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No one ever said he can beat them both? They both ran from him because they were afraid of his hype. He had the greatest hype in the narutoverse and honestly Itachi had no feats in Part 1 except for using Tsukiyomi on Kakashi
itachi was under cover for kohana why wud want to kill jman if he wanted to protect da leaf?
and your honestly tellin me itachi cudnt have done a simple amaterasu or tysukuyomi on jman in that small little hall way?
how cud jman escape a instant amaterasu 5 inches from him?