Back to the first post about Naruto and Pein. I don't think Naruto has to pass Jiraiya in strength to beat Pein. Pein said after his fight with Jiraiya that Jiraiya would have won if he didn't hide his secret. If they decode the message Jiraiya sent it should be possible for Naruto to win after his training without surpassing Jiraiya. I'm sure Naruto will pass Jiraiya eventually but not yet.
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