Norman Osborn used the Headsman as a high profile agent, giving him an energy powered axe and an early prototype of a one-man, vertical-thrust "Goblin Glider." Osborn sent his flunky to negotiate a deal with the criminal Enforcers, however, his efforts were thwarted by Spider-Man. Viewing the Headsman as a potential liability, Osborn terminated his arrangement with him and crafted his identity as the Green Goblin. When the Headsman sought to redeem himself by killing Spider-Man, Osborn secretly assaulted him as the Goblin and left him for dead. Headsman was taken into police custody and remained in prison until Osborn arranged for him to serve as a covert operative of the Thunderbolts.
His first assignment was to impersonate the Green Goblin and attack Air Force One while Osborn and the President were together. Osborn's plan was to serve two purposes: the first was to disassociate himself from the Goblin persona, forcing people to believe they were completely separate identities, and the second was to discredit Doc Samson who was also aboard trying to convince the President that Osborn was not mentally fit to be given control of the country's defenses. Headsman did a superb job, but he still needed to be saved by Ghost when his equipment suddenly faltered. Headsman thought it was a fluke mishap, but Ghost later told him he believed someone tampered with it.
Soon after, Deadpool came looking for Osborn after he was betrayed during the Skrulls invasion of Earth. The Thunderbolts were dispatched to handle the merc-with-a-mouth, but he was proving to be too much for them - that is until Headsman removed his head from his shoulders. Deadpool managed to cheat death with the help of the Taskmaster, but Headsman would have more to worry about than that when Mister X was recruited onto the team. For some reason, X consistently goaded Headsman until such a time he decided to fight back. Not on par with the fighting skill of Mr. X, Headsman was humiliated.
Always looking to prove his worth, Headsman was beside himself when the team caught a returning Songbird and her partner, Natasha Romanova, who was impersonating Yelena Bolova while leading the Thunderbolts, and he was ordered to execute them. Osborn's new team leader, Scourge, threatened Headsman to do as was commanded, but Ghost, Paladin and Ant-Man echoed Headsman's feelings. It was Thunderbolt against Thunderbolt, and Scourge and Mr. X were overruled and beaten, leaving Ghost to alter their memories, and the captives were permitted to leave without incident. Osborn's next victims, Power Man and Iron Fist, refused to be brainwashed into working with his group, but Headsman's sympathies didn't extend to the former Heroes for Hire. He attacked them without mercy, but their experience working as a team was too much for him to handle. They eventually escaped with Ghost's help.
Mr. X, going stir crazy from lack of excitement, went AWOL and the Thunderbolts had to track him down. Initially, Headsman thought he would get his rematch, but the team ran into guerrilla soldiers which they harshly dealt with. Osborn, realizing the lot of them were a bit unstable, gave them a new assignment: kill the Agents of Atlas. Headsman was outclassed, as were the rest of the Thunderbolts, and it was only until Scourge appeared to kill the Uranian that it looked like they stood a chance of winning. Unfortunately, he was feigning death in order to implant a subliminal message into the mind of Scourge to kill Norman Osborn the next time he saw him. This would prove deadly to Headsman, for the next time any of them saw Osborn was during a mission briefing from a holographic image. Once Scourge saw the face of his target he pulled out his gun and shot it. Headsman was standing opposite the pistol, and the bullet passed through the hologram and into his skull - killing him.