Jackson attended Bishop McNamara High School in Forestville, Maryland, and was a student and a starting defensive lineman on the football team.
As a senior football player, he garnered 12 quarterback sacks and more than 100 tackles, and earned All-Metro honors from The Washington Post.
In 1994, Jackson earned a Bachelor of Arts in Labor and Industrial Relations from Penn State University with a minor in Business Administration.
He signed with the Atlanta Falcons as an undrafted free-agent defensive end, and spent most of the 1994 NFL season on the practice squad.
He made his on-field NFL debut as a defensive end with the Miami Dolphins, under Hall of Fame coach Don Shula during the playoffs in 1994–95.
Jackson joined the Tampa Bay Buccaneers in late 1996, and played five seasons with the team for Hall of Famer Tony Dungy.
Jackson finished his career as a member of the Detroit Lions, playing both as a reserve defensive end and tackle and on special teams in 2006–07.