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. He wasn't talking about a 1-on-1. 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. If Itachi at that point fought Jiraiya alone, he'd lose.

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 to be fair, 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 the fight against Kakashi et all since there's no point in fighting the entire village. He's later proven right when they find Naruto guarded only by Jiraiya, in stead of Jiraiya plus a village of Ninja and untold potential backup.

It's not clear how confident Kisame was in his abilities against Jiraiya, but it wasn't just Jiraiya, Naruto was there too. a 2v1 against Jiraiya would be tough (due to Itachi's state) but winnable, but if Naruto were to unleash Kurama in rage then they'd be screwed. And i'm not talking about Naruto with some Kyubi cloak. I'm talking about a proper Kurama unseal and full unleashing of a Tailed Beast. Itachi's call was the right one: there was no point in taking on such a high-risk fight with such a disadvantage.