So, was Itachi one of the the best shinobi in history...

So, was Itachi one of the the best shinobi in history? He basically only lost to Sasuke because of his mysterious illness, and never really had a good match in his entire life.

If this is so, why was he reluctant to fight Jiraiya? Did he just not want to bring the heat on him and Kisame; if that's the case, why not just say it instead of telling Kisame "we can't waste time on this." Instead, he predicts that they would all die in a *best* case scenario.

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Itachi and Jiraiya both are among the best Shinobi in history.

Jiraiya would have whooped his ass

Itachi says as much, but why? Was he just being modest, or overplaying how strong Jiraiya was to Kisame just to keep things from getting messy while Sasuke was there?

The only correct answer is that the Legendary Sanin power level was retconned.

They (Oro, Tsunade and Jiraiya) were supposed to be Op as fuck in original Naruto. In Shippuden they got nerfed A LOT.

Itachi was also Op as fuck in original Naruto too, probably Sanin level. Itachi says it pretty clear, “If I fight against Jiraiya both of us would get killed”. But in Shippuden (Susanoo + Izanagi/Izanami) Itachi becomes way too Op even for legendary sanin levels, humiliating Orochinaru like he was a piece of fucking shit.

Because, in original Naruto, Itachi didn’t have Susanoo and the other asspulled eye powers he gets in the war arc. I get what you are trying to say, with those powers he is almost unbeatable thus making the retcon seem ridiculous.

So in original Naruto Itachi was strong but the power levels were way more balanced. Without Susanoo a Jiraiya vs Itachi battle would have been way more balanced.

>Oro

I see this comparison being made, but Itachi knew exactly how to counter Orochi, and was on a similar power level to the sannin. I think he was more reluctant with Jiraiya because he either

A: didn't know enough about him
B: knew enough about how Jiraiya had sage training, and assistance from the Mt. Frogs and that would seriously hamper Itachi's strengths.
Oro did not have the same relationship with his summons that Jiraiya did. Without Genjutsu, Itachi has to out "power" Jiraiya, and he probably can't.

Logical explanation

We never got to see how much chakra Itachi would have in an ideal situation since he was either in Edo form or dying of AIDs in both instances. However I don't think stamina was ever healthy Itachi's strong suit, can't see him being able to maintain Susano'o for much longer than Sasuke during Kage Summit arc. If Jiraiya can fight with his eyes closed I see him beating Alive Healthy Itachi. Edo Itachi however is absurdly broken

this is probably true

Yeah it actually makes sense. I buy it.

Who would have won?

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Pain, no doubt.

Pain was a whole new level

/THIS

Canon living sick Itachi cannot spam MS techniques like his immortal edo counterpart who has infinite chakra, broken regeneration and most importantly no MS drawbacks no matter how much he spammed amaterasu and Susano'o. So yeah i do thing Sage Jiraiya and canon living sick Itachi is quite balanced match-up. His broken edo form is a whole different story tho.

Pain solo'd whole Konoha, fought Sage Naruto with myoboku backups and then proceeded to fight 8 tailed berserk Naruto. Think about it, dude is on whole another level than Itachi.

Back in the day it was a balanced fight but when Kishi came up with Susanoo in Shippuden, MS users (lets not forget Itachi also has the Totsuka blame, one of the most Op weapons in the whole show) became ridiculously Op and almost unbeatable

If this is true, Pain *also* stated that had Jiraiya knew his secret, he would've won. These are two extremely strong/ skilled shinobi both coming to the same conclusion. Clearly Jiraiya was stronger than we actually witnessed in the entire original run.

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>If this is so, why was he reluctant to fight Jiraiya?
I would say that there could be multiple reasons or explanations for this.
Maybe Itachi was weaker at the time. Jiraiya probably didn't get more powerful from early Naruto into Shippuuden but Itachi was still young and could've easily gotten a fair bit stronger over the few years that the story takes place.
It could also be that Itachi wasn't fully aware of Jiraiya's powerlevel and merely made assumptions based on what he had heard about the sannin and what he had seen of Orochimaru during his time in Akatsuki. He knew that Jiraiya was strong but didn't know much about his abilities while Jiraiya has more experience under his belt and could very well have developed some ways to fight against sharingan.
There's also the fact that Jiraiya chose to take Naruto along with him even when they were leaving the village. That was a power move. It showed that Jiraiya had confidence to keep Naruto safe even when he knew that Itachi and Kisame were after him.

what were his real powers? sage sensing, genjutsu break, frog genjutsu, super speed and strength, rasengan, and high-level elemental jutsus? This seems pretty strong but I wonder because elemental jutsus literally never do anything significant

Pain was being restricted on his home village to not nuke everything to oblivion. Full knowledge Jiraiya might come with some plan using his guerilla tactics.

His undetectable toad dimension barrier was quite broken. He could just take the path one by one into his barrier.

Yeah, but he didn't say the reason was his home village, simply that Jiraiya did not know his secret. Again, this could be modesty or respect for his former master, but there's no reason to believe it's simply that.

>merely made assumptions based on what he had heard about the sannin and what he had seen of Orochimaru during his time in Akatsuki.

One of the things that made me mad is how awful the Itachi vs Orochimaru “battle” is and how bad it makes Oro look.

Orochimaru was Op as fuck, lets not fool ourselves. I’m not saying Itachi wouldn’t be able to defeat him, because he is strong too, but LIKE THAT? With a basic Sharingsn (Not even MS) genjutsu that even Kurenai was able to breakthrough?

I’m not buying into that shit. For me that battle isn’t canon. He also made Deidara look like an imbecile but that’s a whole different story.

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When did that Ita Oro fight take place? It's been a long time.

Itachi’s genjutsu is broken as fuck and it gets annoying. He doesn’t even need to fight or move a finger because he can solo almost everyone using just genjutsu.

Deidara vs Itachi and Oro vs Itachi are great examples.

I'm gonna go with Itachi just *knew* exactly how to deal with Orochimaru. Not sure if it's from Anbu, or just working with him in Akatsuki. But whatever the reason, he had his number. If you can accept that, it makes sense that he was prepared to put him down several times before Orochi even knew what hit him.

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Wouldn’t killing Jiraiya be massively bad for the leaf? It’s one of the few times where Itachi being a double agent actually made sense in hindsight.

I'd guess ~4-5 years before the start of the manga. We know it was between the Uchiha Massacre and the Chunin exam.

Oro is one of the most analytical and smartest ninjas in the whole Naruto universe. Are you telling me he wasn’t prepared for countering Sharingan genjutsu?. Sorry chief, not buying into that.

Kishi had not yet buffed Itachi's powerlevel to match the post time skip era of naruto.
at this point Jiraya was supposed to be among the absolute top tiers so he probably would have beat itachi and kisame.

>analytical and smartest ninjas in the whole Naruto universe

...and then there's Itachi. Oro overplayed his hand many times in the series, so clearly being smart and analytical isn't enough to keep his ego in check.