After playing college football for Delaware State, he was signed by the Eagles as an undrafted free agent in 2003.

Jackson and Fraley appeared on the cover of the August 14, 2006 issue of Sports Illustrated, as they were in a battle for the starting center job—a rare feat for an offensive lineman.

[3] The knee injury turned out to be a torn anterior cruciate ligament (ACL), which kept Jackson from playing the rest of the year.

[7] Jackson was injured in the Eagles' season opener on September 12, 2010, against the Green Bay Packers and left the game.

Jackson competed with rookie Jason Kelce during training camp in 2011 for the starting center job, but lost out as the Eagles changed offensive line schemes.