With a new Maple Leafs general manager about to emerge, reported to be John Chayka possibly working under franchise scoring leader Mats Sundin, we have a ranking of those who've been on hockey's hottest seat. Our five best and worst execs, employed for at least 100 games since the 1917 funding of the team, with their records, points percentages and Stanley Cups in parentheses.
The Five Best
Punch Imlach (1958-69, '79-81)
433-359-159 .539% (4). He was raised in the east end of Toronto, hired as assistant GM, quickly elevating to GM/coach. He epitomized old school, which included brow-beating stars such as Frank Mahovlich, but had complete faith in team elders. Built a heavy roster with defensive acumen to shut down the speed and skill of Detroit, Montreal and Chicago, beating all three in Cup finals.
Best move: Acquiring defenceman/centre Red Kelly from Detroit after talking him out of retirement.
Quote: "I don't believe in age. Ability is what counts for me."
Conn Smythe (1927-57)
774-617-274 .547 (7). Helped buy the St. Patricks and keep the team in Toronto, built Maple Leaf Gardens. A military man, he stressed toughness and ran a strict operation, transforming the post-war Leafs into the franchise's first dynasty.
Best move: Using money won from a long-shot horse race to help finance a trade with Ottawa for King Clancy.
Quote: "If you can't beat 'em in the alley, how you gonna beat 'em on the ice."
Pat Quinn (1999-2003)
145-110-10-15 .559 (0). Hired as coach, took the GM vacancy to protect his job. Re-instilled pride in emulating his former boss Imlach. Fashioned a skilled team that could beat the trap in the worst days of obstruction. His Leafs made the playoffs six straight years.
Best move: UFA signings of Alex Mogilny, Gary Roberts and Ed Belfour.
Quote: "What I have to do is like a car, I have to pick up the hood and look underneath."
Cliff Fletcher (1991-97, 2008)
219-213-58-3 .499 (0). Dramatic transformation of 1980s' drudgery to conference championship appearances in '93 and '94. Moved out youth in many bold trades for proven veterans, while modernizing the hockey department.
Best move: Acquiring Sundin for the beloved Wendel Clark caused an uproar, but landed the franchise's leading scorer.
Quote: "The hardest things about getting this far (losing Game 7 to Los Angeles in the '93 conference final) is not knowing if you'll ever be this close again."
Jim Gregory (1969-79)
334-324-130 .506 (0). Restored a roster twice gutted, first by NHL expansion then the WHA's arrival, while dealing with unpredictable cheapskate owner Harold Ballard. Had a strong junior hockey background, hired new-age coach Roger Neilson and maintained good relations with captain Darryl Sittler and his lieutenants.
Best move: In the 1973 draft landed Lanny McDonald, Ian Turnbull and Bob Neely in top 15.
Quote: "You meet people in this business who think very highly of themselves, but I'd remember Clancy, Syl Apps or Teeder Kennedy. If people like that could be (humble), why not me?"
The Five Worst
Gerry McNamara (1981-88)
166-302-67 .373% (0). History looked back a bit kinder on 'Gerry Mac' before his recent passing, but the '80s are still considered the club's nadir. He made the most of high picks, after a string of poor finishes when he rushed the young talent or failed to insulate it through development.
Worst move: Signing free agent Miro Ihnacak, sight unseen, at Ballard's urging, after paying six figures to spring him from behind the Iron Curtain.
Quote: "Some people said, 'how could you (tolerate) Ballard?' Well, I loved my job, loved where I was at, I loved the money. I was not about to tell him, 'I disagree, I quit.'"
Brian Burke (2008-13)
129-135-42 .490% (0). Instead of reviving Leafs fortunes after his much-anticipated arrival, during Burke's watch they extended their playoff drought a total of seven years. Toronto didn't get team tough as he intended, amid an on-ice leadership void he didn't address.
Worst move: Hiring Ron Wilson as coach. While losses mounted, his old pal didn't get along with top scorer Phil Kessel and was sparred too often with media.
Quote: "It's an 18-wheeler going right off a cliff."
John Ferguson Jr. (2003-08)
226-222-58-9 .504% (0). Had a hard act to follow Quinn, even though it was time for someone younger at the top. JFJ was getting interference from above with CEO Richard Peddie and was the first Leafs GM restricted by the new salary cap, while stars such as Sundin controlled their trade fate.
Worst move: Acquiring Andrew Raycroft for Tuukka Rask, who went on to be the Bruins' franchise goalie.
Quote: "I'm proud of my record. There is a future here. We have not seen the best of it."
Floyd Smith (1989-91)
61-84-15 .428% (0). He inherited neglect from the Ballard era, with a swing year where the team scored a record 337 goals, but gave up 358. After a 1-9-1 start a few months later, he had to replace coach Doug Carpenter with Tom Watt.
Worst move: Trading for defenceman Tom Kurvers with the pick that became Hall of Famer Scott Niedermayer.
Quote: "I've got nothing to say and I'm only going to say that once."
Brad Treliving (2023-26)
139-92-27 .591% (0). Brought aboard when Kyle Dubas' re-hiring suddenly went south, Tree enjoyed early success, only to see a 108-point campaign suffer a club-record one-year drop of 30 this season. Previous depth concerns hampered progress, with injuries and underwhelming trades.
Worst move: While the book isn't closed on it, the loss of valued forward Fraser Minten to Boston for the prospect-thin Leafs, as well as a first-round pick this year or next, looks bad after big defenceman Brandon Carlo made little impact in the 2025 playoffs or this season.
Quote: "It starts with me. I take responsibility for our season."
