Little has been revealed about the origins of the Headsman. All is really known about him is his name; Cleavon Twain. He was equipped with technology devised by Norman Osborn so that it could be tested in the field, even though the Headsman never knew who his employer was. Osborn sent the Headsman to Benson's Department Store where Spider-Man was fighting the Enforcers so that he could help them escape capture. Headsman eventually became an enemy towards Deadpool when he joined the Dark Reign Thunderbolts.