I think the Jedi council should have at least considered sending obi-wan over to Dooku to be like “yes hello I am here for sith training” just to see what would happen

One thing I do like about TOTJ's take on Dooku's fall is that it really highlights that the Dark Side makes you absolutely masochistic. (Mega long post ahead).

One thing TOTJ establishes is that Qui-Gon's death is absolutely on Dooku (no matter if the show itself doesn't seem to be aware of it).

His tone is concerned and his attitude sympathetic and supportive, but he knows. He knows it's a Sith Lord (he even knows Maul's name). He knows Qui-Gon almost died and is marching right into another trap, but he asks questions anyway and affects ignorance.

"I've been warning them about the coming darkness for years," he says, "never to be taken seriously." Using the Council's skepticism as an occasion to complain about how they didn't believe him while lying by omission is a great case of that hypocrisy Dooku loves denouncing in others. Dooku would rather Qui-Gon share his disillusionment with the Jedi than actually do anything to help Qui-Gon. The Council don't believe him? Okay, Dooku, but YOU DO. You can just tell him what's going on.

But he doesn't.

On some level, Dooku has to be aware of what's about to happen. Qui-Gon is walking into grave danger, and Dooku's response to that - before it happens, when there is still time to stop it - is to put the blame on the people who don't know shit while not doing shit himself. (Why can't Dooku be there to protect Qui-Gon, other than because he's already slavishly loyal to Sidious' plans?)

And this moment puts every subsequent action of Dooku's throughout the Prequels in perspective - particularly his relationships with Obi-Wan, Ventress and Yoda.

Dooku is a glutton for punishment.

I've written here about why I think the 'Box' from TCW 4x17 is meant to parallel Obi-Wan and Qui-Gon's mission on Naboo. The dioxis, ventilation shafts, the catwalks and lightsabers, the ray shields, the fire pit... Dooku's idea of a test to find the best mercenaries around is to have them survive what killed Qui-Gon (what he allowed to happen).

During the challenge, it's pretty obvious he starts to suspect Hardeen is Obi-Wan.

Or at the very least, he's taking an interest in the man who supposedly killed Qui-Gon's own apprentice - Dooku's spiritual grandson (see RotS novelization), whom he's been trying very hard to either recruit or kill himself. And what does he do with that interest? Tries to push "Hardeen" to kill Eval in anger.

Dooku, who still mourns the Padawan he knowingly let walk away to his death, watches a pantomime of his Padawan's death, while putting in mortal danger all he has left of said apprentice. If he knows Hardeen is Obi-Wan (and it's pretty obvious that he does), he tries to get Obi-Wan to Fall (or potentially die) in a scenario reenacting Qui-Gon's death. If he doesn't know for sure, then he's encouraging his all but grandson's killer to win the tournament because he admires him (for killing someone Dooku wanted by his side).

Whatever the outcome, Dooku chooses to relive his guilt and chooses to make the same choice to kill his loved one all over again, even though we know he hates that he made this choice:

He misses Qui-Gon and needs him but tries to kill or destroy Obi-Wan, whom he needs and wants by his side. (I haven't counted just how many time he does try killing Obi-Wan in TCW while still expressing his indefectible admiration for him - it's frequent, the Box just stands out to me as one of the most noteworthy occasions.)

And he keeps doing stuff like that!! He keeps choosing the path that causes him the most pain. He does it with Sifo-Dyas, he does it with Yaddle, he does it with Yoda and he does it with Ventress.

Just look at him confronting Sidious about Qui-Gon's death:

He KNOWS following Sidious got Qui-Gon murdered and he KNOWS Sidious will continue to kill or order him to kill people close to him. And yet he's quick to reassure Sidious that this doesn't change anything. Securing his position with Sidious matters more than his rage and grief. The ONLY WAY this behavior makes sense is if Dooku is fully aware that he had a choice about Qui-Gon's fate, and decides that this is the path he's on now: Sidious might make him kill everyone he cares about, but he's going to do it. Every time, things will play out the same.

Sidious tells him to kill Ventress, his new apprentice? Sure, why not!

(And it's not even out of true loyalty for Sidious, because he constantly tries to double-cross him later on. It's pure self-destruction:)

He hates it, Sidious promises him more of it, and he goes along with it!

This is why Yaddle's attempts at bringing him back don't work, in my opinion:

"Whatever lies he's told you, whatever you have done, you can make up for it now by bringing him to justice." This might convince a man who is looking for atonement, except Dooku isn't. He is looking for punishment.

Killing or harming those close to him leaves him broken, furious or in pain? He'll just keep doing it.

Sidious offers him nothing more than agonizing slavery? He'll keep on kneeling.

That's when Yaddle literally offers him the Light - the light that is so much more powerful than the Dark that it has Sidious cowering, the light that can save him if he wants - Dooku just strikes her down, even though he was heartbroken over thinking he had killed her just a moment ago.

He chooses to kill her, regrets it and hates himself for it, and chooses to kill her again. HE KEEPS MAKING THE CHOICE THAT HE KNOWS WILL HURT.

His remedy to guilt is to pick a shovel, because by God if he hasn't hit rock bottom yet he's going to dig!

Snoozing

Eman Esfandi as Ezra Bridger
AHSOKA 1.07: Dreams and Madness

The way she says this, almost like she's relieved to say it, "He was a good Master." like all those years she spent still loving him, still unable to let him go, still remembering the kind things, she wasn't wrong.

We've seen how much Ahsoka doubted herself throughout this series, especially when it comes to trying to resolve her feelings about Anakin and what he did. That she had to work to accept that he became Vader, that he murdered their family and friends, that he took the light of the Jedi out of the galaxy, that he went on to kill so many more, to help an Empire that slaughtered its way through countless lives.

And through all of that, part of her felt so guilty because she couldn't stop remembering the kind things he did, too. "What would have surprised people was how kind he was," she said to Ezra, mere days before they confronted Vader on Malachor, where he was serious about killing all of them, killing her. That there was no reaching him, no matter how badly she wanted to.

But still she loved him.

She couldn't stop loving him and it tore her up because she couldn't let him go, this man who chose to become the worst monster.

And then he came to her in a Force vision, when she was ready to hear him, to really listen to him, and he told her that she's more than just a warrior, just as he's more than that, that he's more than Vader. They're everything of the Masters that came before them and more.

So, now she can remember the good things he did without having to immediately remember Vader. She can remember, yes, he was a good Master to her, that his teachings helped shape her life into something good and worthwhile, that she can still play the holos he made for her when she needs to settle her mind before a fight.

She can remember that she loved Anakin Skywalker and that he was a good Master without having to tear herself apart because of Vader and her inability to stop loving him. He's more than Vader, he was also a good Master and that's just as true as everything else about him.

Him believing in her and encouraging her isn't a sign that she's going down the same path as he is, it's her Master being kind and supportive and good.

And she is so relieved that her love for him wasn't mistaken, it wasn't misplaced, because this was real, he really was good to her and for her.

STAR WARS HELLO??????? HELLO???????