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Even though the Jedi Council greatly disapproved of Anakin becoming a Jedi, Obi-Wan still took him under his wing after promising Qui-Gon Jinn. Anakin eventually becomes Darth Vader...

Has Obi-Wan ever expressed regret, either openly to someone or to himself, in teaching Anakin the ways of the Jedi?

I'm happy to accept any canon source (movies, novels etc.).

Disclaimer: I have seen the first 6 episodes a long time ago in a cinema far, far away.

16

Yes, when he talks to Luke in Return of the Jedi:

According to wikiquote the dialogue was:

Obi-wan: Luke, you're going to find that many of the truths we cling to depend greatly on our own point of view. Anakin was a good friend. When I first knew him, your father was already a great pilot. But I was amazed how strongly the Force was with him. I took it upon myself to train him as a Jedi. I thought that I could instruct him just as well as Yoda. I was wrong.

However, according to IMDB:

Obi-Wan: Luke, you're going to find that many of the truths we cling to depend greatly on our own point of view. What happened to your father was my fault... from a certain point of view. Anakin was a good friend. When I first met him, your father was already a great pilot. But I was amazed how strongly the Force was with him. I took it upon myself to train him as a Jedi. I thought that I could instruct him just as well as Yoda. I was wrong. During the Clone Wars, it wasn't long before the Emperor sensed Anakin's powers and lured him to the Dark Side.

This seems to be a version of the exchange that was in the 3rd Draft (also here as Revenge of the Jedi), which has a different version of the dialogue:

Obi-Wan: I don't blame you for being angry. If I was wrong in what I did, it certainly wouldn't have been for the first time. You see, what happened to your father was my fault.

[Pause]

Obi-Wan: Anakin was a good friend.

[Pause]

Obi-Wan: When I first knew him, your father was already a great pilot. But I was amazed how strongly the Force was with him. I took it upon myself to train him as a Jedi. I thought that I could instruct him just as well as Yoda. I was wrong. My pride has had terrible consequences for the galaxy.

Star Wars Legends

In the novel Kenobi by John Jackson Miller, Obi-Wan has these thoughts about Anakin:

In the Prologue:

I still can't believe the Jedi Order is gone and the Republic, corrupted and in the hands of Palpatine. And Anakin, corrupted as well. The holovids I saw of him slaughtering the Jedi younglings in the Temple still haunt my dreams, and shatter my heart into pieces, over and over again.

In Chapter 13:

It's not like I'm going to suddenly get my friends back. It's not like I'm going to feel any better about what I had to do to poor Anakin. It's not like..

In Chapter 40:

Anakin had flaws of his own. Flaws I failed to see, that I didn't prepare him to deal with. But the Emperor played a role. I don't know if it would have been possible to isolate Anakin from his influence. I tried, but too late.

  • I think I saw a different version of Jedi – chillin Oct 1 '15 at 0:14
  • Absolutely brilliant, thank you very much! +1 – user35594 Oct 3 '15 at 20:16
  • Per the James Kahn novelization: 'I took it upon myself to train Anakin in the ways of the Jedi. My mistake was thinking I could be as good a teacher as Yoda. I was not. Such was my foolish pride. The Emperor sensed Anakin’s power, and he lured him to the dark side.” He paused sadly and looked directly into Luke’s eyes, as if he were asking for the boy’s forgiveness. “My pride had terrible consequences for the galaxy.”'. – Eike Pierstorff Nov 26 '15 at 21:13

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