Board Thread:Versus Debates/@comment-26958911-20151010214426/@comment-27085122-20151018041715

I'm pretty sure itachi would win. I say this because the fights start when they are both at their base form. Jiraiya's sage mode is not instant, and a good bit of his strongest attacks are melee range (Rasengan as a power move and frog kumite as taijutsu). Itachi is a genius, probably as smart if not smarter than shikamaru. His power does lack compared to jiraiya but the way he uses it is much better. He would be able to sense jiraiya going sage, and likely take preventative measures. But lets assume jiraiya makes it into sage mode without qualms, the genjutsu is likely out of the picture unless the terrain allows him to hide considering it takes time to gather the chakra and itachi would see this, and focus on it. And as smart as jiraiya is he would know that getting into itachis range of tsukiyomi is an instant lose so he'd stay ranges, and use summoning jutsu's. Also it could be left to theory that a top shape itachi could use a full-bodied susano'o(Which can fly)so his swamp to try to catch itachi would likely be of no use, but even if he still couldn't it wouldn't be a big deal to burn it. I doubt he would know what itachi's susano'o was equipped with before he see's it in action at least once, considering orochimaru didn't realize it until he had been stabbed, and he had been looking for that same blade. After he see's the totsuka blade seal one of his summons, he might think twice about going into melee with the sword, and once he see's the mirror blocks any attack he would realize he would need to circumnavigate the shield somehow. This would leave jiraiya with Overpower the shield and destroy it anyways, or focus on misdirection and geurrilla fighting. I might think that a sage giant rasengan might be enough to destroy the shield, considering it's jiraiya, but that would leave him susceptible to tsukiyomi and amaterasu, which would be itachi's win. Him focusing on intelligent fighting would usually work, but it sure as hell wont overcome itachi. I think the fight will come down to wether itachi can catch jiraiya in his tsukiyomi, hit him with amaterasu, or seal him, which itachi almost certainly can. In order for Jiraiya to win, he would have to connect in melee range with a super powered move, which isnt impossible, but very, VERY unlikely when fighting someone as intelligent and strong as itachi. I'd give this fight to itachi 8/10 times