[5] During his senior year, 14 of his teammates signed letters of intent to play college football, but he did not receive any offers.

[9] After trying out for the Chicago Bears, Denver Broncos and Green Bay Packers, he went on to play indoor football for the Sioux City Bandits.

He was named the 2005 UIF co-MVP in 2005; in 18 games he ran for 1,770 yards and scored 53 touchdowns (40 rushing, 11 pass receiving and 2 on kick returns).

During this time, he also worked as a youth counselor at Boys & Girls Home Family Services to make ends meet.

[12] Jackson played in NFL Europa for the Rhein Fire in 2006, leading the team with 731 rushing yards.

[23] At the end of the 2009 season, after winning the starting job from Lynch in Week 12, Jackson eclipsed the 1,000-yard rushing mark for the first time in his career with 1,062 yards and two touchdowns.

[26][27] In Week 17 of the 2009 season, versus the Indianapolis Colts, Jackson had a career day with 212 rushing yards and a receiving touchdown.

[32] For his strong performance he was named to the USA Today All Joe Team as he was no longer Pro Bowl eligible.

Despite playing as the backup to C. J. Spiller most weeks, Jackson accumulated 1,283 yards from scrimmage and scored 10 total touchdowns.

[42] On September 7, 2015, Jackson signed a one-year deal with the Seattle Seahawks,[43] reuniting him with former Buffalo teammate Marshawn Lynch.

[46] The Seahawks clinched a Wild Card berth in the playoffs, marking Jackson's first time participating in the postseason.

[49] In April 2018, Jackson confirmed he was in talks with the Bills to sign a one-day contract and formally retire as a member of the team.

[55] In 2018, Jackson signed with MSG Western New York to be an analyst for its weekly postgame series, Bills Tonight.

[56] Jackson is now a part of Spectrum News One's post game show, Buffalo End Zone.