Jackson played football and basketball at Pahokee. He made 188 tackles and caught 21 passes for eight touchdowns as a tight end for the Blue Devils. In 2007, he was named to the Florida High School Athletic Association’s All-Century Team, consisting of the top 33 players in the 100-year history of high school football in Florida. Jackson’s nickname, “City Champ”, came from his days at Pahokee. Jackson went on to play in the NFL for the New Orleans Saints (1981–1993) and the San Francisco 49ers (1994–1995). In 1997, Jackson was inducted into the New Orleans Saints Hall of Fame. Jackson won a Super Bowl ring with the 49ers in Super Bowl XXIX (29) one year before retiring. On February 7, 2010, Jackson was inducted into the Pro Football Hall of Fame.