Born November 4, 1935 in Port Colborne, Ontario, Jim Gregory grew up in Dunnville, Ontario. He moved to Toronto to attend the well-known and loved St. Michael's College School in 1953. Although Jim unsuccessfully tried out for the school's Junior 'B' team, the Buzzers, he instead took a role as trainer of the Junior 'A' Majors, working with highly-regarded coaches Bob Goldham and Honoured Members Joe Primeau and Father David Bauer.
In 1961, by then managing the Majors as well, Gregory was part of an organization that won the Memorial Cup as junior champions of Canada. It was a melancholy summer, as the school made a decision to withdraw from the Ontario Hockey Association, in spite of reigning as Junior 'A' champions.
Instead, a new league was created to address the travel and expense concerns of OHA Junior play. The Metro Junior 'A' Hockey League was formed, and included both St. Mike's and the Toronto Marlboros, as well as a handful of former Junior 'B' teams from the Toronto area. Jim Gregory assumed the position as manager of the Majors once again. But after a single season, the 1961-62 campaign, the school again found the situation unsatisfactory and withdrew from Junior 'A' competition completely.
Gregory found a home for the team with another Toronto Catholic high school, Neil McNeil, and was coach and manager of the Maroons as they won the league championship in 1962-63.
The short-lived league was disbanded, and players from both Neil McNeil and the Marlboros, both junior affiliates of the Toronto Maple Leafs, were rolled into one team under the mantle of the Toronto Marlboros. Gregory executed the merge, coaching the Marlies to a Memorial Cup championship in 1964. The following season, he added the managing role as well and beginning with the 1965-66 season, solely handled the manager's duties. The team won another Memorial Cup championship in 1967.
Already in the employ of the Toronto Maple Leafs, Jim joined the Western Hockey League's Vancouver Canucks as head coach in 1967-68. In 1968-69, he was hired to assist Punch Imlach and Bob Davidson with the Toronto Maple Leafs, focusing on scouting duties. At the age of 33, Jim Gregory replaced Imlach as the Leafs' General Manager during the spring of 1969, and stayed in that position for ten seasons. During that decade, the Maple Leafs made the playoffs eight times.
One of the first NHL managers to recognize Europe as a talent pool for the NHL, Gregory quickly emerged as a strong executive, and in 1979, was hired by the National Hockey League as Director of Central Scouting. In 1986, he was named Executive Director of Hockey Operations for the NHL. Today, Gregory continues as Senior Vice President, Hockey Operations for the National Hockey League. Under his management, the implementation of video goal reviews was introduced.
In addition to his duties with the NHL, Jim has served as Chairman of the Hockey Hall of Fame's Selection Committee since 1998.