Itachi takes this... though not very easily.
Itachi >> Base Jiraiya
Itachi < SM Jiraiya, but easily defeats him before he can activate it.
Actually, it's more like:
Base Itachi (Sharingan) < Base Jiraiya (Jiraiya is stronger in base form with all his summons and Itachi only has Fire Style so not much options for him)
MS Itachi > SM Jiraiya (Itachi has a fully upgraded Susanoo with Totsuka Blade and Yata Mirror accompanied by Tsukuyomi and Amaterasu compared to Jiraiya's imperfect Sage Mode. Nothing in Jiraiya's arsenal with match that)
I'm sorry, but anyone who believes Itachi + Kisame + Further Akatsuki Backup would lose to Jiraiya is a retard.
It was very clearly a diversion to keep Kisame from attacking head on, so as to subvert Akatsuki's goals further.
Yeah, right.
I mean he defeated like 3 of Nagato/Pain's without Intel. He lives up to the hype.
Itachi could have done the same if not more. Most of the Pain's are no match for Itachi's Susanoo which is equipped with Totsuka Blade and armored by Yata Mirror. That does along with the most powerful fire technique to ever exist (Amaterasu) and one of the strongest genjutsus in Narutoverse (Tsukuyomi). Itachi is clearly stronger than Jiraiya with all his feats.
And I think Itachi owned Nagato (not Pain and the Six Paths), but Nagato himself, who is darn powerful. I'm not saying he could have fought on par in a fight though because Nagato is way stronger, he he could have held up better than Jiraiya.
Is this even a question??? Itachi's power is top tier!!!
There guy with sickness defeated Orochimaru who Jiraya could bring home!
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Yeah, exactly! This is a perfect covenant to Itachi's power, and a common opponent both have fought. Orochimaru gave Jiraiya a tough time, and Itachi soloed Orochimaru in a matter of seconds.