The Most Successful Roulette Players

The Most Successful Roulette Players

March 19, 2019 20 By Scott Pilgrim

Roulette is definitely one of the most famous among gamblers from all corners of the world. Ever since it appeared on the gambling scene, it has been attracting numerous players with its fast-paced gameplay and the prospect of quickly winning some money. I have dedicated this article to people who made roulette-playing history either by being absurdly bald, or lucky, or both.

I’m sure that these stories about the most successful roulette players will be inspiring enough for you to rush to the nearest Roulette table and place your bet on a couple of spins yourself.

Winning by Scam

Joseph JaggerThe first success story is about the man who won big by scamming the casino he played in, so I can’t say that you should follow his example. If such an event were to occur today, you would certainly end up behind bars with more than enough time to figure out what went wrong. 

However, the first major Roulette win happened in a casino in Monte Carlo in 1873 thanks to a skillfully devised fraud. Namely, Joseph Jagger was very good at mechanics and had considerable knowledge of how different machines operate. He wanted to use that knowledge to get rich quickly and effortlessly. He offered money to several casino workers to keep track of the winning numbers at a Roulette wheel for some time. 

And when he got his results and analyzed them, he realized that the machine was faulty because certain numbers appeared more frequently than others. Mr. Jagger was ready to take advantage of this finding and took his seat at the Roulette table.

Within a couple of days, Joseph Jagger won an amazing $375,000, thanks to the crooked roulette wheel. Nowadays, this would be millions in winnings. However, the best thing about this story is that once Mr. Jagger left the Roulette table, he never entered a casino again. So although he became rich by cheating, which is never a good idea, James Jagger was a perfect example of a “play big and go home” gambler who was focused on his goal, and once he achieved it, he stopped gambling completely.

An Unbelievable Winning Streak

And now for something completely different. If the first story talked about knowledge and detailed planning of winning big at Roulette, this one is its antithesis.

Charleswells GamblerThis is a short story of one of the most successful roulette players – Charles Wells who had a reputation of a small-time crook known for his numerous shady businesses. When he entered a casino one night in 1891 and started playing Roulette, no one had suspected that he would become the “hero” of an amazing winning story.

This man had beaten the house by winning an incredible 23 spins in a row. He then left the casino with around 1 million francs in his pockets. Although the casino people believed that he cheated, it turned out that he had played clean and that his win was pure luck. 

However, this wasn’t the only time Charles Wells got this lucky at the casino table. He somehow managed to repeat his incredible success and double his winnings by gambling some more. Unfortunately, he wasn’t as smart as he was lucky, because he allegedly died without a penny. It is believed that he wasted all his money investing it into shady business ideas or at a gambling table.

Put It All on Red

This Roulette story should be turned into a Hollywood movie. I am sure it would become a blockbuster in no time because of the unique plot. Ashley Revell woke up one day and decided to take his entire life savings, add them to the money he had earned from selling all his possessions and head straight to a casino in Las Vegas. 

Once he was there, he sat at the Roulette table and supposedly said the line from the heading. Thus, he invested his entire past, present, and future on a single spin. He bet on red, and the ball stopped on 7 red. In this suicidally bald attempt, he doubled his money, which he later used to start an online casino business. If this isn’t silver screen material, then I don’t know what is.

An oddly similar thing happened to an IT expert Chris Boyd who took his $220.000 and started looking for a Las Vegas casino that would accept such an immense amount of money as a single bet.

He eventually found the casino that agreed to take this bet, as well as to cover the double 0 pocket on their Roulette wheel, turning it into the European version of the game. He also put all he had on red, and the ball stopped on 7 red. Chris Boyd took his money and left the casino never to come back. He has successfully managed to stay under the radar since then, so there is no update to this story, but he certainly didn’t end up in some shelter.

Mike Ashley’s Roulette Story

Mike_AshleyThis isn’t a story about a life-changing win at Roulette. Mike Ashley was already filthy rich when he decided to place his roulette bets. This billionaire and Newcastle United football club owner took almost half a million pounds to the Roulette table and covered every single inside bet that involved number 17. In addition to this, he covered several outside bets as well. He ended the game with around 1.3 million pounds won. This amount may be pocket money for Mike Ashley, but it is considered to be one of the biggest wins at Roulette ever.

Lucky Number 32

Gambling Lucky number 32Pedro Grendene Bartelle became famous when he won an astonishing $3.5 million betting on Roulette. His win instantly became breaking news, and many tabloids wrote about it. However, there were some inconsistencies in their reports, as you would expect from tabloids. According to them, Pedro placed his entire bankroll of $35,000 on a single number, a so-called straight-up bet on 32 red. However, this kind of bet brings a 35:1 payout, so if you do the maths, you’ll see that he would have won much less if he had placed only this bet.

So Pedro must have played several other inside bets that included number 32 as well and won them all Whatever the case may be, one thing is certain — the Roulette wheel turned him into a millionaire.


I know that you expected a well-known Sean Connery story about winning the Roulette in real life. However, you must be aware that, in all likelihood, that won’t happen. This success story became evergreen long ago and was an inspiration for many people to try their luck on roulette themselves. In some way, it was an incentive that made all of these previously mentioned stories possible. We can see that Mike Ashley won by betting on 17, and that is a sufficient homage to the timeless Bond gambling scene.

Undoubtedly, all of these stories are equally incredible. However, for every amazing win, there are hundreds of thousands of people whose stories didn’t have a happy ending. In the end, you must understand that all of the people I mentioned above had an unbelievable amount of luck. That’s not to say that you can’t join these people in the roulette hall of fame if you give the game a shot. It’s just that you must be aware that roulette is a game of chance. As such, it features a house edge, and you’re far more likely to lose more than you win in the long run. 

One final piece of advice — do not break the bank to play roulette and try to recover your losses. Only gamble with the money you’re comfortable losing. Play responsibly and remember that the main goal of the game is to have fun.

What is the max bet on roulette?

The max bet depends on the casino itself. Moreover, it can vary from one table to another — some casinos might feature high-stakes tables where you can bet as much as $100,000 per spin. As you’ve seen in the article, if you’re willing to put down a ton of money, you might even get the casino to host a game specifically for you and even cover the double zero. 
Casinos don’t shy away from money. So if you’re planning on wagering large sums, you shouldn’t worry; it won’t be difficult to come to an agreement with a land-based casino. Online, the situation is a bit different. The tables have fixed limits due to the software itself, so you might have to do a bit of digging to find an online casino willing to take really high stakes. 

How do you win money on roulette every time?

The only way to win money every time would be to correctly guess the number every time. As you can imagine, there’s no way to do that; unless you believe in psychic powers. Jokes aside, there are no strategies or systems you can employ to guarantee a win. Roulette is a game of chance, and the outcome of each spin is totally random. It all comes down to luck. The sooner you make peace with that fact, the better.

Can you play roulette for a living?

Of course not. It’s not just roulette, it’s any game of chance. Even if the odds were 50:50, you would be gambling your entire future every single spin. Naturally, the odds aren’t that good — as with any other game of chance, roulette has a house edge that ensures the casino wins out in the end. 
The only casino-style game one could potentially play for a living is poker. The key difference between it and other games is that poker is a game of skill. Although cards are dealt randomly, it takes an incredible amount of skill to see through your opponents and scoop up a large pot.

What is the longest streak in roulette?

The longest recorded streak in roulette happened in an American casino in 1932, when the ball landed on red an incredible 32 times in a row. This goes to show you that you shouldn’t give in to the gambler’s fallacy and believe what know-it-alls at the table tell you. Whoever said the ball has to land black was right, eventually. It’s just that they all would have lost more than 20 bets in a row before their prediction turned out to be correct.