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Drafted out of the Quebec Major Junior Hockey League (QMJHL) first overall by the Pittsburgh Penguins in the 2003 NHL Entry Draft, Fleury played major junior for four seasons with the Cape Breton Screaming Eagles, earning both the Mike Bossy Trophy as the league's top prospect and the Telus Cup as the top defensive player in 2003. He joined the Penguins in 2003–04 and during his 13 seasons with the team won Stanley Cup championships in 2009, 2016, and 2017. He received the William M. Jennings Trophy and the Vezina Trophy in 2021. He is the third goaltender to ever reach the 500 victories mark in the NHL, after Patrick Roy and Martin Brodeur.