Armstrong played multiple positions for the Bruce High School football team, as well as basketball and track and field, before going on to Northwest Mississippi Community College.
[2][3][1] After two years, he joined the football team of the University of Richmond, where he majored in physical education.
[2][4] He became a starting cornerback during his senior year in 1985 and ranked among the top punt and kickoff returners in the country.
[7] Armstrong signed with the Buffalo Bills in 1987 and played with the team in the preseason, but was placed on waivers on August 31.
On September 23, he was interrogated and harassed at a hotel by striking Bills players, including Greg Bell, Joe Devlin, Sean McNanie and Fred Smerlas, for playing as a strikebreaker.