Fletcher spent 25 seasons as an executive with the Maple Leafs, peaking in 1993 when the team came within one win of the Stanley Cup Final.
The Montreal native also led the Calgary Flames to the Stanley Cup title in 1989. He was inducted into the Hockey Hall of Fame as a builder in 2004.
“The Toronto Maple Leafs and its fans will remain forever grateful for the many contributions Cliff made to the organization and the game of hockey,” the team said in a statement. “He will always be remembered as part of our hockey family. The club extends our deepest condolences to the Fletcher family, including his children Chuck and Kristy, their families, and his partner Linda.”
Fletcher, who earned the nickname “Trader Cliff” for his tendency to make deals with other teams, began his career as a scout with the Montreal Canadiens in 1956 before landing his first gig as general manager with the expansion Atlanta Flames in 1972.
He led the Flames through their move to Calgary in 1980 and into a successful decade for the franchise, which included two division titles, two conference championships and culminated in the 1989 Stanley Cup.
Two years after achieving that victory with the Flames, Fletcher moved to the Leafs as president and GM.
In 1992, he executed a blockbuster trade with his old team, acquiring Doug Gilmour as part of a 10-player deal. He also welcomed future Hall of Famers Glenn Anderson, Dave Andreychuk, Mike Gartner and Pat Burns to the organization.
Fletcher brought another beloved Maple Leaf into the mix when he acquired Mats Sundin from the Quebec Nordiques in exchange for captain Wendel Clark in 1994.
He left the Maple Leafs in 1997 and served front-office stints with the Tampa Bay Lightning and Arizona Coyotes before returning to Toronto in 2008 for 19 months, including time as GM.
