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Biggest Roulette Winners 

We should start by saying that roulette involves absolutely zero skill. Of course, you will need to know the basic playing rules. But they only ascertain where and when you should place your bets. The tiny ivory ball is dropped into a spinning wheel and the result is purely down to luck. Because of the nature of the wagers available, it’s impossible to get rich on a single wager unless you lay a huge bet in the first place. On the whole, the largest bets will come from being able to double your bankroll, though they can, as you’ll later see, go as high as 35:1. Nevertheless, there are some players throughout the history of the game who have walked out of the casino has made some serious winnings. Let’s have a look at some of history’s biggest roulette winners.

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Charles Wells – “The Man Who Broke the Bank in Monte Carlo”

Charles Wells was a scam artist and was responsible for many shady “investment” plans in order to make money off foolhardy members of the public. In 1891, having had a successful run thanks to these illegal activities, he took a trip to Monte Carlo. Starting off with an initial bankroll of 4000 Francs, he ended up actually breaking the bank by winning a massive 1,000,000 Francs over the course of a few days. He had a string of amazing luck, having won at 23 out of 30 consecutive spins. Later on, he returned again to Monte Carlo and proceeded to break the bank again, winning another million francs. 

Having won a total of 2 million Francs he was now one of the biggest roulette winners of all time. The operetta musician, W.S. Gilbert, of the Gilbert and Sullivan Victorian theatrical partnership, wrote the famous song about him, “The Man who Broke the Bank in Monte Carlo.”

Of course, many people assumed that Charles Wells won his fortune, not through good luck. But rather through the use of fraud, as he did with his other businesses. Nevertheless, he does go down in history as the biggest roulette winner in the world. Unfortunately for him, later on in life, he actually went to prison after being convicted of his fraudulent activities.  Once he was out he quickly resumed his fraudulent lifestyle though is rumoured to have died in 1922, to completely broke.

Ashley Revell – The Man Who Risked It All 

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There are probably many stories similar to the one involving Ashley Revell. The only difference is that he decided to drum up some publicity about his gambling activities. This young man who came from Kent decided that at the age of 24, he was going to sell all of his worldly possessions and take all the money to Las Vegas for a single bet at the roulette table. After disposing of all his worldly goods, he had a total of  $135,300 as his bankroll. He flew to the Plaza Hotel and Casino in Las Vegas, Nevada, as they were one of the few casinos willing to accept such a wager.  As you can imagine, his crazy bet had attracted worldwide media attention and many sponsors also got involved. 

Ashley Revell had no money to hire a tuxedo and so borrowed one from the casino itself. In front of a cheering crowd, he placed a double or nothing bet on the colour red. As you can imagine, the tension as the wheel was spinning must have been almost unbearable. But once it finally stopped, the ball landed on the 7, which is red. He was able to collect $270,000. This was by far one of the biggest and riskiest bets that have ever been made at the roulette table, made by any of the world’s greatest roulette winners. The TV channel Sky 1 made a mini reality TV series about his adventure called “Double or Nothing.”

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Roulette Winners: Chris Boyd – The Man Who Bet His Savings

Chris Boyd’s roulette story is very similar to that of Ashley Revell. After a lifetime of working manual jobs, he decided that he had enough. Just like Ashley, he sold everything he possibly could and decided that he would also make a single bet in Las Vegas at the roulette wheel. All in all, as a highly paid computer programmer, he managed to save around $220,000 over a period of 3 years. Once he flew into Las Vegas, he came up against a basic problem in nearly all the casinos he visited. That is that all casino table games will have table limits. All the casinos to win the jackpot said the amount he wanted the bet was too much. In the end, as part of a publicity stunt, Binion’s Horseshoe Club agreed to take his wager. They agreed to raise their standard limit of $100,000.

Following Ashley Revell’s jackpot winning strategies, Chris Boyd put it all on the red. And just like that, he won, taking home with him for $220,000, making him one of history’s largest roulette winners.

Pedro Grendene Bartelle – The Big French Roulette Winner

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Pedro was a Brazilian businessman who with his twin brother, Alexander, founded Grandine, who is the world’s largest manufacturers of sandals. In truth, Pedro Grendene Bartelle wasn’t really short of a penny and could easily afford a casino whales lifestyle. Nevertheless, in 2017, he decided to take a trip to a casino, the Hotel Conrad in Uruguay. There he placed a single bet of $35,000 on his favourite number the number 32. A roulette bet on a single number pays out at 35:1. Well, he ended up winning the largest amount anyone has ever won with a single bet. It was an amazing total of $3,500,000. He was playing at the French roulette wheel, which as you know offers the highest payout on any casino game.

Funnily enough, two years earlier, at the same casino, with the same bet on the same number, he also was lucky and won $1,225,000. Rather than go to the real casino, like Pedro, you can certainly try to win the jackpot online by playing at our favourite casino, King Billy Casino. They have a massive number of table game variations, with great live dealer roulette to give you the same feeling of being in a real casino. But whilst playing on your phone, comfortably sprawling out on your sofa at home in your jammies.

Roulette Winners: Sir Philip Green – The Billionaire Spiv

Sir Philip Green was the former high rolling boss of the Arcadia Group.  This had many famous fashion brands under its belt including Topshop, Evans, Burton, Miss Selfridge, Dorothy Parker, Wallis and Topman. Green was well known for his love for the game of blackjack. But one night at Les Ambassadeurs Casino in London, he managed to win £2,000,000 over the course of an evening at the roulette wheel. Unfortunately, now his name has become tarnished. Under their ownership, the company was systematically asset-stripped by Green and his wife. In November 2020 it was declared bankrupt and slipped into liquidation. Worse, they stole directly from the employee’s pension fund. The government voted to strip him of his knighthood.

Roulette Winners: Mike Ashley – The Sports Direct And Newcastle United Football Club Owner

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Mike Ashley is another wealthy businessman who was the CEO of Sports Direct and the Frasers group. As well as being the disastrous owner of Newcastle United Football Club. He comes in at 61st place on the Sunday Times Rich List for 2021. Back in 2008, he paid a visit to 50 St James Street, in Mayfair London, where he made a bet on the number 17 at the roulette table. It was what’s called a “complete bet.” This means that he bet on every combination including the number 17.

After the roulette wheel stopped spinning, he took home around £1,300,000. At first sight, this might make him one of the most successful roulette winners. But keep in mind that he bet a total of £480,000 during that evening. Like Sir Philip Green, his name would later become tarnished as a result of the way he ran Sports Direct and Newcastle United.

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