Chris Chester attended Tustin High School in Tustin, California where he played football, basketball, and threw discus on the track and field team. As a senior he had 815 receiving yards and 11 touchdowns. He also rushed for 450 yards and 5 more scores. He was named first team all-county and league defensive player of the year for his play as a senior. He was considered to be one of the top 10 tight ends in the nation and accepted a scholarship to Oklahoma where he sat out the 2001 season as a redshirt. He returned the following season to catch 2 passes for 25 yards and a touchdown. As a sophomore he served primarily as a blocking tight end and special teams player. He missed five games that season with a knee injury. As a junior, Chester was once again used primarily as a blocking tight end and special teams player. He was switched to the offensive line as a senior where he started three games at right guard and three games at center despite being slowed by a knee injury and a broken hand.

Chris Chester has a good combination of size and athleticism for an offensive lineman. He may be the most athletic offensive lineman in the draft. He is quick off the snap and has the ability to get to the second level in the running game. Chester is athletic enough to pull when playing guard and is excellent at blocking moving targets. He is also a fundamentally sound pass blocker. He is an intelligent player and a hard worker who will do whatever is asked of him. Chris Chester is a converted tight end who has only been starting on the offensive line for less than a year, so he lacks a great deal of experience. He needs to be stronger at the point of attack. He will get pushed around by bigger, stronger defensive tackles at times. He would benefit from bulking up and increasing his strength and he does have a good frame to work with. Durability could be a concern when it comes to Chester. He has had a couple knee injuries and a broken hand the past couple of seasons. He is a bit raw and needs to improve his technique. Chris Chester is a project who could project at guard or center in the NFL. He will take time to develop, but he has a great deal of upside and could be a second day pick in the 2006 NFL draft.