1. the databook scores are irrevelant orochimaru has a 5 in genjutsu yet a teenage itachi managed to get him in a genjutsu, databook arent always a valid source to rely on.
2.itachi also saids even with back up it would be the same outcome, so you agree that itachi+kisame+other akatsuki members can only then take on jman?
3.itachi was on a mission to protect kohana why would he want to kill one of the legendary sannin and cause more trouble? he mainly went their to show danzo he was still alive and that he shouldnt lay a finger sasuke
4. you seriously think if they were really after naruto they couldnt have taken him?
5.last i checked kakashi is still alive, itachi chose not to kill him, what itachi did to kakashi was just a way of him showing that this is the REAL UCIHA POWER
6.
Besides the databook (and various statements made throughout the manga, e.g. Pain stating that Jiraiya could have won their epic battle), I will also like to point out that Jiraiya is an efficient counter fighter. His entire fighting style revolves around him being able to think on the spot, with his humongous /versatile arsenal, and successfully counter his opponent(s). This means that he won’t fight two different fighters the same, and he will specifically design his game plan around his opponent’s strength/weaknesses i.e. he will break down Itachi and realize that he should be worried about Itachi’s genjutsu. He would keep the battle long range, avoid eye contact, and last but not least summon toads and/or Kage bunshins which would raise his odds considerable e.g. Itachi would be hesitant to cast Tsukuyomi when he sees several clones in front of him, of course due to his poor chakra/health.
1. he doesnt have poor chakra
2.your acting like jman is the only genious here, itachi can also breakdown jman's weaknesses and form a plan? are you not?
3. avoiding eye contact wont matter itachi can use his finger genjutsu
4.same goes for jiraiya the amout of times itachi's escaped a situation due to his quick reaction time and shadow crow techs
As I said, we have witnessed Jiraiya’s unique fighting style in a lot of different scenarios. He deduced Konan’s weakness in mere seconds and disposed of her like she was pure fodder. Which we know is false since she technically killed the most invincible man on the planet. He also knows when he is outmatched and when to actually revise your plan. Against the six path of pain he figured out the fact that he needed to separate them and actually meet them one-on –one, which is brilliant. He also realized that one of the paths could turn “invisible” so he decided to use a barrier that is able to detect movement. This again indicates, that Jiraiya can’t be caught with his pants down… unless in a bath house.
it seems you are biased towards jman, you barely went over itachi's great planning and fighting style and his achievements
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tobi even saids if he didnt keep secretes away from him eh would be dead right now that shows how smart itachi is and how dangerous he is.
i shouldnt even have to go over itachi's character because its obvious.