“Obi-Wan Kenobi” Timelines: The Dark Side

This series of articles will look at where some well-loved (and/or infamous) characters from the Star Wars galaxy are during the time frame of the Obi-Wan Kenobi show. We’ve taken a look at where the other survivors of Order 66 could be, what the Skywalker twins may be up to, and theorized where some of the Clone Troopers that Obi-Wan served with may be ten years on. Now, let’s look at where those on the Dark Side of the Force are during this show.

Disney+’s upcoming Star Wars series, Obi-Wan Kenobi, will pick up ten years after the events of Revenge of the Sith. The return of at least one other major character has been teased, but where are other beloved Star Wars characters during the time in which this show is set? A lot happens between the rise of the Empire and A New Hope with many characters playing a part in both the rise of the Rebellion and in shaping the Empire.

 

The following will contain spoilers for Star Wars Jedi: Fallen Order, Star Wars: The Clone Wars, Star Wars: Rebels, Solo: A Star Wars Story, and Star Wars: Dark Disciple by Christie Golden.

The Inquisitors

Though the concept art of the Inquisitor on Tatooine does bear a resemblance to Fallen Order’s Second Sister- fallen Padawan Trilla Suduri, it’s very unlikely that it is her. True, characters in Star Wars don’t always stay dead, but (major Fallen Order spoilers) being cut down by Darth Vader with a lightsaber is probably pretty final!

The Inquisitors have been around for some time, though. Trilla herself was apparently turned fairly soon after her capture during Order 66, and the program continues throughout the events of Star Wars: Rebels.

On the left, concept art from the Obi-Wan Kenobi series showing an Inquisitor dressed in all black (including a full helmet) arriving on what appears to be Tatooine. On the right, the Second Sister from Jedi: Fallen Order arrives on Bracca. The two wear very similar armor to each other, but it’s not likely that the Inquisitor in the Obi-Wan show is the Second Sister.
Concept art for Obi-Wan Kenobi shows a very similarly dressed Inquisitor to the Second Sister, but it’s very likely not her. (Left- Still taken from the Obi-Wan Kenobi preview on Disney+. Right- Still taken from the Youtube video “STAR WARS: JEDI FALLEN ORDER All Cutscenes (Game Movie) 1080p 60FPS” from the channel Gamer’s Little Playground)

In Rebels, we meet the Grand Inquisitor (a former Jedi Temple guard), the Fifth Brother, the Seventh Sister, and the Eighth Brother. The Star Wars: Ahsoka novel introduces the Sixth Brother. The Inquisitor in the concept art for Obi-Wan Kenobi does have a helmet resembling that of the “Sisters,” but it does not match that of the Seventh Sister. We will likely be meeting a new “Sister” numbered somewhere between two and seven, then. Will she be a Padawan that Obi-Wan knew from his time at the Temple, or someone new?

Specific details are still being kept under wraps, but thanks to Entertainment Weekly’s exclusive first look at some brand new stills from the upcoming series, we do have a name now!

a picture from Entertainment Weekly of Inquisitor Reva- a humanoid woman with long dark braided hair and dressed in all black armor
Inquisitor Reva (Moses Ingram) in Lucasfilm’s OBI-WAN KENOBI, exclusively on Disney+. © 2022 Lucasfilm Ltd.; ™. All Rights Reserved. Via Entertainment Weekly

According to captions on the new stills, the Inquisitor that will feature in Obi-Wan Kenobi is called “Inquisitor Reva.” Played by Moses Ingram (The Queen’s Gambit), EW also revealed that she will be joined by the Grand Inquisitor and, of course, Darth Vader.

But while many might’ve assumed that her primary target would be Obi-Wan Kenobi, it appears that Inquisitor Reva will be facing off against Owen Lars, Luke Skywalker’s Uncle. Joel Edgerton returns to the role he played in the Star Wars prequel trilogy!

Inquisitor Reva stares down Owen Lars (a human male with short, brown hair)
(L-R): Owen Lars (Joel Edgerton) and Reva (Moses Ingram) in Lucasfilm’s OBI-WAN KENOBI, exclusively on Disney+. © 2022 Lucasfilm Ltd. ; ™. All Rights Reserved. Via Entertainment Weekly

Darth Maul

Though some may not have known of his survival until the closing moments of 2018’s Solo: A Star Wars Story, fans of the animated series Star Wars: Clone Wars and Star Wars: Rebels already knew that Maul had managed to survive his duel with Obi-Wan in The Phantom Menace. And he really, really has not forgiven Obi-Wan for what he did to him.

Maul’s brother, Savage Opress, was sent on a mission by Dathomirian leader Mother Talzin to find him. After years of isolation and abandonment, Maul went mad by the time Savage found him on Lotho Minor. With Mother Talzin’s help, though, he regains his mind, is given a new set of robotic legs, and sets out to seek his revenge on Obi-Wan.

Savage- a Dathomirian male with yellow skin, black markings, and horns on his head- finds his brother Maul- a Dathomrian male with red skin and black markings. Maul's legs are missing, replaced by spider-like appendages that he's fashioned for himself over the years since he was presumed dead
Savage finds Maul after years of the galaxy at large believing he was dead following his duel with Obi-Wan. While the years of isolation cost him his mind, he knows one thing for sure: He needs revenge against the Jedi. (Still taken from Star Wars: The Clone Wars season 4, episode 21, “Brothers”)

Over the course of his stories in The Clone Wars, Maul tries many different methods of revenge. He battles Obi-Wan several times, but never comes out as the victor. That is, until Maul allies himself with the Mandalorian group, “Death Watch.”

With the help of “Death Watch,” Maul lures Obi-Wan to Mandalore where he has captured a woman named Duchess Satine Kryze. Years ago, when Obi-Wan was still a Padawan himself, he and Qui-Gon had been tasked with the Duchess. Obi-Wan and Satine developed feelings for each other, but ultimately Obi-Wan chose to continue on his path as a Jedi.

But just because he’d left did not mean that Obi-Wan didn’t still have some feelings for Satine. A fact that Maul exploited and used to finally get some fraction of his revenge on the Jedi Knight. After capturing both Obi-Wan and Satine, Maul killed her right in front of Obi-Wan, using the Dark Saber.

Obi-Wan holds Satine after she is murdered by Maul with the Dark Saber

Maul looks on as Obi-Wan suffers the loss of a woman he loved
“Remember, my dear Obi-Wan: I’ve loved you always. I always will.” -Duchess Satine Kryze (Stills taken from Star Wars: The Clone Wars season 5, episode 16, “The Lawless”)

Maul does not immediately kill Obi-Wan as well, though. Instead, he orders Savage to imprison him so that he may fall victim to his sorrow and anger at not being able to save Satine. However, Obi-Wan is rescued by Bo-Katan, Satine’s sister, and former member of “Death Watch.”

Even Maul’s independent, relative victory of gaining control of Mandalore is short-lived, though. Sensing his old apprentice’s work, Palpatine arrives on the planet and takes back his control of Maul. He allows Maul to continue ruling Mandalore and various crime syndicates from the shadows, but ultimately pulls the strings when it comes time to divide the attentions of Obi-Wan, Anakin, and Ahsoka so that he may gain his newest apprentice.

After the events of Order 66, when Ahsoka freed Maul on board a Star Destroyer to create a distraction, Maul started to rebuild what he’d had before. He was successful enough in his endeavors to be at the head of Crimson Dawn less than ten years later. But his obsession with revenge against Obi-Wan would continue, now joined by a determination to take down Palpatine as well.

Maul’s short appearance in Solo takes place in roughly the same year that Obi-Wan Kenobi is set, and it’s somewhat possible that he may pop up again… so long as Obi-Wan finds himself not on Tatooine at some point during the series.

Maul appears as a hologram in Solo: A Star Wars Story. The hood of his robes is down and he holds an activated red bladed lightsaber in his hands
Seeing Maul in Solo was not as much of a surprise for those who’d seen the animated series! (Still taken from Solo: A Star Wars Story)

It’s not until several years later that Maul discovers that Tatooine is where Obi-Wan has been the entire time. Not only that, but also when he combines the Sith and Jedi Holocrons brought to him by Ezra Bridger, Maul discovers that the answer to defeating the Sith is also on Tatooine.

Ultimately, Maul and Obi-Wan engage in one final duel and Maul is defeated. As he dies in Obi-Wan’s arms, he asks “Is he the chosen one?” When Obi-Wan confirms this, Maul’s final words are: “He will avenge us.”

Asajj Ventress

Ventress, a Dark-Side user and Sith assassin, shows up in The Clone Wars as an antagonist many times. She begins as Count Dooku’s apprentice, but Palpatine orders him to kill her when he senses that Ventress is becoming strong in the Dark Side, prompting fears that Dooku may plan on usurping Palpatine’s place.

He fails at this, though, and Ventress returns to Dathomire, her homeworld, and breaks her bonds to the Sith. Mother Talzin, the leader of the Nightsisters, even places Dooku’s replacement assassin under Ventress’ control to help her get revenge against her former Master. This plan fails and eventually results in the destruction of all of the Nightsisters, apart from Ventress.

Ventress, a Dathomirian Nightsister with pale skin and blue eyes, is left on her own
After the destruction of Mother Talzin, Ventress is left to forge her own path ahead. Another pawn of the Sith cast aside without a thought. (Still taken from Star Wars: The Clone Wars season 4, episode 19, “Massacre”)

Within the timeline of the televised episodes of The Clone Wars, Ventress eventually finds work as a bounty hunter – something she does well, thanks to her skill set. At one point, she even finds herself fighting alongside Obi-Wan Kenobi as the pair escape the clutches of Maul and Savage. Then, in her final TV appearance, Ventress assists Ahsoka in finding the true identity of who was behind the bombing of the Jedi Temple on Corascant.

Dark Disciple by Christie Golden picks up Ventress’ story in what had been a planned arc for her in The Clone Wars but was never produced due to the series cancellation in 2013. The plot follows a desperate attempt by the Jedi Council to find a way to end the Clone Wars, or to at least cut down on the suffering the war was causing. To do this, they enlisted the help of Jedi Quinlan Vos to first befriend and then convince Ventress to assassinate Count Dooku once and for all.

The cover for "Dark Disciple" featuring Ventress- now with a short haircut- and Quinlan Vos- a human male Jedi with a yellow facial tattoo
The cover for Dark Disciple by Christie Golden (published by Del Rey)

Quinlan keeps his true identity and intentions from Ventress, but they wind up becoming partners for several different missions. As Quinlan gains Ventress’ trust, he also finds himself falling for her… and touching the Dark Side of the Force. Determined to carry out the mission he was given, though, Quinlan reveals his true identity to Ventress (though she’d more or less worked it out for herself) and even accepts her tutelage in the Dark Side believing that it may be the only way for them to defeat Dooku. Quinlan falls very far from the Jedi path, even seeming to join Dooku at one point.

Eventually, Ventress is able to help Quinlan escape and returns him to the Jedi Temple, having failed in their mission to bring down the Count. But one final opportunity presents itself, and Quinlan asks her to join him once more in another attempt to capture Dooku and make him reveal Darth Sidious’ identity.

But since the opening events of Revenge of the Sith must stand, their plan winds up failing catastrophically. Newly realigned with the Light Side but still with feelings for Quinlan, Ventress winds up sacrificing herself so that he could live. She dies before the Clone Wars are over.

So unfortunately, it is unlikely that we will see a reunion between Ventress and Obi-Wan. Of course, like in the Ahsoka novel, they may choose to change some details of her story, but I’m reasonably sure we will not be seeing Asajj in Obi-Wan Kenobi.

Ventress smiles at Obi-Wan's attempt at a joke while they are escaping Maul and Savage
It’s too bad we are unlikely to see Obi-Wan and Ventress together again. They were great fighting each other or teaming up. (Still taken from Star Wars: The Clone Wars season 4, episode 22, “Revenge”)

Darth Vader

I will start this section by saying that I know there are a lot of comics out there about Vader and the time between his fall to the Dark Side and the original trilogy of movies… but I have not gotten the chance to read them yet (unlike the other books and other extra materials mentioned so far). I don’t want to attempt to summarize what I have not read personally, so let’s just talk about what I do know and what might happen in the show based on the few details we have so far.

One piece of “extended universe” that has Vader in it that I am familiar with is Star Wars Jedi: Fallen Order. That is a pretty big spoiler, yes, but Vader does show up in the closing act of the video game. With Trilla, the Second Sister, defeated and being asked to return to the Light by her former Master, she senses someone else approaching. Over her shoulder appears Darth Vader who only gives her a moment to breathe “Avenge us” before dispatching her with his lightsaber.

Darth Vader- dressed in his iconic all-black armor and menacing helmet- stands behind Trilla- the unmasked Second Sister
“You have failed me Inquisitor.” (Still taken from the Youtube video “STAR WARS: JEDI FALLEN ORDER All Cutscenes (Game Movie) 1080p 60FPS” from the channel Gamer’s Little Playground)

What follows is a desperate escape attempt as Cal Kestis flees – knowing he can’t take Vader himself and fearing that Cere had also been killed by the Sith Lord. Eventually, he finds Cere again, and they’re able to escape… barely. Cal, Cere, and BD-1 are only able to escape when Cal breaks the windows on the underwater base they are in, and it requires all of Vader’s concentration and strength to keep the water back. If you want a look at how impressive (and scary) that is, then I highly recommend this video from The Game Theorists: “Is Darth Vader REALLY That STRONG?! | The SCIENCE of… Star Wars.”

Both from Fallen Order and the later-in-the-timeline Star Wars: Rebels, we also know that Vader has been training (or at least overseeing the training of) various Inquisitors and Purge Troopers. These are the ones hunting down not just the survivors of Order 66, but also children that have the potential to become new Jedi or Force Wielders.

Rebels also shows Vader’s ongoing quest to find Obi-Wan. When Vader and Ahsoka first briefly cross paths during a space battle, he tells Palpatine of this discovery. He believes that, if captured, Ahsoka could lead them to other fugitive Jedi. Vader specifically mentions Kenobi, and Palpatine agrees: “if he lives” he adds.

Of course, it’s already well known that Hayden Christensen is returning to the role of Darth Vader for Obi-Wan Kenobi. Concept art depicts another lightsaber battle ahead between Obi-Wan and his fallen brother. Who knows what might happen, but apparently it may result in something that makes even the Emperor question if Obi-Wan survived.

In a piece of concept art for the Obi-Wan Kenobi series, Vader of the Dark Side and Obi-Wan face off in another lightsaber duel as something crashes and burns around them
A rematch is coming… (Still taken from the Obi-Wan Kenobi preview on Disney+)

We know that an Inquisitor is dispatched to hunt down Obi-Wan (or perhaps Luke). We know that a rematch is coming between Obi-Wan and his fallen former apprentice. Though Obi-Wan had sworn to watch over Luke, some of his greatest fears for the young Skywalker are sure to haunt this upcoming series.

“Obi-Wan Kenobi” Timelines: The Skywalkers and The Clones

“Obi-Wan Kenobi” Timelines: Where are the Order 66 Survivors?

Author

  • Elizabeth

    Elizabeth is a cosplayer, writer, and host for Temple of Geek. Her passions include cosplay, Doctor Who, Star Wars, and traveling to geeky destinations.

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Elizabeth

Elizabeth is a cosplayer, writer, and host for Temple of Geek. Her passions include cosplay, Doctor Who, Star Wars, and traveling to geeky destinations.

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