I'm not sure about this either. He could be referring to escorting the trader you meet at the Lookout Point multiple times. I could be wrong, though. 
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"I have seen the blood and dirt on their faces. I’ve seen young boys turned into soldiers. I’ve seen men ripped apart by bullets. I can’t forget these things I have seen. And so I ask myself: How much more can one man take?" -Sgt. Matt Baker
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