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Originally Posted by amaterasu4
Road to Ninja already depicted this kind of scenario and the results were pretty good. Can't spoil much here though.
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That sounds interesting. I was thinking about Obito testing Naruto, to prove that Naruto is no better than him. So inside the genjutsu he could have both Hinata and Sakura get killed before Naruto's eyes, to prove that Naruto will become like him eventually. Naruto already lost himself once when Pain apparently killed Hinata. I think that for Tobito not only winning is important but also to prove that he is right, and he was already shocked when he heard that Naruto has changed Nagato, so it's probable he would want to prove his dogma by breaking down Naruto. In this chapter he said that Naruto is very similar to his young self but eventually he'll turn out like him, so maybe he will want to prove it if both Kakashi and Naruto challenge his views of the world while they keep fighting. And if he can't break Naruto that could trigger his conversion to the good side and sacrficing himself to save the alliance from Madara.