Obi-Wan Kenobi is consistently one of the most perceptive and tactically capable characters in the Star Wars saga, which makes his repeated failure to notice, address, or prevent Anakin's fall to the dark side an unusually large blind spot for someone otherwise defined by careful judgment.
A close reading of the timeline shows Obi-Wan present at, or immediately adjacent to, nearly every major turning point in Anakin's radicalization, consistently choosing measured half-interventions that address the symptom without ever confronting the underlying trajectory directly.
His final confrontation with Vader on Mustafar is framed as tragic failure, but the outcome, leaving Anakin alive, badly injured, and permanently identifiable as a contained threat rather than dead, is also precisely the outcome a strategist might prefer if killing Anakin outright carried unacceptable political or personal costs.
Obi-Wan alone possesses the specific knowledge of Anakin's psychology, combat style, and emotional triggers, giving him a unique long-term advantage in managing Vader as a known quantity rather than allowing an unpredictable death to create a power vacuum the Sith might exploit differently.
His subsequent self-imposed exile on Tatooine, positioned near Anakin's own family history and conveniently close to Luke, does not resemble simple retreat so much as a permanent observation post maintained by someone still actively managing a long-term outcome he set in motion.
The decision to conceal Luke's parentage entirely, rather than using the information strategically at any point over two decades, suggests less a simple protective instinct and more a carefully sequenced plan designed to introduce Luke into the equation only once Vader had been sufficiently contained and Obi-Wan's own preparations were complete.
Whether Obi-Wan's choices reflect brilliant long-game strategy or the story's tendency to grant him narrative competence he did not always earn remains debatable, but the pattern of near-misses, convenient survivals, and decades-long positioning is difficult to fully explain as coincidence alone.