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This is a....very interesting match by me. Itachi has the Mangekyou Sharingan which enables you to use a genjutsu which can't be broken, Tsukuyomi, and it also gives you Amaterasu. However, Orochimaru has studied hundreds of forbidden techniques and among them could be some that could be used to defeat Itachi. And while Orochimaru himself stated that Itachi is stronger than him, I still think it would be a close match. So what do you think?