Meet The Biggest Blackjack Winners Of All Time

Blackjack has been a popular game in casinos for decades. It’s simple to learn, quick to play, and gives you the chance to try and beat the dealer by getting closer to 21, without going over. But what really captures people’s attention are the rare moments when someone walks away from the table with a massive win.

This blog looks at a handful of real people who’ve done just that—won large sums of money playing blackjack. Each example often comes from games played at high-stakes tables, where large bets and the particular setup of the game contributed to some notable wins.

Whether you’re just learning about blackjack, or want to understand what may be possible in very specific circumstances, this guide will give you an honest look at some of the biggest wins ever recorded—and help you understand how the game actually works.

Breaking Down Huge Blackjack Prizes

Blackjack, often called “21,” is a card game played against the dealer. The aim is to try and get a hand total that’s closer to 21 than the dealer’s, without going over. Each card has a value: numbered cards are worth their number, face cards (Jack, Queen, King) are worth 10, and Aces can be either 1 or 11.

Most large blackjack wins tend to happen at high-stakes tables, where the betting limits are set much higher than average.

In the UK, all licensed blackjack games—whether online or in-person—are regulated by the UK Gambling Commission (UKGC), which means strict standards are in place to ensure fairness and responsible gambling. Limits on stakes may also be applied, either by the casino itself, or as part of the safer gambling tools available to players.

Higher stakes can potentially lead to larger wins, but they also mean losses can add up more quickly when a hand doesn’t go your way. In blackjack, outcomes depend on both the cards dealt and the choices you make during the game—such as when to hit, stand or double down. However, even with good decisions, the final result can’t be predicted or controlled.

Here are a few real examples of players who made headlines with huge blackjack wins:

Don Johnson – Is reported to have won around £10 million across multiple Atlantic City casinos between 2010 and 2011 by negotiating game rules that made blackjack more favourable.
Kerry Packer – The Australian businessman was known for his high-stakes gambling, and it’s widely reported that he may have won substantial amounts during a session at a London casino in the 1990s. While some estimates suggest winnings of over £11 million, exact figures have never been officially confirmed.
Dana White – The UFC president is said to have enjoyed a number of profitable blackjack sessions during visits to casinos outside Las Vegas. Reports have claimed total winnings in the millions over time, though precise amounts and outcomes are not independently verified.
Fred Smith – The founder of FedEx has shared a story in interviews about using blackjack winnings to help cover a critical company expense during its early days. Although the tale is well known, the details and amounts involved have not been independently confirmed.

Las Vegas: Home To The Biggest Blackjack Stories

Las Vegas is often seen as the centre of casino gaming, with many of the world’s biggest blackjack wins taking place in its high-limit rooms. The city is home to dozens of large casino resorts, each with different table rules, betting limits, and versions of blackjack.

Here are real people who have won significant amounts while playing blackjack in Las Vegas:

Archie Karas – During a long winning streak in the early 1990s, Karas reportedly made over £4 million from blackjack as part of his well-known gambling run across several Vegas casinos.
James Grosjean – A skilled player known for using legal advantage techniques in Las Vegas. His exact winnings are not public, but his success led to lawsuits and changes in casino procedures.
Terry Watanabe – Though best known for his overall losses, Watanabe also had periods where he won hundreds of thousands of pounds at the blackjack tables in Vegas before eventually losing much more.
Akio Kashiwagi – A wealthy Japanese businessman who bet £50,000 or more per hand at Las Vegas casinos. Reports from the early 1990s suggest he experienced blackjack wins and losses in the multi-million-pound range.
Bob Stupak – The Las Vegas casino owner himself was known for high-stakes blackjack sessions, once reportedly winning over £750,000 in a single night before retiring from play.

Each of these cases involved very high betting amounts. While some players played under specific conditions, most took part in games with standard rules, but placed large stakes.

High-stakes tables offer the possibility of larger wins, but they also mean that losses can be more significant. Blackjack is a game shaped by both decision-making and chance—players make choices that affect each hand, but the cards dealt remain unpredictable. There’s no system or strategy that can guarantee a particular outcome.

Casino conditions in Las Vegas can differ from one venue to another. For instance, some blackjack tables might pay 3:2 for a natural blackjack (an Ace and a 10-point card), while others offer a lower potential payout of 6:5.

This difference might seem small, but it changes the return you receive if you win with a blackjack, and can affect how much you might win across multiple hands. These types of rule variations also influence the house edge, meaning the odds of the game can shift depending on where and how you choose to play.

Is There A Secret To Frequent Blackjack Wins?

Blackjack is often seen as one of the most “favourable” games in the casino—but only if it’s played with the right decisions and under the right conditions.

In every version of blackjack, the house edge refers to the casino’s built-in advantage. It’s a small percentage of each bet that, over time, ensures the house earns more than it pays out. But that edge can change quite a lot depending on how the game is played.

Here’s how it works:

Using a solid playing method – If you follow what’s called “basic strategy” (a decision guide based on maths and probability), you can potentially reduce the house edge to as low as 0.5% in many standard games. This means that for every £100 bet, the expected average loss is around 50p. However, as blackjack involves an element of chance, any winnings can never be guaranteed.
Making frequent mistakes – If you guess or play based on “gut feeling” instead of basic strategy, the house edge can potentially rise. In many cases, it can go up to 2% or more, depending on how many wrong choices are made—such as hitting when you should have stood or failing to split pairs at the right time.
Game rules and versions – The rules of each table can affect the edge too. Some examples:
- If the dealer is required to hit on a “soft 17” (a hand that includes an Ace counted as 11), the house edge increases.
- Single-deck games (using just one deck of cards) often provide slightly better odds for players, but they are rare.
- Tables that pay only 6:5 on a blackjack instead of the traditional 3:2 payout give a much lower return on potential wins, increasing the house edge by over 1%.

That means even though blackjack can offer some of the best odds in a casino, those odds rely on making the right decisions consistently. And because the game is random, no outcome can ever be predicted or guaranteed, no matter how well you play.

Every time the deck is shuffled, the result is completely independent of past outcomes. No winning streak lasts forever, and betting systems—such as increasing bets after losses—do not improve the odds.

Play Online Blackjack at Ivy Casino

If blackjack stories have sparked your interest, Ivy Casino is fully licensed by the UK Gambling Commission and offers a secure setting for online play. You’ll find classic blackjack alongside other well-known games, like roulette and a variety of slot titles. Whether you’re new to these games or experienced, Ivy Casino’s setup is straightforward and easy to use.

Browse the site and you may quickly spot your preferred games or have a go at something new. Whether you’re interested in blackjack, or simply want to see what else is on offer, logging in or signing up is quick.

Every game at Ivy Casino, including blackjack, follows clear terms and conditions, with outcomes based on chance. It’s important to stick to your personal limits, take regular breaks, and play in a way that feels manageable. If you ever feel things are becoming difficult, support is available to help you keep your experience balanced and enjoyable.

_{*All values (Bet Levels, Maximum Wins etc.) mentioned in relation to these games are subject to change at any time. Game features mentioned may not be available in some jurisdictions.}

_{**The information provided in this blog is intended for educational purposes and should not be construed as betting advice or a guarantee of success. Always gamble responsibly.}