I will just post my thoughts from one of my previous threads:
Kishi made it painfully obvious that these two Kage-level fighters are equals. Yet a lot of people choose, on purpose or not, to underestimate Jiraiya when conversations regarding these two inevitable occur. I think fanboys aside; a lot of it has to do with the whole out of sight, out of mind mentality which isn’t unusual with all the awesome fights we have witnessed after Jiraiya’s death however the facts remain.
Databook scores: 35, 5 vs 35, 5.
They share the number one spot with the exact same score. They excel at each other’s weaknesses while they are also able to master the ability to shield their individual weaknesses e.g. by either entering special modes or by simply adapting their strategy accordingly. In essence they can both beat each other and most likely, most times, it would come down to minor details which would’ve otherwise been irrelevant (condition, surprise aspect, killing intent, etc). Kishi > speculation.
Itachi and Kisame’s infamous meeting with Jiraiya:
Kisame, one of the legendary swordsmen, directly admitted inferiority to Jiraiya, while Itachi claimed that he could only draw with him. These words were stated in the manga.To those who would argue that Itachi wouldn’t hurt anybody from Konoha, well, answer these questions:
Why did Itachi order Kakashi’s murder? Why did Itachi and Kisame go after Naruto? Why didn’t Itachi prevent Kisame from chopping off Naruto’s leg? Last I checked Itachi wasn’t a psychic, so until those questioned are answered nobody can trash the scan.Itachi feared he couldn't get to Sasuke, in one piece, if he engaged in an all out war with him.
Why Itachi can’t just one-shot him every time:
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.
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.
Itachi = Jiraiya
