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Biggest Roulette Winners of All Time - Best Websites to Gamble

Biggest Roulette Winners of All Time

Roulette may not have the jackpot potential of slot machines or Caribbean stud. However, it has still made plenty of people rich.


Roulette may not have the jackpot potential of slot machines or Caribbean stud. However, it has still made plenty of people rich. In fact, some gamblers have won seven figures through this game. A few of these same players even mastered wheel bias en route to winning guaranteed profits. Below, I’m going to discuss seven of the biggest roulette winners in history. Each of these players crushed casinos and became legends in the process.

Joseph Jagger 

Joseph Hobson Jagger (2 September 1830 – 25 April 1892) was an English textile industry businessman from Yorkshire, who in around 1881 is said to have “broken the bank at Monte Carlo” by identifying and exploiting biases in the wheels of the roulette tables there. He used his winnings to buy property in Bradford. In 2018 he was the subject of a biography by his great-great niece Anne Fletcher. Jagger used his insider knowledge to win £65,000 pounds over several days. He finally departed for England after the casino switched the wheels around overnight. He is still a legacy of one of the biggest roulette winners in history over 100 years later!

Billy Walters

William T. Walters (born July 15, 1946) is an American entrepreneur, philanthropist, and retired professional gambler widely regarded as among the most successful sports bettors in Las Vegas, having a winning streak which extended for over 30 years. He was also one if the biggest roulette winners in history! In 1987, Walters stopped all gambling other than sports betting and returned to his roots in business. As of 2016, his holding company owned interests in eight car dealerships with one under construction, one golf course on the Las Vegas Strip, a rental-car franchise, and a number of commercial properties. In 2020, his net worth was estimated at more than $100 million. 

Pedro Grendene Bartelle 

Pedro Grendene Bartelle is the Vice-President of Grendene SA, which is the world’s largest sandal manufacturer. The Brazilian spends most of his free time running the Sao-Paulo-based company. When he’s not in the office, Bartelle likes to gamble. He frequently hits South American casinos and bets big on the roulette wheel.

Bartelle had a particularly strong outing at Uruguay’s Hotel Conrad. He was betting up to $100,000 per round while using the “full and complete” strategy. The latter method involves betting on every variation of a certain number. In Bartelle’s case, he put multiple wagers down involving his lucky number 32. At one point, he won a single-number wager on 32 and booked a $3.5 million payout. This amount could possibly be the largest single roulette payout in history. He won $1,225,000 on a single spin during this trip. His two biggest wins alone add up to over $4.7 million in winnings making him one of the biggest roulette winners of all time.

Charles Wells 

Almost twenty years after Joseph Jagger took Casino de Monte-Carlo for an enormous sum, Charles Wells sought to emulate his feat. However, Wells wasn’t quite as reputable in earning his roulette winnings. Once there, he began an incredible roulette winning streak. Wells won 1 million francs ($5 million today) by the end of his trip. He decided that this wasn’t enough, though, and returned to Monte Carlo. His win streak continued as he collected yet another 1 million francs in profit.

Gonzalo Garcia-Pelayo 

Gonzalo Garcia-Pelayo Segovia ( Madrid , 25 of maypole of 1947 ) is an entrepreneur Spanish has been music producer , presenter , director , broadcaster and in the nineties also gained fame for big profit in casinos around the world with the game of roulette , after designing a legal method to win at the roulette tables of casinos, taking advantage of imperfections in the manufacture of the tables.

He organizes members of his family, mainly his son Iván and Vanessa, and they dedicate themselves to playing at the Casino Gran Madrid . After organizing a team of people who took data from the roulette tables in the casino, they began to play at the end of 1991, being the summer of 1992 when they managed to win some 70 million pesetas in said casino. After being discovered, the Madrid casino prohibits them from entering. It is at this time that they start to travel to different casinos around the world: Las Vegas , Australia , Austria , Denmark , Holland. In total, the García-Pelayo family earned more than 250 million pesetas, a very high figure for the time.

Ashley Revel 

Ashley Revell (born 1971 in Maidstone, Kent) is an English gambler. In 2004 he sold all his possessions, including his clothes, and gambled US$135,300 on a single spin of a roulette wheel in the Plaza Hotel & Casino, Las Vegas. Revell even changed his name by deed poll to “Ashley Blue Square Revell” after the UK online bookmaker contributed to his gambling fund. He raised additional cash through car boot sales and auctions. The ball ended up on 7 red and Revell doubled his money to $270,600. Revell used his winnings to set up an online poker company called Poker UTD, which later went out of business in 2012 due to controversy over US frozen accounts. To this day he is still noted as one of the biggest roulette winners in history.

Paul Newey

Paul Newey (born 6 September 1968) is an English businessman and semi-professional poker player from Dorset, England who co-founded Ocean Finance and later New Wave Ventures. Newey is an avid gambler. On 4 January 2005 Newey nearly broke the bank at Birmingham’s Genting Casino Star City where he won £3 million and forced owner Stanley Leisure to issue a profit warning. The casino value declined by 12% as a result of Newey’s win. Newey lost his winnings later that month.

In 2014, Newey won four times at the $5,000-a-spin machines in Aria Casino located in Las Vegas for a total of $1.75 million. Newey began playing high stakes poker tournaments in 2012 after entering the $1,000,000 Big One for One Drop event at the World Series of Poker. Newey was eliminated without cashing on Day 2 by eventual champion Antonio Esfandiari. In 2014, Newey again entered the $1,000,000 One Drop event; this time, he finished 7th, earning $1,418,667. Newey has had success in the poker world. As of 2018, Newey has cashed for over $4,800,000. Newey plays online under the alias “topdoll827”.


Multimillion-dollar roulette wins don’t happen on an everyday basis. However, the gamblers covered above show that such profits are possible. Jagger, Garcia-Pelayo, and Walters actually used skill to beat the house and win fortunes. They mastered an advantage gambling technique called wheel bias to win big. Ashley Revell bet his entire life’s savings on the roulette wheel. He got lucky when his wager came through and he won $135,000. Wells and Newey also won big with roulette, but they failed to hang onto their winnings. They prove that it pays to know when to walk away.

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