Coach Freeman began his coaching career in 1991 as the Pitching Coach at Robinson High School. He later became the Head Varsity Coach at Falls Church High School from 1994-1998 and then at Fairfax High School from 1999-2007. After a three-year stop at Flint Hill School, where he was the Head Coach from 2007-2010, he landed back at Fairfax High School where he has remained the Head Coach since 2011.
Coach Freeman has coached Travel Baseball locally for the past 10 years where he has guided teams that have been nationally ranked and produced several Power 5 Division I recruits. Coach Freeman was a 1986 graduate of Fairfax High School before he went on to play at both the collegiate and professional levels.