Chester is a native of Fort Worth and attended Arlington Heights High School. As a teenager, he was discovered by Fort Worth diving legend Cal Loock at the Ridglea country club and encouraged to join the Panther Boys Club, where he became one the best age group divers in Texas history. He posted a perfect record in city and regional meets and closed a standout prep career with a Texas state championship in his senior year. Chester’s success earned him a scholarship at the University of Alabama. While in Tuscaloosa, he earned all-America status three times, claimed the 1978 NCAA 1-meter title and was a Southeastern Conference champion and earned SEC Diver of the Year honors in 1981. Wayne returned to his hometown of Fort Worth to coach at TCU for 22 years (1996-2018) earning Mountain West Diving Coach of the Year in 2006.