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From the time Aragorn revealed himself to him in the Palantir, at the Hornburg. This was an explicit part of the strategy: reread "The Last Debate." According to Gandalf, in the rash assault on the Morannon Sauron would see "the arrogance of the new Ringlord."
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The entire plot of The Lord of the Rings could be said to turn on what Sauron didn’t know, and when he didn’t know it.
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