Toronto Maple Leafs: Top 5 General Managers in Franchise History

Dec 15, 2015; Toronto, Ontario, CAN; The Toronto Maple Leafs logo at center ice before the start of the game against the Tampa Bay Lightning at Air Canada Centre. Mandatory Credit: Tom Szczerbowski-USA TODAY Sports
Dec 15, 2015; Toronto, Ontario, CAN; The Toronto Maple Leafs logo at center ice before the start of the game against the Tampa Bay Lightning at Air Canada Centre. Mandatory Credit: Tom Szczerbowski-USA TODAY Sports /
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. Jim Gregory

5. Jim Gregory

Gregory was the Leafs GM from 1969-1979, coming at a time where NHL was starting their post-expansion era. He was a scout for Toronto, prior to replacing Punch Imlach in the spring of 1969.

Gregory had big shoes to fill, considering Imlach was the principal architect of the Leafs’ dynasty during the 1960s. He was brought in during 1959 to work with the Toronto Marlboros, after being introduced to Leafs owner Stafford Smythe  by David Bauer (also known as Father David Bauer).

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The Port Colborn, Ontario native and Smythe built a strong relationship, which helped land him the GM job. During that time, Gregory was working with Bob Davidson, the head scout for the Leafs and the St. Michael’s Majors.

When Gregory replaced Imlach in 1969, the team was coming off a fourth-place finish in the East with a 35-26-15 record, before being swept in the quarter-finals by the Boston Bruins. In his first season in charge, the Leafs finished last in the Eastern Conference.

However, things would begin to turnaround in 1970, when Gregory selected Darryl Sittler eighth overall in the amateur draft. He was also one of the first NHL GMs to bring over players from Europe, realizing they had a strong talent pool of players.

Gregory brought over players like Borje Salming and Inge Hammarstrom from Europe. They helped compliment a strong core including Sittler, Lanny McDonald, Tiger Williams, Ian Turnbull, and Mike Palmateer.

In his 10 seasons as Leafs GM, the team made the playoffs eight times, but when they failed to advance in 1979, Leafs owner Harold Ballard got rid of Gregory and brought back Imlach. Gregory was not even aware he was fired, until the NHL called offering him a job.

Gregory was also responsible for building a proper scouting system with the Leafs, where they hired five full-time scouts. While the Leafs did not make it to the Stanley Cup Finals, he was hired by the NHL as Director of Central Scouting.

In 1986, the 2007 Hockey Hall of Fame inductee was named Executive Director of Hockey Operations for the NHL. He also served as Senior Vice President, Hockey Operations and Supervision for the NHL, with video goal reviews being implemented under his management.

After Gregory’s departure, the Leafs would not enjoy the same success again, with issues between the players and new management undoing all the work he put in. However, his place in Leafs history is assured, as one of the best general managers to ever work in Toronto.

Next: The last GM to be a success in Toronto