(If this post does get an adequate amount of recognition, I will make a YT video elaborating furthermore)
Ok so the title was kinda exaggerated, but don't let that shadow the man point.
We know a lot about Clavicus Vile. He seldom keeps secrets from his followers or practically anyone in that regard. This doesn't mean he's an honest Daedra though. Clavicus is the Daedric Lord of trickery, regret, one sided deals, etc. It's in his nature to disregard the needs and wants of mortals. All of this said, Clavicus is usually regarded as more of a "chaotic neutral" type Daedra rather than just plain evil like Molag Bal or Mehrunes Dagon, but he lacks the mortal interpretation of morals. We know that many regard him as the childish Daedra due to his child-like mischief and trickery, and that his summoning day is the 1st of what would be January, and most important of all, that he has a canine companion named Barbas.
Fields of Regret: The fields of regret are (is) Clavicus Vile's plain of Oblivion. As described by its name and it's appearance in TES: Redguard, his plane consists of green plains and rolling hills, forests, and an abundance of flora and fauna. It is a merchants paradise, and regarded as one of the more pleasant realms of oblivion in the eyes of sane mortals. It is also believed that the floating island of Umbriel was torn from this plane of Oblivion, but that is not relevant to this post. The reason why it is called the Fields of Regret is usually believed to be due to the fact that many mortals regret their deals with the Daedric Lord, but this may or may not be the true reason. Just like other realms of Oblivion, it is an extension of Clavicus Vile himself, with his physical representation acting as a projection for mortals to conceive of his form.
Barbas: Barbas isn't just Clavicus' companion, Barbas is a part of Clavicus himself (but of course most of you know that). As quoted in Skyrim, Clavicus states: "Half my power resides in that mutt Barbas", prompting the fact that his power is split half-half and also that the Dragonborn is about half as powerful as Clavicus Vile, most likely putting him on the weaker side of Daedric Lords.
Now for the important part about Barbas. Barbas is often depicted as the symbolic voice of reason in Clavicus Vile's head. We know this because Clavicus Vile is often not very good at making important decisions such as when he requested the Sword of Umbra to be returned to his realm in TES 3: Oblivion. Clavicus, being the childish trickster that he is, would rather decide based on what he thinks would be benefit him the most in the short term, whereas Barbas decides based on the most logical and beneficial effects.
This inner conflict between Barbas and The Childish Trickster inside Clavicus Vile's head is a constant battle between two opposing forces of Chaos and Reason. More often than not, Clavicus will often be seen pushing Barbas around as he sees him as an annoyance or a fun-stopper, as seen in the Skyrim quest "a Daedra's best friend", even going as far as telling the Dragonborn to kill Barbas so that the two voices can be reunited as one, and most likely be unbalanced with the Clavicus' trickster side taking over.
This internal chaos caused by the opposing forces of Clavicus' personality causes his inner hatred for himself to grow, making him the most human-like Daedra, experiencing many of the same problems us mortals do. Now I know what you're thinking, "isn't that kinda like Sheogorath". Well yes, Clavicus and Sheogorath are the most similar Daedra to each other (sorry Sanguine), but the difference is that Sheogorath IS in himself, purely chaos, with his two sides being the jolly old prankster side of chaos and the depressing demented side of chaos. Clavicus vile experiences a more human (I guess you can say Mer as well, but this applies to real life too) type of inner conflict.
Now remember when I said that one of Clavicus Vile's spheres was regret? Neither do I but it is so let me explain something: For a Daedra to have a certain aspect of reality within their sphere, it must literally be part of their essence (I know you're out there, Daedric Prince of nothing), such as how Namira is literally the ancient evil of darkness, or how Peryite is literally a pest in his annoying voice and god awful quest.
So let's talk about regret. Clavicus' sphere contains regret. This could be interpreted as the mortal regret that comes with striking a deal with him, but it's not just as simple as that.
Just as Sanguine experiences the constant need for stimulation, our boy Clavicus might just be experiencing regret himself.
Here's were stuff gets really spicy, so if I haven't lost your attention yet, you're a champ.
1. We already know that the E'tada (Aedra and Daedra before Mundus) were sentient beings, and although not all existed before the creation of Mundus, It's safe to say there's a good chance Clavicus Vile did, since he is present in many creation stories.
2. It is likely that Clavicus Vile is related to Lorkhan somehow since their "spheres" are somewhat similar, and we all know Lorkhan was the E'tada that came up with the creation of Mundus and then tricked the others into creating it. Lorkhan might even be Clavicus' "father" (or whatever the god-like equivalent is).
3. Since Clavicus is a Daedra, we know that he didn't participate in the creation of Mundus, since the only Daedric lords who we know did are Malacath/Trinimac and Meridia, since both were casted into oblivion later on.
4. So what is it in the first place that Clavicus regrets? What is there for a Daedra to regret? Well there is one thing…
The thing that Clavicus Vile might be regretful of is the fact that he didn't participate in the creation of Mundus. Ok it seems far-fetched for a this to be the thinking process of a Daedric Lord, but hear me out.
We know a lot about Clavicus Vile's personality, and we also know the two things he desires most: Worship (or affirmation from his fellow Daedra and mortal followers), and Harmony (which is actually one of his spheres).
What if Clavicus Vile saw the praise the 8 original divines and some of the Magna-ge got from Mortals, and grew jealous, making him take out his anger in childish ways towards mortals, daedra, and most importantly, himself? The possibilities are endless…
Clavicus Vile is at constant war with himself and suffers many of the problems mortals due cause of it. His greatest desires are appraisal and harmony, which in Lorkhan's eyes could be achieved by becoming a mortal on Nirn, which happened to most of the lesser creators of Mundus. Clavicus missed an opportunity to either experience the true nature of harmony as a mortal, or possibly even achieve divininity in the process.
Clavicus' struggle with Barbas is real, and it is the only way he can truly experience some of the aspects of mortality, which is why he created Barbas. He finds peace in imperfection, as did Lorkhan, and many Daedra as well.
We might just know why he is always making deals and socializing with mortals: He envies them and has a child like curiosity.
Clavicus may not be the most powerful Daedra. He may not be the most altruistic, the most moral, the strongest, most ambitious, most influential, or most worshipped Daedra, but he may as well be one of the most clever and ironically, one of the wisest (in his own way, I'm not saying he's a greybeard or anything).
Feel free to express your own thoughts, i'm open minded to other possibilities.
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