Board Thread:Versus Debates/@comment-36351381-20180802192015/@comment-5085906-20180806094650

I don't think Tsukuyomi is gonna be a deciding factor. Rinnegan was pretty much immune to Infinite Tsukuyomi, which was like a stronger, more intense version of Itachi's version. And even if the Tsukuyomi were to work, a brute fighter like Might Guy had figured out a way to counter it and we all know he's not the smartest tool in the shed. I think a tactical genius like Nagato would be able to avoid looking at his eyes with relative ease.

It's all gonna come down to Deva Path. If Itachi can neutralize Deva Path early on, I believe he can take down the other Paths with Mid to High difficulty. We've seen from Jiraiya's fight with the Six Paths of Pain that even though they're quite troublesome, they're not that hard to kill as one of them died from Jiraiya's kick (granted he was in Sage Mode) and the other died from a normal-sized Rasengan. If, however, he wastes too much chakra dealing with Deva Path and/or Deva Path activates Chibaku Tensei, Itachi's fucked. We saw him escape Chibaku Tensei once, but it was Killer Bee and Naruto's arsenal that enabled him to do so. His Yasaka Magatama would barely inflict any damage on the jutsu.

So, I think Pain wins this 6/10 times.