In the next cell over will be a conversation. Listen in to find out that one of the inmates has carved a key out of wood. Perhaps he can help you get out? Catch a nap and when you are finally let out of your cell, walk down the stairs to the bottom floor. Sitting at one of the tables with a board game is the man you are looking for. Introduce yourself and play a game to find out what he's planning.
After your game, he will explain that he has carved a key but that the key has been stolen by someone else. When you regain control, fast walk up to the top level and find the marked man. Try to walk into the cell behind him but he won't let you. He will then start walking away. Let him by, get behind him and start pickpocketing him immediately. If you do this correctly, you should pick his pocket before he gets to the corner to cross the bridge. If you aren't fast enough, the guard will notice you and you'll fail.
With the key in hand, return to your cell for a rest. After a couple of days, head back down stairs and talk to Mason again. The talk completed, you'll have to start a fight with some of the inmates. You'll start off with three targets. Start a fight with them and more inmates will join in with the fight. The fighters will be a little tough so be sure to mix up your counters with throws and disarms as well. Fight your way through the prisoners and you'll find yourself in the pit, just as you planned.
When you get into the pit, wait for the warden to come and stand in front of your door. Pick the key off his person and wait for him to leave. Open the door when he leaves. When you get into the hall, turn left and you'll see a guard at the corner. He'll turn left and walk up the hallway. Follow him and when he turns right and stops, walk behind his back up the stairs. At the top of the stairs, talk to Mason and he'll open the door to the next area.
You'll find yourself in a new area that looks very similar to the yard from your section of the prison. Walk forward until you see this room and the guard on the bottom floor. At about 1:50, he'll walk up the stairs. Follow him up the stairs but stop before going to the next level because a guard will come down the stairs just to the left. At 1:32, he'll be safely past and you can walk up and go up to the next set of stairs. Wait about halfway up the next set of stairs until you see the guard walk past the top of the stairs at about 1:22.
You are now on the top floor. Once you hit the top of the stairs, immediately turn right and follow the walkway. Keep on the walkway until you see an open door on your left. Go inside. You'll likely have attracted the attention of one of the guards. Inside this cell, take a corner position against the door frame and wait for him to enter the room. If he doesn't come over, whistle to him to draw his attention.
With one guard down, move to the other corner of the doorway and wait for the second guard to go by. As soon as he leaves, go past him and fast walk over to the room that Hickey is in. You should just make it in time.
