Star Wars has finally revealed why Obi-Wan Kenobi never confronted his former Padawan Anakin Skywalker, regarding his marriage to Padmé. Anakin and Padmé chose to marry in secret, but it's long been clear Anakin's best friend - and former master - Obi-Wan knew about their relationship. One scene in Star Wars: The Clone Wars season 7 saw Rex run interference to prevent Obi-Wan from walking in on a holographic chat between the couple. In the aftermath, an irritated Obi-Wan couldn't resist making one of his usual dry remarks. "I hope you at least told Padmé I said hello," he remarked before walking off and leaving Anakin astounded.
Mike Chen's new Star Wars novel Brotherhood reveals Obi-Wan knew about the marriage all along. In fact, he discovered it within days of the wedding, simply because the newlyweds weren't careful enough. Anakin and Padmé spent their honeymoon together on Naboo, with Anakin claiming he was convalescing after the Battle of Geonosis, and when they returned, Anakin was knighted. Padmé bumped into him immediately after the knighting ceremony, saw him without his Padawan braid, and - believing nobody was around - shared a moment of affection with him. Unfortunately, they were witnessed by Obi-Wan, and it didn't take him long to put the pieces together.
He may not have still been Anakin's master, but Obi-Wan was still in a position of responsibility. He had been appointed to serve on the Jedi Council, albeit on a provisional basis, and thus, he knew he should really have reported what he'd seen. Granted, he chose not to do so in large part because he remembered his own past with Duchess Satine of Mandalore. The two met while Obi-Wan was a Padawan, with the Jedi spending a year with her while assigned to keep her safe during a Mandalorian civil war. He fell in love with Satine and would have left the Jedi had she asked him to, but she did not, and so they parted ways, divided by their duty. Obi-Wan couldn't help wishing Anakin the happiness he had been denied, and therefore, he decided to keep the marriage between Padmé and Anakin a secret.
There is a tragic irony to this because, in truth, Obi-Wan shared Anakin's greatest weakness: attachment. Brotherhood makes it clear that Obi-Wan had never gotten over Satine. In truth, he never would, for he took her affectionate nickname, "Ben," for him as a new identity during his years of exile on Tatooine. What's more, although Obi-Wan's early years with Anakin were difficult, he came to care for his former Padawan so much that he preferred hoping for Anakin's happiness over doing what was right. Ironically, the Jedi who earned a reputation for wisdom did not allow himself to consider the hypocrisy of Anakin's position and the fact Anakin's competing attachments would inevitably tear him apart.
Curiously, Brotherhood hints Obi-Wan justified his silence by asking what his own Master, Qui-Gon Jinn, would have done. Qui-Gon was something of a maverick, and Obi-Wan believed he would have been a member of the Jedi Council had he just been able to follow orders. No doubt, a part of Obi-Wan vaguely wondered whether his own appointment to the Council would have pleased Qui-Gon or whether he would have been something of a disappointment. He rightly sensed that Qui-Gon wouldn't have condemned the marriage simply because Qui-Gon had a healthier understanding of balance, love, and attachment than most of the prequel era Jedi and so justified his silence as a strange way of honoring his master. While he was right to believe Qui-Gon would have had a different perspective to the Jedi Council, he was surely wrong in that Qui-Gon would have questioned the healthiness of a life of hypocrisy and challenged Anakin. Obi-Wan was not as wise as he thought - and as a result, the tragedy of the Star Wars saga played out without his speaking up.
