Jiraiya's Like It's All Good - Tumblr Posts

Remember the classic scene in Naruto where Itachi and Kisame go to kidnap Naruto but Jiraiya shows up and stops them? 

One of my favorite head-canons I’ve thought of is that Itachi actually knew Jiraiya before that. I mean, think about it.

Jiraiya: Has an entire spy network

Itachi: Spied on the clan and Akatsuki, probably others tbh. 

So wouldn’t it be cool to think about that? What if Itachi actively knew that Jiraiya was his superior (And Jiraiya would probably some-what know Itachi since he’s spying on such a big project like the Akatsuki).