Let's talk about Sam. He's far more interesting that those Elves anyway......
In my view he DID depart for the West, as why would Tolkien put this in the Tale of the Years if it didn't happen? I can understand why Tolkien wrote it this way, as isn't it actually Hobbits who have written and kept the book (and therefore the tales of the years) up to date? Therefore, if they didn't see him actually depart, they would 'presume' this was the case as he was heading for the Havens when he gave the Book to Elanor. ie
Quote:
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1482 - Death of Mistress Rose, wife of Master Samwise, on Mid-year's Day. On September 22 Master Sam-wise rides out from Bag End. He comes to the Tower Hills, and is last seen by Elanor, to whom he gives the Red Book afterwards kept by the Fairbairns. Among them the tradition is handed down from Elanor that Samwise passed the Towers, and went to the Grey Havens and passed over Sea, last of the Ring-bearers
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And of course Sam left on the same day he did for his other journey, so romantically I believe he was taking another long journey, this time his last.
But I've always wondered if Sam saw Frodo again. In my heart I would like to think so, but isn't Frodo's journey to the West signifying his death? I'm sure someone's mentioned on this site that that's what Tolkien alluded to in one of his Letters.
It was 61 years between Frodo and Sam leaving Middle-earth. I'm not sure if Frodo could have lasted that long with his wounds of Sword, Sting and Bite to contend with. I hope he did, but I wonder if Sam's next view of Frodo was his Grave.........