He is the judge who sent down Jimmy. He is said to have everyone in the city under his control, including all the gangs. He resides in a large mansion in Greenfield that is owned by Frank Vinci in Mafia II. He is apparently very powerful and has a lot of influence over Empire Bay's criminal underworld, including Tam Brodie and his gang, as well as Sal Gravina and the Gravina Crime Family. After Jimmy kills Sal and Tam and their associates, he kills Hillwood and his three associates in the mansion and eventually burns it down.
- In The Big Boss Judge Hillwood looks very similar to Sal Gravina, although this could just be the game designers using the same model.
- The character model used in the cutscene at the end of The Big Boss looks a lot different compared to the model you are ordered to kill. The model you are ordered to kill is Ettore's, while the model in the cutscene resembles Eddie Scarpa's.
- His associates look exactly like Sal Gravina.