Can Jiraiya fight Itachi and Kisame together

Jiraiya before the battle with pein vs itachi before his fight against sasuke. Who wins?
Scenario 2: Add kisame to itachis side
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Murazor

Chief Encyclopedist
Depends on various factors, but Jiraiya needs to achieve surprise or immediately block Itachi's line of sight, because he is not fast enough to dodge Amaterasu like A could, nor durable enough to ignore it even briefly and lacks the means to push it away like Nagato did.
Solo King Itachi solos huehuehuehue

Joking aside, this is actually pretty hard to pin a winner. Jiraiya has immense experience and Itachi has his hax eye powers. I want to give it to Jiraiya as he fought more or less evenly with Pein with Sage Mode

Murazor

Chief Encyclopedist
Solo King Itachi solos huehuehuehue

Joking aside, this is actually pretty hard to pin a winner. Jiraiya has immense experience and Itachi has his hax eye powers. I want to give it to Jiraiya as he fought more or less evenly with Pein with Sage Mode
He kind of didn't.

He got hard countered by three of the bodies, managed to withdraw, pulled what seemed a win thanks to a clever ambush and the frog song, then got ambushed in turn and got steamrolled.

Murazor

Chief Encyclopedist
Susano'o makes this a victory for itachi.
Amaterasu is a likelier path to victory, really. Susano'o is not something that Itachi in the state he was in at the time can spam and it has vulnerabilities that Jiraiya can exploit (re: sonic genjutsu).
Im pretty sure Itachi out right stated that he vs. Jiraya would end with him losing, while he + kisame vs. Jiraya would end in a mutual kill. Or something like that.

And that was before the timeskip. Afterwards, Itachi would likely be already somewhat weaker because illness.

Also, when actually confronted, Itachi and Kisame together decided taht running away was the right thing to do, and had to burn an amaterasu to escape.

Whatever we think, the characters themselves seemed pretty sure on how this would turn out.
I thought the only reason Itachi ran was because they were under orders not to draw attention to themselves or risk losing the kyuubi.
Context is kind of important.

Jiraiya activated his jutsu before Itachi and Kisame knew he was there, transforming the narrow hallways of the hotel into a giant frog stomach that could ooze flesh dissolving acid from every surface and be reshaped on a whim. Oh yeah, and Naruto was stuck in that hallway with them, preventing them from using any jutsu with significant collateral damage because they'd run the risk of accidentally killing him.
Oh, and Itachi didn't even say that Kisame + him vs Jiraiya would end with them losing or a mutual kill.

First, he confirmed that Jiraiya was the source of information onf the Akatsuki, and how Kakashi knew about them. Then, he outright told Jiraiya what the fundamental purpose behind Akatsuki was, which he didn't know till then. After which, he wasted Tsukyomi on Sasuke (which Kisame outright tells him in that very page that it weakens him and that he shouldn't use it that much). Then, after Jiraiya sets up the Iwagama stomach trap, he uses Amaterasu to blast their way out, and when Kisame asks why he didn't deal with Jiraiya then:


Reasons are, in order:
- No need to be hasty, considering the info about Naruto
- Need some rest
- Shouldn't use 'it' until Tsukyomi becomes stronger (or something, that bit's not very clear)

Nowhere is it stated 'man, that guy would totally kill us'.
They totally do say that though.


In the oldest scan I can find of that chapter across multiple sites.

There is also, from the official Viz translation...
In Naruto dubbed 83 not only does Kisame say he thinks Itachi could go toe to toe with him and that Kisame is outclassed, but also Itachi says he would be killed by him, even if he had back-up the result would be the same.
Jiraiya's a scary guy. The one time we actually see him go full-out, he murders his way through several giant summons and kills 3 S-Class threats, one of which has absolutely broken chakra absorption, and hardly breaks a sweat doing it.

If he started out in Sage Mode, I really, really wouldn't give Itachi any chance. Jiraiya would just bullrush through anything Itachi threw at him and lay him out, either with a huge AOE jutsu or sheer physical power. If Itachi pulls out the Susano'o, shits already going really bad for him. He doesn't have the stamina to use it for very long at all. That said, if he nails Jiraiya with the Amaterasu or Totsuka Blade... that's it. In the former case, Jiraiya would be lucky to only lose a limb (which would only slow him down) and the latter is a OHK.

Glass Cannon vs Genuine Tank. Both very fast, both very dedicated. But one of them doesn't have staying power. I'd give it to Jiraiya 7/10, personally.
I say Itachi takes this.

In a neutral area against a high level opponent that fights him seriously, I don't see Jiraiya entering sage mode.

Giant summons also make giant targets, so I don't see them evading Amaterasu.

I don't remember any of Jiraiya's Ninjutsu to be impressive enough to be clearly superior to Itachi's. Coupled with having to constantly watch out for genjutsu, I'd give Itachi the win.
Depends on various factors, but Jiraiya needs to achieve surprise or immediately block Itachi's line of sight, because he is not fast enough to dodge Amaterasu like A could, nor durable enough to ignore it even briefly and lacks the means to push it away like Nagato did.
Keep in mind that in the Sasuke fight Itachi needed quite a bit of time to charge up Amaterasu before he could start using it. Its also not in character to use it as his opening move.
I honestly feel like pre time skip Itachi, who we assume is a lot healthier, would be far more threatening. Itachi was practically blind by the fight with sasuke.
Itachi can bring out his big OHKO guns immediately by staring .. Ama, Tsukuyomi, Susanoo

old man needs time to even go into sage mode

giving it to Itachi if he doesnt hold back
As of his fight with Pein, Jiraiya had already worked out how to hard-counter Amaterasu.

Hell, it took him about 30 seconds after seeing Amaterasu to figure out how to hard-counter it. Jiraiya is fucking scary. He slaps down S-Class ninja who make credible attempts at killing one of the series' main villains like petulant children. At the same time, though, Itachi is easily the next most powerful Akatsuki member after Pein - and those magical doohickeys he's got on his Susanoo will be very difficult to deal with.

That said, I'm going to give it to Jiraiya 7/10 as well - he can definitely take Itachi with a bit of prep, he's good enough at hiding to stay out of sight and gain that prep time, and Itachi doesn't have the same ability to track him that Pein did.