The largest recorded roulette win occurred in 2004 when a player known as "Ashley Revell" from the UK famously sold all his possessions and gambled everything on a single bet at the Plaza Hotel and Casino in Las Vegas. He placed a bet of $135,300 on red, and the ball landed on red 7, doubling his money to a total of $270,600. While this isn't the largest cumulative win in roulette history, it stands out for the sheer size of the single bet and the audacity of the wager.