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Itachi wins high or mid difficulty.
Itachi had Ama, Susanoo and Tsukuyomi since he was 13.
I'd say Jiraiya wins an IC, inteless fight.
I only counter your argument for the Susanoo. The Yomi Numa can be countered by two ways:
1. Chakra control
Itachi can concentrate chakra in his feet to avoid sinking.
2. Katon
He can drain off the mud.
Does Jiraiya start in SM? If not he dies pretty easy. Anyone using the "Itachi said that Kisame and him would stalemate with Jiraiya" bull shit, you are false. Itachi is clearly talking about Kurama.
Chakra control is not helping Itachi with the mud. It has Jiraiya's more potent and stronger chakra. If Itachi needed to walk on water I would agree, but not Jiraiya's swamp of the underworld.
Oh dear god not this again. Anyway, it's my opinion that Jiraiya wins high diff if starting in base and mid-high diff starting in Sage Mode. I will be debating this with Icelerate in a couple weeks. T Bogard, I didnt read your post but im sure those were excellent points, you the real mvp. Giving you rep
How does he counter Amaterasu in base form?
Subsitution is one of the most underrated techniques... Substitution could potentially counter any attack. Think about it..My point is that, substitution has been nerfed. And bringing substitution in battle just complicates things.Oh please. A simple body replacement (substitution) counters Amaterasu.
Itachi did say if ksame and him fought jiraiya in pretimeskip it wouldn't be without consequences. My guess is in the timeskip period itachi improved his sharingan and became much stronger than he were in pre timeskip. He also never used susanoo in pretimeskip, maybe he learned that during timeskip. I would say itachi mid diff