#2 – Punch Imlach
November 22, 1958 – April 6, 1969 and July 4, 1979 – October 1981
George “Punch” Imlach had two stints as the general manager for the Maple Leafs. If those two unique periods could be separated, Imlach would make both this top five list and a bottom five. That makes Imlach’s position as the second-best Leafs manager somewhat controversial. He spent his first years with the team building it into a winning franchise and his second go, dismantling it.
Imlach had an interesting route to the NHL. He played in the OHL for three different Toronto teams before he enlisted in the army during WWII. While with the Canadian Armed Forces, he began coaching hockey.
When the war was over Imlach played in the Quebec Senior Hockey League where he continued his coaching career as the bench boss and general manager of the Quebec Aces. He even had minority ownership of the club.
In 1958, the Maple Leafs hired Imlach after he was fired as coach and GM of the Springfield Indians. He joined the Leafs as an assistant general manager in July that year. By November Imlach was running the team solo. One of his first moves in the role was to assign himself to coach the club.
As coach and GM, Imlach built up a last-place Leafs team. He took them all the way to the Stanley Cup finals six times. His teams won four championships. Imlach even had the good sense to trade for a player who ended up on this list, acquiring Quinn via trade from the St. Louis Blues for cash.
While it’s hard to argue with that level of success, Imlach’s detractors will point to his gruff approach with players and obvious missteps. Imlach traded Jim Pappin to the Chicago Blackhawks who went on to be a 40+ goal scorer. The exchange brought Toronto Pierre Pilote who scored three goals for the Buds.
Imlach also traded away Eddie Shack and in a separate transaction, gave up future stars Bob Nevin and Dick Duff for players who didn’t play beyond a single season. To his credit, Imlach also managed to bring Shack to the team in 1960 via trade. He also scored big by trading for Red Kelly who transformed into a 20 goal scorer in Toronto.
In Imlach’s return to the Leafs, sandwiching Gregory’s time in the office, he was far more destructive. He traded away Darryl Sittler, Ian Turnbull, Pat Hickey, and Mike Palmateer. He even acquired and traded away another future NHL GM, Jim Rutherford.