Are you kidding me... They were not talking about the nine tails. If you put the nine tails in that context, that part of the conversation would make no sense. Kurama was inside naruto at the time and given naruto's strength at the time, all they'd have to do to capture him (assuming there is no further intervention) is put him in a genjutsu or just physically knock him out. Then take him to the akatsuki lair and bam, extract the nine tails out of him.
Yet he was able to defeat those three path's with no previous intel/prep by stalling for time AND one of them, he was able to defeat twice (animal path). He was doing pretty good against them in that battle even though he had no intel or prep time.
Itachi and kisame wouldn't have performed any better against pain than jiraiya had, even with intel, while pain stated that if jiraiya DID have intel, he would have won the battle. The feats that jiraiya showed in that battle back's up itachi and kisame's statement of being inferior to jiraiya.
@bold: Pain was referring to the fact that jiraiya would know where his real body was by using the chakra rods. The same way he figured that out too late when his arm was cut off.
Itachi and kisame together, or seperate? Because if you're trying to imply that itachi and kisame can't take down pain or at least 3 of his paths in the same situation jiraiya had, I don't even know what to say to you...
Don't forget jiraiya only defeated those 3 because of circumstances. he had the perfect position in those pipes to hide and stall for time along with maximize his acoustics to trap them in a sound genjutsu. Without frog song he would have lost. Any other battlefield where he couldn't hide that much to prep the jutsu would get him killed. He was in the perfect location to maximize jutsu usage, just like kabuto vs Itachi and sasuke. It's all circumstantial.
As to your first point. I don't have the viz scan which makes it clearer, but even in this one
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Kisame says jiraiya "
might be a match" solely based on sannin hype.
if Kisame or Itachi can do that to Madara's wood clone talk to me
Anyone can easily do it. It's called a trap. When you set a trap, you make your opponent think they're winning. Madara was being pressured by all of them so he substituted out and let tsunade take on a bushin.
