Top 5 Roulette Players Of All Time

Although roulette players aren’t as popular as poker professionals, these individuals are still skilled gamblers. Here are the top 5 of all time.

Roulette Players & How 5 Of Them Rose To Fame

Despite its apparent simplicity, roulette is a casino game that caters to the house instead of the player. The unwritten casino rule is that the simpler the game, the greater the house advantage. Although it appears straightforward, roulette is actually notoriously challenging. It is a game that even seasoned roulette players associate with risk-prone personalities and significant monetary risk.

Regardless, there have been players who have successfully defied the odds. Several skilled individuals managed to manipulate the game with only the typical bets to make in this game [3]. Examples of several such winnings exceed $2 million for a single number bet.

However, keep in mind that the actual biggest roulette winners are most likely unrecorded. Professionals who rely on proper strategies mostly avoid detection and win big as a result. If you’re looking for the known big names, you’re at the right place.

The Biggest & Baddest Roulette Players To Ever Win

● Phillip Green

● Pedro Bartelle

● Joseph Jagger

● Sean Connery (the true star of this roulette players list)

● Mike Ashley

Phillip Green

Sir Green owns several high-end fashion retail businesses and comes from a successful business background. Even though he preferred blackjack as his game of choice, this successful businessman decided to try roulette on a fateful evening in 2004. His choice proved to be the right decision for beating the odds [4] as Green landed a $2 million win.

This success sparked Green’s ascension as one of the era’s skilled roulette players. In the same year, the same casino, London’s Les Ambassadeurs, demonstrated how much it favors the aristocratic businessman. Green continued to land additional significant wins, one of which bestowed $1 million to his bank account.

However, these wins were not without controversy. Following Green’s lucky breaks, the company operating Les Ambassadeurs issued an interesting statement. The numerous victories depleted the company’s funds, and the continuously decreasing profits resulted in detrimental fund drainage.

Pedro Bartelle

Bartelle was another savvy businessman and multi-millionaire entrepreneur who managed to host Lady Luck on his side. In 2017, Bartelle gambled in a Rio de Janeiro casino [5] when he bet $35,000 on a single roulette wheel number.

This skilled punter went all-in on the number 32 and landed a whopping $3.5 million as a result. Indeed, courage is necessary to bet that much money on a single roulette wager, but Bartelle had an advantage. He was the owner of one of Latin America’s largest shoe companies, meaning he had money to spare.

Additionally, the money ran in Bartelle’s family, as both his father and uncle were equally successful businessmen. His success shows that building gambling skills is available to individuals from all walks of life, including those with pre-existing wealth. Bartelle knew exactly which roulette strategies to avoid and which systems to employ to ensure enormous profit from his risky wager.

Joseph Jagger

This gentleman brings diversity into our top 5 roulette players of all time list due to his unique background. Unlike the previous two entries, which come from a background brimming with old money, Jagger was a textile engineer. His theory of roulette included a belief that the wheels were biased.

Although his hunch was merely instinctual, Jagger’s impressive mechanical sector background as a textile engineer provided him with the confidence to put his theory to the test. As a result, he traveled to Monte Carlo around 1880/1881 [4] and approached proving his hunch in an exciting fashion.

Jagger bribed different clerks at various Monte Carlo casinos into amassing and delivering previous weeks’ roulette results. Upon reviewing the collected results, his intuition proved accurate. There was bias in the wheels, and the ball landed in specific pockets more frequently than the rest. These pockets were 29, 28, 22, 19, 18, 17, 9, 8, and 7.

Armed with the new information, Jagger decided to take full advantage of the bias and eventually landed more than £375,000 in winnings. According to The Times, the textile engineer’s profits measure more than £7.5 million in today’s money. As a result, Jagger’s win became one of the most significant wins in the game’s history and one that allegedly inspired the song “The Man Who Broke The Bank At Monte Carlo.”

Sean Connery

Before you say anything, yes - that Sean Connery. Compared to the previously mentioned roulette players, the legendary Scotsman only won a tiny amount. Connery’s ability to overcome overwhelming odds and turn the situation in his favor granted him the opportunity to succeed in his remarkable career. However, few people know that the actor gambled regularly before choosing the career that made him globally famous.

The story of the actor’s success dates back to his childhood in Edinburgh’s working-class suburbs. He traveled to Saint-Vincent, Italy, in 1963 [6] and frequented a casino where he repeatedly bet on roulette and the number 17. Despite failing numerous times, the James Bond actor wouldn’t cease and eventually won.

The resulting winnings amounted to $27,000, which was anything but modest considering it was in 1963. Fast forward several years, and viewers saw Connery in the legendary Diamonds Are Forever Bond flic. In the movie, you can see the actor also playing roulette and repeatedly betting on 17. Filming trivia reveals this detail was the work of Connery, who decided to use it to pay homage to his gambling career.

Mike Ashley

Last on our top 5 roulette players is a somewhat famous person and another punter boasting prestigious monetary security. Football fans worldwide know the name Mike Ashley as the former owner of the Newcastle football team. Aside from his sporting ventures, Ashley is also a billionaire entrepreneur famous for his lucrative business exploits.

Gambling-wise, Ashley went down the annals of history for a £420,000 wager placed on an inside bet in 2008. The bet occurred at a private Mayfair casino and included the number 17 in a “complete bet.” Roulette enthusiasts know that this complex wager has all six-line, streets, splits, and corners bets that feature this number.

Ashley bagged £820,000 of pure profit as a result and took £1.3 million home. The confidence one must possess to lay down £420,000 on a complicated bet and walk away with their sanity in one piece is impressive. Regardless, Ashley rightfully earned his spot in the luckiest roulette players of all time.