Will Ahsoka meet Obi-Wan again?

The hamster wheel keeps turning at the TumblingSaber! This week I’m wondering:

  1. When did Obi-Wan Kenobi learn about Anakin becoming Darth Vader? and,
  2. How and when Ahsoka Tano can be re-inserted in to canon, in an impactful way?
  3. Can the above two points be combined in to one spine-tingling, hair-raising moment?

One of canon’s great unexplored gaps is of Obi-Wan learning of Anakin survival, and life as Darth Vader. I’m sure Lucasfilm knows how Obi-Wan will discover the truth about his former apprentice. In fact, I’m sure that we’re already seeing the first steps down that story line in the Ahsoka novel. Merely including Obi-Wan in an unrelated plot point hints at that…why else include him if not to lay groundwork of his future story?

Dave Filoni has hinted that Ahsoka will be back following the Rebels season two finale, ‘Twilight of the Apprentice’. But in his typically cryptic style, Filoni was non-committal about when, where, how, or in what form Ahsoka would return. It wasn’t very long before we got more Ahsoka in the form of a young adult novel. Except that it pre-‘Twilight of the Apprentice’ Ahsoka where she becomes Fulcrum, a role she would keep for the next 15 or so years.

Set roughly one year after Order 66, the Ahsoka novel picks up when the Rebellion is in it’s early building stage. Ahsoka has no idea who Vader is, let alone who’s beneath the mask. In the novel, E.K. Johnston reminds usthat Bail Organa knows Obi-Wan is alive on Tatooine. But he preserves Obi-Wan and Luke’s safety by choosing not to tell Ahsoka, a curious choice. I don’t know if Johnston would have revealed that tidbit if there wasn’t more to come…in a sequel novel (of course there will be a sequel novel!).

During the time between being hired as Fulcrum, and learning of Anakin’s fate, could Senator Organa eventually reveal to Ahsoka that Obi-Wan is alive? What would Ahsoka do with this information? Might Bail ask Ahsoka to recruit Kenobi to the rebellion?

Depending on when (and if) Ahsoka returns, she would have to be the bearer of bad news that Anakin is now encased in the Vader armour, no? How powerful a moment would that be when Obi-Wan learns of his galaxy-altering mistake by not finishing Anakin off? At some point Obi-Wan has to learn this news. It’s a must-see moment! It could be the trigger that leads to us meeting the truth-altering, cynical Obi-Wan from A New Hope. And let’s face it: nobody in canon is a more appropriate choice to deliver that news to Obi-Wan than Ahsoka. Except maybe for Qui-Gon Jinn, who could be the one to tell him once Obi-Wan masters connecting with him through the Force.

“But Kyle, both of those things are needless. Obi-Wan could have just felt Vader in the Force and figured it out himself!” In my opinion it’s doubtful that Kenobi could “feel” Anakin’s presence behind that dark suit of armour if Ahsoka couldn’t. Ahsoka would continually reached out to Anakin’s presence after Order 66, but he just wasn’t there. He was gone; consumed by Darth Vader, as Yoda would say.

There are hurdles to jump in order to make this theory work, as is the case with nearly all fan theories. They would have to shoehorn this storyline in to a relatively short window between ‘Twilight’ and ‘A New Hope’. And if Ahsoka returns, why would she run back to the Rebellion?

The Obi-Wan we know in the prequels is much different than who we meet in A New Hope, and it would be a missed opportunity not to hit on this key moment in Obi-Wan’s journey. Sure, years of isolation on a desolate planet following the collapse of freedom that you were partially responsible for would be enough to sour anyone. But seeing Obi-Wan’s reaction to the news that his former apprentice is alive is a must-see.

What do you think? Is Ahsoka the right person to break the news to Obi-Wan that Anakin is alive?

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