Chapter: Graterford, PA: The Pit
After dropping down in to the pit you will need to progress through it a bit. You should keep going till you see what looks like a boiler room you keep going as to beat the level there will be a corridor that will have a leech come after you. Take the first left turn and follow it and you will see a eye patched jack in the box. Shoot it a few times and the trophy will pop.
Credit for video goes to JackieChiles007 at Youtube.