Who Are the Biggest Roulette Winners of All Time?

1) Gonzalo García-Pelayo €5,000,000

A Madrid, Spain music director named Gonzalo García-Pelayo noticed wheel bias when playing roulette and studied the probability. He then worked with his 22-year-old son Ivan, recording thousands of spins at casinos in Spain.

García-Pelayo created a computer program simulating this perceived roulette wheel bias and then put his efforts into work in 1991 with Ivan and other family members in Madrid. They won €1.5 million at the Casino Gran Madrid alone.

When all was said and done, the García-Pelayo family is said to have won around €5,000,000 playing roulette. The History Channel created a documentary in 2004 called Breaking Vegas: The Roulette Assault that covered the biggest roulette win of the García-Pelayo family.

Gonzalo García-Pelayo, who was also a record producer and film director, ended up having heart issues in Sin City and decided to call it quits.

2) Billy Walters $3,800,000

Legendary gambler Billy Walters also studied wheel bias on the roulette table. He and his partners won an estimated $3,800,00 playing roulette.

Walters, a native of Munfordville, Kentucky, and a betting associate noticed a wheel bias at the Atlantic Club Casino Hotel in Atlantic City, New Jersey (now abandoned). They proceeded to place bets on the 7-10-29-27-36 slots.

Thirty-eight hours later, the pair had won $3,800,000, which was $2.5 million more than the previous largest roulette win set in 1971. The casino then asked them to stop playing.

Walters, who employed many runners to help make all of his bets, won $3.5 million backing the Saints in Super Bowl XLIV and $2.2 million on USC when the Trojans beat Michigan, 32-18, in 2011.

Walters, age 76, has an estimated net worth of over $100 million. He had a stint in a Pensacola prison for an insider-trading scandal with Dean Foods. Walters was granted clemency by President Donald Trump in 2020.

Walters, who was convicted in 2017 and ordered to pay a $10 million fine, finished serving the balance of his 5-year sentence under home confinement in Carlsbad, California.

3) Pedro Grendene Bartelle $3,500,000

The Vice President of Grendene SA, Pedro Grendene Bartelle is also one of the biggest roulette winners, winning an estimated $3.5 million 2017.

Visiting Uruguay and the Hotel Conrad, Bartelle made a decision to go all-in for $35,000 on his lucky number 32. Like in the movies, it hit and he walked away with a cool $3.5 million for his risk, employing the “full and complete” strategy.

Billionaire Bartelle spends most of his time running the third-largest footwear company in Latin America, sandal-maker Grendene, with his brother Alexandre.

He also won $1,200,000 on the roulette wheel on another trip to the Hotel Conrad, and if there were a Mt. Rushmore of roulette, Bartelle’s face would certainly be carved in stone.

4) Paul Newey £3,000,000

In 2005, English businessman Paul Newey won £3 million at the Star City Casino in Birmingham, England, causing the casino to have to issue a profit warning after its value decreased by10%.

A native of Dorset, Newey continued to play, however, and lost all of the money he won back to the Star City Casino. Newey is also a semi-professional poker player. He has participated in the World Series of Poker with four cashes and one Main Table finish.

The founder of Ocean Finance and New Wave Ventures, the now 54-year-old Newey, also won $1.75 million playing on a $5,000-a-pull slot machine in Las Vegas at the Aria Casino in 2014.

5) Charles Wells 2,000,000 Francs

Charles Wells might be on a Mount Rushmore of biggest wins on roulette for his legendary winning streak in Monte Carlo in 1891. A known small-time crook, Wells visited the world-famous Monte Carlo Casino Resort, started playing roulette, and went on a dream run.

Wells is said to have won 23 of 30 spins at the Monte Carlo Casino Resort, breaking the bank at the table and forcing play to be stopped. And all on luck. Wells left with close to 1 million Francs.

Englishman Wells then returned to the Monte Carlo Casino Resort and won over 1 million Francs. All by luck, as history tells it, a known scammer, Wells eventually ended up in jail for 8 years. He died, broke, in 1922 in Paris, France.

An all-time roulette winner legend, Wells proved that you don’t always need a computer program, wheel number bias, or a lucky number to strike it rich on the roulette wheel.

6) Sir Philip Green £2,000,000

Another Englishman, Sir Philip Green, also won a bunch of money playing roulette one night. He pocketed a cool £2,000,000 at Les Ambassadeurs Club in Mayfair, London, England in 2004.

Green, a British business mogul and former chairman of the retail conglomerate called the Arcadia Group, was known to frequent casinos in London and is one of the biggest roulette winners.

And like fellow countryman Wells, Green also made a return to the casino where he won his millions. He would go on to win £1 million and many other large amounts from that same Les Ambassadeurs Club.

Located at 5 Hamilton Place in Mayfair, London, and still in operation, Les Ambassadeurs Club has been portrayed in the classic James Bond film Dr. No (1962). It was also used for some scenes in The Beatles film A Hard Day’s Night (1964).

7) Mike Ashley £1,300,000

Former Newcastle United FC (EPL) owner Mike Ashley owns one of the biggest roulette wins on file. He won £1.3 million on the lucky spin of the roulette wheel at the Fifty Casino in Mayfair, London, England, back in 2008.

How did he do it? Billionaire Ashley wagered £480,000 on a “complete bet” on the number 17, covering every combination that included 17. When the black 17 appeared, he won £1.3 million.

Ashley, the owner of Frasers Group Plc (formerly Sports Direct), is still focused on the retail sporting goods market after selling the Magpies in October 2021.

8) Richard Jarecki £1,280,000

When Billy Walters and his partner broke the prior roulette record of £1,280,000, they broke the record held by Dr. Richard Jarecki. He was another pioneer of roulette bias, and set the record back in 1971 at the San Remo Casino in Monte Carlo.

Jarecki was a brilliant German-born American physician who passed away in 2018. He developed a system to try to beat the game through years of observation, looking for patterns, and then executing his plan at various casinos throughout Europe.

9) Chris Boyd $440,000

Yet another Englishman with great luck on the roulette wheel was computer programmer Chris Boyd. Boyd won $440,000 at the Binion’s Horseshoe Club in Las Vegas in 1994.

Boyd decided to save up as much money as he could to place it on a single spin of the roulette wheel. He saved up $220,000 over a three-year period and then headed to historic Binion’s in downtown Sin City, the site of the original World Series of Poker.

The casino only had a $100,000 limit on that roulette table. Therefore, Boyd phoned Binion’s ahead of time and asked if they could take his massive $240,000 one-spin bet. They agreed.

Unlike all of the other historic all-time roulette winners, Boyd went with a color (Red). After the ball finally stopped spinning, it landed in the red 7 slot. Boyd’s life was forever changed, both financially and fame-wise, claiming one of the largest roulette wins in history.

After winning, Boyd reportedly asked Binion’s to lock his money up so he wouldn’t be tempted to bet anymore. Maybe his simple strategy was the best decision. He didn’t spend time studying wheel bias, hoped for good luck, and kept it simple with just one color and one spin.

But asking Binion’s to block out the 00 and then not gambling after he won, may be two of the best decisions that Boyd ever made in his life.

10) William Darnborough $415,000

William Darnborough was an American gambler from Bloomington, Illinois. His biggest roulette win was an estimated $415,000 while playing in Monte Carlo from 1904 to 1911.

Darnborough died in 1958 after totaling what would be millions of dollars today. We don’t know much about him, unfortunately, but adjusted for inflation, he is one of the biggest roulette winners in history.