Biggest Roulette Winners in History

Roulette does not enjoy the popularity level it once did. The overwhelming number of slots and varied table options at land-based and online casinos have dramatically lowered the appeal of everyone’s favorite wheel game. It no longer holds sway over gamblers across the globe as it once did. Though, internet gaming platforms are doing their best to boost the enticement intensity of this casino classic by continuously creating live dealer variations that offer novel twists on traditional roulette gameplay.

One of the main reasons roulette has lost so much ground to reel spinners and blackjack over the past century is that it offers worse odds than the latter and its payouts come nowhere near those that slots supply. For example, the most one can win on a straight roulette wager is a win thirty-five times their stake. In comparison, most reel-spinning games offer progressive jackpots in the millions or at least max prizes of 5,000x a player’s stake. So, win-wise, there is no comparison between these two gambling genres.

That said, roulette has made dozens of millionaires in the past, and if one opts to make even-money bets, the house edge that gambler faces is 2.7%. At many online platforms, the French version has only 1.35%, in addition to offering demo play. So one way to practice is with top online live roulette sites before going into a physical venue, where if one experiences a freakish streak of luck, rewards like those discussed below await.

5. A Brazilian Businessman Snags $3.5 Million

In 2017, Brazilian businessman Pedro Grendene Bartelle was in neighboring Uruguay on a work-related trip when he entered the Conrad hotel in Punta del Este, found in the downtown area, in front of the Playa Brava campsite. The Conard does not rank as South America’s most glamorous gaming establishment, but it is a property where high rollers come to bet big. Pedro chose to do the same as he started his session by making substantial straight bets on roulette. The practice eventually led to him placing one worth $35,000 on thirty-two. The massive gamble paid out, and he left with $3.5 million in winnings from a single wager.

4. Sir Philip Green Cashes Out More Than £2 Million

Philip Green is a British fashion mogul who owns multiple high-end clothing brands like Wallis, Burton, Evans, and Miss Selfridge. In 2004, Green walked into the Les Ambassadeurs, one of the finest Georgian properties in Mayfair, London, where guests get pampered with impeccable service. A frequent gambler, well-known in the London gambling scene, he sat to play roulette, his game of choice, pulling in more than £2 million in one night of wheel wagering. Note that £2 million in 2004 equates to over $4 million in today’s money, a sum attainable in live roulette at various gaming platforms that boast VIP sections.

3. Charles Wells Takes Home One Million Francs

Charles De Ville Wells, nicknamed Monte Carlo Wells, was an English fraudster and gambler born in Hertfordshire in 1841. In his twenties, Wells worked as an engineer at Marseille’s shipyards and docks before moving to Paris, where he defrauded people in various investment ruses. To avoid serving prison time, Wells fled to Britain, continuing his scheming ways in England. In the summer of 1891, Wells visited Monte Carlo Casino, where he enjoyed a three-day winning streak bankrolled with $400, which slowly, over three days, turned into $13 million in 2022 cash. Various speculation arose following Wells’ stunning achievement, many calling it a publicity stunt, with others believing he had cheated his way to victory.

2. Joseph Jagger Takes Advantage of a Bias Wheel to Rake in 2 Million Francs

Known as the Man That Broke the Bank at Monte Carlo, Jagger is an infamous gambler who was a Yorkshire textile industry businessman with vast engineering knowledge. His insights on how machines work helped him identify a flaw in a Casino de Monte-Carlo roulette wheel, making it favor specific numbers. Equipped with this info, he partook in a roulette session lasting several days in 1881 at this venue that resulted in a winning amount that totaled more than 2 million francs. In today’s money, the value of his winnings would come to more than $ 20 million.

1. Drake Wins $25 Million

Multiple sources claim that the world-famous musical artist Drake has gambled billions of dollars in the past few years. His exploits can be viewed on Twitch, with Canada’s best-known rapper seen playing at premium crypto gambling hubs. In July 2022, he live-streamed one of his roulette sessions, accompanied by Moroccan hip-hop artist French Montana. Drake’s take in the round reached a staggering $27 million, but when all was said and done, he only had $1,879 left, losing almost all of his previously secured winnings, proving that it is paramount to know when to walk away.

This article was written in collaboration with casino game experts.