This prospect was talked about extensively years ago, and translators and Japanese people generally agree the context is that they are speaking about Jiraiya.You must be registered for see images
itachi says that if he and him faught they would kill each other
kisame says it was great finding him but his babysitter
itachi was talking ABOUT him
jiraiya cant be the him since jman does not have a babysitter
even kisame says that his babysitter is a sannin which declares that they were referring to someone else before him
after kisame talks about the babysitter(jman) itachi says that everybody has a weakness
the only other person their is the nine tail jinchuuriki
meanin that itachi was talking about the kyuubi
The conversation basically goes:
Kisame: "You might be able to take Jiraiya on, but I can't."
Itach: "Yeah. Jiraiya and I may kill each other, even with your help."
Kisame: "It was great finding Naruto, but with Jiraiya as his babysitter, maybe we should back off."
Kisame was just continuing on after Itachi's response, he didn't change individuals.
Think about it too... if they are so concerned about Kurama, why are they most worried about Jiraiya? They make efforts to get Jiraiya to leave Naruto's side, and then walk up to Naruto without a care in the world; Kisame was even going to chop off his arms and legs and drag him back to Akatsuki, wasn't the slightest bit worried about Kurama.
Think about it too, Kisame specializes in hunting Bijuu, he eats all of their chakra away and leaves the jinchuuriki helpless, and Itachi has the potential to suppress Kurama's because of the Sharingan. They are the perfect pair to capture Naruto, so why would they be so worried about facing him?
They were talking about Jiraiya.
He may, however, Kisame wouldn't even be able to use his full power with Itachi there. If Kisame used Shark Dance, Itachi would drown, or at the very least it quickly becomes a 1 on 1 fight with Itachi being sidelined. I admit Jiraiya would have a hard time with Shark Dance, but he has options at his disposal to win. Then it would come down to Jiraiya vs. Itachi afterwards, making Itachi's statement true; he and Jiraiya may end up killing each other, even with Kisame's help.Kisame alone would give Jiraiya a hard time.
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