Originally Posted by Huinesoron
(Note well the last sentence. Not only were there possibly other messengers 'of their own high order' to different locales, but the Five were only the chiefs of the Istari.)
I can see four possible readings:
1. Tolkien meant the order of the Ainur, not the Valar. Booo-ring!
2. This passage recalls the older version of the Valar, back when the Children of the Valar were still a thing. At that point, there were plenty of Vala-breed folk running around, so sending a handful of them over to Middle-earth wouldn't make a dent. But I think this passage probably post-dates that by decades.
3. 'The Valar' are the canonical fourteen, and the 'chiefs' are five of the Aratar - Manwe, Varda, Aule, Yavanna, Ulmo, Orome, Mandos, Nienna. But which five?
3.1. Saruman has to be Aule. He's the craftsman, there's no real alternative.
3.2. Radagast must be either Orome or Yavanna, the Valar of nature. With Yavanna more focused on plants, I would suspect Orome.
3.3-4. It would make sense for the Blue Wizards, who head off together, to be a natural pair. With Aule already out of the way, that would make them either the sibling group Mandos & Nienna, or the married Manwe & Varda. (Note that, unlike Radagast, there is nothing to indicate that they were male in either this text or LotR - they came as Men, the race, not men, the gender.)
3.5. And Gandalf? As the natural leader, he could well be Manwe - but as the Istar of comfort, he could also be Nienna. Either way, we're left with Yavanna, Ulmo, and either Mandos or Varda holding down the fort at home; I'm most inclined towards the last being Varda, since Mandos has a capable deputy in his wife (making Gandalf Manwe).
4. While Tolkien isn't too terribly sexist, his creations' ideas of authority are. So perhaps 'the chiefs' of the Istari means 'the men', and each was accompanied by his wife? This leads us to a slightly different listing:
4.1. Saruman is still Aule, here accompanied by Yavanna. She may then have gone off to try and find the Entwives. This may explain why Saruman/Aule set up shop near the Ents (so she could find him), but also why he was so angry about them (because they were essentially created to spite him).
4.2. With Yavanna out of the way, Radagast must be Orome, accompanied by Vana. Where would the Lady of Flowers have taken herself off to? The part of Middle-earth most associated with flowers is probably the Vale of Anduin, which has both the Gladden (= iris) Fields and Beorn's bees. It's also right next to Mirkwood, where Radagast/Orome hung out.
4.3-4. The Blue Wizards still need to be a natural pair, and in this case you can't do better than Irmo Lorien and Namo Mandos, the Feanturi themselves. Travelling into Sauronian territory, they're perfectly equipped to influence possible friends of the West (by dreams and visions), and to deal with Sauron's death-cults (like he set up in Numenor). They also take with them Vaire, whose speciality is history - ie, truth, to teach those who have been lied to - and Este, who can bring rest and healing to those faithful to the Valar who are suffering under Sauron's rule.
4.5. Then who is Gandalf? Ulmo has no wife, and would make a decent candidate, except that he's never been shy about revealing his power, and has always preferred to stay out of the Valar's mad schemes. Tulkas we can probably write off. And so, once again, we come round to Gandalf as Manwe, and at his side Varda Elentari, the Elbereth of the elves. While her husband is off talking to the little folk of the world, I imagine her slipping into places like Lorien and Rivendell unseen, simply an elderly woman no-one glances twice at... except that in her wake, the stars seem brighter, and the songs of the elves all the sweeter.
I... didn't actually expect to wind up with Gandalf as Manwe every time; I was assuming based on the name Olorin that he was more likely to be Lorien. But Manwe fits a lot better with the rest of the details, so there we are.
hS
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