This is a great thread in that it details some of Jiraiya's techs, however it's been tainted with some of the posts with... fanboyism?

The original OP is great, though. I agree with it. He was a very versatile shinobi.
It's not a good idea for anyone to get a good thread like this off-topic by posting about another character. This denotes that a) The character the thread is about is not interesting enough for the discussion to be only about him, b) The character's fans are salty and thus need to stealth bash another or demean another, or c) The fandom of the character who the thread is about feels insecure about something.
Now, to address this...
Honestly, he loses mid-diff.
Normal genjutsu wont be very effective on Jiraiya.
He uses abilities like disturbing his chakra while in a genjutsu to break it, as shown in his training with Naruto.
Jiraiya can use kage bunshin. A good tactic vs genjutsu is to let your kage bunshin get caught instead.
He can also summon toads that can pull him out of genjutsu.
Naruto spent 2.5 years under Jiraiya's tutelage. He used the technique Jiraiya taught him and it was proven completely ineffective. And this was just for 3-tomoe genjutsu.
Jiraiya has to have toads already summoned. Animals can get caught in genjutsu as well (crows, snakes ie: Manda have in the past). The frogs get caught and Jiraiya is out of luck.
So, Itachi is going to miss Jiraiya and catch a Kage Bunshin every time he attempts to attack with genjutsu? I doubt this.
Itachi cant last long in a fight.
When he uses Tsukuyomi and Amaterasu once + Susanoo for a short while, than he already needs to rest.
So he needs to kill within those abilities.
Jiraiya has huge chakra reserves and can certainly outlast.
Depends. Itachi has always been one to end conflict quickly, it's not something he enjoys. He knows not to resort to taxing techniques.
Itachi can last as long as he wants to as long as he doesn't use techs that are too draining.
Basing a fight simply on chakra reserves is the equivalent of saying Kushina>Tobirama since she had greater chakra reserves than he did. Better stamina isn't the only factor in the fight, believe it or not it's one of the minor factors.
The only thing in Itachi's arsenal that can be dangerous to Jiraiya is Tsukuyomi (due to the time control), but as said, it is not something that Itachi can spam several times. If Itachi catches a kage bunshin with it instead, than he will basically lose the Tuskuyomi ability in the fight, due to not being able to spam it.
No, everything is quite dangerous. Amaterasu even left Jiraiya in a cold sweat in part one and he spent 1-2 minutes sealing it away while being still. One to two minutes is a long time in a high profile fight like this.
Jiraiya can easily create an opportunity to go SM.
With things like frog summons (he has all kinds of frogs, melee frogs and also genjutsu frogs, the one with the lipstick), kage bunshin, barriers (and frogs he can hide in) and several other jutsus.
While in SM, he doesnt even have to look into his opponents eyes. He doesnt even have to have his eyes open.
Sage mode sensing takes care of knowing where the opponent is and what he does.
So, Itachi is going to stay distracted for the amount of
minutes needed to get SM ready? He's not. He's going to keep his eyes set on Jiraiya and continue looking for openings, whilst attacking.
Jiraiya's SM is incomplete and he failed to notice the Pein body coming at him from behind.
Itachi has no counter vs the special sound genjutsu from ma and pa frog.
Amaterasu is not very fast in general, as in that it has stages, first the eye turns into MS, than it starts to bleed, than the flames appear. With SM you can sense this danger coming (there are even frogs with shields to help blocking like Gamaken).
Without you can make lot of kage bunshins to make sure the real body doesnt get hit (in SM you can do so too).
Itachi cant spam his abilities, so he cant keep Amaterasu up for long and target all the bunshins.
Jiraiya has huge chakra reserves (a requirement for sage mode) so he can make lot of kage bunshins.
A clone on standby can break him out. Or, better yet he wouldn't get caught considering he'd use genjutsu on all 3 before that happens. Or, even more likely considering Jiraiya had to hide from Pein's view for quite some time to get that ready, it never initiates. Ma and Pa probably don't even make it to the fight.
No, Itachi takes it med-diff. Only chance J-man has is if Itachi is ooc and let's him start out in SM, but even then the battle is a win to Itachi for high-diff.
Jiraiya is very versatile.
I agree and it's always great to see his techs. However, versatility doesn't win a fight. It helps, but isn't the main force.
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Jiraiya acts like a pervy goof from time to time, but when it is required, he can be very intelligent and I not only battlesmart. He almost defeated Nagato's six paths of pain by coming up with great tactics and as said by Nagato, if Jiraiya would have had intel on him, than they would have lost.
He can be very intelligent. However, Itachi is moreso. (Databook 3 confirms this.)
Pein said that because he thought Jiraiya would go after the real one, Nagato, if he knew. Also, Pein would have eliminated Jiraiya early on with CT had they not been in the Rain village, which he cares deeply for. CT would have caused destruction...Nagato actually had to hold back on his main OP techs in that fight.
No need to go into that much detail all you need to mention is that Itachi admitted he couldn't beat Jiriaya. Itachi and J-Man are both great, but Jiriaya is stronger and that's no knock against Itachi whatsoever.
No, he's not stronger than Weasel. But, I agree that they're both great characters. U_U
If you want to go by that logic and ignore how it was disproven through various statements in part two (mainly Obito's), then we might as well bring up when Itachi said at that same time "Only one with Uchiha kekkai genkai and blood can defeat me".
Phrases are mainly meaningless, especially when they're dis-proven like Itachi's lie about Jiraiya>himself/Kisame/other Akatsuki.
Itachi cant just win anyone he faces because he wants to.
Jiraiya has a counter or fighting option to everything Itachi has, but Itachi doesnt have one for everything Jiraiya has.
Jiraiya just has to get into sage mode, which he can.
I dont underestimate Itachi.
I think he is a great character, however in a 1 on 1 between the two, I believe Jiraiya>Itachi, due to points I have stated.
No one can win anyone they face just because they want to.
No, he doesn't.
He probably won't, to be honest.
You did underestimate a little. Lol Itachi>Jiraiya on a 1 vs 1.
And both are great characters.
Every reason the guy you were having a debate with stated U_U. Itachi admitted he couldn't beat Jiriaya, even if he had back up.
That was a blatant lie that the majority bar extreme Jiraiya fanboys can acknowledge. Jiraiya is not beating Kisame/Itachi/Obito/Nagato/etc all at once. Lol
didnt Itachi himself say to Kisame that they both would have died even if they together fought Jiraiya Sama? and that is the reason of the duo fleeing away!
that definitely makes it clear how strong Ero sennin was!!!!!
Yes. And then, in the anime Chiyo stated that the reason the Akatsuki stayed away from Naruto wasn't Jiraiya at all, but because they had trouble sealing the beasts in the statue, so they weren't in any hurry to get him. Lol