One of the most powerful moments in Revenge of the Sith is the showdown between Anakin Skywalker and Obi-wan Kenobi on Mustafar. This confrontation is bookended with their final meeting onboard the Death Star twenty years later. As far as we’ve been told these characters never met in the intervening years, but could they have?
While talking to Luke Skywalker, Darth Vader tells him that “Obi-wan once thought as you do.” However, when the prequel trilogy came around and the two friends met on Mustafar, it was Padme not Obi-wan who spoke of the good inside the newly christened Darth Vader. Obi-wan did not seem to make any mention of the good still inside Anakin/Vader. Of course when the original trilogy was being produced, Padme as a character didn’t exist, but that still doesn’t explain the disconnect.
What if the former master and apprentice were to meet again at some point in the intervening years between Mustafar and the Death Star?
We don’t know much about Obi-wan’s time on Tatooine in seclusion. The Legends era EU has very few stories about Old Ben’s time beyond the Dune Sea. The new canon recently published a story of Obi-wan fending off Jabba’s thugs when Luke was a boy. That’s still only a matter of days out of the nearly 20 years he was in hiding.
I’ve worked on the assumption that Obi-wan thought he was leaving Anakin to die on Mustafar, if he was not already dead after the amputation and immolation. Is it possible that Obi-wan left Tatooine after finding out that Darth Vader still lived? If the two faced again, Obi-wan may have tried to talk Anakin back to the light, unable to bring himself to try and kill his brother for a second time.
The only problem I have with this theory is that if they were to fight again, I don’t see any scenario where Vader would allow Obi-wan to walk away. Even if he was beaten again, Vader’s hatred for Obi-wan would seem to be too strong to let him live.
During their final fight onboard the Death Star, Vader steps on Obi-wan’s cloak as if he is testing it to see if it was merely a trick. Could Obi-wan have evaded Vader with a simple disappearing trick before?
This discussion quickly becomes wild speculation and potential fan fiction. The amount of evidence supporting another confrontation between Darth Vader and Obi-wan is limited at best. I know some people complained about the amount of times Anakin and Dooku faced off in the Clone Wars series, so it is possible that too many fights can lessen the dramatic effect on the story. You can have too much of a good thing.
With the Star Wars Anthology films the door is open to this kind of story, I know they would have my $10 easily.