Jimmy Stewart was involved in track and field athletics, soccer, Canadian football, and baseball, but he found the most success in basketball. He joined the Windsor-Walkerville Alumni amateur team in the 1930s and eventually became its captain. He was a member of the Windsor V-8s when they won the Canadian Championship in 1936 and earned themselves a trip to the inaugural Olympic basketball tournament at the 1936 Summer Games. There, the nation defeated Brazil, Latvia, Switzerland, Uruguay, and Poland before being stopped by the United States in the final 19-8 and settling for a silver medal. Stewart played in all six games and scored 27 points. He remained active in amateur basketball through the 1940s and eventually settled into a career with Ford Motors in Windsor. Among others, he has been inducted into the Canadian Basketball and Windsor-Essex County Halls of Fame. His son, Jimmy Jr., also a basketball player, was a member of the 1960 Junior Canadian Championship-winning Windsor A. K. O.