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- Aug 6, 2010
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"His babysitter was one of the three great shinobi....With HIM as our opponent." New subject is established him's refer to it
At that point they're referring to Jiraiya, yes. As Kisame goes on to note that their titles pale in comparison. But in this same discussion, they refer to the him above as Naruto. However, Itachi's reaction is also entirely different.
"Even if we had backup, I doubt the outcome would change" - This opponent is someone Itachi worries about the entire Akatsuki having to fight.
vs
"Even the strongest heroes have their weaknesses" - Itachi notes that Jiraiya, as great as he may be, has his weaknesses. Not worried about needing backup.
And
"I'm not sure about you, but he's out of my league." - Kisame's absolute certain he stands no chance, and questions if Itachi does.
vs
"Why is retreat necessary for you?" - Is not questioning at all that Itachi could have handled Jiraiya, and now that he knows Naruto has little to no control over his kyuubi abilities, he's no longer a threat.
It's also worth noting that Itachi never disagrees that he could have taken down Jiraiya when Kisame claims retreat wasn't necessary.. He only said that he needed rest after having to having to fight the jounin, use tsukuyomi x2 and then use amaterasu.