He played junior with the Toronto Marlboros in 1931-32 and 1932–33 and then with the St, Michael's Majors when they won the Memorial Cup in 1933-34. Jackson joined the Toronto Maple Leafs in 1934-35 but could not stick with the NHL team. He split three seasons between the Leafs and their farm team the Syracuse Stars. He was traded to the Boston Bruins in 1937 and then loaned to the New York Americans in 1938-39. After that Jackson played for six straight seasons with the Bruins, winning the Stanley Cup in 1941, He hit a career high with 28 goals and 41 assists in 1943-44.
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