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?