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i think a battle between itachi and jiraiya could go either way. they are both masters in ninjutsu and they are both very good in taijutsu. obviously itachi has a major plus in genjutsu, but jiraiya has good genjutsu defense in most cases, and and he has a major advanage in stamia/charka. it really doesnt have to be a one or the other debate. either one of them in battle could defeat the other, depending on the situation and how much of there jutsu the other knows about.
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