The Chicago Bears selected Benson as the fourth overall pick in the 2005 NFL Draft, making him the highest drafted Bears player since Dan Hampton in 1979. The Bears’ organization and Benson could not come to terms on a contract, causing him to miss the entire Bears' training camp. After a 36-day hold-out, Benson signed a five-year contract worth $35 million. The Bears wished to make Benson their feature running back, but his lengthy contract impasse had caused him to miss a significant portion of practice. Benson claimed that he received a cold reception upon his return because he claimed he would be starting by the third game despite holding out and not practicing. Jay Glazer reported that certain players even attempted to intentionally injure him during drills, though former Bears guard Ruben Brown has denied such claims.