wins show that Blackjack isn't merely a game of chance; it's also a game of strategy and skill. While luck definitely played a role in Shoeless Joe's victory, many of these other winners were skillful blackjack players who knew how to increase their chances of winning real money through strategic decisions.

So, how can you increase your chances of walking away with a jackpot like these Blackjack champions? Let's check out some proven strategies and tips to maximize your chances at the Blackjack table.

Card Counting: The Controversial Yet Powerful Tactic

Card counting is one of the most famous strategies in Blackjack, largely due to its portrayal in movies and proven effectiveness when done correctly. While it's often misunderstood as cheating, card counting is legal. The premise is that players gain a slight edge over the house by tracking the ratio of high cards to low cards remaining in the deck. This technique has led to some of the biggest Blackjack wins in history, as seen with Australian businessman Kerry Packer and Ken Uston on this list.

The most common method, the Hi-Lo system, assigns values to each card — low cards (2-6) are +1, high cards (10s, face value, Aces) are -1, and 7-9 are neutrals with a value of 0. By keeping a running count as cards are dealt, players can adjust their decisions and bets when the deck is rich in high cards, which favors the player. In multi-deck games, players adjust the "running count" into the "true count" by dividing the running count by the estimated number of decks remaining in the shoe.

Unfortunately, card counting at online casinos is more difficult than in a land-based casino. It's hard to know how many decks are used in online Blackjack, often eight or more. Live Blackjack games also tend to have the Dealer shuffle the cards or use CSM (continuous shuffling machines), making it impossible to track the cards and reducing the advantage of card counting.

Basic Blackjack Strategy: Knowing When to Hit, Stand, Split, or Double

While Blackjack can seem like a game of chance, mastering basic strategy is what separates casual players from the big winners. Unlike other casino table games where the house has a significant edge, Blackjack offers a unique opportunity to lower that advantage through their decision-making. A solid strategy minimizes your losses and puts you in a position to maximize your wins.

The core of basic strategy in Blackjack is understanding the mathematical probabilities behind each decision — whether to Hit, Stand, Split, or Double Down. You can make the optimal choice in every situation by following a basic strategy chart (based on the Dealer's upcard and your own hand). This approach doesn't guarantee wins on every hand but reduces the house edge to as little as 0.5% if you execute it correctly.

Here are some common decisions from a basic strategy chart to guide you on whether to Hit, Stand, or Double Down based on your Blackjack hand values and the Dealer's upcard value.

Player Hand: Hard Totals (No Ace)

  • 8 or less: Always Hit
  • 9: Double Down if the Dealer's upcard is 3-6. Otherwise, Hit.
  • 10: Double Down if the Dealer's upcard is 2-9. Otherwise, Hit.
  • 11: Double Down unless the Dealer has an Ace (Hit).
  • 12: Stand if the Dealer shows 3 - 6. Otherwise, Hit.
  • 13 - 16: Stand if the Dealer shows 2 - 6. Otherwise, Hit.
  • 17 or more: Always Stand.

Player Hand: Soft Totals (Ace counted as 11)

  • Soft 13/14 (Ace +2 or +3): Double Down if the Dealer shows 5 - 6, otherwise Hit.
  • Soft 15/16 (Ace +4/+5): Double Down if the Dealer has 4 - 6, otherwise Hit.
  • Soft 17 (Ace +6): Double Down if the Dealer has 3 - 6, otherwise Hit.
  • Soft 18 (Ace +7): Stand if the Dealer shows 2, 7, or 8. Double Down if the Dealer has 3 - 6. Hit if the Dealer shows 9, 10, or Ace.
  • Soft 19/20 (Ace +8/+9): Always Stand.

Choosing the Right Online Casino

Choosing the right online casino is crucial to having fun and winning big when playing online Blackjack. Not to toot our own horn, but we think you're already in the right place with Rivalry. Regardless, here are some factors to consider when choosing your online casino.

  • Licensing and Regulations: Ensure the casino you choose is licensed by a legitimate authority in the industry. For example, Rivalry holds official certification from the Isle of Man Gambling Supervision Commission, one of the most respected licenses in the biz.
  • Mobile Compatibility: As a society, we're glued to our phones - that's just a fact. That's why you want a casino that is 100% mobile-compatible for iOS and Android devices, so you can play on the go or on the toilet. Luckily for you, Rivalry's online casino is 100% mobile-friendly, so you can play Blackjack in either portrait or landscape mode and start winning big.
  • Payment Options: A good casino will offer various payment options to suit customers from all walks of life. Rivalry has traditional methods like Visa, Mastercard, bank transfers, and cryptocurrencies like BitCoin, Tether, and LiteCoin.
  • Casino Bonuses: The best casinos offer welcome bonuses, cashback, free play, and deposit bonuses. Rivalry's welcome bonus doubles your first deposit up to $100 to use on anything on our website!
  • Customer Support: For any burning questions, you'll want accessible customer support. Rivalry has a dedicated FAQ center and 24/7 customer support, accommodating multiple languages like Brazilian-Portuguese.

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Any NUTZ you collect between now and then will be stored in your NUTZ-sack, which can be later exchanged for $RVLRY. What you do with your NUTZ in your spare time is your business, but it's in your best interest to start storing them, as $RVLRY will mean even more bets on our website and other goodies!

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Bankroll Management: Play Smart & Win Big

Although we could be wrong, we're almost certain you don't have millions of dollars available like some of these Blackjack winners. This means you need to be conservative and careful with your funds. After all, effective bankroll management is the cornerstone to success in all casino games, not just Blackjack.

Set yourself clear limits on the money you bet on each Blackjack game. This should be an amount you're comfortable losing — never wager more than you can afford. A general rule of thumb is to bring 1% of your total bankroll to a session. For example, if you have $1,000 for gambling, only wager $10 per round. This ensures that a few losing Blackjack hands won't wipe you out completely.

Set yourself clear win and loss limits, which you can also do via your Rivalry account settings. Once these limits have been reached, you must know when to walk away. Avoid tilting, especially on a losing streak, as these can lead to emotional decisions like increasing bets to win back losses. Managing your bankroll includes staying disciplined and avoiding emotional betting, which can lead to bigger losses. Our free learning resource, Rivalry Academy, can hold your hand with guides on responsible gambling and understanding odds.

Final Thoughts

With the right strategy, smart bankroll management, and even some card-counting techniques, you can tilt the odds in your favor. From legendary wins that have made history to tips on scoring a jackpot, you're now equipped with the knowledge to tackle the Blackjack tables with confidence.

While chasing huge Blackjack wins can be enticing, it's crucial to approach gambling responsibly. Understanding how the game works, the house edge, card counting techniques, and choosing a trusted casino can boost your betting experience and even increase your chances of winning. With Rivalry, you can always set self-exclusion limits on your account to ensure you never bet more than you can afford to lose.

Ultimately, whether you're playing for fun or aiming to be the next biggest Blackjack win, remember that Blackjack is all about playing smart, staying calm, and knowing what decision to make next. Who knows, you may even become another great Blackjack story!