Master Yoda's greatest defeat was a secret one, long before the events of Star Wars: Episode III — Revenge of the Sith. Famously considered one of the wisest Jedi, by the time of the prequel trilogy Yoda had become Grand Master of the Order — the one whose voice was most respected, whose counsel was sought by the other Masters and whose wishes were seldom overruled. As great as Yoda may be, though, Star Wars has made it clear Yoda was a failure; the Sith returned on his watch, after all. And yet, for all that's the case, his greatest — and most personal — defeat happened years before Star Wars: Episode III — Revenge of the Sith.
The Jedi rules on attachment are often misinterpreted. As celebrated Star Wars author Charles Soule explained, "It’s very easy for a Jedi to love, it’s just you have to love without being controlling and love without being afraid of losing somebody, which is something Jedi are good at, and Sith are bad at." There's a sense in which Daniel Jose Older's novel Midnight Horizon, which is set in the High Republic Era 200 years before the events of Star Wars: Episode I — The Phantom Menace, is essentially an exploration of this theme. The bond between a Jedi Master and their Apprentice is a sacred thing, with the two bound together by the light side of the Force, and thus the pain of losing an Apprentice was very real for Yoda. It's a beautiful exploration of the Jedi Master's character, and it shines a new light on Yoda's greatest, and most personal, defeat — losing Count Dooku to the Sith.
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Cavan Scott's Dooku: Jedi Lost revealed Count Dooku's backstory, transforming him into a tragic figure who was drawn back into the affairs of
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