In 1996, he was part of an offensive line that paved the way for Jerome Bettis to amass 1,431 yards rushing and allowed only one sack per 21.7 pass attempts. He was elected a Pro Bowl alternate that season.
1997, his last year with the Steelers, the rushing unit captured the NFL rushing title with a league-leading 154 rushing first downs and 1,665 yards rushing by Jerome Bettis.
He left Pittsburgh to play for the Chargers in 1998, after signing the largest contract ever offered to an offensive lineman at the time. Jackson always maintained that he would have never left Pittsburgh for the money, and that his decision to go to San Diego was based primarily on family obligations.
He went on to play two years with the Chargers and was then released for salary cap reasons. Signing with the Bengals, he played the 2000 and 2001 seasons with them. He had re-signed with Cincinnati for 2002 but was released in the pre-season due to results of a stress test.
He has since been cleared to play again but has decided that it's time to retire with the team that he had always hoped he would play with for life.