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The sheer number of betting outcomes is why roulette is one of the dramatic table games in a casino. Depending on how daring you feel, you can risk it all or use roulette betting systems. In this case, however, the focus is on the largest roulette wins that come from risky bets.

Where to Play Roulette

Chris Boyd: Double or Nothing

British computer programmer Chris Boyd spend three years saving money to afford a trip to Las Vegas, where he would later stake $220,000 [£170,000] on the colour red in roulette. Chris walked away with double his savings and vowed never to play again.

Sean Connery Wins Three Times on 17

The former James Bond was visiting an Italian casino when he placed five successive bets on 17. After missing the first two, Connery would go on to astound the casino with three-straight wins. It is said Connery walked away with his £163,000 winnings.

Philip Green Wins £2 Million

Philip Green is a UK retail giant who managed to take a Mayfair casino for £2 million back in 2004. Green’s lucky streak happened in the very same night, even leading the casino to warn its investors to expect forthcoming profit decreases.

Ashley Revell: Betting Your Life Savings

Back in 2004, British gambler Ashley Revell sold everything he owned and pooled his life savings before setting off for Las Vegas to place the insanely risky bet. For Ashley, the idea was spawned over drinks with his mates.

And while his friends moved on from the discussion, Ashley could not look go and it eventually became an obsession. After auctioning off his items during a six-month spell, Ashley had accumulated £76,840 and set off to Las Vegas.

The entire experience was even recorded, and you can search for “Ashley Revell” on YouTube to watch it for yourself. Then you will see Ashley betting it all on red and the ball eventually landing on red 7 after a few dramatic spins. Despite that excitement, Ashley has since led a relaxed life with £153,680 winnings.

Mike Ashley: Complete 17 for £1.3 Million

From one Ashley to another, this next winner is famed for owning Premier League football side Newcastle United and a UK chain of sporting shops. But those feats and a multimillion-pound bank account did not hold back Mike Ashley from staking £480,000 while playing roulette at a Mayfair-based casino in London.

On a single spin, Ashley backed a complete 17, which is when all combinations associated with 17 are backed. After just 15 minutes at the table, Ashley saw the ball drop into the number 17 slot of the reel. For seasoned roulette players, this number is significant because it sits in the very centre of the wheel. In May 2008, this enabled Ashley to win a £1.3 million roulette jackpot.

These stories have inspirational outcomes, but don’t forget that smart betting can also be key when knowing how to win in roulette.