Board Thread:Versus Debates/@comment-26636534-20160221124823/@comment-3965545-20160302221735

Jiraiya did have a full on battle with Orochimaru and he lost, he could not keep Orochimaru from leaving Konoha.. in manga and anime, the contents of the entire battle were not shown, only the end result was talked about. Jiraiya even laments that he could not beat Orochimaru and bring him back when he was dying. Your presumptions don't change the fight, Jiraiya may have intel on Itachi, but Itachi always kept intel on Konoha and all of its shinobi past and present.