Gandalf's reply, in my opinion, ought to be viewed as him giving the Council enough information to know that sending it to Tom is not an option here, but not necessarily wishing to linger too long on the concept or topic of Tom. The rest of the Council is left to guess as to the nature of Tom and how he stacks up against Sauron, but these are guesses - Gandalf neither confirms nor denies their conclusions, which ultimately land in the camp of Tom being unable to stand against Sauron.
"But in any case," said Glorfindel, "to send the Ring to him would only postpone the day of evil. He is far away. We could not now take it back to him, unguessed, unmarked by any spy. And even if we could, soon or late the Lord of the Rings would learn of its hiding place and would bend all his power towards it. Could that power be defied by Bombadil alone? I think not. I think that in the end, if all else is conquered, Bombadil will fall, Last as he was First; and then Night will come"
"Do not pursue him! He will not return to these lands. Far off yet is his doom, and not by the hand of man shall he fall."
In a classic case of mistaking the true meaning of prophecy, the Witch King will paraphrase this prophecy (showing that he had both heard of it and believed it) in telling Eowyn that she was a fool for standing up to him:
Hinder me? Thou fool. No living man may hinder me!
But, of course, he misunderstood the prophecy, and his hubris as a result of this misunderstanding led to his downfall.
We may know prophecy, and think we understand them, even when the language seems pretty clear and straightforward (assuming we captured it all correctly), but this example shows there might be a few twists, turns, and surprises even with the simplest of phrases.
In any case, I see something similar in Glorfindel's prophecy regarding Tom, for that is what I take it as, actually. Of course, it is given as a conditional "if" prophecy specific to Sauron, meaning if everything else fell to Sauron, then Tom last of all would also fall. Being a glass-half-full person today, I don't believe it was possible for everything to fall to Sauron (and events of the LOTR proved this be the case), and so don't really think this aspect of the prophecy is worth diving into.
However, it struck me that this is something to this First and Last comment, and Night falling. Meaning, if all else was gone, then Tom would finally also depart, or be removed from his place, I am going to rephrase it as. There is something there that Glorfindel sees and thus generates his statement, amid his guesses as to how events would play out in the specific setting or problem of Sauron at that time.
And I think this will ultimately happen - Night will fall on this world, in the end, perhaps. But in our story, defeat is victory, in a sense. Things are turned upside down.There is no direct confrontation over evil or enemies to destroy and win back the world against. Saruman gets what he wants, in the sense that this world is completely his. For Good, there is only departure - a homecoming.
What I believe Glorfindel saw (or what I am going to use his words to convey) is that Tom will stay on this world (our Earth) until there were none of his family left to be saved or gathered, and then he, last of all, would also depart this world. My story involves the Family of Light being gathered back home to Holy Places. Part of that Gathering, apparently, begins at Tom's House, at the beginning of those "change of days", with the Sawtooth Stone and other Records that are found there. My sense is obviously that this is sooner rather than later given that I now place that Stone at Tom's, but lots of people have thought and written that way about lots of similar things, so I could be way off in that thinking.
What matters is that the purpose of what is at Tom's house is not to turn any tide or take back any world here, I think. Force, power, and strength in that way is not how Good wins here. Rather, those gifts will lead his Family home. Light returns home - all of them.
And then once everyone is safely home, Tom will also leave for home and join his Family there. A time he seems to have been waiting for for quite some time in his little land. It will be just as Glorfindel saw, "Last as he was First".
And then Night really will come on this world, which is Middle-earth. The Family of Light will be completely gone, along with those who wish to go with them, safely in Holy Places not to be moved.
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