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When you cannot retreat and he comes up on you, THEN I would shoot him.

Otherwise I would use my fists or continue to retreat. Not worth risking all you have for some hobo.

Then again, how do you know it's a hobo and not some gang-banger trying to get into a shiny new gang? What if he is armed and is just messing with you as part of the initiation (before he attempts to armed rob you)..

So I would probably have my gun drawn this whole time while retreating (that is how I pictured it anyways)...