In the prequels, it is made pretty clear that Obi-Wan Kenobi doesn’t like flying. He expresses this a couple of times in Attack of the Clones, and in Revenge of the Sith insists that flying is for droids.
But interestingly, Obi-Wan is actually a very skilled pilot. So why did he hate it so much? We now have a canon answer to that question you may not have even known you wondered. In Claudia Gray’s excellent novel “Master and Apprentice”, we are told exactly what happened – and it occurred years before The Phantom Menace.
Spoilers are obviously ahead for “Master and Apprentice”, so don’t read any further if you don’t want to know what happens. We won’t go into full spoilers, but we’ll be discussing a pivotal moment at the book’s climax.
Early in the book, we are told that Obi-Wan actually loves to fly. At one point, we read, “As Qui-Gon well knew, Obi-Wan loved flying” (25). The young Jedi apprentice loved to fly, was fascinated by ships, and was quite good at flying as well.
Well, at the story’s climax, Qui-Gon and Obi-Wan are working to prevent the loss of many lives. Obi-Wan and a scavenger named Pax infiltrate the enemy ship (belonging to the Czerka Corporation, which holds many slaves on board) to rescue their friend Rahara, herself enslaved by Czerka. Qui-Gon, meanwhile, worked to negotiate a peaceful resolution. Obi-Wan stayed with the ship while Pax went to find Rahara, but soon alarms began going off. He climbed into a smaller ship to get better readouts, and then when enemies began coming in, he decided to use the ship’s weapons rather than try to use his (broken) lightsaber. But in doing so, he accidentally triggered the autopilot systems.
Not able to stop it, Kenobi sat helplessly – and screamed – as his ship flew through the narrow corridors of the Czerka ship, narrowly avoiding the walls. Soon enough, he burst onto the bridge, where the Czerka supervisor was at. With Qui-Gon watching via hologram, Kenobi’s ship burst onto the bridge and eventually came to a stop. We then read,
“Obi-Wan’s face was pale, his stare somewhat dazed. He looked at the holo for a long moment, taking gulping breaths, then ventured a weak smile. ‘I don’t suppose you believe I meant to do this?’
‘No.’ Qui-Gon began to smile. ‘But it turns out, you’re right on time.'” (319)
With Kenobi’s arrival, it meant that the official Republic representative was on the bridge of the Czerka ship (there’s a longer story about that too), and he was thus in a position to help free the slaves on the ship. But the damage had been done to Kenobi – he no longer enjoyed flying after the harrowing experience. Gray writes,
“‘You flew through the ship’s corridors?’ Qui-Gon put one arm around Obi-Wan’s shoulders as they walked away from the corvette’s docking bay. … ‘Congratulations on being in one piece.’
Obi-Wan still appeared to be in shock. ‘It was terrible,’ he said, his eyes staring fixedly ahead. ‘I don’t ever want to fly again. Ever.’
‘Oh, come now, Padawan.’
‘I hate flying.’
‘You’re only shaken up,’ Qui-Gon said. ‘That feeling will pass.’
‘No, it won’t.'” (320)
And apparently it didn’t pass. While Kenobi’s skill as a pilot continued, his joy of flying seems to have all but disappeared in this one traumatic moment. And that actually makes plenty of sense, as I’m sure many readers will know someone who suffers from PTSD as a result of a horrific and traumatizing moment that never really leaves and that always lingers. I’m not saying that Kenobi’s was exactly like this, but my point is that one huge event like this is more than enough to scar him for life when it comes to flying.
But I also think that it’s interesting that this is a very similar situation to what Anakin Skywalker experiences in The Phantom Menace. He flies through the Trade Federation ship, flying through the narrow corridors. I like to think that in the years following he and Obi-Wan had some interesting talks reminiscing on their similar experiences.
So anyway, if you ever wondered why Obi-Wan Kenobi hated flying, here you go. It’s all because of one moment years before TPM, where the autopilot of his ship took over and forced him to helplessly fly at high speeds through the narrow inner-workings of a massive ship. It seems that memory never really left him.