After working his way up the ladder with the Quebec Aces (from player to manager to owner), Punch Imlach would become the Assistant General Manager with the Toronto Maple Leafs. As impressive as that title sounds, it was a position that was basically one of a committee, as the Leafs had no General Manager. 

It is safe to say that the Chicago Blackhawks wished they could have that trade back. In Chicago, Phil Esposito was a decent player, but had not shown the fans everything he was capable of, and he often felt like Chicago management had little faith in him.   He was traded to Boston and went on a scoring tear that has been duplicated by only a handful of other players. 

Although Jake Milford never won the Stanley Cup, he was considered one of the top executives in the NHL during his tenure. Milford was a successful General Manager winning the Central League Title four times. Moving up to the big dance, he took over the GM position with the Los Angeles Kings and took them to their best record in the league. He would do the same in Vancouver, assembling a team that went to the Stanley Cup Finals for the first time in that franchise’s history. Again, he may never have won a Cup, but he put together talent in places that gave hope to hockey fans sooner than they would have expected.

An eight time Stanley Cup Champion with the Montreal Canadians, Jacques Lemaire was a Centre who may not have led his team in scoring, but was a vital part of the championships that his team accrued. Lemaire was a point per game player, and played in two All Star games, but he was always at his best in clutch situations and shone brightest during the NHL playoffs. It was likely because of that fact, that Lemaire was considered a Hall of Fame performer as though he was never considered the best player on his team, he was the guy you knew you could count on when you needed it most.