Despite all of Obi-Wan Kenobi’s skills as one of Star Warsmost impressive Jedi Masters, there was one thing that he couldn’t stand doing – flying. It’s kind of a running joke throughout Attack of the Clones that Obi-Wan hates to fly, and Anakin even teases his master about it on numerous occasions. As it turns out, Obi-Wan actually had a very good reason for hating to fly, and it goes all the way back to when he was a Padawan in Claudia Gray's canon novel, Master & Apprentice.

Obi-Wan had his fair share of struggles as a youngling, but he finally found his place as Qui-Gon Jinn’s Padawan. The two of them had troubles of their own, as their styles and views of the Jedi and the Force differed at times. However, they did end up making a good team. One of Obi-Wan’s greatest strengths was his eagerness to learn, especially about flying. No matter what kind of ship they were in, Obi-Wan wanted to fly it and know how everything worked. That was his attitude until he had an experience that scarred him for life.

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Obi Wan and Anakin Speeder chase

Right when Qui-Gon and Obi-Wan were in their roughest patch as partners, duty called. Rael Averross, one of former Jedi Master Dooku’s students, reached out to the Jedi Council for assistance on the planet of Pijal, specifically requesting Qui-Gon. As a fellow student of Dooku’s and a former friend, Qui-Gon felt obligated to lend aid, but he was not thrilled with his assignment. Years ago, Rael Averross had been broken Jedi protocol when attacked by pirates, and it had cost Averross’ Padawan her life. Although cleared of any official wrongdoing, Qui-Gon still held a grudge for the way that Averross had conducted himself.

As a way to distance him from other Jedi and give him a way to atone for his Padawan’s death, the High Council had sent Averross to the planet of Pijal. The planet’s rulers had died, and their six-year-old daughter was too young to assume the throne. So, Averross acted as a Lord Regent and oversaw the princess’ growth into power. However, with rising tensions between the monarchy and the Czerka Corporation, a galactic weapons manufacturer, Averross required assistance and an outsider’s perspective.

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Obi Wan Flying in Revenge of the Sith

Amidst all kinds of trouble, Qui-Gon and Obi-Wan were finally able to unravel some deep political intrigue directly involving the planet’s princess. At one point, though, Obi-Wan found himself sitting in a star fighter in the hangar bay of a large Czerka Branch-class cruiser. As he tried to shoot down droids and other weapons systems in the hangar, he inadvertently switched on the fighter's autopursuit system, and he couldn’t switch it off.

As the ship accelerated, Obi-Wan could steer, but he could not stop. So, he was forced to fly the starfighter though the cruiser’s insides at top speed. Even for Anakin, that would have been a difficult task, and while Obi-Wan survived the incident, he was definitely traumatized throughout the rest of Star Wars. When he finally landed, he was convinced that he hated flying and never wanted to do it again. Qui-Gon was impressed with Obi-Wan for not crashing and tried to tell him that his fear would pass. But for all of Qui-Gon’s wisdom, he was wrong in this case because Obi-Wan still hated flying years later. Clearly, having to repeatedly experience Anakin’s reckless flying habits only served to trigger Obi-Wan’s bad memories, along with his current fear of crashing.

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