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Originally Posted by Boo Radley
Very good point. What would it benefit the Ring if it became trapped in Shelob's cave for another age?
As fot the "Mysterious 10th person"... I really don't think it could have been Bilbo. He was too scarred by the ring and if he touched it again, I believe he would have been lost to it.
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It's clear from conversations between Bilbo and Frodo that Bilbo had NOT seen the Ring. He wasn't completely sure it was even in Rivendell to begin with.
As for Shelob, it seems Gollum, who was most familiar with the dark creature's habits, expected that she would have no intentions or uses for the Ring. It was his hope that he would still be able to find it, cast off along with other inedible objects.