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In the History of Middle-Earth book collection Myths Transformed we learn a lot about how Sauron perceived the Istari and what he knew of them.

Sauron had, in fact been very like Saruman, and so understood him quickly and could guess what he would be likely to think and do, even without the aid of the palantiri or of spies; whereas Gandalf eluded and puzzled him.

(Home X: Myths Transformed)

Gandalf he did not understand. But certainly he had already become evil, and therefore stupid, enough to imagine that his different behaviour was due simply to weaker intelligence and lack of firm masterful purpose. He was only rather a cleverer Radagast — cleverer, because it is more profitable (more productive of power) to become absorbed in the study of people than of animals.

(ibid)

My question now is how does Gandalf elude and puzzle Sauron so much? We know he found Saruman simple to guess down to having similar minds (maybe down to both being maia of Aule?), we also know he must know a fair bit of Radagast as he refers to Gandalf as merely a smarter version of Radagast who was known to have abandoned his task which the Istari were given.

While Sauron went face to face with Saruman via the palantir, it is surprising that he finds Gandalf basically strange, even though Gandalf in reality does the most to circumvent Sauron out of the Istari in the north-west.

  • Gandalf enters Dol Guldur which Sauron flees.
  • Gandalf enters Dol Guldur again in secret and claims he only just escaped with his life, which suggests Sauron may have ended up noticing him.
  • Gandalf pushes White Council to attack Dol Guldur which Sauron foresees.
  • Gandalf fought with all nine of Sauron's greatest servants at Weathertop and played a part in destroying their physical bodies temporarily.
  • Gandalf leads the Fellowship from Rivendell, which Sauron also knows.
  • Gandalf strives with the Dark Tower when Frodo puts the ring on at Amon Hen.
  • Gandalf is present at the Battle of the Black Gate, in which the mouth of Sauron declares they know all about Gandalf.

As I've pointed out, Gandalf is clearly sent to contest Sauron. But I don't understand why Sauron does not see this; throughout the Third Age, well, since the coming of the Istari Gandalf has played a role in almost every contest against Sauron.

So how did he elude and puzzle him?

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    It's probably hard for an egoistic/egocentric person to understand an altruistic person. If you can understand a human as a actor that always picks what is most beneficial for him/herself, one can probably guess what the next move will be. It's way harder to predict the actions of a non-egoistic person. – Willem Van Onsem Mar 13 '15 at 2:04
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    Having just got to the part in the book where Gandalf recounts his story leading him to the House of Elrond. He only fought five of the nine atop Weathertop – ediblecode Mar 13 '15 at 15:12
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    ` But certainly he had already become evil, and therefore stupid, enough to imagine that his different behaviour was...` I didn't know Tolkien thought this way, but it kind of underscores one of the notable weaknesses in his writing: if Evil Is Stupid--which, we see here, he takes as a given--it's hard for the bad guys to do anything truly interesting. Remember, The Villain Makes The Plot, and the smarter the villain is, the more interesting of a dramatic conflict he can create. – Mason Wheeler Mar 13 '15 at 15:57
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    Gandalf's just high on pipe-weed all the time. – ceejayoz Mar 13 '15 at 16:06
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    A good example: Why didn't Sauron guard Mount Doom? "That we should try to destroy the Ring itself has not yet entered into his darkest dream." - Gandalf – Paul Draper Mar 14 '15 at 19:14
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It's an "evil cannot understand good" kind of thing. Sauron can understand Saruman not (only) because they're both Maia, but because Saruman is like him--power-hungry and dismissive of anyone he perceives as lower than himself. It's not that Gandalf is particularly tricky, it's that Gandalf represents a fundamentally different sort of attitude. Sauron's internal, personal game theory predicts what Gandalf will do by asking: what will gain him the most power? which powerful allies is he courting? how will he unseat me so that he can wield power in my stead?

Gandalf, however, simply doesn't operate this way. Witness how Gandalf is really the only character in the series--including the hobbits--who thinks the hobbits have anything to contribute to these great goings-on. He allies himself with the weak, the helpless, and he guides in subtle ways that do not benefit him except inasmuch as he considers the benefit of all to be his as well. So Sauron sees everything Gandalf does, and he's just baffled.

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    Damn, you beat me to it. :P +1. Just to expand: the quote in the question isn't about Gandalf eluding Sauron in the sense of escaping his dungeons, it's about Sauron not being able to understand (and thus manipulate) him, psychologically. Sauron understands that Gandalf's mission is to stop him, he's just completely out of touch with Gandalf's personality and thus has a hard time predicting what he'll do next. By contrast, Saruman thinks along the same lines as Sauron, so Sauron is always one step ahead of him. – Nerrolken Mar 12 '15 at 22:27
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    +1 Gandalf baffles his allies too, with his trust in halflings. – Paul Draper Mar 13 '15 at 4:56
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    I'm tempted to -1 - the reason Gandalf allies himself with Hobbits is not because they are weak, but because he's wise enough to see their strengths. – DVK-on-Ahch-To Mar 13 '15 at 13:41
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    I agree, but they're apparently weak, and their strengths aren't necessarily things Sauron would recognize as strengths. – zeldredge Mar 13 '15 at 13:42
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    @DVK "'Many are the strange chances of the world' said Mithrandir, 'and help oft shall come from the hands of the weak when the wise falter'" - Silmarillion – a_a Mar 14 '15 at 3:17
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Tolkien being a Roman Catholic theist believed that ultimately Good was more free to act than evil. Evil presupposes actions more often centered on the self. Gandalf, a Christ-like representation of Good, was willing to go so far as die in order to accomplish his goals and was unaffected by a desire for the ring (much like Faramir). Gandalf's choices therefore radiated outward and were confusing to Sauron.

Sauron is unable to imagine anyone who would not chose to take the ring. This makes tracking it after the dissolution of the Fellowship difficult for him. His agents largely pursue the remnants of the Fellowship into Sauraman's territories. He ignores completely the path to Mount Doom. This allows the underdogs of the story to win.

This ties in well with jpmc26's comment on Cor 1:27 which likely guided Tolkien's thoughts here. ME is a "what-if noble paganism met Christian morals" world.

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    Not saying that you answer is wrong, but keep in mind that Tolkien explicitly said that his story was not an allegory. It's mystical world was not based on catholic believes. – Skalli Nov 9 '16 at 16:08
  • And to add to what @Skalli says Tolkien also notes that even the orcs look out for their own. Yes they'll fight the others and yes (as Frodo notes) they'll work together if they encounter an enemy but they still have some loyalty. They may be corrupt but to just say they're wholly evil and nothing else is harsh and I always got the impression Tolkien felt that way too - even when using the word 'evil' it wasn't so simple (as the loyalty/disloyalty of orcs show). Oh, and there isn't any religion in Middle-earth, either, to add to the other comment. – Pryftan Jan 1 '18 at 21:37
  • There is no way Tolkien believed that. Evil is freedom. Good IS good because it's inconvenient to be honourable, to sacrifice for the greater good, to accept small defeats for a larger victory. The ritual of religion is to show your god that you are willing to put up with some hassle to please him or her. Destroying the Ring against it's wishes can only be done by someone with a will approaching his own, and in the end, he was correct. That person was Bilbo. He gave up the ring, the only one to do so, and spared Gollum, who then saved his nephew from his own weakness. – chiggsy Dec 15 '18 at 7:31

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