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As is well known and as was stated in a few answers on this site (see e.g. here), Tom Bombadil was unconcerned about the War of the Rings and whether or not Sauron was defeated.

Tolkien himself put it this way:

I might put it this way. The story is cast in terms of a good side, and a bad side, beauty against ruthless ugliness, tyranny against kingship, moderated freedom with consent against compulsion that has long lost any object save mere power, and so on; but both sides in some degree, conservative or destructive, want a measure of control. but if you have, as it were taken 'a vow of poverty', renounced control, and take your delight in things for themselves without reference to yourself, watching, observing, and to some extent knowing, then the question of the rights and wrongs of power and control might become utterly meaningless to you, and the means of power quite valueless. It is a natural pacifist view, which always arises in the mind when there is a war.

The Letters of J.R.R. Tolkien 144

But do we know what would have actually happened to him if Sauron ended up ruling Middle-earth? It seems not unlikely to me that Sauron would have feared him and would have tried to have him killed.

Did Tolkien ever mention what would have happened to Tom in such circumstances? Is there a way to estimate this based on things he had written?

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    I don't have time for a proper answer, but the relevant quote is from the Council of Elrond where it is pointed out that if Sauron were to win, Bombadil would succumb eventually, "Last as he was First". Jun 27 at 8:36
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Bombadil would have fallen at the end

During the council of Elrond they discuss sending the Ring to Tom Bombadil, and Glorfindel says that if Sauron were to get control he would eventually overcome the old forest as well.

'But in any case,' said Glorfindel, 'to send the Ring to [Tom Bombadil] 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.'
The Lord of the Rings - Book II - Chapter 2 - 'The Council of Elrond'

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    @PcMan - Yet at the end he too will fall and the Night will come.
    – ibid
    Jun 27 at 10:45
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    @ibid yep. Sauron would have extreme difficulty in affecting Tom, but Tom could only passively resist, not really oppose. Eventually he would be isolated, and his resistance would be meaningless, and he would pass. Consider how he utterly ignored the influence of the Ring.. Not resisted it, but ignored it. I always got the feeling (but no proof in Tolkien's writings) that Tom was a true Outsider, not one of Eru Ilúvatar's brood, who created Middle Earth. Being a "foreigner", he was not subject to the Rules.
    – PcMan
    Jun 27 at 10:50
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    This quote is talking about what would happen if Tom had the Ring. Sauron would be motivated to get it from him. Can we be sure that if all else is conquered also applies to / includes the case where Tom is totally uninvolved while Sauron captures the ring from the fellowship? I think the question is still open of whether Sauron would choose to eliminate Tom if he regained his full power and was ruling over the whole of middle earth the way he ruled over Mordor. At least without further justification to explain the reasoning. Jun 27 at 19:32
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    "Fall" could, though, mean that Tom picks up and leaves Eä. He may not be able to stop Sauron, but it doesn't mean he can't run away.
    – chepner
    Jun 27 at 20:57
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    @PeterCordes - True. The quote doesn't show if Sauron will conquer him, but it does still show that Sauron could conquer him.
    – ibid
    Jun 27 at 22:42
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That would depend in part on others. If Sauron had won, and Tom didn’t have the Ring, he would IMO probably have been left alone. Tom isn’t someone to fear and isn’t someone it’s desirable to dominate, and he doesn’t have any resources other than the forest itself.

So, until the forest was desirable and worthy of his attention, there would be no need to deal with Tom personally and I don’t think his underlinings could.

The books describe what would happen if Tom had the Ring and Sauron came to dominate. But that is with a great need, and IMO while Sauron’s greed and desire for dominion is unbounded, Tom and his forest aren’t something that Sauron would consider desirable. To him, controlling all of the area around the forest and controlling all of the area around the forest + the forest would be the same thing. It would be like a farmer that was dissatisfied with his control of his barn, not because it had rats, but because one particular rat didn’t hide quickly enough when he came by.

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    To support this, consider that Shelob is explicitly stated not to acknowledge Sauron as master. (scifi.stackexchange.com/a/94406/73281) Yet Sauron was happy to leave her alone, and even let her eat his own minions now and again. Perhaps he would be happy to keep Tom, and even exile naughty orcs to the Old Forest, to be eaten by the trees. If they're lucky! If they're unlucky, Tom might want to read them some of his poetry first. Jun 27 at 22:28
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    @TimeTravellyParadoxySciFiSmeg: I thought about that afterwards, it could be very handy to have an inconsequential but impossible task handy.
    – jmoreno
    Jun 27 at 22:38
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    @TimeTravellyParadoxySciFiSmeg - Tom was a Vogon?
    – Dave
    Jun 28 at 17:13
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    @Dave - The question of who or what was Tom Bombadil is highly debated on this website. I don't think there is a definite answer. But his poetry is, of course, the third worst on Middle Earth. Jun 28 at 22:05
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    @TimeTravellyParadoxySciFiSmeg whose is the second worst? The Azgoths of Kria don't live in Middle Earth, do they? And didn't the very worst poetry perish along with its creator in the demise of Númeror? — Seriously though, Shelob is a good point to bring up but I'm not sure she can be compared to Tom here. Sauron might have kept her only because of the Ungolianth-Morgoth backstory... you know, better give spiders what they want... Jun 28 at 23:08
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I found some evidence suggesting Tom Bombadil would not, in fact, have survived under Saruon's rule:

Ultimately only the victory of the West will allow Bombadil to continue, or even to survive. Nothing would be left for him in the world of Sauron.

From Letter #144.

The only reason I don't consider this to be completely conclusive is that Tolkien might have been describing Rivendell's view on the matter:

Tom Bombadil is not an important person – to the narrative. I suppose he has some importance as a 'comment'. I mean, I do not really write like that: he is just an invention (who first appeared in the Oxford Magazine about 1933), and he represents something that I feel important, though I would not be prepared to analyze the feeling precisely. I would not, however, have left him in, if he did not have some kind of function. I might put it this way. The story is cast in terms of a good side, and a bad side, beauty against ruthless ugliness, tyranny against kingship, moderated freedom with consent against compulsion that has long lost any object save mere power, and so on; but both sides in some degree, conservative or destructive, want a measure of control. but if you have, as it were taken 'a vow of poverty', renounced control, and take your delight in things for themselves without reference to yourself, watching, observing, and to some extent knowing, then the question of the rights and wrongs of power and control might become utterly meaningless to you, and the means of power quite valueless. It is a natural pacifist view, which always arises in the mind when there is a war. But the view of Rivendell seems to be that it is an excellent thing to have represented, but that there are in fact things with which it cannot cope; and upon which its existence nonetheless depends. Ultimately only the victory of the West will allow Bombadil to continue, or even to survive. Nothing would be left for him in the world of Sauron.

It seems to me, however, the most conclusive evidence we have so far. I disagree with ibid's answer, since the quote in it refers to what would have happened if Tom had the ring, not if Sauron had won. The other answer, by jmoreno, seems to me like a good speculation, but it is still only a speculation. There is also a comment by Peter Cordes, suggesting that the case of Shelob might be an indication that Sauron wouldn't care about Tom Bombadil. This is also very interesting, although Tom and Shelob are fairly different.

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