Replay Chapter: Graterford, PA: The Pit
After dropping down in to the pit you will need to progress through it a bit. Once you are near the exit (before picking up the cryogun, after killing some Grims and Leeches.), there will be a small dead-end path on the left side. Go down this short path and look left again to see a small jack-in-the-box, with an eyepatch on it. This is one-eyed Jack. Shoot it a couple of times and the trophy will unlock. For a more direction, see the video below:
when you guys start crawling through the tunnels make sure to hug the left wall; you will eventually come to an alternate path leading to a dead end. look at the pile of rubble and you will see a little toy with an eye patch, shoot it. lol had no clue that was a trophy, guess i lucked out :P
Just to clarify for anyone else, but the toy is a Jack-in-the-box, and it's located in the Sewers, after you first encounter Grims down there, but before you have to hold off waves of them. Look up a video for more detail on what you're looking for.
Best. Trophy. Evarrr! Especially because I just randomly found a jack-in-a-box, melee'd it, then I thought "what if you would get a trophy for that, lol?" and then 10 seconds later I earned a trophy. Laughed so much :D