Jim McKenny was born in Ottawa and moved to Toronto as a child. McKenny played with the Neil McNeil Maroons of the Metro Junior A league in 1962–63. When the league folded in 1963, McKenny transferred to the Ontario Hockey Association\'s Toronto Marlboros who won the Memorial Cup in 1964. As a junior, McKenny was considered by many scouts as the second-best defenceman prospect after Bobby Orr. In later years, McKenny spoke openly of his personal life and career being negatively affected by periods of alcoholism developed during his teen-age years.\n', '

Drafted by the Toronto Maple Leafs in the third round of the 1963 NHL Amateur Draft (17th overall), McKenny had difficulty staying in the NHL early in his career and often played forward instead of his usual position on defence. He was called up from the Marlies to play 2 games with the Leafs in the 1965–66 season. He was given two other opportunities to make the Leafs teams in the 1966–67 and 1967-1968 seasons but only played a total of eleven games. However, on Feb. 24, 1968, he did score the game-winning goal in a 1-0 win over Boston which was the second of his NHL career. He was not promoted to stay on the Maple Leafs for several years, attributed to a poor attitude, possibly his alcoholism and his antipathy towards the high-pressure style of coach and GM Punch Imlach. He played in the minor leagues for the Tulsa Oilers (CPHL), the Rochester Americans (AHL), and the Vancouver Canucks (WHL). McKenny and Don Cherry were roommates when on the road with the Rochester Americans.\n', '

Jim McKenny finally became a full-time member of the Toronto Maple Leafs team during the 1969–70 season and became one of the Leafs top defencemen for eight seasons. McKenny has the fifth highest points total for Leafs defencemen, accumulating 327 points (81 goals, 246 assists) in 594 games, behind only Börje Salming, Tomas Kaberle, Tim Horton, and Ian Turnbull. McKenny was paired frequently with former Marlboro team-mate Brian Glennie, with offensive skills complementing the hard-hitting, defence-oriented style of Glennie. In 1974, McKenny played in the NHL All-Star Game. In 1971, he also appeared in the movie "Face-Off" as the skating stand-in for Art Hindle.\n', '

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