Itachi's style of fighting is a real foil to Jiraiya. Itachi focuses on genjutsu, which Jiraiya hasn't exactly been noted to be amazing at. Jiraiya knows how to break it, but one has to wonder whether he can break genjutsu of Itachi's caliber--not to mention Tsukuyomi, which is on an entirely different level.
But then Jiraiya is a powerhouse. He's got ninjutsu, senjutsu, and genjutsu (from the toads). He can control the battlefield, fight from any range (his taijutsu is still pretty damn good, and ninjutsu is a buffer at mid to long range), and would probably give Itachi a run for his money in terms of intelligence. He's also got shittons of battle experience, and has the clear advantage in chakra and stamina.
So what do yall think?
