3 Craziest Roulette Winners of All Time

The craziest winning roulette bets you probably shouldn’t mimic.

The Craziest Winning Roulette Bets you Probably Shouldn't MimicI’ve seen some pretty wild wagers in my days. I might have even made a few, But none of them compare to the stories I’m going to share with you now. These are the tales of three very different men who took similarly huge risks at the roulette table.

I’m not talking about billionaire businessmen who toss millions at the casino every year. I won’t regurgitate the story of Sean Connery’s 3-in-a-row, let-it-ride wins on black 17. Although considerably crazy roulette winners, players like that have nothing to fear from a loss. The guys I’m going to tell you about put everything on the line!

Craziest Winning Roulette Bets of All Time

Before I get into the details of these stories, please consider just how crazy these actions were. I do not recommend following in their footsteps! Unfortunately, many people have attempted to do so, and have lost everything in the process…

Chris Boyd Wagers Life Savings on Red

Crhis Boyd was an English computer programmer back in the 1990s. Back then, computer programmers made a pretty decent living; enough that he was able to put himself on a strict budget and save up $220,000 in three years time. His plan wasn’t to buy a fancy sports car or a new house. No, his plan was to save for three years then drop it all on a single roulette bet.

That’s exactly what he did in 1994. First, he had to find a casino that would take his wager. Most Vegas properties said “No”, sticking to their $100k limit. But Binion’s Horseshoe Casino (now closed) was willing to take the risk. Not only that, the casino covered its 00, defectively turning the game into European Roulette and giving the young man much better odds (2.7% edge versus 5.26%).

Boyd dropped the full $220k – his entire life savings – on red. You can imagine his elation when the wheel spun to a stop on red. Chris collected his $440,000 in winnings and vowed never to gamble again!

Ashley Revell Liquidates Everything for One Bet

No doubt inspired by the tale of Chris Boyd, Ashley Revell became much more famous for taking a similar risk. However, Boyd saved his money over time. Revell wasn’t so patient. In 2004, the native of Kent, England sold everything he owned – his car, his house, his clothes, any and every possession of value was liquidated to come up with as much money as possible for this one crazy roulette bet. His net worth came to £76,000 (US$135,300).

Revell also ran into the problem of finding a casino to accept his excessive roulette wager. He ended up placing the whole $135.3k on Red at the Plaza Hotel & Casino in Las Vegas. He assumed the greater risk of playing American Roulette, but was lucky enough to see the wheel stop on Red 7.

Ashley walked away with $270,600 (£152k). He’s since become the most famous of the craziest roulette winners, not because he won the most, but because his methodical madness was recorded by UK’s Sky One Channel and transformed into a documentary episode for an E! miniseries called Double or Nothing.

After winning, Revell called it “an amazing experience”, and quipped, “the first thing I am going to do is buy some new clothes…”

Jake Cody Doubles Up on Poker Tourney Win

Last year, professional poker player Jake Cody did something just crazy enough to make the final cut on this list of craziest winning roulette bets. After taking down a high-roller event at the UK Poker Championship, Cody – goaded on by his piers and a few alcoholic beverages – laid his entire tournament prize on the roulette table.

It was only a preliminary event, worth £42,670 ($60,000) in prize money – nothing like the multi-million-dollar payouts we see in major main events. But to Cody, it was a large sum of money that he’d just spent hour after hour working incredibly hard to earn. Nonetheless, he went straight from the poker tables to the roulette table at Dusk Till Dawn and dropped it all on black.

Before the wheel was spun, Jake’s intentions became known throughout the casino. Dusk Till Dawn owner Rob Yong came over, not to witness the event, but to take part as the croupier in the game. Yong spun the wheel and the ball landed in the pocket of black 22. In a matter of seconds, the poker pro’s all-in bet was doubled up.

Best Overall Canadian Casino with Easy Deposits : Royal Vegas


Royal Vegas, the leading Canadian gaming brand, are really going out of their way this month and offering a very lucrative offer to prospective players. Details inside.