18. Hoyt Wilhelm
Photograph By Louis Requena/MLB Photos/Getty Images
Inducted into the Hall of Fame in 1985, Wilhelm posted a 1.92 ERA in six seasons as a reliever with the Sox. Wilhelm was 40 by the time he joined the Sox in 1963. His best season in Chicago was 1964 when he went 12-9 with a 1.99 ERA in 73 games.