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

[Ent]

Was passage granted to Isildur? To Deagol?

Nope

 

[Deimos]

'Zactly. "Nope."

 

[Squint-eyed Southerner]

But they were both dead. 🤔

 

[Ent]

But they were both dead.

Yup

@Deimos asked his question a little incorrectly to match the thread title.
had he said "Would Deagol and Isildur have been granted passage had they lived, since they each possessed the ring for a time?"
In that case, I would have answered:
"nope"

 

[Elbereth Vala Varda]

So your answer would have been the same..?

 

[Rivendell_librarian]

Was passage granted to Isildur? To Deagol?

Didn't they miss the boat being already dead?

 

[Ent]

So your answer would have been the same..?

Yes, it would still be 'no.' Neither Isildur nor Deagol 'earned' any special dispensation. (See #6 below.)

1. Both only possessed the ring for a very short time.
2. Both gave in to its 'power for possession' immediately.
3. Neither ever "willingly" gave it up.
4. Neither ever fought to do 'good' for the 'good' of Middle-earth and others.
5. Neither had a 'natural right' to cross over, both being of the race of man.
6. The reason 'special dispensation' would be given is not "that" anyone possessed the ring for a time. It's about who they are (character) and what they did with and about it (character worked out in action). It doesn't have to do with the ring. It has to do with the person. (Bilbo, Sam and Frodo particularly.)

As to #3 coupled with #6, it could be said that Frodo also never "willingly" gave it up so why did he get to go? He succumbed to its evil in the end.

Well... his dispensation came from his long battle, endurance, and work on behalf of Middle-earth in spite of his final failure. And his willingness to undertake such an impossible task, almost surely one ending in death, on their behalf to begin with.

Compare it to the dispensation Galadriel herself was ultimately given to cross over, and why, though she had previously been banned. And she too resisted the lure of the ring and refused it willingly when freely offered - a test greater than we may realize.

That's all I've got on this one... and the reasons for my conclusion.
(Oh all right I confess... I could say more, but I won't.)😇

 

[Elbereth Vala Varda]

Well said, Ent. Very informative.

 

[Rivendell_librarian]

Does one have to earn "pity"?

 

[Áramandë Amaniel]

Does one have to earn "pity"?

Is pity ever earned, or is it given by a compassionate and loving heart?

 

[Elbereth Vala Varda]

I would say pity cannot be earned. Pity can only be given once something that is wrong is performed.

I don't think you could give pity if someone did nothing wrong or had no problems. Pity is given as a sympathy offering against harsh justice. It is mercy, essentially.

 

[arivista]

It was not a 'burden' to him in the same way as it was to Frodo and Bilbo.

Well, technically speaking, the Ring was not so much a burden for Bilbo. For the most time, he used it rather "selfishly", for lack of better word - first for his own adventurous exploits and later for other advantages (disappering from relatives etc.). He loved the Ring quite voluntarily. Up until the very end when he was encouraged by Gandalf to pass the Ring to Frodo, he didn't really try to resist the fondness for his precious, for he thought it is just a useful magical trinket, not a creation of super-evil tyrant.

 

[Ent]

Well, technically speaking, the Ring was not so much a burden for Bilbo. For the most time, he used it rather "selfishly", for lack of better word - first for his own adventurous exploits and later for other advantages (disappering from relatives etc.). He loved the Ring quite voluntarily. Up until the very end when he was encouraged by Gandalf to pass the Ring to Frodo, he didn't really try to resist the fondness for his precious, for he thought it is just a useful magical trinket, not a creation of super-evil tyrant.

Interesting. I'm going to ponder on this a bit, and pursue a couple little side-channels this brings into my mind as well.
Thanks much.