Armstrong played junior hockey with the Regina Pats before debuting with the Toronto Maple Leafs of the National Hockey League (NHL) in the 1937–38 season. Two years later he was involved in one of the biggest trades of the decade. He, Busher Jackson, Buzz Boll, and Doc Romnes were sent to the New York Americans in exchange for Sweeney Schriner. He played three years with New York before World War II, in which he went to play and coach for the Regina Army Caps. Following his army service, Armstrong was signed by Jack Adams in Detroit, but halfway through his third season he was demoted after Adams called up an 18-year-old named Gordon Howe. In 270 career NHL games, Armstrong scored 67 goals and 121 assists for 188 points.\n', '

Following his retirement, Armstrong went on to coach the Regina Pats from 1950–55, and the University of Denver from 1956 to 1977, winning five NCAA Championships, in 1958, 1960, 1961, 1968 and 1969. He is considered one of the top NCAA coaches of all time.\n', '

He retired to St. Augustine, Florida, where he remained an avid golfer into his 90s.\n', '

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