Itachi Uchiha vs. Jiraiya

Supa

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People say this would be tied, but forgot that when in their altercation in Shippuden Itachi's chakra was nearly drained from owning Kakashi Hatake (Genjutsu), plus the fact that Itachi didn't want to capture Naruto or cause a big scene! If Itachi came with the same intent of Nagato, he would have killed Jiraiya.
 

Drizzy

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do you watch naruto?
Itachi said it himself....Even if he had Kisame with him, they would still lose against Jiraiya..
these threads have been repeated over and over again.....
 
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Lord Snow

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do you watch naruto?
Itachi said it himself....Even if he had Kisame with him, they would still lose against Jiraiya..
these threads have been repeated over and over again.....
itachi did that to avoid conflict. him and kisame together would destroy jman.itachi alone would beat him
 

Haizaki

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People say this would be tied, but forgot that when in their altercation in Shippuden Itachi's chakra was nearly drained from owning Kakashi Hatake (Genjutsu), plus the fact that Itachi didn't want to capture Naruto or cause a big scene! If Itachi came with the same intent of Nagato, he would have killed Jiraiya.
Itachi didn't talk about his chakra being drained to Kisame at that time, he said they he'll lose or it would be a draw
Itachi himself said it would be draw at best or he'll lose so all this talk about not capturing Naruto doesn't change...didn't Pain say he would have lost if Jman knew his secrets
 

Misconception

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Itachi wins... He wouldn't even let Jiraiya get to sage mode... Jiraiya has no decent counter for Amaterasu... All of his summonings will be useless via Sharingan genjutsu which Jiraiya himself doesn't have a counter for... I see no possible way of Jiraiya winning this even if he started in SageMode he could still be one shotted by Amaterasu which he has displayed no speed of dodging it... He cannot sense why?Because Asura path snook up on him and he didn't see it coming which leads me to believe he cannot sense... Even if he could sense doesn't mean he can dodge Amaterasu...
 

Draphsin

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Itachi takes this low diff unless jiraiya starts in SM, then possibly a mid-high diff but leaning more towards mid.

Jiraiya is completely vulnerable to genjutsu, bunshin feints, & blitzes. Ama takes out all of his summons, & susanoo tanks anything he throws.

& Before someone says swamp, itachi reads it via sharingan & evades promptly.
 
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