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Judge Hillwood is the greater-scope villain of the Mafia II DLC pack The Betrayal of Jimmy, and then the main antagonist of the sequel DLC Jimmy's Vendetta. He is a corrupt judge who is the ruler of all the gangs of Empire Bay.
Judge Hillwood is a high-ranking law official in Empire Bay, who has all of the major gang leaders under his thumb. During the events of The Betrayal of Jimmy, he conspires with mob boss Sal Gravina to set up Sal's enforcer Jimmy to be arrested by the police. Following Jimmy's arrest, Hillwood sentences him to 15 years in prison.
Jimmy escapes from prison in Jimmy's Vendetta and begins to take down all the gangs around Empire Bay who were involved in betraying him. He kills Gravina at the docks, and discovers that Hillwood was the mastermind behind all of what has been happening. Gravina heads to Hillwood's villa on the outskirts of the city, and after fighting through his armed guards manages to catch up to Hillwood and guns him down. While Hillwood is on the ground and bleeding, Jimmy douses the manor with gasoline and sets the place ablaze, before then finishing Hillwood off with a shot to the head.
- His boss fight at the end of Jimmy's Vendetta was recycled content from a cut alternative ending from the main Mafia II storyline involving Frank Vinci. The manor that Hillwood resides in belongs to Vinci in the main game continuity, although it didn't appear in the Mafia II storyline due to being incomplete at the time.
- The character's model changes throughout the course of the games, and are recycled from other characters. His model in the text cutscenes for The Betrayal of Jimmy resemble Eddie Scarpa, his appearance during the boss battle in Jimmy's Vendetta resembles a random NPC, and his appearance in the final cutscene is the same one used for Sal Gravina.