Hutchinson was part of a highly publicized quarterback controversy with the Cowboys, when he and Quincy Carter competed for a roster spot in a Cowboys-themed documentary on HBO. Prior to the 2004 season, the Cowboys signed Vinny Testaverde and acquired Drew Henson, creating yet another quarterback controversy. Hutchinson was released on July 27, 2004, ostensibly in favor of Carter; however, when Carter was released under unclear circumstances, Testaverde was named the starter.
Hutchinson was signed as a backup by the Chicago Bears mid-season, and started several games after Rex Grossman suffered a season-ending injury. Hutchinson had been named as the starter for the 2005 season after Grossman suffered a severe ankle injury during the preseason, but was replaced in favor of rookie Kyle Orton after several poor preseason performances. Following his demotion, he was released on August 31, 2005. The Bears would opt to sign Jeff Blake to be a backup behind Kyle Orton instead.