Ok first off i just want to say i beleive Itachi wins this
I want someone who thinks Jiraiya would win to answer this.
Most people say Jiraiya is to smart to be hit with Tsukuyomi but if he doesnt look at itachi in the face how is he going to fight him? Only someone like Mite Guy can predict movements just by looking at thier feet, and you cannot assume Jiraiya can do that. Not because he cant because its not in the manga (you cannot use an argument that isnt factualy based in the manga.)
And everyone says that the natural energy will save Jiraiya or Ma and Pa could put their chakra in him but what happens when Itachi puts all three under Tsukuyomi? Than they are all screwed.
Amaterasu is not something that anyone can just dodge, Sasuke dodged it because he used Orochimarus white snake ability and Itachi wasnt aiming for him completly or that would have defeted the purpose of keeping sasuke alive. Madara just had the fire phase right through him. And When did Jiraiya show any teqnique that shows he can get away from amaterasu?(which is considered almost unavoidable)
And Sussano, Please someone give me a legitament argument on how Jiraiya can beat this. running away counts as a loss so what does he do? He cant hit Itachi because of yatas mirror no jutsu that Jiraiya has will help. If he uses swamp of the underworld Itachi could use those seconds to hit him with the sword of tskota.
I'm a Jiraiya fan and ill try to be concise as much as I can.
1) Genjutsu, people are always looking at only some way to break genjutsu and NOT ALL of them. Not looking at a sharingan is not a way to break genjustu but it's a way to avoid being caught in genjutsu also itachi can cast weaker genjutsu with his finger, but this isn't Tsukuyomi. Anyway lets get started;
- Disrupt your chakra flow within your body, you know the same stuff Jiraiya was trying to teach Naruto during the time skip for any encounters with genjutsu users. So can jiraiya do this? I think he can and if can't and could try to gather some natural energy to disrupt his chakra flow.
- Cause pain within your body to come back to your senses. For example shikamaru broke his finger against the sound genjutsu girl with the flute in part 1. So could jiraiya inflect damage to himself? to break out of the genjutsu off-course he could but at what cost. A simple stab into in his body will break him out of it, Naruto in sage mode stabbed in himself twice and was able to fight in full flight.
- Using shadow clones makes genjutsu useless if itachi gets impatietnt and cast Tsukuyomi on clone the chakra loss would hurt him alot. Jiraiya's use of shadow clones is fantastic look how he stalled nagato before he entered sgae mode. Jiraiya isn't going to sit around waiting for itact to cast away and Itachi knows that which why he respects his stature as a shinobi.
Amaterasu obviously is not something you can negate or can you? Funny enough JIRAIYA is the only person who isn't an uchia that was able to the flames out. Jiraiya sealed them. But obviously this isn't practical in battle, so what can jiraiya do?
- Well speed is the key here like all the other characters that do deal with the black flames. Question is do you think jiraiya is fast enough? I think yes, sage mode has a lot of raw speed.
- Jiraiya is also an earth element user and that so far has shown the best defense against the black flames as the black flames have never burned right through earth due to the slow burning nature of the flame. So jiraiya can give himself time to escape an area scorched with black flames.
Sussano is not invincible, and most people don't understand how dangerous it is to the user aside from the person going against it. Sassano after certain amounts of damage can be visually damaged. And for the user to repair the damage he users his own chakra and physical energy to repair sassano. This was noticeable by sasuke during the kage summit and once again during the fight with danzo. This is how sassano works. Itachi has found a way around this by finding the legendary weapons the haxxed shield and haxxed genjutsu sword. So this obviously a question who last the longest and this where the fight will be won or lost. And it can either way, either itachi will lose all his chakra or jiraiya would get caught with the genjutsu sword.
Even itachi's illness we saw during the sasuke fight I don't believe he would have enough gas to maintain a high level fight jiraya who more less doesn't have to worry about his chakra reserves.
Make your decisions people but the facts as they stand are itachi falls short, also itachi needs the legendary items to compete in the latter stages of this fight, take them out the picture and I'm sorry to say itachi has no chance without them.