Obi-Wan Kenobiwas undoubtedly a brilliant Jedi who was devoted to the Jedi Order, but, unfortunately, that dedication ultimately went from his greatest strength to his biggest weakness and contributed toAnakin Skywalker’sfall to the dark side. Obi-Wan and Anakin have both been massively influential ontheStar Warstimeline. That’s perhaps most obvious for Anakin, as he was not onlythe Chosen Onebut also defined the fate of the galaxy because of his fall.
However, as Anakin’s Jedi Master, Obi-Wan also had a major hand, for better or worse, in these events. In many ways, Obi-Wan was a good fit for Anakin. Obi-Wan was steadfast whereas Anakin was impulsive, and his ability to switch between firm and playful depending upon the situation was the type of flexibility in a teacher that Anakin really needed. Sadly, though,it was in part Obi-Wan’s unwaveringly loyalty to the Jedi that actually created significant problems for Anakin and, ultimately, the larger galaxy.

Obi-Wan Kenobi Would Have Left The Jedi Order For Love
Star Wars: The Clone Warsshocked viewers by revealing that Anakin wasn’t the only Jedi who had a love interest in the prequel trilogy era.Obi-Wan was revealed to have a romantic link of his own, to Satine Kryze, the Duchess of Mandalore. This was very obviously more than a mere flirtation, though. InThe Clone Wars, Obi-Wan told Satine that, had she asked, he would have left the Jedi Order for her.
Obi-Wan told Satine that, had she asked, he would have left the Jedi Order for her.

It was surprising enough to learn that Obi-Wan had a love interest, but to know that he truly loved her so much that he would have left the Order for her was so much more shocking. In a sense, this shows that Obi-Wan was still a much better Jedi than Anakin, even though he did have this romantic connection. Unlike Anakin, Obi-Wan was aware that this was a choice he had to make; he couldn’t have a relationship with Satine and be a Jedi.
Yet, this connection to Satine and Obi-Wan’s decision to remain part of the Jedi Order still ended up causing significant issues. It’s true that Obi-Wan never defied the Jedi Order outright in the way that Anakin ultimately did with Padmé, butObi-Wan’s feelings for Satine ended up informing how he dealt with Anakin and Padmé’s relationship. In fact, his history with his Satine and his devotion to the Jedi Order ended up being (quite literally) a deadly combination.

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Obi-Wan Knew About Anakin & Padmé - But Never Encouraged Him To Leave The Order
It Was Obi-Wan’s Responsibility To Shut This Down, At Least At First
InStar Wars: Episode II - Attack of the ClonesandStar Wars: Episode III - Revenge of the Sith, it isn’t entirely clear how much Obi-Wan really knew about Padmé and Anakin’s romantic relationship, although they admittedly weren’t doing the best job hiding it. Since then, however,Star Warshas made it much more obvious thatObi-Wan knew about Anakin and Padmé, at least in part. He may not have known the full extent, but inThe Clone Warsin particular, Obi-Wan even makes jokes about it.
This shouldn’t really come as a major shock. After all, inAttack of the Clones, Anakin directly tells Obi-Wan that he hasn’t been able to stop thinking about Padmé for 10 years. Many viewers have also pointed out that, in that movie, Padmé runs toward Anakin, and the two embrace and kiss while Obi-Wan and Yoda are in the room. It’s really at this stage that it’s most disappointing to know Obi-Wan did nothing to intervene. ByRevenge of the Sith, Anakin was no longer Obi-Wan’s responsibility, but, prior to that,Obi-Wan absolutely should have addressed this.
At minimum, this should have been brought to the Council. Even in his conversations with Anakin about Padmé, though, Obi-Wan not only doesn’t condemn the way Anakin is speaking about her, but also encourages it in some ways, such as by telling Anakin that Padmé did look happy to see them. As Anakin’s Jedi Master, Obi-Wan should have been the one to tell Anakin he needed to either commit to the Jedi or to Padmé—but his own issues with attachment prevented that from happening.
Obi-Wan should have been the one to tell Anakin he needed to either commit to the Jedi or to Padmé—but his own issues with attachment prevented that from happening.
Obi-Wan’s Own Attachment Got In The Way
Obi-Wan Empathized Because Of Satine, But He Was Attached To Anakin As Well
Realistically, this is a complex, multi-layered problem. On the one hand, Obi-Wan was too dedicated to the Jedi to walk away from the Order, andhe refused to insist Anakin give it up just as much as he refused to give it up himself. Simply by nature of the attachments he had, though, this was a recipe for disaster. Obi-Wan no doubt empathized with Anakin and Padmé’s situation, as he had experienced something similar first-hand with Satine. Had he not had that personal connection, he might have dealt with this much more quickly and firmly.
Obi-Wan also had an attachment to Anakin, though. He said it himself inRevenge of the Sith: Anakin was his brother, and he truly loved him as such. Because of that, he didn’t want to force Anakin to make this brutal decision, nor, in all likelihood, would he really have wanted to see Anakin walk away from the Order. Ironically, in the end,Obi-Wan Kenobi’sdedication to the Jedi became a major weakness for him and even affected Anakin Skywalker’s fall to the dark side.