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For much of Anakin Skywalker’s early life in Star Wars, Obi-Wan Kenobi was his closest paternal figure, his Jedi Master, and the one he spent the most time with. The two spent thirteen years together, during which time Anakin grew from a young boy into a young man, and finally into the infamous Sith Lord Darth Vader.
Throughout the Prequels, Anakin openly acknowledges Obi-Wan as being like a father to him, and Obi-Wan is repeatedly shown to be a good and patient master. However, by the end of Revenge of the Sith, even Obi-Wan admits that he has failed Anakin in his duty as the Jedi’s Master.
10 He Was: Accepted Anakin’s Unconventional Ways
Obi-Wan is a very traditional Jedi, preferring patience and rational action, even in the face of tense situations. Anakin holds less to this ideal, being willing to take rash, reckless decisions, and solve situations through unconventional—albeit usually violent—means.
Nonetheless, despite a few chastising remarks now and then, Obi-Wan is willing to accept Anakin’s different approach. When Anakin is the one to kill Tal Merrik when Obi-Wan hesitates, all he gets is a stern “Anakin” and nothing more. Earlier, when Anakin dives out of a speeder above Coruscant, all Obi-Wan offers is a calm “I hate it when he does that.”
9 He Wasn’t: Furthered Anakin’s Distrust Of The Jedi By Faking His Own Death
In The Clone Wars episode “Deception,” Obi-Wan has to infiltrate a Separatist plot to kidnap Chancellor Palpatine, and in order to do this, he fakes his own assassination at the hands of Rako Hardeen and impersonates him. Only a few people are in on this plot, and Anakin is not one of them.
The result is that Anakin is left traumatized by what he believes to be the death of his father figure, and when the deception is revealed, Anakin is left further hurt by the fact that Obi-Wan and the Council excluded him. This is one of many factors that see him turn to the dark side in Revenge of the Sith.
8 He Was: Knew Anakin Better Than Anyone
Anakin would come to have numerous close friendships over the course of the Prequel Trilogy and The Clone Wars, forging bonds with Padmé, Ahsoka, R2-D2, and more. However, as close as the bonds were, it was Obi-Wan who knew Anakin the best.
It is this knowledge that Obi-Wan used to try and ensure Anakin was kept safe and healthy, and to keep him away from situations or information that might negatively impact him. Tragically, Obi-Wan would also use this knowledge in their duel, baiting Anakin into making a suicidal attack.
7 He Wasn’t: Kept Too Much Distance From Anakin & Padmé’s Issues
It’s indicated throughout The Clone Wars and Revenge of the Sith that Obi-Wan is well aware of the illicit affair Anakin and Padmé are having, behind the backs of the Council.
It is suggested that keeping his distance is Obi-Wan’s way of trying to be a good friend and father figure—he doesn’t want to have to remind Anakin of the rules, or interfere with his privacy. However, the end result is that Obi-Wan cannot help Anakin when the latter struggles with his relationship, allowing the issues to fester and drive Anakin towards the dark side.
6 He Was: Defended Anakin To The Council
The Jedi Council made it known that they were not entirely trusting of Anakin, often viewing him as too reckless and too conflicted to live up to the Jedi way. While Obi-Wan on occasion shared their concerns, and sometimes complained about his difficulties with Anakin, he usually defended his Padawan.
In Revenge of the Sith, the Council worries about assigning Anakin to spy on Chancellor Palpatine, but has to use him because he is the only Jedi close enough with the Chancellor. Obi-Wan steadfastly defends Anakin to Yoda and Mace Windu, reminding them that he is the Chosen One, and assuring them that he has never let Obi-Wan down. Tragically, this is the first time Obi-Wan is wrong in this regard.
5 He Wasn’t: Didn’t Address Anakin’s Resentment
While Anakin and Obi-Wan are always close, throughout Attack of the Clones and Revenge of the Sith, there is an undercurrent of resentment through their relationship. In a rant to Padmé, Anakin accuses Obi-Wan of holding him back, and throughout Revenge of the Sith, there are hints he believes Obi-Wan is trying to have an affair with Padmé.
Obi-Wan either is unaware of this resentment or chooses to ignore it, perhaps hoping that the positive side of his and Anakin’s relationship will win out. Needless to say, this does not happen, and by the time the two of them duel, Anakin is consumed with hatred for his Master.
4 He Was: Provided Stability & Balance
Anakin Skywalker had a turbulent childhood. A mistreated child slave on Tatooine, he was quickly enlisted in a scheme to help Qui-Gon and Obi-Wan get Padmé to Coruscant, and from then dragged into a conflict between Naboo and the Trade Federation. Shortly after, Anakin’s first father figure, Qui-Gon, died, and he was allowed to be trained by Obi-Wan.
From such disrupted beginnings, Obi-Wan provided Anakin with thirteen years of stability and balance. His calm and collected nature allowed him to take Anakin’s difficulties in his stride, and its contrast with Anakin’s own hot-headed nature allowed the two to function together well.
3 He Wasn’t: Too Dedicated To The Jedi Code
Having been raised in the Jedi Temple from almost birth, Obi-Wan is one of the many Jedi who have internalized the Jedi Code, and allow it to guide nearly every decision they make. Anakin joined the Jedi when older, and so has many more struggles following its tenets, often struggling to control his emotions and look at the big picture.
Obi-Wan tries to be understanding, but often his advice towards Anakin simply involves following and obeying the Jedi Code, without getting to the root of Anakin’s difficulties with it. Obi-Wan was simply too used to the Code to be able to relate to Anakin’s problems, leading to Anakin’s issues.
2 He Was: Anakin Learned Much Under His Teaching
A Jedi Master is a lot of things, acting as a teacher and mentor of practical skills in addition to being a philosophical tutor and a parental figure. While much of Anakin’s skills with the Force—lightsabers and leadership—came from natural talent, Obi-Wan’s own contributions cannot be discounted.
Obi-Wan and Anakin trained together for countless hours, and while they favored different styles, they were clearly impactful on one another’s techniques. Obi-Wan similarly taught Anakin numerous Force techniques. Anakin wouldn’t be the Jedi he was without Obi-Wan’s insightful instruction.
1 He Wasn’t: Couldn’t Help Anakin With His Grief
Leaving their parents at a young age and rejecting attachments they see as ‘selfish,’ the Jedi do not grieve like others. Obi-Wan is clearly devastated and shaken by Qui-Gon’s death, displaying a rare bout of anger immediately afterward, but he processes it and is able to move on. Anakin, having formed attachments before joining the Jedi, feels grief more deeply.
As a result, Obi-Wan is poorly equipped to help when Anakin grieves over the loss of his mother. When Anakin is similarly struggling with fear of losing Padmé, he instead discusses his problems with Yoda, who struggles from the same lack of perspective. Had Obi-Wan been better able to work through Anakin’s grief with him, much could have been averted.
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