Board Thread:Versus Debates/@comment-26958911-20151010214426/@comment-26127155-20151017231018

Curse of Hatred wrote: Especially given that he had pretty much just emerged from the snake's mouth and was in the middle of monologuing.

Monologuing isn't an excuse, they are ninja. If they one of the legendary Sannin was caught napping like that, then there is no reason as to why another (Jiraiya) would not be caught out likewise. Jiraiya would have much greater chances of winning if he was completely aware of Itachi's abilities (Jiraiya could have beaten Pain if he knew the secret behind the six pathes) but Jiraya has only shown limited knowledge about Itachi's abilities (Genjutsu, Ameterasu) which means that Itachi's trump card will also have the element of surprise against Jiraiya.