Most Conn Smythe Winners
Patrick Roy leads the Conn Smythe winners list with 3 triumphs in 1986, 1993, and 2001. Roy is also the only player to win with multiple teams.
Wayne Gretzky, Bobby Orr, Sidney Crosby, Mario Lemieux, and Bernie Parent are second on the list. These 5 players have won the trophy twice.
Sidney Crosby, the Penguins Center is the only multiple Conn Smythe Winner still active in the NHL. He won his first trophy in 2016 and in 2017 became the third player ever to win the award consecutively.
Mario Lemieux became the first player to win the Conn Smythe with the franchise in 1991 and 1992. He was the second player ever to do it in successive years. Lemieux was the first overall pick by the Penguins in the 1984 NHL draft.
Wayne Gretzky is one of the only three players to win the Hart Memorial Trophy, Conn Smythe and the Art Ross Trophy in the same year (1984).
Guy Lafleur and Bobby Orr are the other two players. The Great One won his second Stanley Cup Playoffs Most Valuable Player Trophy in 1988.
Both of Gretzky's Conn Smythe came during his time with the Oilers and he won the Art Ross Trophy 10 times between 1981 and 1994. He is still the NHL record-holder for most goals (894), assists (1,963), and points (2,857) which remains unbroken to date.
Patrick Roy won his first two trophies in 1986 and 1993 with the Montreal Canadiens and his third trophy in 2001 with the Colorado Avalanche.
Roy finished his NHL goalie career with a career regular season record of 551-315-131 with 66 shutouts, 2.54 GAA, and a 0.912 save percentage in 1,029 games played. His playoff record in 247 games read 1561 wins, 94 losses, 23 shutouts, 2.30 GAA, and a 0.918 SV%.
Bobby Orr won Conn Smythe playing for the Boston Bruins in 1970 and 1972. Orr is the first player ever to win the trophy more than one time.
Apart from being the first Bruins player ever to win the Con Smythe, he also won the Hart Memorial Trophy, Art Ross Trophy, and the James Norris Memorial Trophy in 1970.
A total of 12 defensemen have won this trophy to date, with Bobby Orr being the only defenseman ever to have clinched the accolade twice.