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Hungry Ghoul
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Re: Gollum and Valinor...
Interesting question, one that probably cannot be answered for certain without any specualtion.
However, first we have to observe what would have happened to Gollum had he survived the destruction of the Ring. I see two possibilities here.
First, Gollum's ties to the Ring were so strong and its influence on him so heavy that he would not have survived it well, if at all. The destruction may have thrown him in utter depression and agony, being a Ring-bearer for so long. The forger died with the annihilation of his creation, and even on Frodo, who had the Ring for a considerably shorter time than Gollum, the destruction had its effect. A part of his former self seems to be missing, he has changed also in a melancholic, desperate way; that sadness could only be cured, if not only eased, in the Realm of Bliss.
So, Gollum may in this case probably have thrown his own life away voluntarily, seeing no more point in it without the precious. This way, he would have also redeemed his prior evil deeds in one way at least.
The other, and in my eyes, likelier possibility, would have been that with the Ring's destruction, the part in Gollum which was dominated by the Ring's influence would have been erased as well. Gollum might have become Sméagol again, although old and desperate (maybe he would have even died of old age very soon, if nature would then take back what the Ring has robbed it of for so long centuries).
Now what would Sméagol have done? Maybe he would have been able to perceive the error of his ways before, and tried to redeem for them in any way. In this scenario, I could imagine that he would indeed have been shown the mercy to respite in the West for the short while of his remaining life. Or Frodo could have taken him under his care.
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