Gary Leeman's journey in professional hockey began when he was drafted by the Toronto Maple Leafs as the 24th overall pick in the 1982 NHL Entry Draft. Initially playing as a defenseman, Leeman transitioned to right wing, a move that would define much of his career. His time with the Maple Leafs was marked by his offensive prowess, particularly during the 1989-1990 season when he scored 51 goals, becoming only the second player in franchise history to achieve the 50-goal milestone at that time.

Leeman's tenure with the Maple Leafs spanned nearly a decade, during which he became a fan favorite for his scoring ability and tenacity on the ice. His performance peaked in the late 1980s, and he was part of the "Hound Line" alongside Wendel Clark and Russ Courtnall, a trio known for their dynamic play and chemistry.

In 1992, Leeman was involved in one of the most significant trades in NHL history, moving to the Calgary Flames as part of a package deal that brought Doug Gilmour to Toronto. His time with the Flames, however, was short-lived, and he struggled to replicate his earlier success. Leeman's career continued with stints at several other NHL teams, including the Montreal Canadiens, Vancouver Canucks, and St. Louis Blues.

While with the Canadiens, Leeman achieved the ultimate team success, being part of the squad that won the Stanley Cup in 1993. Although his role was more limited compared to his peak years, being part of a championship-winning team was a notable highlight in his career.

Leeman's NHL career concluded with the St. Louis Blues, after which he briefly played in the minor leagues and overseas before retiring from professional hockey.

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