Obi-Wan Created A Sith Lord Even More Powerful Than Darth Vader
If you ask any Star Wars fan what Obi-Wan Kenobi's greatest failure was, they would say it was letting Anakin Skywalker become Darth Vader. That's a no-brainer. He admits it at least a couple of times. For years, it would haunt him because he protected Luke Skywalker, Anakin's son. Master and Apprentice would meet again in the original Death Star and have another duel. There, Kenobi would sacrifice himself and become more powerful than anyone could really imagine, while Anakin would return to the light and finish off Darth Sidious, bringing the Sith to an end for a time at least. That was the end of Vader as well.
But was that the only Sith Lord Kenobi inadvertently created? In the Legends continuity, at least, there was another. A Sith Lord who would one day revive the Sith and bring unbalance to the Force. A Sith Lord who would lead an entire army all fanatically dedicated to serving him. A Sith Lord who would conquer the galaxy, bringing about a new age of chaos and warfare, which they hadn't seen since the fall of the First Galactic Empire. A Sith who came into conflict with the Jedi, only to be opposed by the heir of Skywalker.
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His name was A'Sharad Hett, and he was the son of a Jedi and a Tusken Raider. Tusken Raiders were considered a proper species during the Legends continuity, but some other humanoids were occasionally "adopted" into the group. A'Sharad's father was the Jedi, Sharad Hett, while his mother, a Tusken Raider called K'Sheek, was lost in a sandstorm shortly after his birth. Although Sharad would be killed by the bounty hunter Aurra Sing during a conflict between the Tuskens and the Hutts, his last wish was for Ki Adi-Mundi to take on his son as his Padawan. A'Sharad Hett's story begins in Star Wars #10: Outlander Part 4, published by Dark Horse Comics in 1998.
Fast forward past the Great Jedi Purge, Obi-Wan was, of course, living on Tatooine. At one point, he came across another survivor, A'Sharad Hett. Hett had become a war leader and was waging a crusade against the human settlers. Their next target was Owen Lars's farm. Kenobi, feeling as though Hett was dangerously close to the Dark Side, and wishing to protect the young Luke, engaged Hett in a duel. Obi-Wan won, and rather than killing him, urged him to leave Tatooine before unmasking him in front of his followers. Breaking a taboo of the Tusken Raider, the army left Hett behind.
A'Sharad followed Obi-Wan's advice and became a bounty hunter, eventually hunting down a bounty hunter to the Sith tomb world Korriban. After killing his bounty, Hett would hear a voice, which led him to the Sith Holocron of XoXaan, an ancient Sith Lady. There, she opened his eyes to the Dark Side. Though he tried to stay on the light, it was naught. Obi-Wan's mercy, meant to save Hett from the Dark Side, had only brought him fully within its reach.
Hett would eventually take on a new name, Darth Krayt, and create a new Rule of One, meant to replace the Rule of Two. With his new reborn Sith Order, the One Sith, loyal to him, Krayt would spark a new war between a reformed Empire and the Galactic Alliance, the successor to the New Republic. Then, at the war's end, Krayt would betray the Empire and rule the galaxy in the name of the Sith, with promises of order and peace through the Rule of One. However, little did he know that a new Skywalker would one day oppose him. That is a story for another day, however.