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We all know the house has an advantage in roulette over the long term, but there are no laws of physics that say it is impossible to win big in roulette. Isn’t that possibility the reason we all play? The house may have the advantage over the long term, but people do win. Some people win big.

This post is all about the people who have beaten the odds and taken the house for astronomical sums of money. I originally planned to rank these winners in order of the amounts of money they won. However, that soon proved to be a fruitless task as the time value of money, time’s effects on purchasing power and currency conversions make it difficult to accurately rank these winners.

All technicalities aside, there is some degree of relativism when we talk about “big winners.” Does Bill Gates placing a $200,000 bet (equal to about one hour of work for Mr. Gates) mean as much as the guy who sells everything he owns and bets it all on red? In pure money terms, sure. In “holy $%&@ that was a ballsy bet” terms, not so much.

Also, you can bet there are even bigger winners than these that we never hear about. High rollers in Las Vegas tend to guard their privacy so we’ll never know about some of the biggest wins of all time. Also, this post only includes live roulette winners. Online roulette is a private endeavor and so we don’t hear about the big winners at online casinos.

1. Ashley Revell

Total take: $135,500

Method: Wagered life savings on red

One day in 2004, Ashley Revell took his life savings to Las Vegas and wagered everything on a single spin of the wheel. And when I say life savings, I mean everything. He sold his house, his car, favorite watch, old trophies, all of his clothes except for the ones on his back and then added every penny in his bank account to create a gambling fund of $135,000.

With not a single possession except for the clothes on his back, Ashley Revell flew to Las Vegas and bet everything on red. Sky One (a UK TV channel) heard about his crazy plan and made a mini TV series out of the event.

On the big day, Revell threw down a $135,500 wager on red in front of an audience of millions. The roulette ball began making smooth trips around the wheel and then began to slow. The orbit wobbled, the ball clanged down into the bottom of the wheel, took a few bounces and eventually came to rest on red 7. With one spin of the roulette wheel, Ashley Revell had doubled his net worth.

$135,000 probably isn’t even near the top 50 largest roulette bets ever placed in Las Vegas, but it ranks very near the top in terms of pure ballsy-ness. This one bet represented everything Ashley had accumulated over 32 years of life.

Where is he now?

After winning the big bet, Ashley Revell started an online poker site by the name of Poker UTD. The site is still live, but I saw a few rumors on the internet that he was looking to sell the site in 2012. It looks like he might still run that site though, so take that rumor with a big grain of salt.

As of March 2013, he helps people find online casino jobs at igamingrecruitment.com (a WHOIS search on the domain can confirm this). The site is only a few months old, but it looks like Ashley Revell is staying busy and doing well for himself.

2. Charles Wells

Total take: 2 million francs in 1891

Method: Luck

Charles Wells won a million francs at the Monte Carlo in a single night in 1891. He returned later that same year and won another million francs. Unfortunately, his luck came to an end after that.

Charles continued gambling and lost everything. Then, he was arrested for running business scams and sentenced to 8 years in prison. His total take over the long haul was zero, but he did have one beautiful night in which he won a million francs over the course of a few hours.

Most people say he just experienced the lucky streak of a lifetime. Wikipedia even says that at one point during his escapade, he won on 23 out of 30 consecutive spins of the wheel. But keep in mind, this guy was a known scammer who did at least 3 stints in prison. Was it dumb luck or something more? We will never know for sure.

It is tough to quantify a million francs in modern times. Even if you convert francs to dollars and then calculate the effects of inflation, it still doesn’t give us a clear idea of the purchasing power that kind of money had back in the real world back then. The only thing that’s clear is that it was a massive amount of money at the time.

Where is he now?

Underground. It is said he died broke in Paris in 1922.

3. Mike Ashley

Total take: £820,000

Method: A “complete” bet on 17

Mike Ashley is a billionaire businessman and owner of Newcastle United Football Club. News outlets reported in 2008 that he visited a private Mayfair casino and threw down a complex roulette bet worth nearly half a million pounds.

In one spin, he wagered a total of £480,000 on every possible inside wager that includes the number 17. This includes a straight-up bet on 17, all the splits that include the number 17, all the streets, corners and six-line bets. This is called a full complete.

The same news reports also state that he placed wagers on black, odd, the first half, middle column and middle dozen. In the end, he took home roughly £1,300,000 for a net profit of £820,000. It’s not a whole lot of money for a billionaire, but it is impressive that the ball landed exactly where it needed to land to make the bet a perfect winner.

Where is he now?

Mike is still doing whatever it is that billionaire businessmen do. In recent news, he purchased the fashion chain “Republic” and saved 2100 jobs in doing so.

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4. Joseph Jagger

Total Take: $375,000 in 1873

Method: Identified biased roulette wheels

Joseph Jagger worked in the cotton mechanics industry and took his experience with machines to the Beaux-Arts casino in Monte Carlo. There, he paid six clerks to secretly note the results of many spins of the roulette wheels there. He found that one of the wheels showed a clear bias which resulted in the numbers 7, 8, 9, 17, 18, 19, 22, 28 and 29 hitting more often than they should have in a truly random wheel.

Joseph Jagger then visited the casino himself, placed his bets accordingly and won the equivalent of $375,000 over the next few days. The casino eventually wised up to his strategy and got rid of the biased wheel. Jagger kept his winnings, retired from his job, invested the money in his own property and never again returned to the casino.

To put that in perspective, $375,000 back then would have a purchasing power of more than $7,000,000 today. The exact numbers are actually different everywhere you look, but $375,000 seems to be the most frequently cited number. Whatever it was, it was a lot of money.

Where is he now?

Joseph Jagger resides at the Bethel Chapel cemetery in Shelf, England.

5. Chris Boyd

Total take: $220,000

Method: Wagered $220,000 on red

Chris Boyd was a 40 year old computer programmer from England who saved $220,000 over a three year period. He took the money to Las Vegas and searched for a casino that would take such a massive bet. Many casinos refused, but he eventually struck a deal with Binion’s Horseshoe Club.

Binion’s had a max bet of $100,000, but they agreed to take his wager this one time. They also covered the 00 slot on their American roulette wheel, which effectively turned it into a European roulette wheel.

Chris bet all $220,000 on red and won the bet. Legend has it that the ball landed on red 7. If you’ve been paying attention, you will have noticed that this is the same exact slot the ball landed on for Ashley Revell.

Where is he now?

I can’t find any recent information on Chris Boyd. It is said that he vowed to never gamble again. Considering that he was a computer programmer and that it only took him 3 years to save an extra $220,000, I would guess that he’s still doing well barring any health issues.

6. Francis Farrugia, Francesco Baioni and Frank Camilleri

Total take: Unknown, millions

Method: Cheating / past posting

Francis Farrugia, Francesco Baioni and Frank Camilleri traveled the world for 20 years ripping off casinos using the age-old trick of distracting croupiers in order to add high value chips to wagers after the ball had come to a rest.

The trio was eventually banned from every major casino in the world but that didn’t stop them. Using fake IDs and disguises, they continued to travel around the world to ply their trade. Major casinos launched investigations and eventually the three-man team was busted.

But the story doesn’t end there for these crooks. The only charges that stuck were related to possessing false identification. Francis Farrugia was eventually sentenced to 9 months in jail, but the sentence was suspended and he was released on supervision. His accomplices also served no time.

News articles are saying these guys were “top hatting” but nowhere does it mention that casino staff were involved (top-hatting is similar to past posting except the croupier purposely helps the cheaters). I think these guys were just traveling past posters.

Where are they now?

The trio has managed to stay out of the news since 2011. It is anyone’s guess as to whether they have retired with their money or are back in the game. The next time you visit a casino, keep your eyes open for a trio of three well-disguised Italians.

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Total take: Undetermined

Method: online casino and good luck

If you’re feeling motivated after reading about these stories of the biggest roulette winners of all time, you’re not alone. Millions of people around the world gamble at online casinos with similar hopes of making it big.

The only thing you need to try your own luck at roulette is an account at an online casino. It is impossible to cheat at online casinos, but think of that as a good thing. It eliminates the possibility of ending up in jail (or worse).

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