 He was the oldest of three brothers and part of a track and field family; his younger brothers John Simpson and Chauncey Simpson followed him in the sport, as did his cousin, William Sylvester.Simpson first became an athlete at Bosworth High School, but did not yet take up hurdling; instead, he excelled in the long jump and high jump and also competed in the sprints, becoming known as the "one-man track team".In addition, he played baseball and basketball.