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Would Gollum have sailed from the Grey Havens had he survived?

I don't honestly think that Gollum intended to die with the Ring, but here is what I think was going on:

Gollum was tied to the Ring because of how long he had taken it into his possessions. And so because of that, his need for it was exponential, and his desire for it surpassing even that. I don't know if Gollum would have died instantly after the destruction of the Ring, or if he would have survived a bit longer, but I firmly believe the only thing still suppressing his age and inevitable death, was the pursuit of the Ring.

It was the one thing that actually gave him something to live for. We can see throughout the other chapters, his appearance, his solitude, Gollum had nothing more than the Ring and his desire for it. He did not have ornamental clothes, or any form of family, or even a home. He simply had the Ring, and when even that abandoned him, he was left with his desire for it.

When the Ring was destroyed, it would be the end. It was the only thing that Gollum would have ever desired or hoped for, and the only thing left for him to live for. I don't think it was necessarily as much the evil of the Ring that preserved Gollum from death, but maybe the fact that he had not fulfilled his purpose. Once he did, he died. Instantly.

And while, it happened due to his fall into the Cracks of Doom, that was still his end. I believe that Gollum would not have sailed away, because he would not have been alive. Most likely, with nothing, he would succumb to grief, mourning the loss of his 'Precious'.

Or dare I say, he would have cast himself into the fiery chasm, in hopes of finding the Ring.

While it seems Gollum takes a mis-step, and accidentally is cast into the Cracks of Doom, I might even argue that a subconscious part of him, tied to the Ring and his love for it, purposely made a leap, in a false hope that he would have his Precious forever with him, and no one could take it.
 
It's not certain that Gollum's "prophecy" that he would die if the Ring was destroyed is bound to happen. Neither is it certain that 'bound up with the fate of the Ring' means that the destruction of the Ring inevitably means the death of Gollum. Here Gandalf advises Frodo not to be too eager to 'deal out death'. Pity is a strong theme in the LOTR, and I like to think that pity could be extended to Gollum/Smeagol.

Many that live deserve death. And some that die deserve life. Can you give it to them? Then do not be too eager to deal out death in judgement. For even the very wise cannot see all ends. I have not much hope that Gollum can be cured before he dies, but there is a chance of it. And he is bound up with the fate of the Ring. My heart tells me that he has some part to play yet, for good or ill, before the end; and when that comes, the pity of Bilbo may rule the fate of many - yours not least​

 
I think that even if it was granted to him a passage to Valinor he simply wouldn't survive.
Gollum is old... very old..., and the only thing that kept him living is the one ring.
With the destruction of the one, I think he would die of old age, week or 2 after the destruction, and since they didn't go to Valinor right away (but after year or 2), he simply wouldn't have lived long enough to be "transported" to Valinor.

Poor Gollum.
 
For me, it's not too difficult to imagine a different turn of events at The Cracks of Doom. If The Ring went into the fire after a struggle between Gollum and Frodo, Gollum might have passed out from the trauma of its destruction. Then, would our good friend Frodo have left him lying on the ground to die in the eruption? No way! He'd have carried him outside. Then, the eagles would have carried three away to safety, and the bond between Smeagol and Frodo would continue. I could easily see an interesting relationship with a tamed and healing Smeagol living with Frodo for a few years in the shire. Frodo would be a caretaker for Smeagol. Then eventually...it's The Straight Road for the duo.

Within the confines of "The Lord of The Rings", allowing non-elves into Valinor doesn't seem to be problematic at all: Frodo, Bilbo, Sam, Gimli

Evil Gollum would have died with the ring, but victim Smeagol would have remained. I think having Smeagol sail to Valinor would have made a nice alternative ending. Moral of the story: it's never too late for forgiveness and redemption.
 
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Within the confines of "The Lord of The Rings", allowing non-elves into Valinor doesn't seem to be problematic at all: Frodo, Bilbo, Sam, Gimli
Might just be my opinion, (honestly it probably is)

But I have always thought that the reason they were permitted passage was because of their heroic deeds as a fellowship. Not only did they save Middle-Earth, the unheard-of bonds between Elves and Men, Dwarves and Hobbits, and opposing kingdoms that they established were almost the herald of a new age where the races were put aside for once, and the many peoples of Middle-Earth became allied under the love of the land they had been blessed with.
 
I think we're considering if he would have been permitted to have sailed, without considering if he would want to. Bearing in mind his hatred of all things Elvish, I doubt that he would.
 
Speaking as a simple Hobbit, I'd like to point out that my revered ancestor Bilbo Baggins spared Gollum's life. 'It's pity that stayed Bilbo's hand.' As a celebrated Man once wrote: 'The quality of mercy is not (con)strained / It droppeth as the gentle rain from heaven.' One of his compatriots confirmed this idea: 'To err is human, to forgive, divine.' Another author, in whose name we debate, was a Catholic for whom forgiveness was key to Christ's and therefore God's nature. As Gandalf suggests, Bilbo's action was prompted by something both in and beyond himself, perhaps 'the Divine' which, in Professor T's sub-creation, equates roughly with the Valar. Who are we therefore to deny poor old Sméagol even the possibility of passage to eternal rest? There may be, after all, many roads to the Undying Lands. Anyway, drink up, it's only a story. More beer here good Barliman!
 
I think we're considering if he would have been permitted to have sailed, without considering if he would want to. Bearing in mind his hatred of all things Elvish, I doubt that he would.
Exactly my thoughts. He was under influence of evil far too long to be just immediately free from it even after the Ring was destroyed. The Ring was main influence for evil in Gollum's life, but not exclusive. Plus some influence of the Ring remained even after its destruction. Bilbo still asked about it with fondness in the last chapters of RotK. He was not completely free. Only like, say, a recovering alcoholic. He is OK without a liquor, but he is generally not freed enough to be able to drink again, however moderately. His addiction is still in some small degree a part of him.
 
Don't want to trigger a thread derailment with a Star Wars reference, but I found this thought too interesting to hold back:

After the destruction of The Ring, Smeagol (formerly Gollum) sails away beside Frodo and Gandalf to live in peace in the Undying Lands.

After the destruction of The Emperor, Anakin (formerly Darth Vader) fades away beside Obi-wan and Yoda to exist in peace with The Force.
 
One could only come if one were an Elf, or had special dispensation somehow.

Gollum was not an Elf, nor would any give him special dispensation.

Like Melkor, he never bore the ring as a 'burden' on behalf of the good peoples of Middle-earth. It was not a 'burden' to him in the same way as it was to Frodo and Bilbo. He had no "goodness" in him that required his resisting its drag and draw on him toward evil.

Just like Melkor, he bore it only for his own selfish purposes, and for no other reason. His possession of it started with murder, he murdered many along the way for his own selfish needs, and it would have ended with murder of Frodo and Sam had his efforts at several points not failed.

His reason for desiring it in the end was not to destroy it for others' good, but remained only for his own 'evil.'

I believe the Ship itself would have prohibited his passage by the same power that enabled its passage back and forth from and to Middle-earth to begin with.
 
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