Top 5 Toronto Maple Leafs General Managers of All-Time

#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.