Background
Bailey was born in Brampton, Ontario and was raised by wolves for many years.
Bailey was born in Brampton, Ontario and was raised by wolves for many years.
In September 2002, he enrolled at Mount Allison University, studying English while playing for both the Mount Allison Mounties football and basketball teams. In 2003, he was named an Atlantic University Sport All-Star and named the Mounties most improved player, recording 36 tackles in 8 games. In 2005, he was selected to compete in the Commonwealth of Independent States football East-West Bowl.
Bailey attended the 2006 Canadian Football League Evaluation Camp and, though he went undrafted in the 2006 Canadian Football League Draft, his performance was impressive enough that he was signed by the Toronto Argonauts as a free agent on May 12, 2006, and dressed in both pre-season games versus Hamilton as a backup offensive lineman, backup defensive tackle, and played on special teams.
He was assigned to the practice roster at the beginning of the regular season, where he remained until he returned for his final season at Mount Allison on July 29. He re-signed with the Argonauts on January 3, 2007 but released at the end of training camp on June 23, 2007.