The two would have won. I think Itachi alone is actually strong enough to beat Jiraiya. Kisame too? Please.
This is of course based solely on feats and what all the characters have proven to be able to do. Dunno, or care, if they got boosted during the time skip.
I'm pretty sure they'd beat Jiraiya- though it's worth noting Itachi had already used his mangekyo twice before they even really began so he's probably going to have to limit usage more than usual, making it a harder fight than a two-on-one should be, and there's no way it'd be over before reinforcements show up.
Yeah, Guy would show up sooner or later. I just think the two would be too much for Jiraiya on his own. Granted, Itachi being tired presents a problem but he really only needs one Tsukuyomi for a distraction.
wait a sec, people are still sticking with the plot here so nothing would change as itachi didn't want to cause a war in konoha
you'd have to remove sasuke, remove the goal nobody can kill: naruto, and take the fight our of konoha just for itachi to fight and let kisame go nuts.
According to both Itachi and Kisame Jiraiya would of beaten their monkey asses.
The fact that he is physically strong enough to make Kisame a non-factor supports this, as well as possessing a mode that arguably would make his movement faster than Itachi's.
I'm fairly certain that that statement came from his Sanin rep more than anything. And it doesn't help that the meaning of the statement has changed since the revelation of Itachi's hidden alliance.
Though what indicates that he is stronger than Kisame out of Sage Mode? Out of curiosity?
I thought the whole lifting of giant rock toads was that indication. Then the giant Rhino toss which borders on being the best strength feat in the who manga...
Is Jiraiya weaker than Naruto in Sage Mode? I always thought they were about the same with Jiraiya having a more diverse set of Jutsus to use in Sage Mode due to his experience.
Also, it looks like Jiraiya can enter sage mode faster...due to Ma and Pa.
What did he think he was going to accomplish? Did he really think his genjutsu were greater? I can see ways how it could (and did) go wrong, but I can't see what could have gone right. Even if he was immune, why leave himself open to the possibility? Just look somewhere else.
I answered already: He thought his eye was enough to make himself immune to Itachi's sharingan.
It wasn't that he thought his genjutsu was greater...he just thought his Sharingan made him immune.
And he looked because he thought his eye was immune (true...for the most part...but not against someone who had mastered the eye much further than a 3-tomoe user) and the eye offers an awesome precog ability. Seems fairly reasonible if you consider that Kakashi was not aware of the MS at the time. Or at least not aware that Itachi had an MS.
Out of Sage Mode feats please, not Sage Mode feats.
And to answer your question, I don't think so. Jiraiya made it clear that he was going to hit Pain with full force from the start. And then he implies that he needs time to call them. Since he is not as good at Sage Mode as Naruto, I figured he needed help from the Toads to actually enter it.
As to why Kakashi bothered with keeping his sharingan eye open, it would be worse if all of them closed their eyes.