- Never thought of it that way with the chakra recievers. I guess his approach might have been different all the way if he had any info on Pein, but saying he would defeat Pein with all 6 present is just crazy. He had trouble dealing with 3paths and the strongest path Deva was not present and didn't use any of his powers against Jiraya.
- Jiraya never gave much info on Akatsuki so it's likely he didn't know much about them aside from Itachi who was already well known in the leaf. The Akatsuki was pretty much a mystery to everyone and no one knew anything about anyones powers in their first encounters.
-Itachi doesn't need to close his eyes to use his Mangeykou sharigan and so what if he does? No one notices besides us when he slowly closes his eyes to use Tysukomi. Jiraya is already disadvantage of fighting Itachi while only looking at his feet and body. Itachi can still place Jiraya in a genjutsu that tricked more powerful Sm users.(Kabuto) Itachi has other ways than his MS powers to defeat Jiraya and that goes without saying.
- Orochimaru was stronger than Jiraya but that is just my opinion. This thread isn't so much about them. If they both were fighting with the intent to kill one of them would be dead right now.
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On the first bold: No one knowing about Akatsuki the organization is true, but saying they didn't know about the people in the organization is stupid. Kisame is probably one of the most known S-class ninjas because he, among other people are in the bingo book, you fail at saying no one knew his abilities.
Itachi doesn't need to close his eyes to activate MS?? Are you stupid or are you stupid? lol He does have to close his eyes, not saying Jiraiya can take advantage of that, but others might be able to (cough cough Minato).
Itachi's only way of defeating Jiraiya is if he uses MS, do not downplay Jiraiya as if he is some fodder smdh Itachi would certainly loose if he doesn't use MS, that's plain and simple.
Last bold, just your opinion.