Schoolboy missed the 1944 and 1945 seasons to wartime service in the U.S. Navy. He was assigned to the Great Lakes Naval Training Station where his former manager, Mickey Cochrane, put together an All-Star baseball team that included Schoolboy, Bob Feller, Johnny Mize and Billy Herman. The 1944 Great Lakes team compiled a 48–2 record, including an 11–1 record against major league teams. Schoolboy played as an outfielder as well as a pitcher and led the Great Lakes team with a .446 batting average.