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When Itachi was saying that he has to retreat because he overused the Mangekyou sharingan, maybe he wanted to make an excuse to retreat because he didn't want to kill Jiraiya or capture Naruto. I think he wasted tsukiyomi twice just to make an excuse that he is about to faint so that he can persuade Kisame to retreat. Also just because Kimimaro got a 4.5 in stamina does not mean that healthy Itachi would have low stamina. Kimimaro was probably a stamina beast before he became sick but this is just speculation at this point so I have nothing to say really.Hold on, I don't recall Itachi constantly feeling unwell whenever he was fighting. Don't overexaggerate things, the real Itachi, the one with the disease, was the one which fought Kakashi and co. The one who was warned against overusing his MS due to his low chakra reserves. People have a false idea of what sick Itachi is due to the fact that it was sensationalized in his fight against Sasuke. He was only coughing up blood to that degree because he was already close to death and had used up practically all of his chakra.
@OP: I somewhat agree with what you said. Itachi is definitely overrated by many but I think you are somewhat underrating him. His power and skills as a ninja rivals that of Minato, Sasuke, Mu and Killer Bee and he is a somewhat stronger than sage Jiraiya.
The manga does portray Jiraiya to be stronger than he really is so I guess what you say is correct. Remember though, Jiraiya is also portrayed to be equal to Orochimaru and Itachi is portrayed to be well above Oro's level. This means that Itachi is on a tier above both Jiraiya and Orochimaru.
Jiraiya got a lot of false hype in the manga. He can not hold his own against both Itachi and Kisame at the same time. He can't beat the six paths of pain at the same time either. Pain said he could do this only because he wanted to give respect and a tribute to his dead sensei. He clearly had respect for Jiraiya and his powers.
On the other hand, Itachi got some false hype as well. He is not invincible like zetsu said he was.
:rofl::rofl:_O-_O-