Despite his endless list of achievements--one of the legendary Sannin (Three Ninja), teacher for the Fourth Hokage, Naruto's trainer during his time away from the Hidden Leaf Village--Jiraiya is a modest ninja. Taking his personal philosophies from his personal experiences, Jiraiya keeps his stories close to himself.
After training Naruto for two and a half years, Jiraiya finally returns home. His next mission was to track down Orochimaru, once a comrade from his days as a Sannin. After hearing of Orochimaru's sudden death, he confronts the new enemy, the Akatsuki, only to discover that the core members happened to be his former students.
Once the battle was over, Jiraiya encountered three orphans from Amegakure. While Orochimaru suggested they kill them to spare them the cruelty of the world, Jiraiya decided to look after them for a time and taught them ninjutsu. During which, he grew close to the three children and even wrote a book that was inspired by one of them, Nagato. Eventually however, he left them so that they could pursue their own goals. Although news of their exploits reached him from time to time, he thought them to have died during an undisclosed incident.
Once becoming a Jonin capable of leading a squad, Jiraiya became the teacher of Minato Namikaze and two other unknown Genin. Years later, when Orochimaru betrayed Konoha and fled the village, Jiraiya pursued him, trying to convince his friend to come back. Orochimaru refused, and attacked Jiraiya. While he tried to find a reason for Orochimaru's defection, he eventually realized that his friend wasn't coming back. Feeling he was responsible for Orochimaru's escape, Jiraiya left Konoha so he could follow Orochimaru's movements as well as the organization Orochimaru eventually joined, Akatsuki. In doing so, Jiraiya was unable to fulfill the Third's wishes of taking on the role of Hokage, knowing that tracking down Orochimaru was more important.
A few years before Orochimaru's defection, Jiraiya finished his first book, The Legend of the Utterly Gutsy Shinobi (ド根性忍伝, Dokonjō Ninden), that had failed as a seller. Minato, now the Fourth Hokage, however thought the book was excellent, he and Kushina Uzumaki decided to name their son after the main character in his book, Naruto, thus making him Naruto's godfather.