First let's see the fight:
[video=youtube;SqpKvdLKnRM]http://www.youtube.com/watch?v=SqpKvdLKnRM[/video]
here are the contradictions:
1/ It's said that Itachi can't defeat Jiraiya even with Kisame's help, and we all know that Jiraiya failed to force Oro to return to village, let's just say Jiraiya = Orochimaru (it's not what the thread is about)
2/ Orochimaru got trapped into a usual Sharingan Genjutsu (not a MS one), In the fight between Itachi, Kisame vs Kakashi, Asuma and Kurenai, the latter one was able easily to dispell It by simply biting her mouth.
2/ The databook says that Orochimaru has 5 in Genjutsu, Jiraiya for exemple has 3 and he is able to dispell Genjutsus while Orochimaru couldn't.
3/ Itachi cut Orochimaru's arm when he wanted to dispell it, He actually helped him getting out of it !
4/ By cutting his arm Orochimaru can regenerate his body so he was able te make it grow again and use handseals and Ninjutsu to fight.
Conclusion: The fight is a plot hole and Kishi is an Itachi fanboy.
On the 'It's said that Itachi can't defeat Jiraiya even with Kisame's help note'. You really can't use that statement to justify anything. We all know that Itachi was working for Konoha all along, obviously he'd say anything, and do anything (without being too obvious ofcourse) to prevent the capture of Konoha's jinchuuriki, I mean, he even went as far as killing his own family for that place.
Now lets recap. Kakashi (having found out from Jiraiya) accuses Akatsuki of trying to capture the Kyubi. Itachi doesn't have to explain or deny anything, but than he goes ahead and explains exactly what their intention is for no good reason, and he's very quick to point at Jiraiya as being the one who must have passed the information to them. Here, he is using Jiraiya as a smokescreen for the fact that he is confirming/giving out information almost blatantly.
I also believe that Itachi allowed Oro to live in order to cover for his own tracks. If Itachi was making sure that Konoha (Jiraiya) receive information about Akatsuki behind the scenes, he'd obviously need a smokescreen for his activities, and who better than the traitor Orochimaru to use as a scapegoat. If he kills Orochimaru, they'd obviously suspect him to be the one dishing out information. But with Orochimaru alive....well, that one is self explanatory, and even if they suspected him, he'd still have someone to point a finger at in Orochimaru.
Another thing is that Itachi, almost immediately upon Kakashi, Kurenai, and Asuma catching up to them, makes it clear that they should allow them to pass as he 'doesn't want to have to kill them', this is so clear I don't understand how people constantly miss it, they guy practically told em he don't wana hurt them.
Kakashi, after being hit with Tsukiyomi, admits that Itachi could have easily killed him, and than asks himself why Itachi didn't in fact kill him. Another blatant display of Itachi's killing intent against Konoha shinobi, or rather, lack of it.
Kisame and Itachi were not unanimous on the Jiraiya issue, Kisame believed Itachi could take him, and Itachi made up excuses. Ofcourse Kisame would believe that because he would have known that Itachi defeated Orochimaru, another sannin, but Kisame didn't believe that he himself could take Jiraiya.
There are alot of plot holes in that conversation I must admit, for one, most of the Akatsuki, in fact, all of the Akatsuki members were hell bent on killing Orochimaru and showed absolutely no fear of him, in fact, it was the other way around, Orochimaru was scared of them. Now how can Kisame speak of himself as if he is that far below a sannin (Yes, they were not argueing on the facts of Jiraiya as an individual, but their conversation was based solely on the fact that he's a sannin)? It totally doesn't make sense, and it doesn't make sense for Itachi to say all that nonsense when he himself knows, and Kisame knows that he took care of a sannin easily a few months prior.
Another factor is that Orochimaru showed zero percent fear of Jiraiya, in fact, he considered Jiraiya to be inferior to him, yet for some reason, Kisame and Itachi, who have no fear of Orochimaru, now suddenly have this strong fear for Jiraiya? More so with Itachi, considering how much Orochimaru feared him in particular.
Anyway, on a side note, have you ever thought that Itachi might have intentionally put a fault in the genjutsu he placed on that girl so that she would tip off Jiraiya when they were out of site? Lets not forget how much time Itachi was intentionally wasting in that meeting of theirs with Naruto. It could have been an easy snatch and go mission, but he wasted time with niceties and played around with Sasuke. Maybe he was waiting for Jiraiya to come back.
