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Which makes me wonder why our Steef did so well. I can think of two things that separate the Stranger from other Steef: his crossbow and his scrawniness. Might his inferior strength actual allow him the agility he needed to succeed where past Steef haven't?
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Maybe the Steefs who guarded the Grubbs got used to just enjoy the glory and fame Grubbs gave them, and got spoiled like little pet poodles in the time there were no threats.
Our Stranger might have had a wilder, more independent backround and actually knew how to fight or use a crossbow.