Might be Josh Heeren. He was assistant producer on the game, as well as producer and assistant editor on the pre-rendered movies. Maybe he has monogramed undergarments, and OWI wanted to include this hilarity in the game.
Or maybe one of those mortars is just called Josh.
I found a cardboard cut-out Outlaw Shooter! In the waters in front of the beach the Freely Gang are tossing expired explosives about on, there are three explosive barrels about halfway across the river. Leaning up against one of them is a flat Outlaw! I couldn't quite understand what it was doing there - maybe target practice for the mortars?