Leafs extend front office member who brought Sundin and Gilmour to Toronto

At 89, Cliff Fletcher has been involved with the NHL in some capacity since 1956 or 68! years. Upon entering the 2024-2025 season, it will be his 24th with the Leafs as the Leafs have extended his contract as a senior advisor for the upcoming season.

Throughout his 68 years, Fletcher has made some very good moves and some not-so-good ones, but will be remembered most by Leaf fans as the architect behind two of the biggest trades in Franchise history. He acquired Doug Gilmour in 1992 and two years later, he traded away Wendel Clark to bring in Mats Sundin.

Fletcher broke into the NHL in the 1956-57 season with the Montreal Canadiens where he spent 10 years as a scout before joining the St. Louis Blues as an assistant general manager. He then jumped to the Atlanta Flames in 1972 to be their general manager, a position which he held as the team relocated to Calgary and guided them to their only Stanley Cup in franchise history.

In 1991, Fletcher joined the Leafs until 1997 and then left for the Tampa Bay Lightning where he spent 2 seasons before joining the now defunct Phoenix/Arizona Coyotes. Finally, he reunited with the Leafs ahead of the 2007-2008 season where he has been since.

As Lance Hornby noted, Fletcher doesn't make it to many games anymore, but keeps himself occupied with a wall of TV's that allow him to watch any game he wants to. He clearly still has the drive in him to chase another Stanley Cup, now if the Leafs could show that drive, maybe they'll make it past the first and/or second round this season.

Source: Elite Prospects: Cliff Fletcher management history