On December 8, 1962, his 23rd birthday, Jackson caught an 85-yard touchdown pass for the Redskins from quarterback Norm Snead in a 34–21 loss to the Baltimore Colts. He had been a first-round NFL draft pick of the Cleveland Browns, the 11th player selected in the 1962 draft. Jackson, along with Bobby Mitchell, was traded by the Browns to the Washington Redskins in exchange for Ernie Davis in 1962.
Jackson was the Illinois state champion in the 100-yard dash three years in a row for Bloom High School from 1956 to 1958.