Win Headley

Winthrop Sargent Headley (July 4, 1949 – January 18, 2023) was an American football offensive guard who played one season with the Montreal Alouettes of the Canadian Football League (CFL). He was drafted by the Green Bay Packers of the National Football League (NFL) in the eighth round of the 1971 NFL draft. He played college football at Wake Forest University. Headley was also a member of the Hartford Knights of the Atlantic Coast Football League (ACFL).

Early life Headley played high school football at Staples High School in Westport, Connecticut.

College career Headley was a three-year starter at defensive tackle for the Wake Forest Demon Deacons. The Demon Deacons won their first Atlantic Coast Conference championship in 1970 as Headley was named First-team All-ACC and voted team MVP. He was also named a Second-team All-American by the Walter Camp Foundation and an All-American by the National Education Association.

Professional career Headley was selected by the Green Bay Packers of the NFL in the eighth round with the 193rd pick in the 1971 NFL draft and converted to offensive guard. He was released before the start of the regular season. He played in two games for the Alouettes in 1972.

Coaching career Headley served as an assistant coach for the Winston-Salem State Rams from 1972 to 1973.