<P> The Conn Smythe Trophy was introduced in 1964 by Maple Leaf Gardens Limited to honor Conn Smythe, the former owner, General Manager, and coach of the Toronto Maple Leafs and a member of the Hockey Hall of Fame as a builder . The centerpiece of the trophy is a stylized silver replica of Maple Leaf Gardens, the arena built under Smythe's ownership of the Maple Leafs, and their home from 1931 to 1999 . Backing the arena replica is a large silver botanically - accurate maple leaf . The arena replica and leaf are set atop a square wooden foundation, the front of which bears a dedication plaque . Additional tiers below the foundation, sloping outward, contain maple leaf - shaped plates bearing the inscriptions of the winners' names . </P> <P> The base of the Conn Smythe Trophy has been expanded twice over the years to accommodate more winners . Although the 16 nameplates on the original base tier were filled up after 1980, a new tier was not added until the 1983 - 84 season . Following the 2000 Stanley Cup Finals, the 20 nameplates on the new tier were filled up, so the first nine winners' nameplates were moved up to the remaining three sides of the foundation tier, with the remaining nameplates shifted accordingly to keep the winners in chronological order . Due to the cancellation of the 2004 - 05 season, the trophy wasn't filled up again until 2010, after which a new tier was added, making room for 24 more names . </P> <P> The first winner of the award was center Jean Béliveau of the Montreal Canadiens in 1965 . The first player and only defenseman to win it twice was Bobby Orr, who scored the Cup - clinching goals for the Boston Bruins in 1970 and 1972 . Goaltender Bernie Parent (for the Philadelphia Flyers) and centers Wayne Gretzky (for the Edmonton Oilers), Mario Lemieux, and Sidney Crosby (for the Pittsburgh Penguins) have also won it twice each, with Parent, Lemieux, and Crosby each winning theirs back to back (1974 / 1975, 1991 / 1992, and 2016 / 2017 respectively). Goaltender Patrick Roy is the only player to win the trophy three times, and also the only player to win it as a member of two different teams (with the Canadiens in 1986 and 1993, and with the Colorado Avalanche in 2001); his wins also fall into three different decades . Ken Dryden, the 1971 Smythe winner, is the only NHL player to win this trophy before winning the Calder Trophy as rookie of the year (in 1972): Montreal called him up to play only six regular season games, which is not enough to qualify as a rookie season . Dave Keon's eight playoff points in 1967 is the fewest ever by a non-goalie Conn Smythe winner, as he was a defensive forward and is the only Maple Leafs player to win the trophy donated by his club's parent company . </P> <P> Though the award rewards a player who performed particularly well over the entirety of the playoffs, it has never been given to a player whose team did not at least reach the Stanley Cup Finals . The trophy has been awarded to members of the team that lost the Finals five times, most recently Jean - Sébastien Giguère of the Mighty Ducks of Anaheim in 2003, who backstopped his team's surprise run to the Finals, where they pushed the New Jersey Devils to seven games . The only skater to win the award in a losing cause is Philadelphia's Reggie Leach, who won it in 1976 as he had set a league record for most goals in the playoffs (19), which included a five - goal game in the semifinals and four goals in the Finals, even though the Canadiens swept his Flyers . </P>

Who has won the most conn smythe trophies