Bailey made his debut in 2001. In June 2003, along with the owner of the promotion IWA Mid-South Ian Rotten and Corporal Robinson, he "invaded" CZW on behalf of IWA Mid-South. In the same year, he competed in the 2nd CZW Tournament of Death where he lost to Nick Mondo in a deathmatch involving light tubes, and the 5th IWA Mid-South King of the Deathmatch where he lost to Mad Man Pondo after defeating 2 Tuff Tony, Necro Butcher and Ian Rotten.