Gerry James joined the Winnipeg Blue Bombers in 1952 as the youngest CFL player at age 17. During his eleven years with Winnipeg, James won four Grey Cups and rushed for over 1,000 yards in 1955 and 1957. He won the league scoring title in 1957 and 1960, and was voted top Canadian in 1954 and 1957.
James also played five years of National Hockey League (NHL) hockey with the Toronto Maple Leafs, from1955 to 1960. He made history as the first person to play in the Grey Cup and Stanley Cup finals in the same season (1959/60).
Gerry James also coached hockey in Saskatchewan at the minor league level for 19 years.