Obi-Wan Made One Critical Mistake That Led To The Fall Of Anakin Skywalker & The Jedi Order

Jedi Master Obi-Wan Kenobi made one huge mistake that greatly contributed to Anakin Skywalker’s turn to the dark side and the execution of Order 66. There is no question that Obi-Wan is a highly skilled Jedi, but just like all the others, Obi-Wan made mistakes. Many of these mistakes were small and correctable, but there were a few that were catastrophic.

His biggest mistake directly concerns Anakin. In Star Wars: Episode I – The Phantom Menace, Qui-Gon Jinn makes it clear that he believes Anakin is the Chosen One and refuses to accept the Jedi High Council’s answer when they tell him that they sense too much fear in Anakin to allow his training, as he instead tells them that he will train Anakin no matter what. Later on, when Qui-Gon lay dying in Obi-Wan’s arms, he makes his newly-knighted apprentice promise to train the boy in his stead, and Obi-Wan decides to follow through on this promise.

Obi-Wan Kenobi Wasn’t Ready To Be A Jedi Master

The Newly Knight Jedi Had Just Finished His Own Apprenticeship

Obi-Wan wasn’t ready to be a Jedi Master at the time he was knighted. Throughout The Phantom Menace, Obi-Wan struggles to remain in the moment and center himself in the Force. This is best demonstrated during his and Qui-Gon’s climactic fight with Darth Maul. During the confrontation, Obi-Wan, Qui-Gon, and Darth Maul get separated by a series of ray shields. Rather than taking the time to meditate like his master, he paces angrily. This prevents him from using an ability such as Force speed to get to Qui-Gon. This struggle continued throughout the prequel trilogy.

To make matters worse, Obi-Wan was only knighted when he was because Qui-Gon wanted to take on Anakin as an apprentice. While Qui-Gon confidently said that he believed Obi-Wan was ready, his desire to train Anakin was a contributing factor to his push for Obi-Wan’s trials. This suggests that Obi-Wan’s knighthood was rushed to an extent, and it was worsened by him taking on a Padawan straightaway. He hadn’t had the chance to come into his own as a Jedi Knight and get used to his new rank before gaining an apprentice.

Not only that, but he felt pressured into it by Qui-Gon. He cared deeply for his master and didn’t want to let him down. When Qui-Gon asked Obi-Wan to promise to train Anakin, Obi-Wan couldn’t resist fulfilling his master’s dying wish. He was traumatized and felt obligated, which isn’t a good combination.

Anakin Skywalker Was Too Traumatized For Obi-Wan’s Teaching Style

Obi-Wan’s Rather Harsh Teaching Style Contributed To Anakin’s Internal Struggle

Obi-Wan’s teaching style mainly consisted of sarcasm and lectures, which was the worst teaching style Obi-Wan could’ve used on Anakin. Anakin was deeply traumatized by his childhood, and to make matters even worse, he also had trauma from how the Jedi Council treated him. From the moment they met him, they told him that he was both special and extra powerful as the Chosen One and someone to be feared and mistrusted. These confusing signals led to resentment, an inflated ego, and frustration at being treated like a loose cannon.

Obi-Wan’s teaching style reinforced these toxic messages. He belittled Anakin – sometimes in front of others – even though he knew Anakin had spent years being humiliated and dehumanized as a slave. He would tell Anakin that he was a great Jedi, particularly in Star Wars: Episode III – Revenge of the Sith, but then treat him like a child. This was not a teaching style that Anakin could handle, and it strained their relationship. While they became close after Anakin was knighted, the resentment was still there, with Anakin even telling Padmé he struggled with Obi-Wan’s harshness.

Anakin Fell In Part Because Of The Jedi’s Mistreatment… That Obi-Wan Defended

Rather Than Sticking Up For Anakin, Obi-Wan Took The Council’s Side

The Jedi Council played a large role in belitting Anakin over the course of his life, especially when he was given a seat on the Council without the rank of Jedi Master. Rather than standing up for his former Padawan, Obi-Wan defends the Council’s decision, telling Anakin he should be grateful to be the youngest member of the Council. Even worse, he tells Anakin that the only reason he is on the Council at all is because he’s close to the Chancellor, essentially telling Anakin that he doesn’t deserve what he got.

This is extra insulting in light of Star Wars: The Clone Wars. Anakin – at Obi-Wan and Grandmaster Yoda’s insistence – had already been acting as a Jedi Master. He was an overall good master to Ahsoka Tano and would’ve successfully guided her to knighthood if it weren’t for the Council betraying her and causing her to leave the Order permanently. Obi-Wan supporting this behavior was unacceptable, especially since he didn’t fight hard enough for Ahsoka, even though he was against her expulsion.

This is just one of many examples of the Jedi mistreating Anakin that pushed him closer to then-Chancellor Palpatine. Obi-Wan supporting the Council in decisions like this and belittling Anakin himself gave Anakin real reason to distrust the Jedi. It isolated Anakin, and Palpatine was always there to pick up the pieces. This made him feel grateful to Palpatine, as though he was the only one who truly recognized his talent and respected him as a person. It made it far easier for Palpatine to push Anakin to the dark side and convince him to execute Order 66.

Obi-Wan Should Have Recognized He Wasn’t A Good Fit For Anakin

He Still Had The Power To Help Anakin Select A Different Master

Obi-Wan should’ve realized that he wasn’t ready to train Anakin so soon after being granted the rank of Jedi Knight. Further, he should’ve recognized that he and Anakin had trauma-bonded over Qui-Gon’s death; it’s what pushed them together. Once the Council approved Anakin’s training, Obi-Wan should’ve requested that a more experienced Jedi Master train Anakin, who likely would’ve recognized the signs of the dark side in Anakin and been able to deal with them. They also likely would’ve had the wherewithal to adapt their teaching style to be more sensitive to Anakin’s needs.

The fact that Obi-Wan decided to train Anakin after trauma-bonding with him is evidence that he wasn’t a good fit for Anakin and should’ve never been his master. The Jedi Code bans attachments, and while there are big issues with how strictly the Jedi enforce this rule, it is a rule that Jedi Masters must follow. Yet, Obi-Wan Kenobi allowed himself to grow attached to Anakin, and this stopped him from thinking clearly enough to request a more qualified Jedi Master for Anakin – which led to Anakin’s eventual fall, as well as that of the Jedi Order.

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