Had defining moments in Anakin's fall to the dark side were also driven by the actions of the Jedi.
Obi-Wan and Anakin may be one of Star Wars' best duos, and it's clear that Obi-Wan tried his best with Anakin, but, the reality is, Obi-Wan Kenobi also played a role in Anakin's fall to the dark side. This is precisely why many argue that, had Qui-Gon Jinn lived and been Anakin's master instead, he could have prevented Anakin from turning to the dark side. In truth, had Obi-Wan made just this one change, he very likely could have stopped Anakin's fall and all that transpired because of it.
Obi-Wan Loved Anakin, But He Didn't Tell Him Soon Enough
This Painful Revenge Of The Sith Moment Came Too Late
In the final moments and Anakin and Obi-Wan's confrontation on Mustafar, Obi-Wan heartbreakingly said, "You were my brother, Anakin. I loved you," as he watches Anakin rolling around in agony after losing his limbs and being burnt near to death by the lava. The past tense of this statement is particularly painful, but this revelation from Obi-Wan is significant—and it came too late. Clearly, Obi-Wan had long been proud of and loved Anakin, yet he didn't tell him that until it was already too late.
Obi-Wan had long been proud of and loved Anakin, yet he didn't tell him that until it was already too late.
Inadvertently, this laid the groundwork for Palpatine to manipulate Anakin to the dark side and worsened Anakin's obsession with Pé because he felt he needed her. Obi-Wan was likely being mindful of the Jedi rule against attachments and battling an inner conflict about whether it was 'right' to love Anakin and see him as a brother. This really couldn't have backfired more, as Obi-Wan withholding these feelings and affirmations from Anakin made Anakin so much more susceptible to all that happened in Revenge of the Sith.
Anakin Needed That Affirmation, For Better Or Worse
It Was Against The Jedi Way, But That Didn't Make It Any Less True
The truth is, Anakin needed to hear these things from Obi-Wan, but Obi-Wan didn't vocalize them until Anakin was effectively dying on Mustafar (and after too much damage had been done for them to ever reconcile). It was incongruent with the Jedi way for Anakin to need to be told Obi-Wan loved him and was proud of him, but, really, that should have been expected. Anakin was never a traditional Jedi.
In addition to being the Chosen One, Anakin was raised with typical family love for 9 years. This was the very reason the Jedi Council expressed concern about accepting him into the Order; he had developed familial attachments and was therefore dangerous. The Jedi were clearly hoping that as Anakin was trained he would abandon those attachments, but that ended up being far from the case.
While that doesn't mean Anakin was right for feeling that way, much less for doing all that he did, the reality is, Anakin was always going to need to feel loved, accepted, and ed. When neither Obi-Wan nor any other member of the Jedi Council gave him that acceptance or those affirmations, Anakin found comfort in Pé's love for him and felt validated by Palpatine's (manipulative) and encouragement. In fact, Palpatine directly exploited this fact, constantly pointing out to Anakin that the Jedi didn't trust him.
Anakin was always going to need to feel loved, accepted, and ed.
Anakin Was Angry And Egotistical, But His Biggest Issue Was Insecurity
Anakin's Issues With Insecurity Are Too Often Overlooked
Anakin clearly had an ego throughout Star Wars: Episode II - Attack of the Clones and Revenge of the Sith, but, beneath that surface, Anakin actually struggled considerably with insecurity. This is precisely why, when he is listing his grievances with Obi-Wan to Pé in Attack of the Clones, he particularly emphasizes that Obi-Wan is "overly critical." Obi-Wan was almost certainly just trying to be a good master, but to Anakin, it felt as though he was never good enough for Obi-Wan.
This issue was compounded by Anakin's rather brutal introduction to the Jedi Order. He was just 9 years old when he stood before the Council, and he faced their judgment and their rejection. They also essentially told Anakin he was at risk of becoming 'bad' because of his (natural) feelings about leaving his mother.
Anakin never let go of that first encounter entirely, especially because he knew the Council only changed their minds because Qui-Gon died and this was his dying wish. However egotistical Anakin may have been, he always felt as though he was inferior in the eyes of the Jedi. This made him all the more desperate for validation from other sources, such as Pé and Palpatine.

When Did Anakin Skywalker's Fall To The Dark Side Really Begin?
Anakin Skywalker's fall to the dark side and transformation into Darth Vader has defined Star Wars for decades—but what really caused his fall?
Obi-Wan Could Have Saved Anakin Had He Voiced His Pride
Obi-Wan's Validation Could Have Been Enough
It's not Obi-Wan's fault that Anakin fell to the dark side, nor is it really any one person's fault. That doesn't negate the fact that had Obi-Wan validated Anakin and verbalized how proud he was over the years, he could have seriously diminished Palpatine's ability to manipulate Anakin, which played a major role in Anakin's decision to side with Palpatine. From the beginning, Anakin just wanted to be accepted. That is something that Palpatine directly exploited, and the Jedi routinely deprived him of.
With Obi-Wan in particular, Anakin told Pé that he saw Obi-Wan as a father figure. Like any father-and-son dynamic, that means Anakin looked up to Obi-Wan and worked hard to gain his approval. Yes, Anakin fell short at times, but it would have gone a long way for Obi-Wan to affirm Anakin—especially given Obi-Wan loved Anakin as a brother.
In the end, Palpatine and Pé addressed Anakin's insecurities, which is why his loyalties were with them. It's a shame, because the burden of this issue doesn't fall entirely on Obi-Wan or perhaps even primarily on Obi-Wan. Had the rules of the Jedi been different, Obi-Wan may have been more willing to praise Anakin and reveal how deeply he cared for him. As it stands, Obi-Wan Kenobi withholding how he really felt about Anakin Skywalker contributed to his fall in Star Wars: Episode III - Revenge of the Sith, and that's truly devastating.

Star Wars: Episode III - Revenge of the Sith
- Release Date
- May 19, 2005
- Runtime
- 140 Minutes
- Director
- George Lucas
Cast
- Obi-Wan Kenobi
- Anakin Skywalker / Darth Vader
- Writers
- Jan Duursema
- Prequel(s)
- Star Wars: Episode II - Attack of the Clones
- Franchise(s)
- Star Wars
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