Top 5 Toronto Maple Leafs General Managers of All-Time

The Toronto Maple Leafs have won 13 Stanley Cups. The general managers in charge played an important role. We will rank the five best in team history.

The Toronto Maple Leafs have a storied history. The organization has been in place for 102 years and in that time there have been 17 general managers. As with any franchise, some who occupied the position, made decisions yielding positive results, while others were less fortunate.

With a history that long, there are many great lists that can be built to help demonstrate how impactful some have been with the organization. Such is the case here. We will identify and make the case for the top five general managers in Leafs history.

In order to break down the group of 17 and rank them, we will share the most significant moves that were made. The general managers will be based on their entire body of work and the results that came from it.

This puts current Leafs GM, Kyle Dubas, at a disadvantage. His tenure in the role is limited to just one season and his decision making has not fully borne its fruit. That provides an incomplete picture that cannot truly be assessed. As a result, Dubas does not qualify for the top five.

There may be a time where Dubas’s moves can be scrutinized and evaluated. He has already been credited with acquiring John Tavaras, Jake Muzzin, and Tyson Barrie. He was also the man who has let negotiations with Mitch Marner and William Nylander drag on far too long. Hopefully, before his time is up, he can clinch his place among the greats with multiple Stanley Cups to his name.

#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.

#4 – Charles Querrie

GM: Toronto Arenas (1917–20) and Toronto St. Patricks (1920–27)

Charles Querrie was one of the most important general managers for the organization. He was the first to take on the position, even before the team adopted the name Maple Leafs. He ran the team for a decade.

Queerie was not just the general manager, but also owned a majority share of the team. He helped shape the business of the sport. He was instrumental in facilitating the very first radio broadcast of a hockey game in 1923. It took place in Toronto at Arena Gardens.

Arena Gardens, which was sometimes just called Arena was the home for Queerie’s teams. While he held the reins, the franchise underwent name changes. It was first known as the Torontos, then Toronto Arenas. In 1919 the name was changed once again, this time to the Toronto St. Patricks. The name Maple Leafs came only after Querrie sold his stake in the team and relinquished control.

Querrie wasn’t just making personnel decisions, but he also served as the team’s coach for three years. He had a record of 29-38 and never qualified for the postseason as the bench boss. Luckily, as GM, he had better fortune.

Under Querrie, Toronto qualified for the playoffs four times. They also won a pair of Stanley Cups. They captured the title in 1918 and 1922. He put together the original roster, which included talents such as Jack Adam, Corb Denneny, Harry Cameron, and goaltender Hap Holmes.

The most significant of Querrie’s roster moves had to do with future Hall of Famer Adams. Querrie not only signed him, but also traded him away for cash. It didn’t take long for Adams to lead the league in scoring for the Vancouver Millionaires.

As an established star, Querrie re-acquired Adams and played him alongside a young Babe Dye. The two together were a lethal combination as Dye became the league’s top point-getter of the 20s and owned an incredible point per game average of 1.28 with Toronto. Like Adams, Querrie later traded Dye for a cash return.

#3 – Jim Gregory

GM: April 6, 1969 – July 4, 1979

Number three on the list is a Hall of Fame builder, Jim Gregory. Gregory’s legacy in hockey began when he was cut from St. Michael’s College Junior B tryouts. He decided to stop pursuing a playing career and joined the Junior A team to keep stats.

He ascended in the ranks and eventually managed the team and even won a Memorial Cup. That success followed him where he won a championship with the Toronto Neil McNeil Maroons. When the team changed their name to the Toronto Marlboros Gregory stayed on as coach. With them,  he captured his second Memorial Cup.

Gregory eventually earned the opportunity to run the Maple Leafs. The organization hired him in 1959, which turned out to be an excellent move. He first started with Marlies and was even given the title of Director of Scouting for a period.

Starting in 1969, Gregory spent a decade managing the Leafs. He took them to the postseason eight times. He was also the interim manager of the team in 1967 when the Leafs won their last Stanley Cup.

Though the Cup is attributed to Punch Imlach, Gregory took over when he got sick. Gregory ran both the Toronto Maple Leafs and the Marlies at the time. His name was never etched into the Stanley Cup.

Gregory may be best remembered for his willingness to think outside the box. He was one of the first to search for talent outside the continent. Gregory turned to Europe to find players, which at the time was incredibly rare. The gamble worked as Gregory brought Borje Salming and Inge Hammarstrom to Toronto in 1973.

Gregory was also the man responsible for starting the Maple Leafs scouting system. He personally hired the organization’s first group, Frank Bonello and five full-time scouts.

#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.