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so i see a lot of discourse on whether or not itachi was retconned into being a heroic or good character, and i (being an itachi fan, as well as a kishimoto defender) disagree.
what always comes to mind is this 2 page interaction between kakashi and itachi in chapter 257 (well before itachi’s redemption)
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kakashi directly asks how much eyesight Itachi has lost. something kinda unusually personal for a battle. it doesnt seem mocking at all; kakashi knows the cost of the sharingan, and the paneling makes it feel almost like genuine concern.
itachi doesn’t respond immedietly, and instead we get this weird, almost vulnrable moment of silence. he looks down, pained. sort of odd for a character people swear up and down was pure evil devil incarnate until his "random redemption," but i digress. he doesn’t threaten, or get angry, like a true villain would in the face of their weakness; he just looks tired.
kishimoto rarely tells the audience character emotions or motivations, it’s all in the subtext and the little downward glances or averted gazes.
on the second page we see itachi start to ask a question. it seems like he may be trying to bridge a connection here by asking something hard for him to say ("kakashi…are you…?") he can’t finish the sentence. this is the closest we get to him reaching out, but whatever he was about to say is closed off by kakashi restablishing the aminosity of their relationship. ("i don’t make the same mistakes twice.")
it’s been shown before in kakashi’s character his aversion to open vulnrability; the first time we hear anything about his past from kakashi himself is right before sasuke leaves the village, and even then its cryptic at best ("everyone you are talking about is already dead .") itachi may have been about to offer a personal inquiry about the sharingan or their eyesight. but kakashi, surrounded by his students, shrinks back from the exposure and burns the tentative bridge between himself and itachi. instantly, the scene is reframed as a fight, not a conversation. naruto regains his footing, and itachi falls silent.
kakashi slinks back into his comfort zone, unknowingly slaming the door on itachi’s face. i dont think it’s a cruel thing, i don’t think be was trying to force itachi back into his role, i think it was merely a bad habit. showing the affects of pushing people away for your own comfort, as well as the cruelty of the shinobi world, snuffing out every last flicker of connection. the ache of almost.
so back to the point. this excerpt clearly shows kishimoto’s foreshadowing of itachi’s redemption arc in as early as the 257th chapter. it establishes him as a tragic character through this subtext and his silent moments. and he was NOT retconned.
Kishimoto dropped hints of Itachi's truth before he was even introduced. Although they were very vague, they get better and better later on.
I like how you put it, especially the bond between Itachi and Kakashi, because they're both aloof. I love the look on Kakashi's face. It's sad and a little wistful.
Makes me sad that nobody cared about trying to understand Itachi, and while I think Kakashi asked about his eyesight because he wanted to gauge how strong and efficient Itachi would be as an enemy right now, it's Itachi's reaction that breaks my heart. He probably doesn't see it that way and expresses his vulnerability briefly.
