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In part 1, Jiraiya told Kakashi he was on Orochimaru's trail ever since he left the village, Jiraiya then says he discovered Akatsuki through Orochimaru.
But this is where it gets odd....Jiraiya then says to Kakashi he knows about Akatsuki's structure. Orochimaru left, and the other 8 split up in to pairs. Jiraiya was also aware all 8 of them (Zetsu and Tobi were unknown) were S class criminals. He then gives Itachi as an example. Was specifically mentioning Itachi more than a coincidence maybe? I know Itachi had just been introduced in the story, and Kishi was holding off on introducing the others until part 2, but is that far fetched?
Up until the beginning of part 2 it seemed none of the villages knew about Akatsuki except for the Stone because they had been using Akatsuki as cheap labor. Kakashi, and Jiraiya knew, but the village itself didn't seem to be alarmed about Akatsuki even though Itachi and Kisame had been within reach of Naruto (yes they knew Itachi was good, but Kisame was still there!). Actually, the Sand seemed to know as well but the Sand never showed any national worry up until the Sand saw two members approaching.
^ What i'm trying to say above is that Jiraiya never got his intel from the villages because they never looked in to Akatsuki. The Stone MAY have been Jman's source of intel, but it seemed even Jiraiya knew too much. Even Itachi and Kisame seemed to be alarmed (Itachi secretly happy) with the amount of intel Kakashi had on Akatsuki. Itachi was also supposed to be a spy in Akatsuki, it is too bizarre that Itachi wouldn't do anything, yet sit and watch Kisame capture Roshi.
The next point that needs to be brought up is Pain. How the hell could Jman figure out Pain's whereabouts? No one outside of the Hidden Rain knew of Pain except Obito. If memory serves me right, he said he gathered intel that Pain was located in the hidden Rain, meaning Jiraiya had discovered Pain's location from a source outside of the village itself. But there is one issue with this, how could Itachi himself find out Pain's location, it's not like he's a sensor. But at the same time Itachi had been in Akatsuki for 7 years. This is also Itachi after all, the smartest character in the whole story.
Anyway, the thing is...how could Itachi leave clues behind discretely. Obito had to have had Zetsu on Itachi's ass 24/7. There's no reason he wouldn't. Which is likely why it never seemed like Itachi acted like a spy in the first place, because of the risk of Zetsu fidning out.
Anyway it's only a theory, I doubt 677 chapters in to the story Kishi is going to confirm it blindly, but I definitely feel that Kishimoto should have put more emphasis on Itachi's role as a spy, to give more depth to his character.
But this is where it gets odd....Jiraiya then says to Kakashi he knows about Akatsuki's structure. Orochimaru left, and the other 8 split up in to pairs. Jiraiya was also aware all 8 of them (Zetsu and Tobi were unknown) were S class criminals. He then gives Itachi as an example. Was specifically mentioning Itachi more than a coincidence maybe? I know Itachi had just been introduced in the story, and Kishi was holding off on introducing the others until part 2, but is that far fetched?
Up until the beginning of part 2 it seemed none of the villages knew about Akatsuki except for the Stone because they had been using Akatsuki as cheap labor. Kakashi, and Jiraiya knew, but the village itself didn't seem to be alarmed about Akatsuki even though Itachi and Kisame had been within reach of Naruto (yes they knew Itachi was good, but Kisame was still there!). Actually, the Sand seemed to know as well but the Sand never showed any national worry up until the Sand saw two members approaching.
^ What i'm trying to say above is that Jiraiya never got his intel from the villages because they never looked in to Akatsuki. The Stone MAY have been Jman's source of intel, but it seemed even Jiraiya knew too much. Even Itachi and Kisame seemed to be alarmed (Itachi secretly happy) with the amount of intel Kakashi had on Akatsuki. Itachi was also supposed to be a spy in Akatsuki, it is too bizarre that Itachi wouldn't do anything, yet sit and watch Kisame capture Roshi.
The next point that needs to be brought up is Pain. How the hell could Jman figure out Pain's whereabouts? No one outside of the Hidden Rain knew of Pain except Obito. If memory serves me right, he said he gathered intel that Pain was located in the hidden Rain, meaning Jiraiya had discovered Pain's location from a source outside of the village itself. But there is one issue with this, how could Itachi himself find out Pain's location, it's not like he's a sensor. But at the same time Itachi had been in Akatsuki for 7 years. This is also Itachi after all, the smartest character in the whole story.
Anyway, the thing is...how could Itachi leave clues behind discretely. Obito had to have had Zetsu on Itachi's ass 24/7. There's no reason he wouldn't. Which is likely why it never seemed like Itachi acted like a spy in the first place, because of the risk of Zetsu fidning out.
Anyway it's only a theory, I doubt 677 chapters in to the story Kishi is going to confirm it blindly, but I definitely feel that Kishimoto should have put more emphasis on Itachi's role as a spy, to give more depth to his character.