- "Listen up, assholes! My name is Captain Terrence Stone, and this is my prison. You're here on the inside because you can't behave like normal human beings on the outside. Make no mistake - your ass belongs to me now, and you'll do what I say or you'll be sorry that you didn't. Fuck with me and I'll fuck with your sorry ass all day long. You were sent here to be rehabilitated, and rehabilitate you, we will."
- — Captain Terrence Stone's welcoming speech
Hartmann Federal Penitentiary is the main federal prison serving Empire Bay. As you walk in you walk along the gates of the prison yard which seem to separate the Asian (on the left) African American (on the right) and the White (straight ahead) groups. This could be a reference to gang violence that still exists in prisons today. It is a hell hole in all ways. During Vito's stay there, he gets into fights, is forced to clean dirty toilets, and is abused regularly by the guards. Leo and his gang have a lot of influence here being able to roam the prison when presented with a task.
It only appears in Chapter 6, Time Well Spent and in the first mission of Jimmy's Vendetta, Too Good to be True. It's not on the map of the Empire Bay so its exact location is unknown, but presumably somewhere outside the city.
- Vito Scaletta (1945-1951)
- Leo Galante (1943-1948)
- Pepé Costa (1927-1947)
- Brian O'Neill (1945)
- Derek Pappalardo
- Steve Coyne
- Mr. Wu
- Wu's Fighter
- Jimmy (Jimmy's Vendetta)
This was Vito's home while he was in the penitentiary. However he soon moved into Leo's Cell after killing Brian O'Neill.
Leo Galante's Cell
- The prisoners banging the fence and threatening the new inmates as Vito enters is similar to the popular movie The Shawshank Redemption.
- The warden has a Toothbrush style mustache, commonly known as a Hitler Mustache, made famous by World War II dictator, Adolf Hitler. Hitler committed suicide the same year the warden first appears in 1945.
- In Jimmy's Vendetta, Jimmy breaks out during a prison riot.
- When released into the Prison yard to find Leo there is a man sitting on the ground near a guard tower, he appears to be talking to himself, talking about a bomb, and being tricked.
- A picture of "The Last Supper" by Leonardo DaVinci can be seen in Leo's the cell.
- In the final cutscene of the chapter Time Well Spent, Leo, Pepe Costa and Vito can be seen cooking dinner themselves in Leo's cell. This might be a reference to the 1990 Martin Scorsese movie, Goodfellas, where one of the characters Paul Cicero, played by Paul Sorvino, can be seen cooking sausages in a skillet very similar to Leo cooking the spaghetti mixture in his skillet.