Obi-Wan Kenobi has one of the most storied histories of any Star Wars character, and what story is complete without a few villains? Though fans know Obi-Wan as a great hero, the Jedi master made several enemies throughout his life, from cyborg Jedi Killer General Grievous to Sith Assassin Asajj Ventress.
However, two of Obi-Wan's enemies stand above the rest, Dark Lords Of The Sith Vader and Maul. These two adversaries have struck the most personal blows to Kenobi, but which one comes out on top? Let's compare their dark accomplishments to find out.
10 Vader: A Former Friend
There are few things more tragic than seeing close friends become enemies. Obi-Wan and Anakin Skywalker occupied the roles of master and student for a decade, then grew as close as brothers during the tribulations of the Clone Wars. Alas, their friendship was not meant to last. After falling to the Dark Side, Anakin becomes convinced that Obi-Wan has betrayed him, while Obi-Wan is forced to confront Anakin, knowing his reign of terror can't be allowed to continue.
The denouement of the pair's duel on Mustafar is one of the few moments where Obi-Wan's composure breaks; tears welling in his eyes, he shouts to the man once called Anakin that he loved him while his former apprentice boils in pain and rage.
9 Maul: Killed Obi-Wan's Master
The first time Obi-Wan experienced tragedy was when Maul killed his Jedi Master, Qui-Gon Jinn, on Naboo. Separated from them by a force shield, Obi-Wan could only watch as the Sith apprentice mercilessly stunned then stabbed Qui-Gonn. Still a Padawan learner when his Master passed on, the death forced Obi-Wan to grow up quicker than he had anticipated and is the very reason he was left to teach Anakin in the first place.
Despite the Jedi Code of non-attachment, Obi-Wan's failure to save Qui-Gon clearly cast a shadow across the remainder of his life; when Maul rubbed the killing in Kenobi's face during their second confrontation years later, the Jedi responded with uncharacteristic rage.
8 Vader: Obi-Wan's Own Failure
While Obi-Wan may have failed to save Qui-Gon, it was his failure to save Anakin that yielded truly disastrous consequences for himself and the galaxy. Having never intended to teach Anakin in the first place, Obi-Wan often, albeit unintentionally, alienated his pupil, doing little to help Anakin work through his issues beyond reciting Jedi dogma.
This reached its head during the Clone Wars, where Anakin never trusted Obi-Wan enough to confide in him about his forbidden relationship with Padmé. It was his uncertainty about that relationship's future, more than anything else, that spurred Anakin on the path to becoming Vader. As Obi-Wan admits to himself and Vader, "I have failed you, Anakin."
7 Maul: Killed Obi-Wan's Love
Qui-Gon was the first of Kenobi's loved ones who Maul killed, but, tragically, he wasn't the last. During the last legs of the Clone Wars, Maul allied with Mandalorian terrorists Death Watch in overthrowing the pacifist government of Duchess Satine before slaying Death Watch leader Pre Vizala in combat and taking the throne for himself.
The Duchess happened to be an old flame of Kenobi, with the two having become acquainted during Obi-Wan's apprentice to Qui-Gon, though they had decided not to act on their feelings. When Obi-Wan surreptitiously arrived on Mandalore to rescue Satine from imprisonment, Maul captured them both and executed her in front of the Jedi. With the swing of his blade, Maul took not only Obi-Wan's mentor from him, but the love of his life as well.
6 Vader: Destroyed Obi-Wan's World
Raised in the Jedi Order since infancy like the vast majority of his comrades, the Jedi way of life was the only one that Obi-Wan had ever known. He lived within the Jedi Temple's walls throughout most of his early life, and almost all of his friends and peers were his fellow Jedi.
While Obi-Wan himself may have survived the Order 66 slaughter, the destruction of his Order and the Republic he'd fought for meant the destruction of everything he'd ever known. While Palpatine may have masterminded these events, it was Vader who marched into the Jedi Temple alongside legions of Clone Troopers and carried out the massacre.
5 Maul: Obi-Wan's First Enemy
Every student has a moment where they must face a great challenge themselves, without their teacher standing by to counsel or assist them. Obi-Wan's moment was witnessed in The Phantom Menace, and it was a baptism by fire like no other. As his master lay dying, it fell to Obi-Wan to defeat Darth Maul, the Sith's bloodlust unquenched by Qui-Gon's coming demise.
Relying on skill and luck in equal measure, Obi-Wan defeated his opponent, sending the bisected Maul tumbling to his seeming demise. Though Maul would return to menace Obi-Wan for the remainder of their lives, this duel was not just the first time in millennia that a Jedi had defeated a Sith Lord, but the first time Obi-Wan triumphed by himself.
4 Vader: Haunted Obi-Wan During His Exile
While Obi-Wan did not meet Vader for two decades after their fateful duel on Mustafar, they were omnipresent in each other's thoughts. Canon comics published by Marvel show that Vader often recalled the duel, indulging in fantasies of killing the man he once considered a friend who left his physical form a ruined carcass. It's likely Obi-Wan had similar visions, albeit ones of a guilt-ridden and sorrowful nature rather than a viscerally cathartic one, especially since he had little else to do aside from meditating during his exile on Tatooine.
By the time Obi-Wan finally meets Luke face-to-face, Obi-Wan has come to regard Vader as an entirely distinct entity from Anakin, for that point of view was the only way he could live with himself.
3 Maul: The Two Had Many Duels
While Anakin Skywalker may well have been the most important person in Obi-Wan's life, he only ever encountered the man as Darth Vader twice. In contrast, Obi-Wan and Maul met in battle several times, beginning of course with their iconic duel on Naboo.
The pair then dueled on three separate occasions during the Clone Wars, the first time Obi-Wan had to run from Maul, the latter two times Maul had to run from Obi-Wan. Then, almost two decades later, the two enemies brought their rivalry full circle with a final clash on Tatooine.
2 Vader: He Killed Obi-Wan
Obi-Wan finally met Vader again on the Death Star twenty years after their previous confrontation, the latter unrecognizable in his black armor designed for the Sith to overcome the very injuries Obi-Wan had inflicted upon him. This meeting would be their last, at least in the physical realm, for Obi-Wan allowed himself to be cut down so that Luke and co. could escape.
One killing the other was really the only way Obi-Wan and Vader's relationship could've ended by that point. However, while Vader may have taken momentary satisfaction in finally striking down his friend turned foe, the passing allowed Obi-Wan to become more powerful than the Sith had ever imagined.
1 Maul: Obi-Wan Killed Him
Sensing Kenobi still lived after accessing a Sith holocron, Maul set out to find his old foe. After a long, delirious trek through the Tatooine desert, he eventually locates the exiled Jedi Master. Maul is eager to finally have vengeance for his defeat on Naboo all those years ago, while Obi-Wan concludes that Maul is a threat to Luke.
Their thirty-year long rivalry finally concludes in a brief but memorable Lightsaber duel, with Maul attempting the same move he used to kill Qui-Gon, while Obi-Wan instinctively blocks it. In their final moments together, Obi-Wan offers his enemy something unexpected: solace, that the Chosen One will avenge the misdeeds of the Sith.