What Itachi Meant When Talking About Jiraiya
This is an age-old argument. "Itachi solo's J-man" "J-man solo's Kisame and Itachi" "They are dead even" and I'm sure there are more than that. There are those that believe that Itachi was just saying that due to his loyalties to the village and that could be true. The only one to know that for sure is Kishi. But seeing as we are not him, I will try and lend a theory on this to see if it can be put to rest. Here goes:
Ok, you have Jiraiya. He is a legendary ninja with a vast array of jutsu in his arsenal. He is skilled enough to counter most genjutsu, (prob not a Tsukuyomi from Itachi)and has the stamina to go the whole nine yards. Jiraiya is the definition of a whole-person ninja. He ranges from profficient to master grade in Ninjutsu, Taijutsu, and Genjutsu (countering it).
Then you have Kisame. While he is no push-over, whatsoever, he is still not on J-man's level. Sure, Kisame has him on strength, but he is only equal to J-man in stamina. All other aspects, J-man takes the cake. He can only match J-man in 2 aspects.
Finally you have Itachi. Itachi has proven that he is one DEADLY ninja. He can go toe-to-toe with the big guys. But he has an achilles heel: His sickness/stamina. If Itachi wasn't sick then him, by hisself, would be able to battle J-man on equal footing. Let's face reality, after 1 use of an MS tech, Itachi is almost spent. In my opinon, I find it doubtful that J-man would get caught in a genjutsu, to Tsukuyomi's level, early on. If anything, the fight would push J-man to use Sage Mode just to nullify Itachi's Tsukuyomi. Now, with him and Kisame going against J-man, it makes it a draw because Itachi himself could not last against J-man and Kisame wouldn't have enough techs to do him in. Kisame makes up for Itachi's lack of stamina and Itachi makes up for Kisame's lack of jutsu arsenal. Now calm down Kisame fan-boys, I'm not saying he doesn't have any jutsu, I'm just saying to the high levels of Itachi and J-man? No.
Summary: Itachi was noting that he and Kisame compliment each other; through Kisame's stamina and strength and Itachi's vast aresenal of powerful jutsu. But all they could do is stalemate J-man because he has all of that. The 2 of them = J-man. In regards to Itachi, this is only true because of his sickness.
Thanks for reading..or not.