This article should probably come with a warning, because it’s enough to make you excited. Remember though, these events could just have easily gone the other way, and the game of roulette is weighted against you.
That said, there have been some incredible wins over the years.
It’s not possible to know about every big win that has ever occurred, since many will have happened without report or fanfare, some perhaps online, but some do make it into the news and those are the ones we can tell you about here.
The thing with roulette, is that your payout odds will be the same for all the different bets regardless of how much you stake. However, the more you stake, the more that payout is worth in pounds notes if you win. This means that only those with lots of money in the first place can make really large amounts from a single bet, everyone else has to claw their way up to big numbers one bet at a time.
Still, some of the people on this list managed to win large amounts over long play sessions, and they will be included too.
So here we are, the biggest and best known roulette wins in no particular order, and making no alterations for how the value of money has changed over time.
The Buried Life Cast – $250,000 – 2010
This win actually led to the biggest roulette bet in Las Vegas history.
The lads were on some sort of MTV reality show trying to complete a 100 strong bucket list, and at number 75 was to win $1 million dollars.
The plan was to bet $125,000 on an even money bet to try and get $250,000. They would then take that $250,000 and put it on another even money bet in the hope to get $500,000. Next, you guessed it, they would put that $500,000 on another even money bet and try to win the big $1,000,000.
They chose the Golden Gate Casino for their big bet, and the four boys all felt good about red, so with the crowd and the TV cameras watching they pushed their stack of chips onto the board and went absolutely insane when their bet won.
They were split over what to do with their next bet, with half saying red again and half saying black. Eventually they settled on black, slid their even bigger pile of chips a few centimetres in the other direction making history as they did so… and lost the lot.
The ball landed on red again and their dream of winning $1,000,000 was over. They may have broken a record, but they didn’t break the bank.
Mike Ashley – £1,284,000 – 2018
The well known, and some might say infamous, retail business owner, was a regular at the casino in London where he placed his big bet.
The venue has actually never been confirmed, but we know it cost £650 a year to join at the time and dates back to 1827.
Ashley’s favourite roulette bet was a complete 17 – so he would cover every single bet that included the number 17.
This meant he had the following bets on with the stakes broken down besides:
- 1 x straight bet = £2,000
- 4 x split bets = £16,000
- 4 x corner bets = £32,000
- 1 x street bet = £6,000
- 2 x line bets = £24,000
- 1 x column bet = £50,000
- 1 x dozen bet = £50,000
- 1 x black bet = £100,000
- 1 x odd bet = £100,000
- 1 x 1-18 bet = £100,000
That’s a total stake of £480,000.
Unbelievably, his bet won. The ball landed on number 17 and every single bet paid out, netting him a massive £1,284,000.
Supposedly, the table was surrounded with onlookers when this happened, and Mike Ashley is reported to have shown very little emotion, but looked at the dealer and said “That’ll do me. Thanks very much”.
He than gathered his winnings and left. He had been at the table for about 15 minutes.
Phillip Green – £2 million – 2004
Way back in 2004, billionaire businessman Phillip Green (he’s got a knighthood but we refuse to call him sir) was at Les Ambassadeurs in London.
He was known as the retail King at the time, and owned some of the biggest brands on the high street so he could afford to be frivolous with his money (and other people’s too as it would turn out many years later).
He won over £2 million in one night and rumour has it took another £1 million from them a few weeks later. It hurt the casino so badly that they had to issue profit warnings and reduce table limits.
He didn’t win it all in one spin, but was betting tens of thousands of pounds on each spin of the wheel, favouring a mix of even money bets and single number bets.
Green’s empire has since crumbled and his reputation is in tatters after some dodgy dealings plus sexual harassment and bullying accusations. 100 MPs voted for him to be stripped of his knighthood.
Joseph Jagger – £65,000 – 1880s
If you are looking at the amount in the title and thinking it doesn’t sound like that much, then remember, this was back in the 1880s, and that £65,000 would be worth around £7.5 million in today’s money.
Jagger was an unremarkable man in many respects, a mill worker from Yorkshire who taught himself to read and write, he was also an engineer and knew that a roulette wheel could not be truly unbiased.
Back then this was true, as manufacturing techniques were not as advanced, so Jagger planned a trip to Monte Carlo where he would observe the roulette wheels, identify their biases, and then exploit them.
This is exactly what he did, and after months of rinsing the casinos for all they were worth, he and his small team headed back home to rainy England very rich men.
He continued to live fairly modestly though, and his tale is only known today because his family passed it down through the generations, and a distant relative decided to write a book about him in 2018.
Ashley Revell – £153,680 – 2004
This man has gone down as a hero in roulette folklore, simply because of the guts it took to do what he did.
Ashley Revell was out with friends when they ended up talking about the stress a person would feel if they bet everything they had on one spin of the roulette wheel.
For some insane reason, Ashley couldn’t shake the idea and decided that this was exactly what he wanted to do.
He sold literally everything he had, down to his spare clothes, got Sky involved to make a documentary about him, and headed to Vegas to place his bet.
The Plaza Hotel and Casino was the only venue willing to take his bet of £76,840, which might not sound much compared to some of the other big hitters on this list, but remember, it was 100% of everything he had.
The wheel was spun and he chose red at the last minute, and the ball did indeed land on red, winning him £153,680 and making him a legend in gambling circles for decades to come.
He was invited back to the casino on the ten year anniversary of his big win, and he placed a £7,000 bet on red to recreate the fateful night. He won again.
Sean Connery – $27,000 – 1963
Ok, this win is tiny, but it was Sean Connery so it’s going on the list. The original bond casually won $27,000 in an incredible string of luck.
He was playing at the Casino de la Vallee in Saint Vincent, Italy – no doubt staking out some international bad guy with evil intentions upon the world – and bet on 17.
He lost, made the same bet again, and lost again. He bet on 17 for a 3rd time though and this time it came in, netting him a 35:1 payout. He stuck to number 17 for another spin and against the odds it came in again.
Unbelievably, he stayed with his lucky number one more time and even more unbelievably it came in for a 3rd time in a row. The odds of this happening are 50653/1, and Connery (or Bond, not sure which one of them it was at this point) decided to call it quits, walking away with $27,000 in his pocket.
Not only is that the most James Bond thing anyone has ever done, but it was also written into Diamonds are Forever where Bond himself bets on number 17 and wins.
Chris Boyd – $220,000 – 1991
Computer programmer, Chris Boyd, is a bit like a lesser known, but more successful, version of Ashley Revell.
It was further back in 1991 that Boyd made his bet, but he essentially did the same thing. He saved up as much money as you could and took it all to Vegas to make one huge make or break gamble.
He had more trouble than Revell in finding a casino that would take the bet because he wanted to use a European wheel, but eventually Binion’s Horseshoe agreed to his demands, covering the double 00 on their wheel with a card.
Chris had a few practice spins and then it was time for the spin that would count.
He bet on red, and much to his relief the bet won, netting him a very tidy $220,000 which he asked the casino to lock away until he left so he couldn’t lose any of it by betting more. He also apparently vowed to never make another bet again.
We will never know if he kept his promise though, because he took the money home and no one ever heard from him again, which is probably why Ashley Revell gets all of the attention in this department.
Charles Wells – £50,000 – 1890s
Probably the most mysterious name on the list, Charles Wells was a gambler, con man and trickster who hit Monte Carlo in the early 1890s.
He had a history of stealing people’s money by convincing them to agree to invest in his inventions… which he would never go on to invent.
No one really knows how he managed to win so much money but it’s widely accepted that he must have been cheating in some way, especially given his dubious past.
In one instance he won 23 out of 30 consecutive spins, and ‘broke the bank’ many times over during several marathon sessions at the tables.
The song “The Man Who Broke the Bank at Monte Carlo” was written about Wells.
He is another who did not win one certain amount from a single bet, but he managed to extract around £4 million in today’s money from the casino before moving on. Remember, that £50,000 in the title is in 1890s money.
It didn’t do him any good though, and he ended up in jail before being released as a very poor old man. When he died, he was buried in an unmarked grave because his wife didn’t have the funds for a proper funeral.
Pedro Grendene Bartelle – $3.5 million – 2017
This one was caught on camera, and it’s incredible.
Pedro Grendene Bartelle is a Brazilian businessman and co-founder of the biggest sandal manufacturing company in the world – not to mention being the nephew of a billionaire.
That makes his $100,000 wager on number 32 seem insignificant, and to him it probably was, but the 35:1 return that he got on that money when the bet won was anything but.
He pocketed $3.5 million dollars that night at Hotel Conrad in Uruguay, and the large crowd that was watching seemed just as excited as he and his friends were when they witnessed it.
The story gets even more ridiculous though because Pedro had actually done the exact same thing, at the exact same casino, playing the exact same number once before.
On that occasion he only had $35,000 on number 32, but it came in nevertheless, bagging him over $1,000,000 on that day.
So if you’re ever in a casino and you see Mr Bartelle make a bet, pay attention.