Early positions

Fletcher started his career in 1956 for the Montreal Canadiens as a scout under Sam Pollock, then later became the general manager of the Verdun Blues junior team.

He joined the expansion St. Louis Blues in 1966 as a scout for Eastern Canada worked his way up to the assistant GM position. With Fletcher's help, the Blues advanced to the Stanley Cup Finals in each of their first three years, a feat unmatched to this day.

Fletcher's general manager career started in the Central Hockey League with the Kansas City Blues when he was awarded the top job in January 1971 during a mid-season shake-up that also saw John Choyce appointed as the team's new head coach.^[3] In 1972, he accepted the opportunity to run an NHL team when offered the GM position in Atlanta.

Flames

Fletcher joined the newly minted expansion Atlanta Flames team as general manager, remaining with the Flames in that capacity through and after the team's move to Calgary, Alberta in 1980. Over the next 10 years, he oversaw the Calgary Flames to two Smythe division titles, two Clarence S. Campbell Bowls as Campbell Conference champions, and two Presidents' Trophies, given to the team with the best NHL regular season record. During his tenure in Calgary, he was the first GM to bring a player from the Soviet Union when Sergei Priakin played in 1988. The Flames won the Stanley Cup Championship in 1989 against the Montreal Canadiens.

He also served as the GM of Team Canada for the 1981 Canada Cup.

Maple Leafs

Fletcher moved to the Toronto Maple Leafs in 1991, to serve as chief operating officer, president and general manager. He made a blockbuster trade with Doug Risebrough, his successor as the Flames' General Manager, sending Gary Leeman, Michel Petit, Jeff Reese, Craig Berube, and Alexander Godynyuk to the Flames for Doug Gilmour, Jamie Macoun, Ric Nattress, Rick Wamsley and Kent Manderville on January 2, 1992. That year, Fletcher also hired Pat Burns as head coach for the upcoming season.

Fletcher's hiring occurred shortly after the death of longtime Leafs' owner Harold Ballard. To his undoubted benefit, unlike Ballard the team's new owners had no desire to meddle in hockey operations, thus giving Fletcher a free hand in managing the team. The positive impact on the Toronto team was immediate. During the 1992–93 season, his second year as GM, the Leafs set team records with wins (44) and points (99), while Gilmour emerged as a superstar and scored a franchise-high 127 points. During the postseason awards ceremony, Gilmour finished as runner-up for the Hart Trophy and won the Frank J. Selke Trophy as best defensive forward, while Burns won the Jack Adams Award as coach of the year; the first major NHL individual awards that Leaf players had won since 1967. Fletcher himself was named as the "Man of the Year" and the "Executive of the Year" by The Hockey News in 1993.

Ultimately, Fletcher did not match the postseason success he enjoyed in Calgary, as the Leafs failed to reach the Stanley Cup Finals during his tenure. The Leafs did reach the conference finals in 1993 and 1994 - the only team in the NHL to make it that far in the playoffs in both seasons and the only one of the seven teams from those two years to not make a Stanley Cup Finals since expansion.

He remained with the Toronto Maple Leafs for six seasons before retiring to Florida.

Lightning

In 1999, Fletcher joined the Tampa Bay Lightning as Senior Advisor to the GM for two seasons at the request of Jacques Demers, then Tampa's coach and GM. When Demers left the franchise in 1999, so did Fletcher.

Years later, Demers revealed that he had sought the assistance of Fletcher (as well as that of Jay Feaster) largely on account of his own functional illiteracy, which Demers managed to keep concealed from NHL circles before leaving the game. In his biography, Demers acknowledged that Fletcher and Feaster did most of the work a general manager would normally do because Demers knew he could not do it himself.^[4]

Coyotes

Fletcher joined the Phoenix Coyotes on February 17, 2001, as general manager and executive vice-president. On August 28, 2001, he passed his GM role to Mike Barnett and became senior executive vice-president of hockey operations.

On April 11, 2007, Fletcher and General Manager Mike Barnett were fired after the Coyotes finished the 2006–07 season with its worst record since relocating from Winnipeg to Phoenix in 1996.

Return to Toronto

Fletcher was officially named the interim general manager of the Toronto Maple Leafs on January 22, 2008, replacing John Ferguson Jr. Fletcher signed a nineteen-month contract with the franchise; serving as GM for six months before becoming an executive for the Maple Leaf Sports & Entertainment organization. He was replaced as GM of the Toronto Maple Leafs by Brian Burke.

Team President Richard Peddie announced that Fletcher would likely be the general manager through the 2008–09 NHL season,^[5] although it was later announced on November 27, 2008, that Brian Burke had agreed to a six-year contract as the Maple Leafs' GM.^[6] Fletcher served the remainder of his contract with the Maple Leafs as an adviser for the Maple Leafs management team. During the off season of 2009, Fletcher signed a multi-year contract extension.