Itachi vs Pain

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Ashura San

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Itachi is much more analytical than Naruto. He would've found a way to beat them.
His intellect is often not taken into account.
Kakashi figured it out on his own and they're on par when it comes to intellect.
 
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shusui uchiha

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ill have to say itachi if itachi thought nagao it would be different but i dont think pain would win itachi would be able to get inbetween the 5 second interval we have seen in the fight against pain vs sage jiraiya that genjutsu very effective against all pains and itachi has that in the bag with tsykiyomi amaterasu and sussano i believe would be to much for him also itachi smart and can find weakness in a jutsu like that as we have seen him destroy planatery devestation (with help) at a stronger form when nagato used it i believe if pain used it it wouldnt be as strong as nagatos as hes at his prime in reanimation also izanami would be very effective against pain because of his life im not saying it would be easy but i think itachii takes this oneguys :)
 

Davy Jones

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Itachi is much more analytical than Naruto. He would've found a way to beat them.
His intellect is often not taken into account.
Kakashi figured it out on his own and they're on par when it comes to intellect.
This is very true... people do not take this into account. Itachi with intel will smash, Itachi without gets smashed.

No intel: Pain 8 times outta 10

With intel: Pain 6 times outta 10
This is the most plausible answer
 

Sleipney

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Tho i like both of them i think Pain would take this one just cause he can absorb all ninjutsu and the planetary-jutsu is too much for the susanoo alone.
Now that i think Itachi's susanoo has Yata Mirror and it can reflect all ninjutsu too so hard call, but still going with Pain high-diff.
 
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