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People need to stop being so think. Orochimaru is more familiar with Jaraiya and Itachi than, those 2 are of each other. Why you might ask?
Orochimaru-
A. Was on the same team as Jaraiya.
B. Was in the same organization as Itachi.
Orochimaru has a better grasp of what Jaraiya and Itachi are capable of than those two have of each other. There is no evidence that Itachi knows a whole lot about Jaraiya. Based on what he knows is probably based on "legend" while Orochimaru grew up with the guy. There is however evidence that Jaraiya doesn't know much about Itachi. Jaraiya like Naruto thinks he can beat anyone if given good reason. After seeing the effects of Itachis techniques however he realized that he underestimated him. I mean why would he do the frogs stomach technique if he knew it would have been useless? He obviously doesn't know a lot about itachi. In fact I bet the Uchiha clan keeps a lot of secrets. (Under the tile)
What does that mean? These two characters will either be cautious of each other or overconfident.
I say, Itachi >Orochi AND Jaraiya, why? I hate Itachi but lets face facts, Itachi had
to give Orochimaru a reason to leave the Akatsuki. That reason made Orochimaru leave and most likely caused him to seek out an Uchiha body. He probably never had a run in with an Uchiha at Itachis level before, that's why Kimmaro was his FIRST choice.
Orochimaru doesn't like fighting unless he's at a disadvantage and he showed little pause at all even before he knew Jaraiya was drugged. Orochimaru isn't stupid he knows when he's outclassed, and apparently he thinks Jaraiya is a joke. You don't consider someone better than you a joke, a rival sure....but not someone who's obviously more powerful than you are and like I said Orochimaru is most likely VERY familiar with Jaraiyas ability. Frankly I think Itachi has something to do with the cut off hand with the Akatsuki ring on it in Orochimarus quarters. They focused on it during his discussion about the Akatsuki in the manga AND anime.
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