#charlie said in an interview some time ago that he doesnt know whether sauron was truly repentant but he knows he wished he could be

[ghostinthetumbchine]

This but i also feel like it's important how they're starting from very different footing with very different slates.

(Im sorry OP im about to go into a yap session on your great post, hope you dont mind)

Stranger does not know who he is nor do people around him. In many ways he's a blank slate. He has no preexisting tendencies and convictions and people around him have no hangups nor reasons to have them other than maybe him being a bit strange. Its easy to love him, even when he makes mistakes because he just seems like an innocent baby lost in the world. And people do love him, and that makes all the difference.

We also know he is Olorin, a maia who has remained in valinor and spent his existence serving Manwe, Nienna aka caretakers, leaders, people who tend to and nourish what already exists, rather than focus on creation and progress and invention.

In comparison, we have Sauron with all the existing baggage, his own knowledge of his past and others justifiable hatred and prejudice towards him. He has thousands of years of living in darkness and brutality, negative conditioning and enforcement of ruthless, nihilist perspective. He's for sure cynical, disillusioned to the extreme and he already had a distincly non-incarnate perspective on existance before that. This position - which, granted, he mostly put himself into by switching to Morgoths side in the first place, ensures that he has no option for honest connection with anyone in vicinity.

And so maybe Im nitpicking, i don't mean to get in your parade op because your post is amazing, but i feel like its also making an inevitable - even if not intended - point about circumstances and context.

When you are innocent and do not actually have a history of doing really wrong things to people and watching them be done to others and to you and justified, this kind of messaging from your friends or "guides" - in this case I guess we can say Nori and Diarmid - will be valuable and it is for Gandalf and the viewers. And Sauron simply functions as a narrative mirror/negative example of someone who has already been making bad choices.

But i would love to see more exploration of the fact that to rehabilitate a genuinely bad person who on top of it has very self-righteous and cynical perspective on the world and has been in a brutal war with a significant part of it for a long time based on those principles, you would need an entirely different/more detailed approach. But ofc its not that kind of story, nobody truly awful for all the "i believe im right" reasons ever got that treatment in tolkien, they just get killed of or get the "maybe one day he will manage to redeem himself but hell if i know how"

The Stranger (Gandalf) and Sauron

 The thematic parallels in their storylines are one of the key threads of the show. Save or rule? Why action carries more weight than intent. Choosing every day to do good. To be good. Your actions reveal your nature.

Season 2 opens with Sauron given the opportunity to choose a new path. He seems to have moments where he leans toward repentance, as seen in this scene with Diarmid and “Halbrand”: 

-“Find forgiveness. You are alive because you have chosen good.” -“But what of tomorrow?” -“You have to choose it again. And the next day. And the next. Until it becomes a part of your nature.”

Consider then these scenes with the Stranger and Nori: 

-“You're not a peril. You're good.” -“I’m good?” -“You're good. Because you're here to help.” -“Get away from me. Or I wi… I will hurt you. Again.” -“What? What have they done to you?” -“They showed me what I am.” -“Only you can show what you are. You choose by what you do. You're here to help. I know it.”

In such conversations, there is an acknowledgement of harm caused: Sauron’s “I’ve done evil” (something he says to Galadriel as well in Season 1) and the Stranger’s “I am peril”/“I will hurt you again”. Throughout the season I think you see them both struggle with this. The difference being in season 2 that it may be Sauron’s intent to choose good (and maybe he thinks he is) but his actions are causing harm. The Stranger has the intent and acts congruently. He does not mean to cause harm and he does try to avoid it, because he recognizes that his actions can cause harm. 

In season 2 - Friends over power

The stranger chooses to save his friends over what power he might learn from the Dark Wizard, the promise that they would succeed Sauron (save or rule - he makes the choice to save)

Sauron calls Celebrimbor “friend” mockingly, tortures him and impales him with a spear. Calls himself the Lord of Eregion while he torments Celebrimbor into serving his purpose. He thinks he is healing Middle-earth while he causes destruction and he cannot see the difference. 

The Stranger sees the difference between “save” and “rule” and he chooses to do good. 

One is a peril to Middle-earth, the other an instrument of salvation. The irony being that Sauron sees himself as Middle-earth’s salvation and the Stranger calls himself a peril.

(Not sure I love the narrative choice to pair the morally questionable man with a woman whose purpose it seems is to guide him toward goodness, but that may be a little reductive of me, so I digress…)