Jackson attended St. Xavier High School where he was a three-year starter at Linebacker in football, as well as a center in basketball.
As a junior, he recorded 120 tackles, seven sacks, 19 tackles-for-loses, seven forced fumbles and five tipped passes that resulted in interceptions.
In football, he was a Parade, Blue Chip Illustrated, National Recruiting Advisor, and PrepStart All-America selection.
He earned his second start of the season in the Cotton Bowl Classic, a game in which he recorded five tackles, including two for losses.
As a senior in 2001, he played in 11 games, starting 10, missing one due to suspension for a violation of team rules.
Prior to the regular season games against LSU, Jackson worked his way into the starting Left end position.
Jackson went unselected in the 2002 NFL draft, however on April 25, he was signed by the Washington Redskins as a rookie free agent.
However, on September 1, 2003, he was released again during the team's final cuts,[4] after being sidelined for three weeks with a high ankle sprain.