Jimmy Montgomery was a multi-sport athlete took up basketball in high school, but was also proficient in boxing and rugby football. His talents in the latter sport earned him a stint with both the Rosemont Bombers of the Quebec Junior Football League and the Verdun Shamcats of the Quebec Rugby Football Union in the late 1950s and early 1960s. His most notable success came in boxing, however, when he was selected to represent Canada at the 1956 Summer Olympics in the light-middleweight division. At the Games he was eliminated in round one by decision by Germany’s Ulrich Kienast. Following his retirement from active competition, he took up a job at Shell Oil, where he worked for nearly four decades, and also volunteered as an ice hockey coach with the East End Boys Club of Montreal.