Obi-Wan Kenobi is renowned as one of the Jedi Order’s best for good reason, but Star Wars: Episode I – The Phantom Menace shows us his biggest mistake – thus proving why this prequel movie is so essential. Following Anakin Skywalker’s fall to the dark side, Obi-Wan burdened himself with a great deal of guilt, as did others.

His greatest mistake, however, had nothing to do with Anakin’s actual fall to the dark side. Instead, it traces back to long before Anakin had ever become Darth Vader, and it’s shockingly rooted in what Jedi like Obi-Wan were misguided about for the duration of the prequel trilogy era: feelings.

Obi-Wan Did Everything He Could To Uphold Qui-Gon’s Dying Wish

Obi-Wan was put in a tough spot in The Phantom Menace as he held his dying Jedi Master in his arms. Qui-Gon Jinn chose to use his last breath as a plea for his Padawan to train Anakin, and who was Obi-Wan to say no to him in his dying moments? Unfortunately, this is where Obi-Wan truly went wrong.

Obi-Wan treated his promise to Qui-Gon like a vow, to the point of insisting to Yoda that he would train Anakin regardless of the Jedi Council’s approval, just like Qui-Gon would have. Obi-Wan, however, wasn’t the Jedi Master Anakin needed, and he would learn that lesson too late.

By doing everything he could to uphold Qui-Gon’s dying wish, Obi-Wan prioritized his feelings over his intuition, and it would ultimately lead to Anakin’s dark side fall. While that’s not to put the full weight of Anakin’s fall on Obi-Wan himself, it certainly was a contributing factor as Anakin progressed through his Jedi training.

Obi-Wan Was Willing To Overlook The Warning Signs In Anakin

This is where Obi-Wan does shoulder responsibility in Anakin’s fall, and it has everything to do with upholding his word to Qui-Gon, in addition to his genuine, brotherly care for Anakin. Obi-Wan wanted Anakin to succeed as a Jedi so badly that, when faced with warning signs, Obi-Wan was willing to outright ignore them.

The most obvious of these was Anakin’s relationship with Padmé. We know from stories such as Star Wars: The Clone Wars and the novel Brotherhood by Mike Chen that Obi-Wan was very aware of what was going on between Anakin and Padmé. In fact, he could relate, based on his own past with Mandalore’s Satine Kryze.

Still, Obi-Wan ultimately chose the Jedi Order over Satine, and he wasn’t willing to tell Anakin that he had to make that same choice, too. Obi-Wan let it slide, and while many of us are in support of that lenience, he truly should have confronted Anakin about it and instead encouraged him to leave the Order behind.

That’s solely because the Order wasn’t going to easily change their ways when it came to romantic relationships, and Anakin felt trapped by his inability to get help with his premonitions about Padmé’s fate. Had he left the Order, he might have felt more confident in reaching out for help about the entire situation.

That wasn’t all. There were several instances of Obi-Wan seeing Anakin succumb to feelings that surrounded the dark side, or exhibiting a willingness to go to darker places during the war than any Jedi ever should – including outright murder. Obi-Wan turned a blind eye all in the name of maintaining Anakin’s Jedi status.

While it’s still important to stress that Anakin’s wrongdoings are his own, Obi-Wan also willingly ignored ways in which he could help Anakin simply to uphold that promise he made to Qui-Gon all those years before. He wanted Anakin to remain a Jedi at all costs, even if it meant overlooking warning signs like these.

Qui-Gon’s Death Truly Sealed The Deal On Anakin’s Own Fate

Qui-Gon’s death really did seal Anakin’s own fate beyond the obvious, which was him not being able to train Anakin himself. By pᴀssing that responsibility onto Obi-Wan, who then made it his own personal vow, everything about Anakin’s training and life as a Jedi was formed on the basis of obligation at best.

While it was clear that Anakin was very talented and had the makings to become an incredible Jedi, Obi-Wan’s own dedication to Qui-Gon’s dying words caused him to focus too much on that potential rather than the evidence presented right in front of him. Had Qui-Gon survived, then this wouldn’t have been the case.

Qui-Gon shouldn’t have burdened Obi-Wan with such a responsibility, but he did, and that weight was transferred onto Obi-Wan – and has since become his biggest mistake. Everything Obi-Wan does wrong up until his death in A New Hope can be traced back to that very moment on Naboo with his dying master.

Ironically enough, the Jedi who truly did uphold the flawed vision of the Order in terms of neglecting feelings ultimately succumbed to the wrong one. He let his immediate and everlasting grief over Qui-Gon overshadow his better judgment time and time again where Anakin was concerned, making The Phantom Menace his ultimate turning point.