Was Obi-Wan Complicit in Anakin’s Fall and the Order 66 Massacre? Let’s Get Into It.

“Why didn’t you stop him? He was your padawan. Where were you when [Anakin] was killing my friends?”

This was what the Third Sister (now Grand Inquisitor) asked last week after Obi-Wan deduced she was a youngling at the Jedi Temple during Order 66. And it begs the question for the audience too.

Where was Obi-Wan Kenobi and could he have stopped it?

First, some history, Obi-Wan started out Revenge of the Sith on Coruscant but was later assigned to take down General Grievous on Utapau by the Council—after rejecting Chancellor Palpatine’s request that Anakin be sent instead. This, of course, played right into Palpatine’s hands, as it both emotionally and physically divided the former Master and Padawan. Despite seeming to part on good terms, Anakin was hiding both life-threatening secrets and brewing resentment for his teacher, father figure, and friend.

Could Obi-Wan have done more to prevent Anakin’s fall to the Dark Side?

Okay, let’s get out of the way that even though Palpatine was a master manipulator (who had literally been grooming Anakin for the role of his apprentice from the tender age of 9), Anakin’s fall was ultimately no one’s fault but his own. He chose to prioritize Padme’s life over the fate of the Jedi and the galaxy, and even Padme couldn’t stop him. But the question is, was there a possibility that Obi-Wan could have done more to prevent it all?

Obi-Wan wasn’t just Anakin’s friend, after all, he was also the one who raised Anakin. And to really talk about blame, we need to analyze their relationship from the start.

Obi-Wan as a father figure

One part that people forget about The Phantom Menace is Obi-Wan somewhat resented Anakin a little at the start, feeling like his own Master was casting him aside for this supposed Chosen One. And that had to have influenced their relationship at the beginning, at least on a subconscious level.

Still, Obi-Wan fulfilled Qui-Gon Jinn’s dying wish to train Anakin, though, in hindsight, the two were ill-suited to each other. Obi-Wan was a stickler for rules and authority, while Anakin was much more a free-spirit like Qui-Gon. Perhaps opposite attract (or balance each other out), but Obi-Wan seemed more determined to bring Anakin to heel than listening to him and learning from him in Attack of the Clones. It doesn’t help that he seems to take every opportunity available to remind Anakin of his place as padawan.

Their relationship does improve in The Clone Wars after Anakin is knighted, but Anakin remembers this association of authority and continues to brew resentment after being denied the Master title—despite being on the Jedi Council AND having trained a padawan who was now leading the Siege of Mandalore.

In Season 2 of The Clone Wars, Anakin discovers Obi-Wan had a former ‘relationship’ and teases his master about his girlfriend, Duchess Satine Kryze of Mandalore. It’s then that Obi-Wan opens up about the undercurrent of remorse left by the Jedi code of non-attachment.

But at the same time, Obi-Wan refuses to use Republic resources to help Satine’s sister, Bo-Katan, retake Mandalore after the Duchess’ death—due to the risk of violating treaties between the Jedi and Mandalorians. Anakin oversees the argument, clearly disagreeing with his Master’s stance that the Jedi Code is more important than Obi-Wan’s attachment.

This is made even more complicated by Obi-Wan having revealed that he knows Anakin and Padme are having secret correspondences, if not an outright affair. Instead of seeing his former Master as a confidant, Anakin seems to be more worried than ever. Obi-Wan has made it clear where his loyalties lie. And I feel like the combination of these past experiences is why Anakin doesn’t confide in Obi-Wan about his concerns for Padme.

Anakin’s fall to the Dark Side

Season 3 of The Clone Wars sees Anakin, Obi-Wan, and Ahsoka trapped on a planet that is a manifestation of the Force, including three personifications of its sides: The Daughter (Light), the Son (Dark), and the Father (Balance).

During this, the Son shows Anakin his future as Darth Vader and Anakin turns to the Darkside to…prevent himself from turning to the Darkside. Which is just about the most Skywalker-sounding oxymoron if I ever heard one, but let’s move on.

Anakin’s memory is eventually erased, but Obi-Wan seems to shake off any concerns over Anakin’s darker nature. Granted, a lot of Anakin’s darkest moments in The Clone Wars were done out of Obi-Wan’s view (a couple of impalements excluded), but he never seems to follow up with Anakin about this inner darkness. You know, maybe check in on that. Seems important.

Rako Hardeen

And here we come to the event that probably fractured Anakin and Obi-Wan’s relationship more than anything else: Obi-Wan faking his own death in order to go undercover as his own murderer.

Not only did Obi-Wan traumatize Anakin, Ahsoka, Satine, Padme, and all his other friends by not letting them in on the charade, but he doesn’t reveal the truth to Anakin until his former padawan’s “Roaring Rampage of Revenge” threatens his mission. Anakin’s rage is pretty justifiable in this case.

Seriously, Sidious barely needed to do anything at this point, the cracks were already there, he just exploited them.

Revenge of the Sith

Revenge of the Sith is a true tragedy in that you can imagine how easily the disaster could have been avoided if everyone had just taken another minute to talk things through.

• If Obi-Wan hadn’t asked Anakin to betray Palpatine’s trust, maybe Anakin would have trusted him more.
• If Obi-Wan hadn’t gone after Grievous, he would have been there to help Anakin with the conflict of finding out his friend was a Sith Lord.
• If Obi-Wan hadn’t snuck aboard Padme’s ship, maybe she could have talked Anakin down (or at least would have avoided getting Force choked).

Could’ve, Should’ve, Would’ve.

In the end, Obi-Wan certainly feels responsible himself for Anakin’s fall to the Dark Side, saying he failed him during their duel on Mustafar, and doesn’t want anyone else to die for his own mistakes during the events of Kenobi. But Anakin’s one-track mind (and fractured relationship with Obi-Wan) means he doesn’t deny Sidious when he declares all Jedi, including Obi-Wan, traitors of the Republic, meaning by that point, he’d lost all trust in his former master.

And while there are hundreds of time-travel fics dedicated to Obi-Wan or some other Star Wars character going back in time and fixing the mistakes of the past, we can never know for sure if Obi-Wan’s presence would have changed things.

But what do you think? Was Obi-Wan responsible? How would things have changed if he had been on Coruscant during Anakin’s fall?

(Featured Image: Disney Plus/Lucas Films)