Jessie Armstead was playing football at a very high level from an early age, and he was the first high school player in history to be named a three-time All-American. He then continued that success at the University of Miami, where he helped lead the Hurricanes to a pair of NCAA National Championships. Following his standout college career, he was selected by the New York Giants in the 1993 NFL Draft.

The Dallas native spent the first nine seasons of his NFL career with the Giants. He was a four-time All-Pro and five-time Pro Bowl selection there, registering five straight seasons with at least 100 tackles. Following his time with the Giants, he then played his final two years with the Washington Redskins. Over 11 seasons in the NFL, Armstead recorded 752 tackles, 40 sacks and 12 interceptions. After retiring, he was named to the Giants Ring of Honor, which is the highest accolade that can be awarded from the franchise. He has since returned to the Giants as a Special Assistant to the General Manager, and he was with the team when it won Super Bowl XLII.