We all know Darth Sidious didn’t respect the Jedi. To him, they were naive, blind to the truth, and easy to manipulate. He spent years planning their destruction, and by the time Revenge of the Sith hit its peak, he had pulled it off almost perfectly. But here’s the thing: not all Jedi were equal in his eyes. One of them made him pause—Obi-Wan Kenobi.
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Obi-Wan Never Gave Him a Weak Spot
Sidious always found a crack in every Jedi’s armor. He used Anakin’s fear of loss, twisted Mace Windu’s pride, and threw the Jedi Council into chaos by exposing their hypocrisy. But Obi-Wan just never slipped.
Even after everything—losing Qui-Gon, training a friend who turned into a monster, barely surviving the purge—Obi-Wan still held to the Jedi Code. No rage, no revenge, no grabbing for power. Just pure Jedi discipline. And the thing is, Sidious noticed. He didn’t say it, but I think deep down, he respected that kind of strength.
Mustafar Changed Everything
If there’s one moment that really made Sidious take Obi-Wan seriously, it was the duel on Mustafar. Anakin was his ultimate project—years of manipulation, grooming, and training, all to create the perfect Sith. And then Obi-Wan cut him down. That wasn’t just a loss. That was a disaster.
We get a direct quote from Dark Lord: The Rise of Darth Vader that spells this out clearly. Sidious actually says:
“Obi-Wan triumphed because he went to Mustafar with a single intention in mind: to kill Darth Vader. If the Jedi Order had shown such resolute intention, if it had remained focused on what needed to be done rather than on fears of the dark side, it might have proven more difficult to topple and eradicate. You and I might have lost everything.”
I don’t think Sidious ever saw that coming. He placed all his faith in Anakin. And then the one Jedi he hadn’t paid much attention to completely wrecked everything. Obi-Wan didn’t just win—he nearly ended the Sith then and there.
Sidious Never Underestimated Obi-Wan Again
There’s another line that really stuck with me:
“But even Sidious hadn’t foreseen Anakin’s defeat by Obi-Wan Kenobi on Mustafar. Anakin had still been between worlds then, and vulnerable. The failure to defeat his former Master had worked to prolong that vulnerability.”
That quote tells me everything I need to know. Obi-Wan wasn’t powerful because he chased power—he was powerful because he stood firm, stayed true, and did what had to be done. Sidious didn’t make the same mistake twice. He never tried to manipulate Obi-Wan directly. He never picked a fight with him. He knew Obi-Wan was dangerous.
The novel goes even deeper. There’s this chilling part where Sidious reflects on that day. He remembers racing to Mustafar, dragging what was left of Anakin’s body back to Coruscant, and doing everything he could to keep him alive. That’s not just concern. That’s fear. The book says:
“Sidious recalled the desperate return trip to Coruscant; recalled using all his powers and all the potions and devices contained in his medkit, to minister to Anakin’s hopelessly blistered body and truncated limbs. He recalled thinking: What if Anakin should die?
How many years would he have had to search for an apprentice even half as powerful in the Force, let alone one created by the Force itself to restore balance, by allowing the dark side to percolate fully to the surface after a millennium of being stifled? None would be found.”
That’s wild to read. Sidious, the Sith Master who planned everything, was panicking. He realized just how badly Obi-Wan had ruined his plans—and how hard it would be to ever find another like Anakin again.
The Jedi Who Could’ve Ended the Sith
If Obi-Wan had ended Anakin completely, there might never have been a Darth Vader. And if there was no Vader, there’s a good chance the Sith wouldn’t have survived. Sidious knew that. That’s why he feared Obi-Wan—not because he was the strongest, but because he was the most unshakable.
Even later, Obi-Wan helped set Luke on the path to become the Jedi who would bring Sidious down for good. In a way, he still beat him. Not through brute force—but by staying true to the Jedi way, all the way to the end.