Versus Battle Is Pain vs Itachi a debate?

This is definitely a debate! Probably the most classic Naruto vs. debate due to the big fanbase of both, lol. I feel like this is one of those fights that are just impossible to predict, since with 7 fighters and so many diverse Jutsu involved there are thousands of ways this could go. It'd be an extreme-diff fight either way. However, a few pro-Itachi considerations:

Sick Itachi's stamina
For peak performance healthy Itachi is often considered, but honestly, even sick Itachi did quite a lot if you recap the whole fight. Itachi endured:
  • 1 x Tsukuyomi
  • 2 x Amaterasu, the 2nd time spamming it for an extended period and producing huge amounts of flame
  • 1 x Extinguishing Amaterasu, which takes another big toll on the body as was seen when Sasuke did it vs. Bee [X]
  • V3 Susano'o for an extended period of time non-stop
So, if we rule out purposely extinguishing Amaterasu, which is not gonna happen vs. Pain, that's at least 4-5 Mangekyou techniques, prior to extended V3 Susano'o. And mind you, this is worst-state, almost blind Itachi who also took a blade to the thigh and got half-toasted by Kirin. Pt. 1 Itachi did 2 x Tsukuyomi and 1 x Amaterasu and was exhausted, but could still perfectly move [X].

Susano'o versatility
Susano'o, even without Yata and Totsuga, is imba. Even incomplete base form cushions massive impacts as long as it's not broken [X, X], its activation is instant, also allowing for surprise attacks [X, X], and its base attack power is huge, e.g. a simple hand swipe cutting Shurado's metal body [X] that resisted even Raikiri. This means that any simple Shinra Tensei is basically negated, and a careless Bansho Tenin could be deadly to Tendo.

Summonings
I don't think summonings play such a big part in this. Itachi can see the chameleon and the others are way too telegraphed and slow, so the only actual threat I see here is Ceberus. And that can also be dodged or disposed of with Amaterasu. Also, Itachi's Sharingan should be able to control or at least paralyze the beasts (like Itachi did Kabuto or Sasuke did Manda). They are still beastly in behavior, so are unlikely to avoid eye-contact like the paths themselves and/or can be forced into eye-contact way more easily.

Genjutsu vs. Rinnegan
This is I think one of the most important and complex aspects of the fight, and imo it's just way too speculative to have strong opinion on. Some thoughts:
  • I think a visual Genjutsu cast on one of them wouldn't affect the others, since it's only the actually hit Pain's "eyes" that are being affected? It's hard to explain, but I imagine it kinda like a Medusa situation where you're immune if you look at her indirectly through a mirror. Nagato has knowledge of Pain's conversations, that means they share not only vision but also hearing. Despite that, Nagato and the other Pains weren't affected by J-man's acoustic Genjutsu. So I imagine it's similar for visual. Or they were affected after all and J-man simply wasn't aware because they were in another location, lmao.
  • I think that visual Genjutsu on Itachi's level does work on Pain. General Genjutus proficiency and the ability to see through them have been portayed as specific Sharingan traits. Natural Rinnegan evolves when Uchiha and Senju genes are combined, and it's the culmination of both. So a natural Rinnegan, which includes Sharingan abilities, would most definitely be able to counter Tsukuyomi. However, Nagato's is an incomplete Rinnegan, as he lacks the Uchiha genes, and is devoid of any Sharingan abilities. So imo there's no base to claim that Pain/Nagato could escape Tsukuyomi just because "it's Rinnegan to it's superior lol".
  • That being said, I think Tsukuyomi could work on Nagato but not on Pain, since on paper they're corpses, and thus shouldn't have a psyche that can be broken. Paralyzing Genjutsu could work, but might be easily broken by Nagato breaking and then re-assuming Chakra connection to that body. But it could still be used as an opening for Itachi regardless.
As I said, too speculative. But I love that the manga gives such a rich base to speculate from.
 
Good for him, Konan and Pain were also talking like they could take on Obito lol

Obito wanted to solo edo akatsuki if it wasnt for Madara's edo
I am not saying Itachi beats Obito, just pointing out that there was a point where a healthy Itachi existed and we have a sense of his strength as he was bold enough to threatened Obito
 
I am not saying Itachi beats Obito, just pointing out that there was a point where a healthy Itachi existed and we have a sense of his strength as he was bold enough to threatened Obito
Empty words.
Even "Healthy" itachi doesnt defeat obito

and we dont know how or when itachi got totsuka blade and yata mirror, he might or not have it at the time

and in anime fillers, "Healthier itachi" struggles with Amaterasu like sasuke at the beginning, cause he is not comepletly use it.
 
Healthy alive Itachi gets outlasted. Can't see him beating Pain. I don't blame the fans for forgetting how taxing the Sharingan abilities are.

Edo Itachi may actually come close to but Nagato is broken man.
I have edo itachi over edo nagato but alive itachi unfortunately loses due to ninja aids and MS being way too risky to use, i think he used one tsukiyomi and 2 amaterasus and was done vs sasuke. He was particularly blind
 
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