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Famous Blackjack and Roulette Players and Their Strategies

In this article, I’ll provide an overview of how some of the most renowned casino players managed to beat the games of blackjack and roulette.

What strategies did they employ? Did they resort to cheating? Or were they merely capitalizing on loopholes that emerged on specific tables?

Most importantly, I’ll address whether their strategies can be replicated and whether you can utilize them to generate profits in land-based and live dealer blackjack and casino games.

I’ll focus on players whose exploits mean something to you. I’ve left out the following:

  • Players from the 19th century, as what they did, no longer apply.
  • Outright cheaters who use electronic devices – you don’t own the device.
  • Blackjack card counters – this is a subject in its own right.
  • Billionaires who gambled big and won big just for fun – that’s just nasty!

Consider this article as fun reading that might give you some fresh ideas. Afterwards, you should have a decent overview of what it takes to be a successful blackjack or roulette player and how these two games differ.

famous blackjack and roulette players

Legendary Blackjack Players

The world of legendary blackjack players is primarily composed of two groups: advantage players, predominantly card counters, and thinkers who ponder over blackjack in an almost scientific way.

The two groups often overlap, which perhaps shows the direction your training should go.

The best blackjack players are in some way involved with card counting. I won’t include the famed MIT card counting team, as they used their immense skills in a coordinated effort to beat the casino.

There are many good blackjack players and researchers, and many of them wrote books on the subject. There’s a neverending stream of books about blackjack from the 1960s onwards, and game fans like to read them.

I will look at two players, a Don, who approached the game from a scientific standpoint and our representative of this entire group. The other Don, an advantage player, famously created an advantage for himself and then exploited it.

Let’s see what we can learn from the duo of Dons.

Don Schlesinger

Don Schlesinger’s work in the field of blackjack spans over five decades, and it contributed significantly to the modern understanding of the game.

Some of his research touches on card counting, but Schlesinger was more concerned with the overall mathematics of the game.

It’s incredible how deep the blackjack game is, which you’ll learn by reading one of Schlesinger’s books.

Don Johnson

No, not the actor. However, we’ll have one for you a bit later. This Don Johnson is a hustler who played blackjack for high stakes. During six months in 2011, he took over $15 million from Atlantic City casinos.

This was because casinos at that time, right after the 2008 crash, were so desperate to attract high rollers that Mr Jonhson could negotiate several rule changes that gave him a mathematical advantage.

This won’t happen ever again, but we can learn from Mr Johnson’s way of exploiting that edge. You might try to do something similar at blackjack tables with favourable rules.

Once he knew he had the edge, he played for big stakes. And we mean big.

During a 12-hour marathon at Tropicana, he won $1.2m across three hands, including a single hand in which he won $800k on an initial $100k bet because he split twice and then doubled down on all hands, after which the dealer went bust.

This can be seen as the perfect example of how to push your luck when you have the edge and how beneficial the Double Down After Split rule can be if you play it right.

Legendary Roulette Players

Numerous roulette players have become celebrated figures within the community, often for their remarkable feats of breaking the bank and amassing millions.

This diverse group often includes billionaires, cheaters, organized criminals, and scoundrels. I am fond of the following five individuals because they weren’t cheating, even if the first two exploited the system just a bit.

Carol & Richard Jarecki

The US duo of Carol Jarecki, nee Fuhse, a chess referee, and doctor Richard Jarecki devised a system for detecting and exploiting the biases in roulette wheels.

The duo did the damage in the 1960s and 1970s at various Italian land-based casinos.

They made more than $1.2m over the years. That’s $8m in today’s money. They were discovered by a casino in San Remo and banned from entering the casinos and Italy altogether.

The system relied on discreetly keeping track of more than 10,000 spins for an individual roulette wheel and seeing if any of the numbers showed a bias.

If they did and the bias was significant, the Jareckis would apply their betting strategy. Sometimes it took over a month to find a biased wheel, but they were ready to make loads of money when they did.

Carol used the money from the scheme to fulfil her dream and buy a Cessna Turbo 210 Airplane that she flew solo with Cricket, her Jack Russell terrier. She logged more than 4,200 flight hours. Carol died in 2021 at age 86.

Could this scheme be replicated? It most certainly could if you could find a biased wheel and apply the correct betting strategy for exploiting the bias.

However, most modern roulette wheels are perfect and include technology to self-report a bias. So this scheme is unlikely to occur in more modern times.

Chris Boyd, Ashley Revell

Mr Boyd, a UK programmer, became the poster boy for the only roulette strategy that makes sense. Make a wager on an even-money bet and walk away if you win. He did that with a $220,000 stake in 1994.

The man decided to save as much money as possible, which took three years of persistence, to give himself a 50-50 chance to win big.

It took some time to find a casino that would accept the bet, which shows how risky a single bet of this size is, even for a casino. Eventually, Binion’s Gambling Hall and Hotel in Las Vegas agreed to raise the standard 100k limit. The roulette wheel spun and landed on 7 Red, winning Boyd’s bet on Red. The man cashed out and walked away with $440,000.

Can this be replicated? It most certainly could, even with smaller amounts, and you could do this online, as some high-stakes live roulette tables will even take a £20,000 bet.

Many individuals agree that the 50-50 gamble is worth it if it saves you years of working to achieve the same outcome. However, it would have been a different story if he lost!

The critical thing here is that Mr Boyd managed to walk away. He did not place another bet, not even a small one. To the best of my knowledge, he never gambled again.

Could you do that?

Ashley Revell did.

Except that Mr Revell didn’t keep his possessions out of the equation but sold everything he could, even his clothes.

He ended up cashing in on everything he owned and gambled it all. In 2004, Mr Revell wagered $135,000 on Red at Plaza Hotel & Casino, Las Vegas. If he lost, he would have become homeless on the streets of Las Vegas.

Thankfully, the ball, just like 20 years before in a different Las Vegas casino, landed on 7 Red.

Sean Connery

Yes, we’re talking about the iconic actor this time.

He was a gambler before he became an actor, kudos. In 1963, he travelled to Saint-Vincent, Italy, where he wagered numerous times on number 17. He persisted through a losing period and eventually won big, getting $27,000, which would today be worth around $270,000.

Eight years later, Connery would star in the James Bond film Diamonds Are Forever, where he’d place a roulette bet on the number 17 as an hommage to his previous real-world exploits. How cool is that?

Can you replicate this? No, because you lack the poise, the accent, and the sheer grandeur of one Sean Connery. It can’t be done. You might place a bet on 17 Black, though, knowing that it’s Connery’s number.


By looking at the top players that have played some casino games, we can understand how the game is supposed to be played because these guys have figured it out.

As it turns out, blackjack is all about card counting and favourable rules. At the same time, roulette is all about embracing the randomness and making it work in your favour instead of attempting to tame it, which is what many progressive betting systems players want to do.

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About Neil’s Casino Comparer Reviews

I have tried to be objective and consistent with all my live casino reviews. Hopefully, they will strike a chord with you, but I thought it might be helpful to explain the criteria I use to mark each of the casinos. Hopefully, the categories and explanations make sense.

Playability – What is the overall impression of the casino? Did I have a good time? are the dealers nice and chatty and is everything easy to understand? Does it have a good set of games and is there a comprehensive set of betting options? Are high stakes players taken care of?

Software – What is the software like to use and does it integrate well with the rest of the casino?. Are the images clear and is the video streaming fast? Have they taken more than the default shared tables? Is it available on mobile?

Payment Options – Does the casino have a good variety of payment options? Do they payout quickly and on time?

Security – How good is the reputation of the casino amongst other players? Do they hold a valid gaming license? Are they transparent about the security measures they have in place? Are they regularly audited? Do they publish this information?

Support – Do they have multiple methods for communication with me? Is support available 24×7? Do they have instant chat and are they quick to respond? Are they able to help me immediately? Do they have an online FAQ and self-help library? Are the support people knowledgeable about the product I’m playing?

Bonuses – Do they have bonuses?. How strict are the wagering requirements? Do they offer repeat bonuses?. Do they offer loyalty points and can they be redeemed for cash or playing credits?

After all that, would I play there regularly?

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