Obi-Wan Kenobi is acknowledged in Star Wars as one of the finest Jedi to ever live. Aside from his masterful skills with the Force, with a lightsaber, and as a diplomat, he embodies the control, willpower, and adherence to the Jedi Code that the Order so emphasizes.
Obi-Wan is fundamentally one of the most principled characters in the franchise, but he isn’t perfect. At several points throughout the films and TV shows like The Clone Wars and Obi-Wan Kenobi, he proves that he can be pushed to violate his principles as much as anyone else. Obi-Wan sometimes fails to live up to his own expectations.
9 Letting A Fellow Jedi Be Killed By Inquisitors
Obi-Wan is in a very dark place at the beginning of Obi-Wan Kenobi. He’s almost completely cut off from the Force and eking out a miserable, unremarkable existence on Tatooine while trying to keep Luke safe. Due to the threat posed by the Inquisitors and the Empire as a whole, Obi-Wan can’t afford to be his usual heroic self.
As a result, Obi-Wan has to compromise on his principles and his other responsibilities, even to other Jedi. Although he has to tolerate a lot of injustice, the worst comes when fugitive Jedi Nari asks him for help. Despite his love for the Jedi Order and his loyalty to the others, Obi-Wan can’t bring himself to help, and is clearly guilt-ridden when Nari ends up dead.
8 His Time As Rako Hardeen
Although Obi-Wan isn’t above using intelligence and guile to resolve things, he has principles to how far he’ll go, particularly with his loved ones. To foil something as desperate as an assassination plot against Chancellor Palpatine, however, Obi-Wan shows that he’s willing to go further than usual with an undercover mission.
Faking his own death and replacing Rako Hardeen is an extreme move for Obi-Wan to make, but the most extreme part is keeping up the deception to Anakin and Ahsoka. They are both devastated, something that Obi-Wan usually tries to avoid in his duties as Anakin’s master.
7 The Depths Of His Feelings For Satine
Although Obi-Wan is a master of restraint and willpower, he does have temptations as much as anybody. Much like his apprentice, he has his own forbidden romantic attachments. He doesn’t pursue it, but Obi-Wan is shown several times to be desperately in love with the Mandalorian duchess Satine Kryze.
When Obi-Wan first sees Satine again during the Clone Wars, he insists that they both loved duty more. Later, he says to Anakin that such feelings are natural if not acted upon. However, Obi-Wan also admits that he would have left the Order for her, and openly defies the Jedi Council by trying to rescue her later. This flies in the face of his typical devotion to the Jedi Code.
6 Taunting His Opponents In Combat
Despite his immense skill with a lightsaber, Obi-Wan is something of a pacifist, largely adhering to the Jedi way of only using violence when it is absolutely necessary. He frequently has to reprimand Anakin, having to remind his apprentice to not be overly confident or arrogant in combat.
As much as Obi Wan is reproachful to Anakin, he shows a notable tendency to mock his opponents while fighting them. Due to his naturally deadpan and sarcastic nature, Obi-Wan often quips while fighting enemies, and even devolves into mock flirting against opponents like Asajj Ventress.
5 Letting Anakin Live On Mustafar
The master-padawan relationship between Obi-Wan and Anakin is one of the emotional cores of the prequel trilogy and The Clone Wars, and Obi-Wan is devastated by Anakin’s fall to the Dark Side. Their clash on Mustafar forms the climax of the trilogy, and there’s a moment where Obi-Wan fails to keep to his principles by letting Anakin live.
As a Jedi, Obi-Wan has an obligation to fight the Sith at every turn. Yet, he refuses to put an end to one of the most dangerous Sith Lords to ever live. By leaving Anakin to slowly burn to death, Obi-Wan is letting him suffer in a fashion that goes against his own gentle nature and the principles of the Jedi.
4 Wishing To Challenge The Emperor Himself
After Order 66 devastates the Jedi, Obi-Wan Kenobi and Yoda are the only two able to respond quickly to events on Coruscant. Due to the seriousness of the situation, they decide they each need to fight either Palpatine and Vader. Because of his personal ties with Anakin, Obi-Wan pleads with Yoda to be allowed to fight the Emperor.
Obi-Wan wanting to challenge the Emperor is an entirely understandable reaction. However, he has spent a lot of time admonishing Anakin for being ruled by his emotions and not focusing on the best course of action. By pleading to fight the Emperor instead of Anakin, Obi-Wan slips into the same trap briefly.
3 Fighting Darth Maul In Anger After Qui-Gon’s Death
One of the most famous rivalries in Star Wars is that between Obi-Wan and Maul. Maul kills Obi-Wan’s master. In return, Obi-Wan mutilates him and leaves him near death, giving them both enough reasons to despise each other. Maul is one of the few people to momentarily cause Obi-Wan to struggle with his feelings, even though Kenobi resists the Dark Side every time.
The first occasion is immediately after Qui-Gon’s death. As soon as Obi-Wan can rejoin the fight, he does. He mounts a fierce offensive against Maul and even lands several hits. Although Obi-Wan doesn’t speak, it’s clear from his face that he is furious. He fights with anger, despite his usual emotional control and the stoicism required by the Jedi.
2 Getting Involved In Rescuing Leia
After the fall of the Republic, Obi-Wan dedicates his life to watching over the young Luke Skywalker to keep him safe until he can be trained as a Jedi. Obi-Wan suffers a miserable existence on Tatooine to do so, unwilling to leave Luke or do anything that could paint a target on their backs.
When bounty hunters kidnap Leia Organa, her father Bail comes to Obi-Wan for help. Obi-Wan initially does refuse for a number of reasons, including protecting Luke. Eventually, however, his own guilt and Bail’s faith win him over. Although Obi-Wan does a lot of good in going after Leia, he does break his promise by leaving Luke unprotected.
1 Letting Anakin Fall To The Dark Side
Obi-Wan is a good master to Anakin, and the two have one of the closest emotional bonds in the entire franchise, somewhere between paternal and brotherly. However, to the detriment of the galaxy, Obi-Wan fails to uphold the standards that he expects of himself and are expected of a Jedi Master by letting Anakin fall to the Dark Side.
While a number of factors drove Anakin’s fall, Obi-Wan isn’t blameless in the matter. Despite promising a dying Qui-Gon to train Anakin as well as he can, Obi-Wan finds himself unable to give Anakin the complex emotional support he needs at times. Obi-Wan lets Anakin fall under the sway of Palpatine instead.