This post is about Itachi and the fact that he was an insider. When Itachi left the village he was still a spy. He wanted to keep an inside eye on the enemies of Konoha. The question is who did Itachi tell the inside information too? My guess is that he told the shinobi that he could trust to use the information to help Konoha to survive. He gave information to the Third Hokage on Akatuski's actives up until the 3rds death. My guess is that Itachi was relaying information to Jiraiya. Jiraiya was very informed with Akatuski actives, as well as what their goal was. Jiraiya was informed by Itachi that Madara was sending Pein for Naruto and Jiraiya appears out of nowhere. Post what you think, but answer me this; If Itachi was an insider, then who did he relay his information too?
You have a very good Q and a lot to back it, I have been giving this Q a thought for a lot longer time than it have been posted and I would have agreed with you to, but the biggest reason that I would not go with this argument is the fact that the Jman have captured them in the big toads belly when Kisame and Itachi wanted to kidnap Naruto, the Jman would not have captured them if Itachi have relayed info to him, otherwise how would then keep him informed? Also if it all was a hoax and it was a mok fight, how come Jiraiya didnt know about the Amaterasu that Itachi used on the frog? If he did know "as part of the plan to make it look real" Why then did he seal the Amaterasu to study it later?
Honestly I dont think that he was the informant, I think that Konan was the Spy, since she never fought seriously with Jiraya up and until Pain got there, and I think that she have some sort of connection to Konoha? Just my guess??
Then again, Itachi was so loyal that he killed his own clan for Konoha. And I think that Itachi might not have anybody reliable to report to, since the Jman died?
