Star Wars: 10 Times Obi-Wan’s Past Haunted Him Again


Obi-Wan Kenobi played an important role in important parts of galactic history in Star Wars. He was a prominent and powerful Jedi who fought against the Separatists, as well as pirates, the Sith, and more. On top of that, he helped train other important Jedi like Anakin Skywalker, Luke Skywalker, and Ahsoka Tano.

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All that said, this doesn’t change the fact that he made some major mistakes that eventually came back to bite him. Some returned to him long before others, but they all turned against him, and the galaxy, eventually.

10 He probably should have told Luke about his family

Luke Skywalker with his yellow lightsaber

Even though Obi-Wan Kenobi was one of the most respected Jedi in the galaxy, he really did seem to have trouble telling the truth. Hiding a variety of things from Anakin was a big part of his former Padawan turning to the Dark Side. It wasn’t much better with Anakin’s son, Luke.

Obi-Wan and Luke only spent a short time together before Darth Vader killed him. Obi-Wan was able to return as a Force ghost, and he still didn’t tell Luke the truth about his family until it was absolutely necessary. There was no reason not to tell Luke about Vader and Leia earlier, which would have made things much easier.

9 Not paying attention to your instincts about Palpatine

Darth Vader Emperor Palpatine Star Wars Return of the Jedi

During the Clone Wars, the Jedi were aware that there was a disturbance in the Force. They could sense that the Dark Side was gaining power and that the Sith were rising again. That said, if the Jedi had believed in the threat when he first appeared on Tatooine with Darth Maul, things would have gone a lot better.

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Somehow, the Jedi constantly overlooked the fact that Chancellor Palpatine was Darth Sidious. Obi-Wan, in particular, repeatedly told Anakin not to trust Palpatine as something was wrong with him. Obi-Wan probably should have listened to his own advice; he might have discovered the truth much earlier.

8 Go ahead with the war

rookies clone wars star wars

The Jedi Order established itself as a peacekeeping force that tried to make the galaxy a safe and just place. That didn’t necessarily make everyone happy, but it was the best the galaxy had at the time. But the war brought out a different side of the Jedi.

Like the rest of his order, Obi-Wan found himself embroiled in the Clone Wars and firmly entrenched himself in them. Despite constantly talking about seeking a peaceful solution, Obi-Wan’s actions painted a very different picture. Obi-Wan helped spark a war that ultimately handed the galaxy over to Palpatine.

7 Leaving Duchess Satine

At some point before the events of the Clone Wars, Obi-Wan ended up on a mission to Mandalore. It was there that he met Satine, a young woman who would become the Duchess of Mandalore. They fell in love and even had a relationship that went nowhere as they both put duty first.

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Duchess Satine and Obi-Wan met again during the Clone Wars, as the galaxy was crumbling. If Obi-Wan had stayed by Satine’s side, he might have been able to save her from her fate and prevent Mandalore from falling.

6 Don’t take Anakin seriously

After leaving Tatooine behind, Anakin Skywalker became Obi-Wan’s Padawan. He was supposed to be Qui-Gon Jinn’s Padawan, but Darth Maul made sure that didn’t happen. But even though he grew in skill and power, Obi-Wan’s opinion of him didn’t.

A large part of Anakin turning to the Dark Side felt disrespected and underestimated by other Jedi, especially Obi-Wan. It was almost as if he had never gotten over his initial doubts about training Anakin, something Obi-Wan really only did as a favor to his own dying master.

5 Faking his death and not telling Anakin

When the Jedi learned of a plot to kill the Emperor by Count Dooku, Obi-Wan went into hiding by faking his death to prevent the assassination attempt. What they didn’t know was that Palpatine was involved in the whole thing, as Dooku was secretly his apprentice from the Dark Side.

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But the biggest mistake Obi-Wan made was not telling Anakin. He did this because he believed that Anakin’s actual emotional response to his death would help sell the plan. That might be true, but it hurt Anakin a hell of a lot. Looking back at the whole thing, this was the moment that created the first major rift in their relationship.

4 Don’t kill Anakin on Mustafar

After being converted to the Dark Side by Palpatine on Coruscant, Anakin took the name Darth Vader. His first act was to slaughter the Jedi in the temple and then head to Mustafar to take down the Separatist leaders. It was there that he faced Padmé Amidala and Obi-Wan. And it didn’t end well.

First, Vader drowned Padmé with the Force. Then he and Obi-Wan engaged in a wide-ranging lightsaber duel that Vader ultimately lost. While Obi-Wan cut off several of Vader’s limbs in the final moments of the fight, he didn’t finish the job. If Obi-Wan had struck the killing blow, he could have saved the galaxy a lot of pain and suffering.

3 Turning a blind eye to Anakin and Padmé

Darth vader

Anakin and Padmé first met on Tatooine. Although Anakin was a bit young to establish a relationship with Padmé, much older, it was easy to see that the boy was in love. Many years later, they reconnected on Coruscant and secretly married.

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It was pretty evident in both the prequel movies and The Clone Wars that Obi-Wan was aware of what was going on between them. He didn’t need to hand them over to the Jedi Order, but helping Anakin get through this might have kept Palpatine from digging his claws deeper.

two Don’t kill Maul before

Battle with lightsabers in Star Wars: The Clone Wars

Obi-Wan killed Darth Maul for the first time on Naboo, years before the start of the Clone Wars. But in an unexpected twist, Maul would survive his injuries and eventually return to prominence, chasing Kenobi across the galaxy for years.

Maul was eventually killed by Obi-Wan during the events of Rebelsand buried in the deserts of Tatooine. The wandering Sith Lord caused a lot of trouble throughout his life, which was only allowed to happen because Obi-Wan never chose to properly deal with him.

1 Training Anakin Skywalker in the first place

Darth Vader kills Obi-Wan Kenobi Star Wars A New Hope

The first Jedi Anakin met was Qui-Gon Jinn when he and Obi-Wan were stranded on Naboo. Sensing its power, Qui-Gon decided to train Anakin. The Jedi Council objected to this due to Anakin’s age, to which Obi-Wan initially agreed.

But Obi-Wan relented after Qui-Gon’s death and agreed to train young Anakin. That would turn out to be one of the worst decisions Obi-Wan ever made. Every instinct had told him not to do this, but he did it to honor his master. Obi-Wan giving in to his emotions almost cost the galaxy everything.

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