Of course, when they first met, their division was clear.

The Padawan of Qui-Gon Jinn, Obi-Wan Kenobi became a Jedi Knight after his master’s death.

Obi-Wan trained Anakin Skywalker as a Jedi, with his own apprentice knighted after the Battle of Geonosis.

Star Wars Tales of the Underworld TV Show Poster

He sacrificed himself for his two charges, becoming a Force Ghost and continuing to mentor them.

Hailing from the Nightsisters of Dathomir, Asajj Ventress became Count Dooku’s apprentice during the Clone Wars.

This all happened when they were genuine enemies.

live-action Obi-Wan Kenobi and Asajj Ventress from Star Wars: The Clone Wars

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Vos and Ventress love story is complex and tragic, but Obi-Wan played a role in bringing them together.

The Jedi Council ordered Quinlan Vos to execute Count Dooku, and Obi-Wan suggested Ventress could be of use.

Their dynamic is worth exploring further.

Darth Maul in Star Wars: The Clone Wars, Cad Bane in Star Wars: Tales of the Empire, and Boba Fett in The Book of Boba Fett

The Padawan of Qui-Gon Jinn, Obi-Wan Kenobi became a Jedi Knight after his master’s death. Obi-Wan trained Anakin Skywalker as a Jedi, with his own apprentice knighted after the Battle of Geonosis. The Jedi Master became a key player in the Jedi during the Clone Wars, and was heartbroken when Anakin turned to the dark side; Obi-Wan critically wounded Anakin before taking to the shadows, watching over the young Luke and Leia for years. He sacrificed himself for his two charges, becoming a Force Ghost and continuing to mentor them.

Even though the Hidden Path feels like an easy way to bring them together, its not.

That story takes place just beforeA New Hope.

It would feel incredibly forced.

Ewan McGregor as Obi Wan in Obi Wan Kenobi TV show

The Padawan of Qui-Gon Jinn, Obi-Wan Kenobi became a Jedi Knight after his master’s death. Obi-Wan trained Anakin Skywalker as a Jedi, with his own apprentice knighted after the Battle of Geonosis. The Jedi Master became a key player in the Jedi during the Clone Wars, and was heartbroken when Anakin turned to the dark side; Obi-Wan critically wounded Anakin before taking to the shadows, watching over the young Luke and Leia for years. He sacrificed himself for his two charges, becoming a Force Ghost and continuing to mentor them.

Star Wars: Tales of the Underworldpremieres May 4 on Disney+.

Asajj Ventress in Star Wars The Bad Batch Season 3

Hailing from the Nightsisters of Dathomir, Asajj Ventress became Count Dooku’s apprentice during the Clone Wars. Betrayed by her master, she sought revenge - even forming a surprising alliance with Jedi Master Quinlan Vos at one point. Asajj has reinvented herself as a bounty hunter, and survived into the Dark Times of the Empire’s reign.

Obi-Wan Kenobi in Obi-Wan Kenobi in the foreground and Asajj Ventress from the new Tales of the Underworld trailer in the background

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Headshot Of Nika Futterman

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Star Wars: Tales of the Underworld

Obi-Wan Kenobi

Asajj Ventress