I have this hc that Sauron’s obsession with vanity led him to spend years studying Maedhros’ features and trying to emulate them. When he couldn’t get it right, the proportions always a little off, red hair never deep enough, he took his anger out on Mae and when that option was gone, tried to pull from others also renown for their beauty instead.
Fast forward a few centuries and turns out all that work wasn’t entirely useless. And Sauron knows exactly what to do with the features he was able to recreate. Weaving them into his new face, the line of Maitimo’s smile, the set of his eyebrows, the crease of his eyes, he puts just enough to be familiar, but not enough to set off any alarms.
Celebrimbor doesn’t know *why* he trusts Annatar so easily, just that he’s got a good feeling about him. The Maia reminds him of someone he can’t quite put a finger on, but it’s a good association and he doesn’t think on it too deeply. Grows to call him a brother in all but blood.
Of course we all know how that ends. And the last thing Celebrimbor sees is his eldest Uncle’s smile, a mockery of the warmth it should hold as Sauron finally ends his torture.
(Elrond, on the other hand, never saw Maitimo who used to laugh easily and play silly games with children. Only grim Maedhros. The gentle features Sauron steals are alien to him. A stranger with too many familiar features he can’t quite place, twisted the wrong way, leaving him deeply unsettled. It’s why he immediately tells Gil Galad to send Annatar away, hiding trembling hands in his sleeves.)
Makes perfect sense! If Maedhros was really The Prettiest, Sauron would be so jealous seeing him all the time during Mae's imprisonment in Angband. He would be OBSESSED by recreating that look. Until inevitably admitting it's impossible.
It would also explain why some would love Annatar so easily, as Maedhros was beloved by Fëanorians. I know in Lindon probably nobody would associate Maedhros with good things (except for Elrond, of course), but as you said, the resemblance could be really subtle - enough for Fëanorians to unconsciously notice it, but not enough for the others, who would just see a pretty face, actually a VERY pretty face.
What I love the most about this idea is the fact that Elrond wouldn't need any visions to recognize there's something wrong with Annatar. While Elrond's life is basically "A Tragedy: To Be Continued", this would be a perfect example of bad things that ultimately led to something good (just as Glum stole the Ring from Frodo at Mount Doom and, without meaning to, caused its destruction). It would be enough to just look at Annatar, his experience allowing him to recognize this stranger's twisted nature - something that used to be good, but no longer is; although Elrond wouldn't be able to put a finger on it, or he would think it wrong for different reasons, the fact still stands.
(Also, it's quite sad that Elrond would consider cheerful Maedhros unsettling, as he never got to see Maedhros in Aman, before all the darkness become ever-present in the life of Noldors.)
I think that Tolkien himself would approve.
Yesss exactly!! Love your analysis into it!
Also Maedhros was probably known as trustworthy, and I believe that would reflect in his face if you know what I mean. Throughout Aman pre-drama he was known across the land for being mature, kind, and fair. The kind of guy you could leave valuables with and come and collect them in perfect condition. Or go to for advice and know you’re getting an honest response. Even in Beleriand he lost the softness but retained that trustworthy nature, which is how he was able to build the Union for the Nirnaeth.
Sauron would mimic that and mostly succeed, at least in giving that kind of warm trustworthy vibe he had in Aman that you have to be Very Good to see through. He is a deceiver after all and has been doing this probably as long as elves have existed, if not longer.
I like to think there were many elves across ME confused why Gil Galad’s herald immediately refused Annatar’s aid. Some even thought it was due to a Fëanorian upbringing until Celebrimbor welcomed Annatar and silenced those rumours.
(Yep. Maedhros really did try for Elrond and Elros, but he only really smiled at most, and usually with his eyes rather than his mouth. Even that was shadowed in agony and grief, especially with the elves even now inexperienced with dealing with constant loss, and not knowing how to help.
I like to think it’s what really pushed Elrond and Elros to become healers before warriors.
Sorry I’ve gone off topic, these poor elves give me all the feels 😅)
I love YOUR analysis! Don't forget YOU started it😉
I can vividly imagine Maedhros as the beloved and wise prince and people adored him. And yeah, it's really said to know all the things he survived and how his life became more and more miserable.
I bet that there were all kinds of rumour about Elrond and not just during the Second Age. Actually, I think it started with Elwing's escape and that it has never stopped.
Don't apologize, Tolkien was master of complicated situations and relationships. And anything concerning Elrond gives me feels. He just deserves a break❤️🩹