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You know I did forget that he was drugged but still Itachi > Jiraiya and it's really not that close. Full strength Jiraiya wouldn't handle Oro with the ease Itachi could.Bringing up Jiraiya vs Orochimaru when Jiraiya was explicitly drugged by Tsunade and not full power
Pain even admitted he would have lost if Jiraiya had known his secret
DefinitelyCould Itachi take on pain?