The tragedy of Darth Vader is the central story of the Star Wars film franchise. Luke Skywalker redeeming his father is so engrained in the cultural lexicon that even those who have never seen the film know that plot line. Though audiences were first introduced to this story in the Original Trilogy, chronologically, multiple other people tried to break through Vader’s defenses to bring Anakin back — most notably, his old master Obi-Wan Kenobi and his old padawan Ahsoka Tano.
The central plot of Return of the Jedi focuses on how Luke believes he can redeem Darth Vader and bring him back to the light side. It works by itself in the context of the Original Trilogy because those were the only stories available at the time, but at its place in the timeline, Luke would not have been able to bring Anakin back if not for the failed attempts of Obi-Wan and Ahsoka, who both tried on multiple occasions and were unsuccessful.
How Obi-Wan Failed to Redeem Darth Vader
The audience is first made aware of Obi-Wan and Anakin’s relationship in A New Hope, where all the information divulged is that the two are good friends and Obi-Wan shows excellent admiration for Anakin. Of course, the Prequel films showed audiences how those two came to be so connected. Obi-Wan admits that Anakin is a brother to him, but even given how close the bond between the two is, it isn’t enough to stop Anakin’s fall to the dark side after the seduction of Palpatine. Obi-Wan attempts to talk sense into Anakin during their climactic battle in Revenge of the Sith by trying to break down his emotional defenses before being forced to break his physical defenses.
The Obi-Wan Kenobi show on Disney+ features Obi-Wan’s second attempt to bring Anakin back, although it’s slightly different this time, as Obi-Wan is plagued with guilt over his failure to save Anakin the first time. During the battle when Obi-Wan tries to reach Anakin and fails yet again, Vader explains, “You didn’t kill Anakin Skywalker, I did.” This line is the nail on the head for why Obi-Wan has failed to redeem Vader.
Obi-Wan’s failure to save Anakin is driven by the fact that in his mind, Anakin Skywalker is dead. Even though the body of Anakin is encased in this evil armor, Anakin’s mind and soul are gone and cannot be retrieved. In Obi-Wan’s mind, which is reiterated by Vader’s words, Anakin Skywalker simply no longer exists. His guilt in the show comes mainly from the point that he failed and allowed his padawan, his closest friend, to be killed. However, there’s no doubt that Obi-Wan’s pleading with Vader has some sort of emotional impact on the latter.
Ahsoka Likewise Failed to Redeem Anakin Skywalker
Anakin is given Ahsoka as a padawan in The Clone Wars movie before being brought to the show. Used initially by the Council as a kind of tool to help Anakin learn to not be so wild and rash, he ends up teaching Ahsoka quite a bit of those mannerisms, and the two form a very close bond. When Ahsoka chooses to leave the Jedi Order in The Clone Wars Season 5, Episode 20, “The Wrong Jedi,” she bids an emotional goodbye to Anakin, showing that even after all the Jedi Order put her through, she still cares for and respects him.
Her admiration for her master is still shown throughout Season 2 of Star Wars: Rebels while helping the Ghost Crew. The Season 2 finale results in a climactic engagement between Ahsoka and Darth Vader over the life of Ezra Bridger. Unlike Obi-Wan, Ahsoka does not know that Anakin and Vader are the same person at this point, and this duel reveals it to her. Similar to Obi-Wan, Ahsoka breaks Vader’s mask and makes contact with Anakin, which results in a confrontation very similar to Obi-Wan’s, with Ahsoka pleading for Anakin to come out only for Vader to say, “Anakin Skywalker was weak. I destroyed him.”
Ahsoka’s failure to redeem Anakin features many of the same traits as Obi-Wan’s. Ahsoka truly believed that Anakin Skywalker was dead. It’s not until her confrontation with Darth Vader, and she slices his mask that she finally discovers who Darth Vader truly is. She attempts to reach her old master but is unsuccessful. The man that trained her is well and truly gone.
Obi-Wan and Ahsoka’s Failure Led to Luke’s Success
So how is it that Luke, who had very little interaction with Vader before their battle in Empire Strikes Back where the revelation occurs, can redeem the irredeemable monster that is Darth Vader where his closest friends, Obi-Wan and Ahsoka, both failed? Part of it is that Luke not knowing Anakin Skywalker in the flesh gives him an advantage. To Luke, Anakin is a mythical entity of which he’s only heard stories from Uncle Owen and Ben Kenobi. Unlike Obi-Wan and Ahsoka, Luke did not witness Anakin’s fall to the dark side firsthand, so despite Vader being notoriously evil, Luke can separate the things Vader has done from the things that Anakin could be. Because of this, Luke can focus more on getting Anakin out of Vader rather than trying to get him back to the man he used to be.
The other advantage that Luke has is the timeline. During the height of the Empire, between Episode III and Episode IV, Vader is portrayed as an irredeemable monster, and there probably isn’t much that anyone could have done to redeem him. It’s been shown in various comics, novels, and video games set in the era that Vader is an unstoppable force. By the point of Return of the Jedi, the Empire has already suffered some significant defeats from the Rebellion, and Darth Vader is no different. Luke has the distinct advantage of attempting to redeem Vader after Obi-Wan and Ahsoka’s failures. These two attempts literally and metaphorically broke down Vader’s defenses. In each fight, Vader’s mask was broken, exposing the Anakin beneath, but the emotional conversations also broke Vader down and exposed the Anakin beneath, allowing Luke to be able to fully break through and bring Anakin back.
The Only Way to Save Vader Was Together
In the end, it was never going to be just one person who could save Vader. Obi-Wan would never have been able to have done so himself, just as Ahsoka would never have been able to do so. Likewise, Luke was never going to be able to do it without both Obi-Wan and Ahsoka failing before him. Obi-Wan and Ahsoka were both able to get through the armor and by the time Luke rolled around, it was metaphorically cracked enough for Luke to get in and pull Anakin out.