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.

Over 50% of players betting $4 on a specific number (Straight up) lost everything before enjoying a single winning game round, as these players lost 25 rounds in a row. When playing live roulette, this adds up to about 45 minutes of play time. But after several hazardous investments, he lost everything and has to pay a debt of nearly €600,000! 8 – Vivian Nicholson - $5,4 millions. Online Roulette. 7 Life-Changing Lessons From Someone Who Lost Everything If you woke up tomorrow without the use of your arms and legs, would you think life was fair? The answer just might surprise you.

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.

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.

7. Spot Reserved for [Your Name Here]

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).

My top pick for roulette fans is Lucky Red Casino. Lucky Red has a long reputation for fair games and lots of bonuses for both new and existing players. They have a no-download option (compatible with Macs) and a downloadable software package that will let you get started today.

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Many gamblers strive just to win meager profits. But a small percentage of players have actually managed to become rich through gambling.

The biggest winners often have the perfect mix of talent, fearlessness, and bankroll management. Unfortunately, some big winners are lacking in the latter category.

These same players have won and lost fortunes due to their inability to handle money and/or walk away. The following 7 gamblers serve as cautionary tales for knowing when to quit.

1 – Stu Ungar

Stu Ungar is best known for winning three WSOP Main Event titles. He took down this prestigious tournament in 1980, 1981, and 1997. The latter title earned him the nickname “The Comeback Kid.”

However, Ungar was proficient in more than just poker. He first became a professional gambler through gin rummy.

After standing out in the New York gin rummy scene, Ungar travelled to Las Vegas in search of action. He dominated the competition so badly that nobody would play him anymore.

Ungar was also extremely good at blackjack. He was so good, in fact, that he could count a six-deck shoe and know what the final card was.

While Ungar was excellent at various forms of gambling, he did poorly with sports betting. He also developed a bad cocaine habit that would fester throughout the years.

The combination of sports betting and coke led to Ungar losing everything he made on the gambling tables. But he still experienced a shining moment after winning the 1997 WSOP Main Event.

Ungar split the $1 million prize with his backer, Billy Baxter. Sadly, he blew his $500,000 share on drugs and sports gambling.

Just a few months later, he died in a seedy motel of a heart attack. The heart attack was the result of years’ of cocaine usage.

2 – Erick Lindgren

Erick Lindgren was one of the biggest beneficiaries of the poker boom (2003-2006). He won multiple WSOP gold bracelets and World Poker Tour titles at the height of poker mania.

“E-Dog” also landed a sponsorship deal with Full Tilt Poker that paid him $300,000 per month. Lindgren used his wealth to bet on sports and fantasy sports.

The latter caused his sports gambling problem to surface in 2012. Fellow gamblers began complaining that Lindgren failed to cover a $100,000 buy-in into a private fantasy league.

Soon, others came forward with stories about the two-time WSOP champ owing them money. He eventually declared bankruptcy after realizing that he had no chance to cover some $12 million worth of debt.

He owed $3.8 million in back taxes to the IRS. Lindgren also owed fellow gamblers, including poker pro Andy Bloch, an estimated $6.1 million.

He’s since gone into gambling rehab multiple times and continues to play poker. But Lindgren will never be able to pay all the people whom he owes money. Of course, bankruptcy court probably took care of most of this debt for him.

3 – Terrance Watanabe

Unlike many other gamblers on this list, Terrance Watanabe has never been a professional. Instead, he’s a whale who formerly ran Oriental Trading Co.

Watanabe took over the family business in 1977 and helped it become a prominent brand. The Japanese-American businessman sold his stake in Oriental Trading in 2000 and retired a wealthy man.

He set out to be a great philanthropist in his retirement. However, he spent far more time in Vegas casinos.

Watanabe was the biggest fish in the casino and would play everything from keno to slot machines. He lost big playing these games and others.

Of course, Vegas was more than willing to offer him generous comps. Caesars, for example, created a special “Chairman” VIP level just for Watanabe.

The CEO would proceed to lose over $200 million through gambling alone. He eventually sued Caesars Entertainment in an effort to avoid paying up on a $14 million debt. The two sides settled out of court.

4 – Ryazan

“Ryazan” became one of the most-famous daily fantasy sports (DFS) pros in the mid-2000s. He won a fortune through football and other games in 2015.

Feeling good about his skills, Ryazan began challenging other noted pros like Martin “Papagates” Crowley and Saahil Sud to matches.

In fact, he used credit cards to fund his initial bankroll. Ryazan spent much of his 2015 fortune and used credit cards to reload his account.

The result was mounting credit card interest and a diminishing bankroll. His career took a downswing in 2016 that left him unable to cover the massive taxes on his 2015 earnings.

5 – Charles Wells

Charles Wells is similar to Terrance Watanabe in that he didn’t become famous for being a professional gambler. In fact, he was a conman long before his gambling ventures came to light in the 1890s.

The Englishman funded his initial gambling bankroll via a phony musical jump rope. He duped investors into giving him a collective £4,000.

Wells took the money and headed to Monte Carlo. Here, he played roulette using the Martingale system and got lucky enough to break the bank (win every chip at a table) multiple times. By the time the trip was over, Wells had earned 1 million francs.

He went back to Monte Carlo shortly after the first big win. He did even better this time, breaking the bank 17 times.

Wells became a celebrity upon returning to Britain. He even toyed with the press that he had a secret roulette strategy.

This notion was just another con. Wells simply got lucky while using an aggressive betting strategy.

The luck would finally run out when he returned to Monte Carlo for a third time. He lost everything and returned to Britain penniless.

As if this wasn’t bad enough, Wells was also arrested for fraud. He spent the rest of his life in and out of prison.

6 – Harry Findlay

A professional sports bettor, Harry Findlay has won millions of pounds through different sports and horse racing. He’s also become a celebrity in the UK due to his outspoken ways.

Findlay started drinking his own Kool-Aid in 2007. He placed a £2.5 million bet on New Zealand beating France in the Rugby World Cup.

Findlay was so sure of a win that he held a big party at the stadium. His huge bet looked like it would pay off when New Zealand led 13-3 at halftime.

Despite the big lead, Findlay hedged with a relatively small bet on France making a comeback. This wager promised to pay £600,000 if the French pulled off the miracle.

They indeed did so and dealt Findlay a massive lost. He at least salvaged £600k thanks to his halftime hedge.

This was just the beginning as Findlay continued to lose more bets over the years. He also poured money into saving Coventry Stadium’s greyhound racing program only to get burned.

Findlay is now worth far less than he used to be. He’s still a successful horse bettor but not to the same extend as previously.

7 – Archie Karas

No story beats Archie Karas’ fall from gambling grace. He managed to pull off the greatest gambling run in history only to lose everything.

Karas’ tale began in Los Angeles where he was down to his last $50. Rather than saving up money to reload, he headed to Las Vegas in 1992.

Once here, he borrowed $10,000 from a friend and won enough to build a decent bankroll. Karas proceeded to win millions of dollars through a combination of pool and poker.

By the time he was worth $17 million, nobody would play Karas in pool or poker. He resorted to playing high-stakes craps at Binion’s Gambling hall.

In 1995, Karas switched to baccarat and lost $11 million. He returned to the craps tables only to lose an additional $18 million.

Following a brief visit back to his native country of Greece, Karas began playing baccarat, craps, and poker in Vegas. All three propelled his losses until he was left with nothing.

Karas has since gone on other large runs only to lose the money. He was arrested in 2013 for marking cards at a San Diego casino.

Conclusion

Lost Everything Roulette Meaning

All the gamblers on this list have had to think ‘what if’ when reflecting back on their careers. Each of these players was up big at some point and lost everything.

Ungar is arguably the best all-around gambler ever. But sports betting and cocaine proved to be powerful addictions that he couldn’t overcome.

Erick Lindgren once appeared set for life thanks to his poker winnings and Full Tilt sponsorship. But like Ungar, he couldn’t resist betting big on sports — much to his detriment.

Terrance Watanabe built Oriental Trading into a well-known international company. He cashed out in 2000 only to lose over $200 million of his fortune to Vegas casinos.

Ryazan was one of the earliest success stories in DFS. However, his good fortune took a downturn when mounting credit card debt and bad bankroll management caused him to go broke.

Charles Wells was a nineteenth century conman who got extremely lucky playing roulette. He pushed his luck too many times and lost everything.

Harry Findlay won millions of pounds through sports gambling. But big bets and a failed bid to help UK greyhound racing cost him his fortune.

Lost Everything Roulette Movie

Finally, Archie Karas won $40 million after starting with just $50. He couldn’t quit at the top, though, and ended up losing the entire amount.

Lost Everything Roulette Games

You may never win as big as any of these gamblers. But if you do, heed their stories so that you can quit with some of your profits.