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Originally Posted by The 1,000 Reader
He never says that directly, and I've always interpreted that as meaning Mordor would destroy Tom's "environment" and it would be harder to live and be happy, making Tom face the same problems a bear would. Overall though, a battle between Tom and Sauron would be a battle where Sauron would be dead on the ground and being danced on in a matter of moments.
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The quote in question is this:
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Originally Posted by Council of Elrond, FotR
Could that power be defied by Bombadil alone? I think not. I think that in the end, if all else is conquered, Bombadil will fall, Last as he was First; and then Night will come
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There are some interesting refferences: if all else is conquered and Night will come. Perhaps the coming of the night is simply a figure of speech - a victory of evil similar to the one mentioned in the Last Debate, one "so complete that none can foresee the end of it while this world lasts"); but then how could Bombadil be the last? Maybe Sauron will indeed follow the "same ruinous path down into the void" of Melkor (cf Valaquenta) and will resort to nihilism, complete destruction.