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I've just come across a point that I've thought about before, and thought it would be good to get some other stances on it. See this letter, emphasis mine:

In the 'Mirror of Galadriel', 1381, it appears that Galadriel conceived of herself as capable of wielding the Ring and supplanting the Dark Lord. If so, so also were the other guardians of the Three, especially Elrond. But this is another matter. It was part of the essential deceit of the Ring to fill minds with imaginations of supreme power. But this the Great had well considered and had rejected, as is seen in Elrond's words at the Council. Galadriel's rejection of the temptation was founded upon previous thought and resolve.

In any case Elrond or Galadriel would have proceeded in the policy now adopted by Sauron: they would have built up an empire with great and absolutely subservient generals and armies and engines of war, until they could challenge Sauron and destroy him by force. Confrontation of Sauron alone, unaided, self to self was not contemplated.

One can imagine the scene in which Gandalf, say, was placed in such a position. It would be a delicate balance. On one side the true allegiance of the Ring to Sauron; on the other superior strength because Sauron was not actually in possession, and perhaps also because he was weakened by long corruption and expenditure of will in dominating inferiors. If Gandalf proved the victor, the result would have been for Sauron the same as the destruction of the Ring; for him it would have been destroyed, taken from him for ever. But the Ring and all its works would have endured. It would have been the master in the end.

Gandalf as Ring-Lord would have been far worse than Sauron. He would have remained 'righteous', but self-righteous. He would have continued to rule and order things for 'good', and the benefit of his subjects according to his wisdom (which was and would have remained great).

-Tolkien, Letter #246

I've always wondered why this was left and not explained. I know in the margin of this letter it does say he'd make good seem detestable, but would he still be helping others? What's so bad about a leader who knows what's best for everyone? Surely that's what a King does after all albeit sometimes very badly.

My thoughts were that he'd be so overzealous with his wisdom that he'd relinquish anyone's free will to the point where people would start taking their own lives for the sake of freedom or there lack of, something I guess which could be worse than Sauron, since he didn't really give you a choice about life or death.

So what's everyone else's thought on this? BTW, I looked around the web for an answer or at least something on this, and very little popped up for me, so I thought it would be a good question.

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    I was going to suggest that Sauron had been long-exhausted, and that all his strength was tied up in the ring. Gandalf was not so exhausted - he can go one-on-one against a Balrog while only wielding an elvish sword, and still win. Gandalf also knows the "full counsel of the light" - their capabilities, plans, and modes of thoughts with a clarity that neither Sauron nor even Morgoth had. The Valar spent eons battling Morgoth in order for creatures to live on Middle Earth - they too are spent. Gandalf would look like a resurrected Morgoth - it would have been bad for creation. – EngrStudent - Reinstate Monica Sep 29 '15 at 16:03
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    @EngrStudent: The Valar have not actually spent eons battling Melkor - the Noldor have. The Valar caught him once and fought him once again, and even that second time IIRC it was Elves and Mayar which did most of the work. So they're certainly not spent. – einpoklum - reinstate Monica Sep 30 '15 at 13:47
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    'What's so bad about a leader who knows what's best for everyone?' No such thing. Anybody - leader or no - who believes and acts as if they know what's best for everyone or even a single person always is 100% wrong. This is something that can only come within. Obviously this excludes things like you shouldn't do drugs but even then nobody will have the full story 100% of the time. But forget the cost. The war on drugs is harmful to those who unfortunately are on drugs, much more harmful than if they were to be given help rather than treated like criminals; they're just people who suffer. – Pryftan Jul 12 '17 at 22:13
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The key point is in the margin note to that letter:

In the margin Tolkien wrote: 'Thus while Sauron multiplied [illegible word] evil, he left "good" clearly distinguishable from it. Gandalf would have made good detestable and seem evil.']

(The Letters of J.R.R. Tolkien 246: "To Mrs. Eileen Elgar (draft)". September 1963)

This is reminiscent of something said by Mandos, written in an essay called "Laws and Customs of the Eldar":

We may indeed in counsel point to the higher road, but we cannot compel any free creature to walk upon it. That leadeth to tyranny, which disfigureth good and maketh it seem hateful.

(History of Middle-earth X, Morgoth's Ring, Part 2: The Second Phase, Chapter 3: "Laws and Customs of the Eldar": Of the Severance of Marriage)

It would appear as though Tolkien has a strong moral opposition to compulsion, even the compulsion towards "truth." He says something similar in another letter:

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.

(The Letters of J.R.R. Tolkien 144: "To Naomi Mitchison". April 1954)

I would say, then, that though there may be a path that is unambiguously "right", Tolkien believed that free creatures should have the freedom to choose whether to follow it, or not. To deny that freedom would, at least according to my reading, conflate the "right" path with the wrong.

When Mandos says that tyranny "maketh [good] seem hateful," I interpret that as suggesting that compelling a free creature to walk the "right" path would ultimately drive them farther away from it. The "good" path would seem evil, because the all-powerful Gandalf is forcing you to follow it, and the "evil" path would seem good because you're choosing it of your own will.

According to Catholic doctrine, which would have greatly informed Tolkien's views on morality, the intent and free will of an action is almost (if not more) important than the action itself. In comments Binary Worrier, who went to Catholic school, provides an anecdotal perspective on this:

I can remember being [taught] (in Catholic school) that intending to steal something when the opportunity arises, is still a sin even if the opportunity doesn't arise. The choice to commit the sin is as bad as committing the sin. Freedom to sin is an important part of Catholicism. Removing that freedom (forcing them to walk the correct path) removes the truth of their redemption (because they did not make the choice). It will demonize the "good path" because it is a thing you are enslaved to, and so one will eventually rebel against it.

This is the disfigureth good and maketh it seem hateful part from Mandos above. Also the act of forcing another to the right path corrupts you, for you are enslaving them to it, and removing their free will.

If you're interested in a doctrinal perspective on this moral question, our friends at Christianity.SE are happy to oblige you.

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    This sounds very much like Catholic reasoning, in which not just a given deed, but the reason why you do it, is important in evaluating its morality. – Matt Gutting Sep 29 '15 at 17:07
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    I can remember being thought (in Catholic school) that intending to steal something when the opportunity arises, is still a sin even if the opportunity doesn't arise. The choice to commit the sin is as bad as committing the sin. Freedom to sin is an important part of Catholicism. Removing that freedom (forcing them to walk the correct path) removes the truth of their redemption (because they did not make the choice). It will demonize the "good path" because it is a thing you are enslaved to, and so one will eventually rebel against it . . . – Binary Worrier Sep 29 '15 at 17:24
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    Trying to find the appropriate item in the Summa Theologica. I know it's in there somewhere. – Matt Gutting Sep 29 '15 at 19:59
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    I think I found it - though it may not be easy to understand :-D – Matt Gutting Sep 29 '15 at 20:06
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    Great answer. Perhaps the one thing you do not get into is how Sauron is any better. Basically, the idea here is that Gandalf would control absolutely, as would care for each of his subjects he would exert his will upon them to force them to this good path. While Sauon, being evil, ultimately does not care about his subjects, and therefor mostly leaves them to their own devices. – Jonathon Nov 3 '15 at 23:34
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What's so bad about a leader who knows what's best for everyone?

In addition to the excellent points made by Jason Baker, consider the words of C.S. Lewis, who was good friends with J.R.R. Tolkien (emphasis mine):

Of all tyrannies, a tyranny sincerely exercised for the good of its victims may be the most oppressive. It would be better to live under robber barons than under omnipotent moral busybodies. The robber baron's cruelty may sometimes sleep, his cupidity may at some point be satiated; but those who torment us for our own good will torment us without end for they do so with the approval of their own conscience.

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