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The Uchiha Clan Massacre remains his defining tragedy - ordered by Konoha's elders to prevent civil war, Itachi slaughtered his entire clan yet deliberately spared his younger brother Sasuke, choosing to bear the weight of infamy alone. This act forced him into the Akatsuki organization while secretly remaining Konoha's most effective double agent. Itachi's philosophical battles against Kakashi, Orochimaru, and ultimately Sasuke revealed his "win without fighting" approach and the depth of his sacrifice.