Star Wars has confirmed Obi-Wan Kenobi knew about Anakin Skywalker's marriage to Padmé Amidala all along. By the end of the Clone Wars, Obi-Wan Kenobi was considered one of the greatest Jedi alive. The sad truth, though, is that Obi-Wan was never really the right Jedi Master to train Anakin Skywalker; Anakin would have been better with Qui-Gon Jinn. But Qui-Gon died in battle with Darth Maul, and Obi-Wan vowed to train the Chosen One in his place.
Obi-Wan could never fill the void Qui-Gon's death left in Anakin's heart. Anakin had grown up longing for a father figure, and Qui-Gon became a surrogate father, albeit for a tragically brief time. Obi-Wan was still grieving his Master's death when he took Anakin on as a Padawan himself, and the two never enjoyed the kind of relationship Anakin so desperately craved; instead, they became like brothers. Their partnership became much easier when Anakin was promoted to the rank of Jedi Knight, and they fought side by side throughout the Clone Wars. But, as close as Anakin was to his former Master, Anakin kept his marriage to Padmé a secret.
Or so he thought. Mike Chen's new novel Brotherhood is set shortly after the beginning of the Clone Wars, with Anakin Skywalker newly promoted to Jedi Knight - and it reveals Obi-Wan knew about his marriage all along. Anakin and Padmé crossed paths in the Jedi Temple's corridors immediately after Anakin's knighting ceremony, and Padmé was struck to see him without his Padawan braid. There was a moment of spontaneous affection, which they believed was unobserved - but they hadn't noticed Obi-Wan, who unwittingly viewed that moment of intimacy. The newlyweds were nowhere near as subtle and secretive as they had believed.
Obi-Wan knew Anakin was indulging in a forbidden Jedi attachment and initially considered confronting his fellow Jedi Knight. He decided not to, however, because he remembered his own time as a Padawan and his own feelings for the Duchess Satine. Then, he would have left the Jedi Order if she asked him to, but instead, they parted ways, and he was never able to fully let go of the regret he felt for the life he could have had. Obi-Wan wanted Anakin to have the married life he never had, and so he resolved to remain silent.
This revelation adds a new degree of tragic irony to Obi-Wan Kenobi's story, for, in truth, there's a simple reason he decided to ignore Anakin's marriage: he was more attached to his former Padawan than he was to his oaths as a Jedi. It is striking that Obi-Wan, renowned as one of the wisest Jedi Masters, continued to overlook Anakin's romance even when he served on the Jedi Council. There are signs the secret began to irritate him a little as the Clone Wars continued, though. In Star Wars: The Clone Wars season 7, there's a scene toward the end of the conflict where Obi-Wan throws shade at his brother, and he no doubt enjoys Anakin's shocked reaction. The tragedy of the Star Wars saga is, of course, that Obi-Wan should have done a lot more than just throw shade, for he knew his fellow Jedi was living as a hypocrite.
