Star Wars has revealed Obi-Wan Kenobi shared Anakin Skywalker's greatest weakness: attachment. Every Jedi must strive for balance, and a key part of this lies in their rejection of attachment. As Star Wars author Charles Soule explained so memorably, there is a difference between love and attachment. "It’s very easy for a Jedi to love," he pointed out. "It’s just you have to love without being controlling and love without being afraid of losing somebody, which is something Jedi are good at, and Sith are bad at."
Anakin Skywalker, of course, was certainly not good at loving without fear of loss. His competing attachment ultimately left him living a life of hypocrisy, because he could not live without his beloved Padmé, and yet he was also unable to leave the Jedi Order he cared so much about. This underscores the tragedy of Anakin Skywalker, because his attempt to cling onto both ultimately led him to lose everything he was so devoted to. Ironically, Anakin's own Padawan Ahsoka conquered the attachment he could not not when she chose to leave the Jedi rather than live a lie.
Kiersten White's novel Padawan subtly reveals Obi-Wan Kenobi shared Anakin's weakness. The book is set during Obi-Wan's apprenticeship to Qui-Gon Jinn, and it sees him realize - for probably the first time in his life - that the Jedi rules had cost him as much as they had given him. The conflict within Obi-Wan's heart is clearly portrayed as a battle of competing attachments, one similar to the battle his own Padawan would face decades later. While Obi-Wan reaches a different conclusion, the way the internal battle plays out underscores the fact he was more similar to Anakin than he realized.
Star Wars Keeps Making Obi-Wan & Anakin's Story Even Greater
This isn't the first time Star Wars has hinted at Obi-Wan's flaws. Obi-Wan's need for attachment drove so many of his most important decisions; Mike Chen's novel Brotherhood revealed he knew about Anakin and Padmé all along, but he chose not to act, simply because he wished Anakin the happiness he had been denied with Duchess Satine. It is telling that, during their fateful duel on Mustafar, Obi-Wan forgot all his Jedi training and lashed out with just as much passion and ferocity as Anakin. "You were my brother, Anakin," he cried out in rage, giving voice to the depth of his pain. Ironically, years later - in the Obi-Wan Kenobi Disney+ TV show - the Jedi Master's attachments were the reason he was able to defeat Darth Vader again. Obi-Wan remembered the people he cared for so much, young Luke and Leia, and he fought on for their sakes.
It's easy to criticize Obi-Wan for his attachments to Anakin and to others. In truth, his struggle with the same problem as his Padawan simply underscores the impossible ideal Jedi pursue. Love without fear of loss is easy to talk about but hard to achieve, even for the greatest Jedi. What's more, there's a sense in which the similarities between Obi-Wan and Anakin were the real reason their relationship - as Master and Padawan - was so flawed. They were too alike, and so Obi-Wan couldn't possibly help Anakin deal with his greatest issue, his deep need for attachment. Thus the tragedy of the Star Wars saga became inevitable.