Gilchrist was signed to (what had to be an illegal) contract by the Cleveland Browns to a contract when he was still in high school.  The Browns reneged, and he would forego college to play in an amateur league in Canada before he was old enough to play in the Canadian Football League.  He played there for five years, winning a Grey Cup with the Hamilton Tiger-Cats, and in 1961 he would finally play pro in the United States when he traveled around Lake Ontario to play for the Buffalo Bills of the American Football League.