Because Jiraiya was perhaps the strongest character back in Part 1?
Even with later Shippuden knowledge we know that he's still a force to be reckoned with, in a battle they didn't need to fight or risk themselves to even if Itachi was a villain.
Not to mention, his Sannin hype was godly and probably scared even the Akatsuki- who had never met him.
That is true which is why he question Itachi.
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Kishi just hyping Jiraya.
Coming from the guy who thinks konoha 9 fodder can beat ems sasuke. lol
OP: Orochimaru was so certain in itachi's power that he even said w/ him on his side nothing could prevent his evasion. lol and mind you that was without knowledge of his mangekyou techiques, the same techniques jiraiya knew nothing about when he made that outrages claim of beating two akatsuki's at once. underestimating jiraiya's strength is irrelevant if he has no counter to them, a counter that conveniently most opponents sasuke has faced since awakening MS were fortunate enough to possess and even then sasuke had yet to reach itachi's lvl.
You get that i'm talking about hype right? Itachi probably is stronger than Jiraiya. But if we're thinking about hype in the NV & from the POV of a part 1 reader, there is no reason they wouldn't be concerned about his appearance. Even the Akatsuki WHO HAVE NEVER MET HIM would be and were fearful.
Reread my post, i'm not denying any of this stuff you're saying. Plus how long are you gonna hang onto that one thread lol. At least I presented an actual argument, a well-organised Shikamaru-led K11 defeat MS Sasuke and can contend with EMS, though I never stated a clear 100% winner if you remember.
Back in part I (keeping the whole double agent Itachi thing in mind) Kisame was hesitant on confronting Jiraiya knowing he had Itachi on his side (who dealt with Orochimaru easily by himself). I know that Itachi was hyping him up to avoid combat, but in Kisame's perspective those two should have been able to handle Jiraiya. Hell, i think in Part II Sasori (assuming by himself since Deidara had no knowledge of their upcoming meeting) was prepared to face Oro when he was going to meet Kabuto on the Tenchi Bridge.
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This scene was clearly hyping Itachi and the later threat of the Akatsuki. Why would you not hype upcoming villains who you intend on keeping in the shadows for a couple years?