Two major Star Wars characters, Obi-Wan Kenobi and Anakin Skywalker, failed as Master and Apprentice respectively. That said, it is worth noting that Anakin and Obi-Wan's failures are not negative aspects of the iconic Star Wars characters. In fact, it is the duo's failures and flaws that make them relatable characters, allowing them equally to become two of the franchise's most compelling protagonists - or antagonists in Anakin's case.

When watching the Star Wars movies in order, these failures of Anakin and Obi-Wan become even more clear. Throughout Star Wars: The Clone Wars, for example, Obi-Wan's struggles with overcoming attachment were highlighted. Similarly, Anakin's attachments to characters like Ahsoka Tano, Padmé Amidala, and his mother Shmi Skywalker were the primary reasons for his fall to the dark side. Through these attachments, both characters were doomed to fail as Master and Apprentice which upcoming Star Wars movies may even detail further.

Anakin Never Overcame His Attachment To Obi-Wan

While the aforementioned attachments led to Anakin becoming Darth Vader in Star Wars: Episode III - Revenge of the Sith, two attachments stuck with him even into the original trilogy: Luke Skywalker and, most importantly, Obi-Wan Kenobi. The Obi-Wan Kenobi show revealed that Vader was still consumed by the need for revenge against Obi-Wan, going out of his way to hunt him down personally across the galaxy due to his past attachment to his former Master. This continued into A New Hope where his desire to defeat Obi-Wan led to Luke, Han, and Leia escaping only to return to destroy the Death Star.

This failure to let go of Anakin's attachment to Obi-Wan was teased in Star Wars: Episode III - Revenge of the Sith. At the end of the film on Mustafar, Anakin is consumed by anger against Padmé that is primarily driven by his thoughts of Obi-Wan. Anakin thinks Padmé was sent to him as a spy by Obi-Wan, proving how much his Master was on his mind. While the anger, rage, and resentment he felt toward Obi-Wan were not positive emotions in any sense, they proved that Anakin could not overcome his attachment to Obi-Wan even long into his time as the dark lord of the Sith.

Obi-Wan's Attachment To Anakin Meant He Turned A Blind Eye To His Marriage

However, this attachment between Anakin and Obi-Wan has also been shown to go both ways. Star Wars: Episode III - Revenge of the Sith and other elements of Star Wars canon from The Clone Wars to the novel Star Wars: Brotherhood have hinted that Obi-Wan knew about Anakin's marriage to Padmé. The latter canon installment outright confirmed that Obi-Wan knew of Anakin's marriage, proving that not only was the Padawan's fondness for his Master an issue, but vice versa.

Related: Star Wars Confirms Obi-Wan Knew About Anakin & Padmé All Along

Obi-Wan turning a blind eye to Anakin's marriage stemmed directly from his connection to his Padawan. The Clone Wars revealed that Obi-Wan once fell in love with a Mandalorian named Satine Kryze yet chose to stay true to his Jedi upbringing. In a way, Obi-Wan allowing Anakin's marriage despite it going against the Jedi Code was a way in which he could allow his Padawan to live a life he never did. No matter Obi-Wan's reasoning, it is clear that his love for Anakin saw him overlook something that was instrumental in the latter’s fall to the dark side proving that he failed as a Master due to attachment.

Neither Anakin Nor Obi-Wan Ever Learned To Be True Jedi Master & Apprentice In The Prequel Era

Due to these individual failures, neither Anakin nor Obi-Wan learned what it truly meant to be a Jedi Master and Padawan, at least in the prequel era. While Obi-Wan overcame this through his teaching of Luke and Anakin with his final lessons to Ahsoka Tano shown in Ahsoka, both of them failed to become what they needed to be in the prequels. Obi-Wan's failings as a Master directly contributed to Anakin's fall to the dark side, something largely chronicled in the prequel trilogy. The guilt of this was adequately highlighted in Obi-Wan Kenobi, proving that the character had to go through this to become a proper Master to Luke.

While Anakin eventually overcame his issues to become a true Master to Ahsoka, his time as a Padawan was a failure. In struggling to overcome his attachment to his Master, Anakin could not flourish. This led to his downfall in which he was consumed by his feelings toward his Master. If Anakin had overcome his attachment to Obi-Wan, he may not have fallen to the dark side and could have become what the Jedi Council saw as a Master. Instead, both protagonists did not learn what it meant to be Master and Apprentice in the Star Wars prequels, making for two of the most compelling characters in the Saga's history.