Sage Mode Jiraya vs Itachi

blackbullet

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This is Sage mode Jiraya with Ma and Pa vs living Itachi
Personally I think Itachi wins but Jiraya has some good chances of winning together with the frogs but high diff

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Bronze

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Itachi, low diff.​
 

Unorthodox

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Amaterasu gg
 

RustledJimmies

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I've lost count of how many times this has been made, Itachi wins mid difficulty.
 

Kamui Sama

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Jiraiya high diff U_U
 

LustyLover

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Itachi med diff v.v, sweet damn. This has been almost as much as Minato vs Itachi.
 

Beans2

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Jiraiya mid-high diff.
 

TRE MERCER

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Jiraiya cannot dodge Amaterasu so it's quite clear who's the winner hear.
 

ARGUS

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Itachi wins this high diff
 

Lytes

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Jiraiya wins...
 

eagle8

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jiraiya wins high diff.
 

Legendary Toad Sage

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This match-up heavily depends on the knowledge, location, starting distance, and mindset. Low and medium difficulties do not exist in the face of two ninja of this caliber. Whoever does win, is just barely doing so.
 

genii96

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Jman wins this,
 

Bogard

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Jirays wins. First of all, i'd like to say that if we're talking about alive Itachi, his techniques are close range only because

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And we know how badly his eyes deteriorated(he had MS for 8 years after all)

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Even the databoook repertoriated Amaterasu and Tsukuyomi like close range jutsus and now we know why

Here is the databook of Amaterasu

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Jiraya being a powerful long range fighter, he can easily overwhelm Itachi with his arsenal

Amaterasu

User(s): Uchiha Itachi
Rank: -
TNG: Ninjutsu (Bloodline Limit)
Range: Close
Type: Attack

Description:
"The ones reflected in these eyes turn to ash!! A black world-destroying
conflagration that scorches all on heaven and earth!!"

The Uchiha clan, originally significant as "those with the fans which manipulate
fire", traditionally specialize in Katon jutsu, but there is a legendary jutsu
unknown outside the clan. This is "Amaterasu". The appearance of these flames
are jet-black. The high temperature is like the sun, and one time touching it is
the last. It is said that this is named after the Goddess of the Sun as it
continues to burn for seven days and seven nights. However, the Mangekyou
Sharingan is necessary to activate this jutsu, and for this reason there are not
many who have learned this jutsu. Therefore, the details of this jutsu are yet
unrevealed...

Picture text:
Top: The black flames that only the owner of the Mangekyou Sharingan can control
are even able to instantly break through the side of a rock toad who breathes
fire!!
Bottom: Jiraiya, whi has mastered many jutsu, did not know of the existence of
Amaterasu. What he does understand is the power of the suspicious conflagration.

And every time there is a Amaterasu usage, there is some kind of air pressure that Zetsu or Nagato were capable to detect. Jiraya doesn't need to dodge it physically. All what he needed is either to shield himself with needle jizo(it's harder than steel despite being made of hair and we've even seen Amaterasu fail to burn Madara's hair in this war anyway when it was left alone) or block eye sight with his AOE katon attacks, or even pulls out with a kawarimi jutsu(Killer-Bee escaped through this method), or even use clones with Itachi not knowing where the original actually is

During Amaterasu usage, Itachi is also practically defenseless. We've seen Sasuke was capable to summon large shurikens and throw it in Itachi's direction to try and prevent it, same goes for Killer-Bee when this time Itachi got saved by Nagato's Shinra tensei. So while the casting jutsu is instant, the prep behind the technique leaves openings

Genjutsu isn't an issue either. Besides the close range eye contact i previously mentioned, in SM Jiraya has Pa and Ma as partners who continuously deliver him external chakra, so either genjutsu attempt would prove to be futile considering it would be broken in an instant

Susanoo is no problem either

Gaara helped us to know that . Well, Jiraya has a perfect counter for this with (Jiraya even said it was ). 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 like he already did in part1. He can also create an opening to capture him in the like he did against Pain

Sasuke made us understand because of sound vibration. Well, Pa and Ma have (able to paralyse Pain summons). With this jutsu, it would be easy for SM Jiraya to paralyse Itachi and finish him either with his or or even something else in his arsenal.

We also know thanks to Kabuto, that , so Pa and Ma use this and he is done for:
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Not to mention the heavy drawbacks of MS techniques on Itachi that could leave openings or the fact Jiraya possess a large stamina advantage. All in all SM Jiraya is superior to alive Itachi
 

blazekev90

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Jman wins high difficulty.
 

Latios

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Itachi Low-Mid Dif.
 

Demonic.

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No one is winning this low difficulty. Pain the strongest akatsuki member took it high difficulty. Itachi is sick and Jiraiya has better stamina. Kishi says they are both equal in the databooks. I don't know why people say Itachi low difficulty.
 

Sweg

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Itachi mid-high diff.
 
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