Webb played shortstop for the Championship Kilmarnock High School team in 1937. He went to Babe Ruth Baseball School in Florida in 1939 and in 1940 was with the Orioles Spring Training Camp when he became the first person drafted from Lancaster County. Webb was the 3rd baseman for the Fort Story, Va. Post Team that played against Major and Minor League Teams in exhibition games for nearly five years, while in the Army. Upon discharge in 1945 he ended his baseball career with the Chesapeake League.
Northumberland High School Athlete of the Year in 1956 was named MVP in baseball at Ferrum Junior College in 1959. He served in the Army where he led the Regimental Baseball Team in hitting with a .387 average. Returning to Northumberland High School, as Athletic Director and Coach, he won two District Championships in Junior Varsity Basketball. He was named the Coach of the Year in 1987 and 1988 in Varsity Baseball where he coached for 21 years making State Quarter Finals in 87 and Regional Finals in 1988; was Varsity Basketball Coach for 20 years where he was named Northern Neck District Coach of the Year in 1983, 1985 and 1996. He was also Group “A” Regional Coach of the Year and East All Star Coach 1983 and won the Group”A” State Championship in 1996. Jett retired at the end of the 2000-2001 school year after completing 30 years at NHS.
Ashburn won more than 500 games while player-Manager-Coach of the Texacos fast pitch Softball Team, including the State Championship in 1970. Ashburn won over 100 games as Coach of Texettes Girls Fast Pitch Team. ASA, Virginia High School League and Little league Umpire for more than 30 years, he has also been a radio sports broadcaster for over 25 years. Ashburn has also served as a tournament and special event organizer for Lancaster County Dream Fields.