Sidney Crosby has won three Stanley Cups in the first 12 seasons of his 13-year career.
Crosby's first championship came in 2009 when he helped the Penguins reach the Stanley Cup Finals for the second time in his career. Pittsburgh defeated the Red Wings in seven games to capture the third title in franchise history, just one year after Detroit knocked off Pittsburgh in six games to win the Stanley Cup.
After winning that championship, the Penguins failed to reach the Stanley Cup Finals for six straight seasons, until in 2016, they went through the Rangers, Capitals and Lightning to set up a matchup with the Sharks for the Stanley Cup. Pittsburgh won that series in six games, and the next season, they beat the Predators in six games to become the first back-to-back champions in the NHL since the Red Wings did it in 1997 and 1998.
Crosby won the Conn Smythe Trophy for Pittsburgh's last two playoff runs. In 2016, the Penguins captain had six goals and 13 assists in 24 playoff contests and in 2017 he had eight goals and 19 assists over 24 contests to help Pittsburgh claim its fifth Stanley Cup.