My theory is that Itachi was Jiraiya's "Inside Man". Why? Because Itachi sacificed His own clan to protect Konoha. Madara alluded that Itachi was one of his biggest threats to his Goal. It is the Backed up by the fact that He rigged Sasuke's Sharingan To "self-activate" when gazed upon by an other sharingan: that being Madara's. Since Itachi fans brag on Itachi ginus(wich he does have somewhat ) Madara informed Sasuke that it was a "fail-safe" on stoping him from contacting Sasuke (wich He then added, " But Itachi only completed the "fail" part." !!Burnnn!!.)
But realy Itachi tried to take Madara out Before He Got to Konoha. Jiraiya , before he left for Amegakure, told Tsunade and mentioned it a couple of times in the manga that he had some one giving him the Info an accomplise. Um.. Hum.. :y and Jiraiya was tailing the Akatsuki but how could he when Nagato put up a Barriers around the areas that can sense intruders. Jiraiya only got pass one and got caught. If He had been tailing them, he would have got caught a long time ago. The only sufficient way to uptain Info like where the main leader's hide out is, Is to get it from someone close to the group>like Itachi. They both are shown to have strong love for Konoha:
- Both were close to Hurizen/Hurizen being very close to Jiraiya.
The 3rd Might have new indirectly that Itachi would be joining a terrorist group but he didnt know the full details.
- Itachi with his sacrifice for Konoha
- J man with his life sacrifice to unmask the truth about the Rinnagan ( wich he sussesfuly did in vane
It is Highy possible that this was the deal and Itachi could have been J man's inside man. Im not sayin that they new eachother or that J man New his accomplise.
This just came to thought, Maybe Jiraiya was getting info from some one and that Itachi was giving it to some one. Hum.. This would mean that there was a ""middle-man"""
, a person who was receiving info and passing it along to J man.
Wow Mind- Boggling :crazy: