I said it once and im going to say it again, Itachi is stronger than Jiraiya, he just didnt want to fight him because it was the perfect excuse to make Kisame believe that Jiraiya was a reason to retreat and abort the mission, they were sent by Akatsuki to capture the 9 tails, Itachi just said everything to not capture Naruto, i even think that the genjutsu to the girl wasnt to take Jiraiya out of the picture, Itachi knew Jiraiya would see such a basic Genjutsu and realize Naruto was in danger. He didnt kill Kakashi, Kakashi himself was confused on why Itachi didnt just killed him. The only thing Itachi didnt expect was encountering Sasuke. Itachi is 35.5 overall status in the third databook, that was part 1 of the series mostly, im pretty sure he will be like 37 in the 4th, because most of his feats were done and shown in the second part( Sasuke fight and Edo), so please dont bring the stats up to the discussion, i seriously believe Masashi Kishimoto loves the Sharingan and specially Itachi, thats why he figured out a way to bring him back, while taking Nagato and the other Kage summons out really fast, and thats why 4 of the strongest ninja now are sharingan users( Itachi, Tobi, Sasuke and Kakashi), I also think Kisame could take Jiraiya since he could defeat Killer Bee, the perfect Jinkuriki of the 8 tails, possibly a character just as strong as current Naruto maybe slighty weaker.