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Originally Posted by narfforc
I do not think that Sauron considered that the Ring would be sent Westward anymore than he thought it would be destroyed, I believe he fully expected someone like Gandalf or Aragorn to appear wearing it in opposition to himself, his thoughts were that if any of his enemies found the Ring, they wouldnt/couldnt fail to use it, that is how three little hobbits managed to sneak into Mordor.
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So you disagree with Elrond and other big guys? Elrond said that the westward road looks easiest and should therefore be avoided and the only thing I can conclude from this is that Elrond meant that Sauron might guess that they are sending the Ring over the Sea and guard the way.