Obi-Wan Kenobi is seen in the Star Wars universe as one of the best Jedi to ever live. Apart from being a diplomat, he embodies the willpower, control, and adherence to the Jedi Code that the Order emphasizes so much.
Fundamentally, Obi-Wan is among the most principled characters, but he isn’t really perfect. At many points throughout the movies and shows like Obi-Wan Kenobi and The Clone Wars, he goes on to prove that he is someone who can be pushed hard to violate his principles like anyone else. On occasions, Obi-Wan fails to live up to his own expectations.
Letting A Fellow Jedi Get Killed By Inquisitors
Obi-Wan seems to be in a very dark place at the start of Obi-Wan Kenobi.
He’s completely cut off from the Force and living out quite a miserable existence on Tatooine while he keeps Luke safe thanks to the threat posed by the Empire.
Despite his absolute love for the Jedi Order and his well-known loyalty to everyone else, Obi-Wan just can’t bring himself to help and is guilt-ridden when Nari dies.
Taunting His Opponents During Combat
Despite his impressive skills with a lightsaber, Obi-Wan Kenobi is more of a pacifist, mostly adhering to the Jedi way of using means of violence only at a time when it is absolutely necessary.
He frequently reprimands Anakin, reminding his apprentice to not be very confident or even arrogant in combat.
As much as Obi-Wan was reproachful to Anakin, he also showcased a tendency to mock his other opponents while fighting them. Obi-Wan quips a lot while taking on enemies, and even devolves into mock flirting against enemies like Asajj Ventress.
Wishing To Challenge The Emperor Himself
Once Order 66 destructs the Jedi, Yoda and Obi-Wan Kenobi are just the two able to respond very quickly to Coruscant events.
Due to the entire seriousness of the whole situation, they come to a decision that they need to fight either Vader or Palpatine. Thanks to his personal ties with Anakin, Obi-Wan literally begs Yoda to be allowed to battle the Emperor.
Fighting Darth Maul After Qui-Gon’s Death
The most famous rivalry in Star Wars is that between Maul and Obi-Wan. Maul takes the life of Obi-Wan’s master.
In return, Obi-Wan goes on to mutilate him in anger and left him to death, giving them a lot of reasons to despise one other. Maul is among the first ones to cause Obi-Wan to struggle with his feelings, even though Kenobi manages to resist the Dark Side.
The first occasion is right after Qui-Gon’s death. Obi-Wan rejoins the fight, and he mounts an offensive against Maul and even landing many hits. Although Obi-Wan does not speak, it’s quite clear that he is furious on his face.
Letting Anakin Fall To The Dark Side
Obi-Wan has always been a good master to Anakin, and the two of them have a close emotional bond in the whole franchise, somewhere between paternal and brotherly.
However, Obi-Wan is not able to uphold the standards he expects of himself and is expected the Jedi Master by letting Anakin fall to the Dark Side.
While many other factors drove the fall of Anakin, Obi-Wan isn’t very blameless in this matter. Despite the promise he made to a dying Qui-Gon to train Anakin, Obi-Wan is unable to give Anakin the emotional support that he needs most. However, Obi-Wan allows Anakin to fall under the evil sway of Palpatine instead.