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During the mission "Bounty Hunter", Red Harlow unknowingly walks into the Bloody Tom Gang's base of operations, Twin Rocks. After most of the gang is dispatched, "Bloody" Tom himself, along with Big Oaf and Loaf, come out and attempt to kill Red.
While Tom and Big Oaf charge at Red, Loaf stays behind, hiding behind bushes. After Tom and Big Oaf are killed, Loaf will come out of hiding and be killed as well.