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I think any weakness Sauron saw was tied into the Ring. He did not believe anyone could destroy the Ring and it was not destroyed voluntarily. Gollum fell into the pit and Frodo's will could not bring him to do so. So he was looking at it from the angle that his enemies would try to use the power of the Ring to overthrow him.
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"For believe me: the secret for harvesting from existence the greatest fruitfulness and the greatest enjoyment is - to live dangerously!" - G.S.; F. Nietzsche
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