Leroy has been the Director of Operations at Mathews-Dickey since 2010. Witherspoon began umpiring in 1995. He has worked high school, American Legion, and Reviving Baseball in the Inner Cities (RBI) League games. He is president of the Lysander Baseball Association of Umpires, an organization he founded to provide umpires for high school games. Since 2011, his group has been chosen to officiate the High School Senior All-Star Games at Busch Stadium in St. Louis. He works as an umpire in the games.

In 2007, he received the James Whiteside Award for Baseball Officials. In 1973 and 1974, Witherspoon played second base for St. Louis Country Day High School and was captain of his team. He was selected to the All-League team, and voted All-Star second baseman of the ABC Tournament of Champions in 1997. Witherspoon was an infielder at Monmouth College. From 1973-75, he played for the St. Louis Barons. Leroy played semi-pro ball for the GBU Athletics and Troy Dodgers. Witherspoon has coached and managed youth teams in the Khoury League and the RBI League, managing the St. Louis 2011-13 Girls RBI softball teams to Central Regional Championship titles. In 2012, Leroy received the Osbie Savage, Junior Award for Excellence in the RBI program.