He played college football at Wake Forest University and attended Staples High School in Westport, Connecticut.
[2] He earned All-County and All-State honors as well as being selected to the New York Giants Tri-State Football Team his senior year in 1969.
[2] He also participated in wrestling, earning All-County honors and winning the state heavyweight championship in his senior season.
The Demon Deacons won their first Atlantic Coast Conference championship in 1970 as Headley was named First-team All-ACC and voted team MVP.
[2][3] He was named co-recipient of the Arnold Palmer Award, which is given to Wake Forest's best male athlete, in the spring of 1971.