Hugh Stephens graduated from Randolph-Macon in 1941 and became the athletic director of Henry Clay High School. In 1948, he was named the graduate manager of athletics at R-MC and was promoted to full-time athletic director and head baseball coach the following year. The Yellow Jacket baseball team had 32 successful seasons under his direction. As director, Stephens oversaw the additions of the Crenshaw Gymnasium and the Chenery Press Box.

His enthusiasm for the love of the game showed in his daily life as well. Stephens was an active member of Duncan Memorial United Methodist Church, and served as president and secretary of the Ashland Kiwanis Club. His affection for this community and for Randolph-Macon was evident throughout his entire life.