All-Time Famous Roulette Players, Bets, and Stories

by Enrico
Updated Roulette strategy guides and tips how to win

Famous Roulette Players
Over the years, roulette has gained a reputation as one of the most dramatic and exciting casino games around. Part of the reason is due to the dramatic tension of this solely number-based game, anyone and everyone really will feel like they have a shot at winning big. It also helps that this game is super simple to play.

Basically, all you need to do is to think of a number from 0 to 36 (in total 37 numbers), place a bet, and watch the wheel spin. When the ball starts rolling from one square to another, every player hopes that it will eventually fall on his/her lucky number. At the same time, roulette’s allure is also based on the chances of betting on just a single number and scooping up a huge payday.

Since the emergence of roulette as a casino game all those years ago, many brilliant bets have made some players famous overnight. These are the players that have truly broken the bank and rode the famous roulette wheel right into the history books.

Below are some of the most famous roulette players of all-time and the bets that earned them that claim to fame. We’ve also looked at a few famous fictional stories too, as while they may not have been real, they’ve certainly not stopped short in serving up some roulette-based drama.


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The Famous Names and Faces

We just mentioned it above, but it certainly needs reaffirming. Some names are synonymous with the game of roulette, often as big winners that have blasted the casino. The following are three names that over a series of bets and casino visits have shown that there is money to be made from roulette – even if some of their methods have raised more than just a bit of suspicion.

Joseph Jagger’s Bank-Breaking Efforts

The first roulette winning pioneer roulette is and always will be Joseph Jagger, also known as “the man who broke Monte Carlo Casino“. In 1873, Jagger realized that not all roulette wheels were absolutely perfect. In an attempt to tilt the odds in his favor, he hired several people to record the numbers on every roulette wheel in the world-known Monte Carlo Casino.

After several days of research, Jagger determined that there was a roulette wheel that was particularly biased towards 9 numbers over others. Over the next few days, Jagger took advantage of this bias and won approximately £65,000 pounds. If we convert it to today’s money, the amount would exceed £3 million pounds.

Among serious roulette players, Jagger’s story drums up plenty of debate, as some consider his methods cheating. In many ways it is, but to play devil’s advocate, Jagger simply had the street smarts to find a weakness in the casino’s armor and exploit it. You could certainly argue that Jagger would not have found such success had the casino been on the ball if you pardon the pun.

Charles Wells Almost Kills the Casino

A few years after Jagger beat the famous Monte Carlo Casino from pillar to post, another player stepped up and won big. In July 1891, Charles Wells, a young rogue from London, showed up with thousands of pounds from his series of scams. In about eleven hours, he almost “killed the casino” by winning all the money on every roulette table he participated in. In the November after, he repeated his greatest show again, by winning more than a million francs across two roulette games.

Unlike Jagger, Wells apparently did not have any tricks up his sleeve, and later he admitted that his success was nothing more than a combination of luck and the then-radical martingale system. However, historians feel that Wells’s winning streaks weren’t exactly above board. Odds dictate that sweeping through every roulette wheel a casino has and winning on every one of them is near enough impossible. Wells protested his innocence, but his backstory and the sheer winning streak itself tell a different story.

Gonzalo Garcia-Pelayo Plays His Way into History

Another gambler who has won a lot of money on roulette is Gonzalo Garcia-Pelayo. While a little more unknown than the names mentioned above, don’t write off Gonzalo, as he’s earned his way onto this list. Although it was 100 years after Jagger discovered the Monte Carlo Casino’s biased tables, Garcia-Pelayo still boldly believed that if you observe carefully enough, you can still find a table that can be taken advantage of. Facts have also proved that this was the case. He found such a roulette table in Casino de Madrid and won more than €1 million in the process.

Again, the performance of Garcia-Pelayo raises a few questions like the other names we mentioned. Whether it’s cheating or a fair win is generally up for debate. Yet, what can’t be debated is the fact that roulette has made Garcia-Pelayo a millionaire and in that sense, he is undoubtedly a roulette success story.

Some You Win, Some You Lose

Famous players in the world of roulette aren’t always the hardest to come by, as there are winners at roulette tables around the world every single day. However, things are a little bit different when it comes to looking at famous bets. The idea that one person can risk it all and win big is the stuff that Hollywood movies are made of. The players below threw the betting strategies out of the window and went for it – luckily for them the roulette wheel was kind rather than cruel.

Ashley Revell’s All-or-Nothing Wager

In most cases, a single bet made by a player in one roulette game is more dramatic and exhilarating than a long-term win at a casino across multiple games. For example, the famous story of Ashley Revell is one that will without question stand the test of time.

The man from London decided to take the risk and put all his money on a roulette bet. After selling all his assets, Revell raised $135,300. The professional gambler then put all his money on red on a roulette table at the Plaza Hotel and Casino in Las Vegas. In the end, the ball stopped at Red 7. Revell won $270,600 in one bet, leaving $600 in “change” as a tip.

Is this the biggest roulette win you’re ever going to see? Absolutely not, but that doesn’t take anything away from what Revell managed to achieve here. Literally going all in, he bet the house and then some on red and walked away from a winner, that takes guts, nerves, and a whole lot of guile to pull off.

Derren Brown Comes Unstuck on National TV

In 2009, TV star and magician Derren Brown tried to predict where the roulette ball would fall on British television. Any British readers of this article will be well aware of Derren Brown, as he’s famous for his so-called mind tricks. His abilities have often been criticized for being nothing more than camera trickery, with this being his attempt to prove those critics wrong. Sadly for Derren, things didn’t turn out as he had hoped.

In order to raise the stakes a bit, he bet £5,000 (somebody else’s £5,000 we might add) and put it all on one number. According to Brown, he can predict where the ball will finally fall based on the laws of physics – he selected number 8. However, the outcome was not as Brown expected, it was a loss for both Brown and the person who paid for the bet, as the ball landed on the square right next to number 8 which was number 30. Unfortunately, a close guess is still determined as a failure.

Roulette Goes Hollywood

There is nothing Hollywood loves more than splashing a great gambling tale all over the big screen. For most blockbusters, it’s craps that command the most attention, with a bit of poker and baccarat sprinkled in for good measure. While these card games more often than not command the spotlight, roulette certainly isn’t without its admirers in twinkle town.

Run Lola Run Revs Up Roulette

How can you talk about roulette in cinema without mentioning Run Lola Run? One of the most famous world cinema films of all-time. Roulette has often been used in movies to create a dramatic atmosphere, usually when a character has a chance to win money because he or she needs to do something really important (normally for a life-saving reason). In the German movie “Lola Run”, the protagonist (Lola) bets 100 marks on the number 20 twice and strikes it rich both times. She won a total of 129,600 marks, with 100,000 marks left after paying off her boyfriend’s debt and saving his life – the life-saving reason we spoke about.

Run Lola Run is a thrill-a-minute affair on-screen that certainly does the game of roulette plenty of justice. If you are a roulette fan and fancy a night at the movies, make sure you check this movie out, but be warned, when it’s over you’ll be itching to spin the roulette wheel all over again.

“Roulette Rick” Steals the Show in Casablanca

Casablanca is undoubtedly an all-time cinema classic. Part of that is because it is packed wall-to-wall with quotable lines and impressive soundbites. Roulette also plays an important role in this famous movie from 1942.

Rick (played by Humphrey Bogart) owns a restaurant in the film, and in the restaurant, there is a roulette wheel that has some questionable “alterations”. Although he usually uses it to defraud customers for money, he also helped a Belgian couple to bribe a local police captain. He suggested to the couple to put their money on number 22, they won without doubts.

After winning the next round, he told them to keep betting on 22 and they won again. At this time, Rick warned her husband to stop playing, but cash out the money when it was enough, and it was best not to play that roulette wheel ever again-for their own good.

Putting roulette in the spotlight, Casablanca certainly helped raise the profile of the game back in the 1940s. Many argue that this is why the game saw a huge surge in popularity throughout the decade and early 1950s. Learning from Casablanca, it’s clear that a little bit of silver screen magic can work wonders for a casino game.

James Bond Proves That Diamonds Are Forever

No look at casino games in cinema is complete without mentioning James Bond. The famous British agent has been around the world dropping wagers, but while he’s famous for his baccarat and craps play, he’s no stranger to the roulette wheel either. Way back in 1971, Mr. Bond played roulette on screen for the first time, with it doing plenty to boost the flagging reputation of roulette during the 1970s.

The film in question is Diamonds are Forever, the seventh James Bond film in the series, with his roulette play, certainly bringing plenty of atmosphere to the film. The movie’s roulette scene happens just before its famous craps scene takes place, helping to set the tone for one of the most exciting Bond films of all-time.

Be the Next Big-Time Roulette Winner!

One thing is for sure, winning big on roulette doesn’t need to be a dream after reading these stories. Whether it be in real life or in the world of La La Land, roulette serves up its fair share of winners. Will you be the next lucky roulette player? Everyone has a chance to make it onto the most famous players list, and today, well, it could be your day!

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