ackson played for three Major League teams during his 12-year career. He spent 1908–1909 as a member of the Philadelphia Athletics and 1910 with the minor league New Orleans Pelicans before joining the Cleveland Naps at the end of the 1910 season. He remained in Cleveland through the first part of the 1915; he played the remainder of the 1915 season through 1920 with the Chicago White Sox.