Board Thread:Versus Debates/@comment-26104757-20170917032219/@comment-734582-20171104102814

Vinuth123 wrote: Itachi could have fought jaraiya alone (not that he would definitely win, but would put up a fight) but they were pretending to attack konoha. He was with Kisame and fought together with Kisame before. 1 on 1 Itachi was never going to win since he already used his MS 2-3 times. The Databooks imply that Itachi and Jiraiya are roughly equivalent (equal final stats, down to the half-point), so the fight wasn't close.

Kisame was definitely not kidding about capturing Naruto, so no they weren't just pretend-attacking Konoha. Itachi had no problems with capturing other Jinchuriki and didn't even try to delay or stop it. Although they weren't attacking Konoha: they were there to see if they could easily capture Naruto, with a side-effect of reminding Konoha of Itachi's deal. Itachi tells to retreat from this since there's no point in fighting the entire village, and prove this later when only Jiraiya defends him.

It's not clear how confident Kisame was in his abilities there, but it wouldn't be the first time a Jinchuriki went beserk and could kill them. a 2v1 against Jiraiya would be tough but winnable, but if Naruto were to unleash Kurama in rage then they'd be screwed. Itachi's call was the right one: there was no point in taking on such a high-risk fight with such a disadvantage.