Obi-wan regrets are layered. He regrets training Anakin and him regrets failing to train Anakin. He regrets hurting Anakin and he regrets not dying there.
A very crucial scene in Return of the Jedi established that Obi-Wan Kenobi (a Force ghost by that point) blames himself for Anakin's fall to the dark side. He explained to Luke, “I took it upon myself to train him as a Jedi. I thought I could instruct him just as well as Yoda.
Yes, when Darth Vader turned back to Anakin Skywalker and sacrifice himself to save his son, he dies and Obi-Wan uses the force to connect with Anakin's spirit. In that time Anakin apologizes to Obi-Wan, desperately asking him to forgive him for everything he has done to him and everybody over the years.
After defeating Darth Vader in the Obi-Wan Kenobi finale, Obi-Wan broke down and began tearing up when he saw Anakin's scars. It was the first time he had seen Anakin's face since leaving him to burn on Mustafar, and so he apologized for everything that had happened.
Originally Answered: Did Obi Wan ever care about Anakin, or was he just a kid that his ex-master cared about? Of course he did. Obi Wan's tone, body language, and ultimately his friendship speaks to the fact that he cared deeply for him.
Before he discovered Vader had survived Mustafar, Obi-wan lived with the regret of killing his son, brother and best friend. After, he regretted not killing him and wondered if he had only made things worse by pushing Anakin further into dark side and Palpatine's arms.
Arguably, most Star Wars plot points revolve around characters simply not knowing something, very often about their family history. But, on top of all of that, the biggest reason Obi-Wan doesn't know Anakin is alive is that the last time he saw Anakin Skywalker in Revenge of the Sith, Ben literally left him for dead.
With his helmet shattered and his fleshy parts poking out, Vader gurgles his disgust toward Obi-Wan. He refuses to accept Obi-Wan's wet-eyed apology. “I am not your failure,” he wheezes. “You didn't kill Anakin Skywalker.
Obi-Wan : I have failed you, Anakin. I have failed you. Anakin Skywalker : I should have known the Jedi were plotting to take over!
Yes he did. And the saddest thing is that there was nothing he could do about it. He was broken. The first case is shortly after ROTS when Vader was making his Sith lightsaber.
It is unclear whether Yoda would be more or less forgiving than Obi-Wan but one thing is certain - the former Grand Master would be ready to treat Anakin as an ally, following the events on the second Death Star. In Star Wars: Revenge of the Sith (2005), Yoda never really lost faith in Anakin in the way Obi-Wan did.
Now we know why Anakin Skywalker said Obi-Wan was "holding me back!" “I'm really ahead of him.” In Attack of the Clones, Anakin Skywalker makes this casual boast about his master to Padmé Amidala and later, claims “It's all Obi-Wan's fault! He's jealous!
The canonical comic Star Wars: Darth Vader #7 confirms the younglings' deaths caused Anakin grief, self-loathing, hatred and pain, fueling his descent even further into the dark side. Those negative emotions also power the dark side, meaning Anakin likely felt stronger as he killed the younglings.
The only reason we may consider Obi-Wan saving Anakin after their battle is because we know that there is still good inside Vader, and that we was never totally lost. It's just that, from Obi-Wan perspective and experience with Anakin that day, there was no possibility of that.
At most, they would scold him for his behavior. The Jedi Council was too passive when it came to Anakin's education, and it fostered a toxic relationship with him. He knew that they did not trust or approve of him, and as a result, he lost trust in the Council.
Anakin Skywalker, in one last digged-effort, before his imprisonment as Darth Vader for the next 23 years, cries out for help. He yearns for his beloved Padme, with the words, “Padme, help me.”
What he did not see, at the time at least, was that Padmé used her last breaths to tell Obi-Wan that she was certain that in regards to her husband, "there's still good in him." Now, those words are set to be revealed to someone other than Darth Vader himself.
In the annals of Star Wars history, many believe Obi-Wan Kenobi was the key to saving Anakin Skywalker's soul before his fall as Darth Vader. However, as Kenobi's recent Disney+ series showed, that was never really the case. Anakin lost himself to the Dark Side way before Obi-Wan's intervention.
Obi-Wan knew it was only a matter of time. So, he made the difficult decision to use his learnings and become one with the force, rather than let Vader decapitate him.
In the material around the film from the Legends timeline, it's established that by the end of Star Wars: Episode III - Revenge of the Sith, Kenobi was one of the characters who knew Anakin's Sith name was Darth Vader. However, what he didn't know was that he was still alive after Mustafar.
The Tragedy of Anakin Skywalker was a Jedi history that detailed the fall of Anakin Skywalker. It gave full account of his romance with Padme Amidala, his desperation to save her that led to his fall to the dark side and the terrible deeds he committed in betraying the Jedi.
because his Padawan Ahsoka. never became a knight. She left the order when she was still a padawan. This is why Anakin was denied the rank of master.
The clear implication is that all the Inquisitors knew Darth Vader's true origins, which is indeed something of a surprise. Still, it does make sense from an in-universe perspective. Inquisitors were not Sith, but they served the Sith's purposes, trained in many dark side arts to hunt Jedi across the galaxy.
Anakin needed to be killed to keep him from turning into a galactic dictator. But Obi-Wan couldn't bring himself to kill someone he considered a brother. As Anakin jumped off the floating platform, his intentions were evil-- he was looking to cut Obi-Wan in half the way Kenobi himself had once done to Darth Maul.