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What if 🧙Gandalf had recognized the One Ring immediately?

The answer to ALL such Hypotheticals is:

”It depends upon the needs of the Narrative.”

Others have addressed some specifics of what Tolkien had done with the early writing of the Sequel, where the formulation that the Ring found by Bilbo in Gollum’s lair under the Misty Mountains (re: Hithaeglir).

Some seem to have missed that the Watchful Peace ended 400 to 500 years prior to the events of The Hobbit, and that Tolkien did not even realize that the events in his first Novel were intimately connected to his original Mythology until he began formulating the sequel to it.

Another point that many seem to have missed:

• Sauron and the Witch-King were already back in Mordor before the White Council lead the storming of Dol Guldur, where Khamûl led the 25,000-odd defenders against the 10,000-odd assailants led by the White Council (odds are also pretty-good that this is where Legolas was, leading his father’s forces in that battle).

So by the time Bilbo could have ”revealed” that he had a Magic Ring, and iff Gandalf had recognized that it wasn’t just a minor study in the craft, but a Ring-of-Power, and not just any Ring-of-Power, but THE Ring-of-Power, Sauron’s Ruling-Ring, the One-Ring, Gandalf would have been too late to intervene in the events at Dol Guldur and with Sauron reaching Mordor where Barad-dûr would be nearing completion.

The best Gandalf could have done in this case would have been to have Gondor and Rohan (and Lórien) block the flow of Orcs and other Allies of Sauron into Mordor. And... Of course.... Begin figuring-out what to do about the problem, as-well-as searching for everything he had to search for in LotR as it was concerning the fate of the One Ring, and Isildur’s possession of it, and what made the writing on it appear.

He would still need these things to demonstrate to others that it was the Ruling-Ring.

But the question of “What would have happened if...”

Well... The exact same thing would happen there that would have happened had Clement Attlee, Neville Chamberlain, and Winston Churchill had known that Adolph Hitler was going to rise-to-power in Germany in 1933, and that he would eventually put Adolph Eichmann in charge of the “Final Solution to the Jewish Question,” leading to the Shoah.

And that answer is:

• “Something different than what has been recorded, whether by Actual History or a Fictional History.”

MB
 
The answer to ALL such Hypotheticals is:
”It depends upon the needs of the Narrative.”
...
Another point that many seem to have missed:

• Sauron and the Witch-King were already back in Mordor before the White Council lead the storming of Dol Guldur, where Khamûl led the 25,000-odd defenders against the 10,000-odd assailants led by the White Council (odds are also pretty-good that this is where Legolas was, leading his father’s forces in that battle).

So by the time Bilbo could have ”revealed” that he had a Magic Ring, and iff Gandalf had recognized that it wasn’t just a minor study in the craft, but a Ring-of-Power, and not just any Ring-of-Power, but THE Ring-of-Power, Sauron’s Ruling-Ring, the One-Ring, Gandalf would have been too late to intervene in the events at Dol Guldur and with Sauron reaching Mordor where Barad-dûr would be nearing completion.
...
"The needs of the narrative" are the ultimate trump card, or in terms of another card game the Joker, or even Jolly Joker.
JRRT managed to make his narrative needs seem logical; PJ didn't, but that was the fault of his narrative being nutty in parts ... 😈

But as to the other two points of yours I quote, I register objections from Appendix B "The Tale of Years" for the Third Age:

2941: Saruman [finally] agrees to an attack on Dol Guldur, since he now wishes to prevent Sauron from searching the River. Sauron having made his plans abandons Dol Guldur [after the attack].

(I'm also keenly interested about the source of your statement of 25,000 defenders of DG against 10,000 attackers. Until the advent of (crushing) air force superiority in WW II this would have been a suicide mission; 3 to 1 numerical superiority for the attackers was considered an absolute minimum, even up to WW II.)

2951: Sauron declares himself openly and gathers power in Mordor. He begins the rebuilding of Barad-dûr [ten years after having abandoned DG].
 
... as soon as Gandalf saw the ring that Bilbo had picked up, through a combination of intuition and memory, and ignoring his better judgment, Gandalf had realized that it was the One Ring.

I actually thought about this, too. I think everyone who knew about the ring were either dead or thought the ring was lost. Then again, did Gandalf see the ring before it was lost? I don't think he saw it when it was forged or when Isildur took it. So, that may explain why he didn't recognize it at first.

Then again, he may have known what it did to its wearer. Isildur was invisible when he wore the Ring, so when Bilbo went invisible, that should've given Gandalf a clue.

I agree with Saruman - he was high on weed. muddled his brain.

My question is: how much easier would it have been at that time to destroy the Ring, or would it have even been possible? Some points I'm considering:

* Would Gandalf have known that a hobbit was the best choice for a ring bearer without the hindsight of 77 years of hobbits having the Ring?

Honestly, I don't think Bilbo would be a good choice over Frodo and Sam. I still believe that Sam was the reason why the ring was destroyed - but he wouldn't be there if Frodo wasn't there to begin with. So, they both were essential in the destruction of the ring.

* Although he probably still would have avoided it out of safety, was there as much of a risk if someone like Gandalf or Elrond took the Ring at that time? Could they have borne it long enough without corruption to get it to Mount Doom?

No, as they are the most susceptible to its corruption because the do possess power. The more powerful you are in Middle Earth, the more you are tempted to use the One Ring.
 
I don't believe any of the others are described. Gandalf's narrative in "The Shadow of the Past" seems to imply that the One looked like one of the lesser rings.

On thinking about the nature of both Sauron and the Ring, the thought occurs that, although the Elves were of course aware of the One, it's possible that the only people who ever actually saw it were those present when Isildur took it from Sauron's hand.
 
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