#5 – Pat Quinn
GM: July 15, 1999 – August 29, 2003
Kicking off the list at number five is Pat Quinn. He first started with the Maple Leafs as a player in 1968. He played under general managers who finished second and fourth on our list. As a professional defenceman, there wasn’t much notable about his contribution to the team.
Quinn was however in the middle of a key moment that grew the rivalry between the Leafs and Boston Bruins. In April of 1969, the two teams squared off in Game 1 of the first round of the playoffs. In their last encounter, Quinn fought superstar Bobby Orr.
In their first postseason meeting, with the Bruins up six-nothing, the two connected again. Quinn watched Orr begin to skate the puck out of his zone. Before Orr was able to reach his own blueline, Quinn delivered a devastating elbow to his head.
Orr lay in a heap as all the Bruins on the ice, including goaltender Gerry Cheevers, tried to get a piece of Quinn. He was forced to fight his way free, even getting punched from a fan who reached over the glass. The fight with fans continued when he reached the penalty box. Orr luckily only suffered a concussion on the play.
Once Quinn’s playing days were through, he continued in hockey as a coach. The Maple Leafs were his fourth NHL team. He joined them for the 1998-99 season. He was surprisingly successful, as the Buds exceeded expectations. That played a big part in Quinn being given the responsibility to manage the team while also coaching the following year.
Quinn held the dual role for four seasons and made the playoffs every year while he was the general manager. The team’s best success under Quinn’s watch was when the team progressed to the 2002 Eastern Conference Finals. They were eliminated at the hands of the Carolina Hurricanes.
Quinn stayed on as a coach after his duties as a general manager were removed in 2003. When the Leafs didn’t qualify for the postseason in 2006, Quinn was terminated as the team’s coach.
The Leafs made good selections in the entry draft under Quinn. He was responsible for selecting Brad Boyes, Mikael Tellqvist, Carlo Colaiacovo, Jay Harrison, Kyle Wellwood, Alexander Steen, Matthew Stajan, and others who went on to have careers in the NHL.
Quinn also won more trades than he lost as the GM in Toronto. He traded for notable players such as Owen Nolan, Darcy Tucker, Phil Housley, Doug Gilmour, and Bryan McCabe.