Judge Hillwood is the main antagonist of the Mafia II DLC packs The Betrayal of Jimmy and Jimmy's Vendetta. He is a corrupt judge who has control over the criminal underworld in Empire Bay. He is responsible for sending down the protagonist Jimmy.
After freelance criminal Jimmy's arrest at the end of The Betrayal of Jimmy, he is sent down for 10 years by Judge Hillwood. Jimmy survives attempts on his life in prison by his former employer Sal Gravina (the supposed main villain of the DLC packs) and breaks out to kill those who have wronged him.
After killing Don Gravina by the docks, Jimmy heads to Judge Hillwood's mansion. After finishing off his henchmen, Jimmy faces off with Hillwood and guns him down. Jimmy begins burning down the mansion and finishes off Hillwood with a bullet to the head.