Mindset: Jiraiya is holding back just as much as Itachi was, his objective is to tire Sasuke out of chakra so that Orochimaru will come out so he can defeat him. Sasuke's objective is to kill Jiraiya. Knowledge: Sasuke has as much knowledge on Jiraiya as he did on Itachi (he knew about Itachi's genjutsu, Tsukiyomi, Amaterasu but not Susano'o. So however you translate that into Jiraiya's arsenal), Jiraiya has as much knowledge on Sasuke as Itachi did (alternatively; if you believe manga knowledge is more fair since some characters should be able to benefit from their experience then consider it the knowledge stipulation instead). Location: Uchiha hideout. Jiraiya starts in base.