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Why didn't the Men of Gondor kill Shelob when they had the chance?
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When did they have the chance? If they had the chance, why didn't they just enhabit all of Mordor so that Sauron couldn't get back in? Perhaps they didn't think that they had the chance and had other things to worry about. If they didn't want to get into Mordor, killing Shelob wouldn't help them any.
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