Ryan went on to co-form the Montreal Hornets and the Montreal Alouettes in the mid 1940s. With the Alouettes, Ryan was a manager and a secretary until 1949.[5] He also won the 1949 Grey Cup as the manager for the Alouettes.[6] After a break from football, Ryan joined the Canadian Football League in 1960 to become the general manager of the Edmonton Eskimos.[7] With the Eskimos, Ryan served as general manager from 1960 to 1965 and executive assistant in 1966. He ended his football career in 1967 and moved to Victoria, British Columbia.[8] Outside of football, Ryan became a sportswriter for the Winnipeg Free Press in 1938[9] and worked at an Ottawa tax office in 1942.[10]