Its hard to calculate how much cash he actually won converted in modern money, but its in the tens of millions of dollars. We couldnt find any information on his following activities, but we bet he is doing pretty good.375,000 in 1873, how? Conclusion Those were, in our opinion, the greatest roulette wins in history. It looked like he really knew what he was doing. Plus, a straight-up bet on 17 itself. Instead, here are the stories of the biggest roulette winners, who defied the casino advantage and walked into the sunset as very rich men. Reports claim that he also put money on other bets the first half, middle dozen, middle column, black and odd. Connery wagered his winnings one last time, again on 17 and he was lucky again. Ashley wagered his life savings on red. After all, Wells was a known scammer, so the casino would take extra interest in the manner in which he won this fortune. Multiple bets. Mr Wells won close to a million francs that night, inspiring the once-popular song The Man Who Broke the Bank at Monte Carlo. Note: to turn off these warnings you need to set the 'safe mode' to OFF (on the top right) 27 Man Shoots Foot Playing Russian Roulette. This clip is available in 4K resolution. In the end, Mike Ashley managed to win a total of 1,300,000. That alone earns him a spot in this list. One day, he went to a casino in Monte Carlo and bribed six of the clerks into writing down all the results of all roulette wheels in the joint for a couple of weeks. We initially wanted to rank them according to the amount of money they won, but due to the value of money changing over the years, that proved quite difficult.