He played college football for the Oklahoma Sooners and was selected by the Baltimore Ravens in the second round of the 2006 NFL draft.

He was also a Golden West All-League as a junior and senior and a first-team All-Orange County by the Los Angeles Times.

[citation needed] Chester played college football at the University of Oklahoma.

Chester was selected by the Baltimore Ravens in the second round (56th overall) in the 2006 NFL draft.

[7] He helped to protect the quarterback and only 17 sacks were allowed, the 2nd fewest in the league.

[8][9] He was the only member of the Redskins' offensive line to start and play in all 16 games of the 2011 season at the same position.