Education
He played college football at Wake Forest University and attended Staples High School in Westport, Connecticut.
He played college football at Wake Forest University and attended Staples High School in Westport, Connecticut.
He was drafted by the Green Bay Packers in the eighth round of the 1971 NFL Draft. Headley played high school football for the Staples High School Wreckers. 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 1996.
He also participated in wrestling, earning All-County honors and winning the state heavyweight championship in his senior season.
Headley was a three-year starter at defensive tackle for the Wake Forest Demon Deacons. He was also named a Second Team All-American by the Walter Camp Foundation and an All-American by the National Education Association.
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. He was inducted into the Wake Forest Sports Hall of Fame in 1994.
Green Bay Packers
Headley was selected by the Green Bay Packers with the 193rd pick in the 1971 NFL Draft and converted to offensive guard.
He was released before the start of the regular season. Hartford Knights
Headley played for the Hartford Knights of the Atlantic Coast Football League in 1971. Montreal Alouettes
Headley was signed by the Montreal Alouettes in March 1972.
He played in two games for the Montreal Alouettes in 1972.
Winston-Salem State University
Headley served as an assistant coach for the Winston-Salem State Rams from 1972 to 1973. Wake Forest University
Headley was an assistant coach with the Wake Forest Demon Deacons from 1973 to 1975.
Princeton University
Headley served as an assistant coach for the Princeton Tigers from 1975 to 1982. High school football
Headley returned to coaching at the high school level in 2003 and has served as a coach at several schools, including Princeton Day School in Princeton, New Jersey and Montgomery High School in Skillman, New Jersey.
Headley was also a member of the Hartford Knights of the Atlantic Coast Football League.