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In this thread i'm comparing SM Jiraya to Itachi. To compare them i'll try my best to show you effectiv counters that SM Jiraya would have against Itachi and what makes me believe he would defeat him if there was a fight between them. Hope you enjoy reading 
How SM Jiraya counters Itachi's genjutsus:
How Jiraya counters Amaterasu:
How does Jiraya counter Susanoo:
These are the reasons why i believe SM Jiraya has all what it takes to defeat Itachi
How SM Jiraya counters Itachi's genjutsus:
Pa and Ma are there to collect natural energy in every instant, and it's the reason why Sage Mode is unlimited for Jiraya
So the fact that he continuously receive sennin mode chakra makes the use of genjutsu useless against him
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How Jiraya counters Amaterasu:
Jman already has
Jman who even already has knowledge on the jutsu, also has natural counters for this like
In Sage Mode, he even has sensing abilities, and we've seen that a sensor like Nagato
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. So he would be really cautious if he were to fight Itachi. Contrary to the popular belief, amaterasu is a
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that appears instantly withing a certain range, and from there begins
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(it's the reason why eventhough it almost appeared on Raikage, he had time to shunshin out of the way) and
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depending on where the user focuses. What i mean by that is that if a target is outside the range of amaterasu, it would be easier for him to notice it and therefore counter it with something in his arsenal. Sasuke for example was able
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during a while and
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to counter the jutsu. Killer-Bee also used a subtitution when he had no knowledge on the jutsu, and with knowledge he has shown that it was even able
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before he uses Amaterasu(which shows btw that Amaterasu needs some time of concentration to be released).Jman who even already has knowledge on the jutsu, also has natural counters for this like
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(burning a KB is useless). Even without knowledge in part1, he directly created a counter for it in an instant with a fire sealing scroll
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In Sage Mode, he even has sensing abilities, and we've seen that a sensor like Nagato
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by noticing the pressure. Therefore, he can attack the user before he even uses it like Killer-Bee did. Since Itachi needs some concentration, at that moment, Itachi could be killed by
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for example, or even
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or by this:
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How does Jiraya counter Susanoo:
Gaara helped us to know that underground is
If they are fighting in an enclosed area, Jiraya could capture him(Susanoo or not) in
Sasuke made us understand
We also know thanks to Kabuto, that
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. Well, Jiraya has a perfect counter for this with
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(Jiraya even said it was
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). It would totally make sink Itachi in this position with or without his Susanoo If they are fighting in an enclosed area, Jiraya could capture him(Susanoo or not) in
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like he already did in part1, or capture him in the
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like he did against PainSasuke made us understand
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because of sound vibration. Well, Pa and Ma have
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(able to paralyse Pain summons). With this jutsu, it would be easy for SM Jiraya to paralyse Itachi and finish him either with
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or
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or even something else in his arsenal.We also know thanks to Kabuto, that
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, so Pa and Ma use this and he is done for:
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These are the reasons why i believe SM Jiraya has all what it takes to defeat Itachi