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Jillette was a dirty cop who helped crime boss “The Owl” gain power by being a go between for the criminal and the police force. He made sure cops were paid off so they wouldn’t go after the owl. Eventually almost everyone on the police force was being paid off and Jillette was in charge of the dirty cops and did everything he could to make sure the owl and the corrupt police officers who worked for him didn’t get arrested.
Jillette began to get worried when Frank Castle wouldn’t take any money. Not only wouldn’t he take money but he told other police officers who were on the take what he truly thought of them and that the city would be better off without them. This caused Jillette to become worried and he began to discuss with other paid off police officers about possibly needing to kill Frank Castle to prevent him from talking to internal affairs which could’ve very well lead to them being incarcerated.
Frank Castle’s partner detective Bruce Greenwood informs Jillette that Castle has already talked to internal affairs about them all taking money. Jillette than along with others go after Frank to kill him so they don’t go to prison. They failed and ended up only wounding Frank Castle and instead murdered his family, Castle than after healing up goes after criminals and the corrupt cops who killed his family now calling himself the Punisher.
The Punisher kills all those who were involved with his family’s death including his old partner Bruce Greenwood. The Punisher eventually tracks down Jillette and is about to kill him but gets interrupted by Daredevil. Daredevil tries to talk Punisher out of murdering Jillette; however Spiderman shows up unexpectedly and attacks Punisher knocking him out, Jillette tries to get away but is caught by Daredevil. Later in Prison Frank is assigned to the same jail cell as Jillette and the guard informs him that Castle does have friends in blue and the guard walks away allowing the Punisher to kill Jillette.