A Dudley High School graduate who later earned a degree from North Carolina State University, Free was a standout baseball player and an outstanding collegiate athletics administrator. Free played in the Negro Leagues and professionally with the Hickory Rebels and Raleigh Capitals along with three seasons in the New York Mets system. In five years he had a .289 average. Free moved into athletics administration and in 1978 he became the first full-time commissioner of the MEAC, a post he held for 18 years. Free served on the NCAA Executive Committee and became the first Black appointed to the NCAA Basketball Selection Committee. He also served as Commissioner of the Eastern Intercollegiate Athletic Association. Free is a member of the N.C A&T State University, Dudley High School Sports, and CIAA Sports Officials Halls of Fame.