Just one eye contact during the whole fight ends the battle against Itachi. Just one successful hit with Amaterasu ends the battle with one glance. One hit with Susanoo as well. The techniques of Itachi's Mangekyo Sharingan are far easier ways to finish an opponent than what Jiraiya could throw at Itachi, under the consideration of constant fear and care of Tsukuyomi and Amaterasu. A summoned Boss toad is killed with Amaterasu, by Susanoo (slaughtering it with Totsuka or sealing it away) or controlled by simple 3T Genjutsu. Itachi's agility and speed will nevertheless allow him to dodge whatever the Boss toads will do against him; even Tendo managed to dodge their attacks with foot speed.
Same with Pain, who fought neither Jiraiya nor Naruto with full power - with Tendo's abilities absented. Pain would take this quite comfortably with all Six Paths present at full power.
Same with Obito. I only need to read the chapter 595, consider his Katon, Uchiha Kinjutsu (Uchiha Kaenjin for example) and Izanagi on top of all that, to consider him the winner.
Jiraya has tactics to deal with Itachi one shot jutsus. First is to ruin his Line of Sight. Jiraya can strictly close his eyes and rely strictly with his SM senses[
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]. So what he can do is have Shima use Dust Cloud[
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] her and other Summon don't get hit with Sharingan. Itachi unaware with his vision block, can get shotted with Oil Bullet, and Kisame too. Itachi is force to use Sussanoo early, which takes a toll at him in thee end.
I can see Pain getting one shot in these scenario. Since Jiraya's Oil is much different in this scnerio, taking or even touching to oil= Toad Stone. So Goemon can end it.
Did you read the OP concerning Obito..
