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Chūnin Exams During an unannounced return to Konoha, Jiraiya visits the Konoha Hot Springs in order to spy on the women bathing there. He is discovered by Ebisu who, not realising who Jiraiya is at first, tries to stop him and reprimand him. Jiraiya uses a toad to knock Ebisu out so that he won't interfere in his "research". Jiraiya is immediately confronted by Naruto Uzumaki, who Ebisu was training to improve his chakra control and who now, because Ebisu is unconscious, needs somebody else to teach him. Jiraiya refuses to be that somebody until Naruto demonstrates his Sexy Technique, at which point Jiraiya eagerly agrees. While watching Naruto struggle with his training, Jiraiya notices two things: Naruto is the jinchūriki of the Nine-Tails; his access to the Nine-Tails' chakra is being restricted by the Five Elements Seal, which Jiraiya correctly guesses was placed by Orochimaru. Jiraiya removes the seal, making it easier for Naruto to control his chakra, and offers to start teaching him to use the Nine-Tails' power the next day. He informs Ebisu of this decision later that night. Ebisu doesn't mind, but asks that Jiraiya meet with the Third Hokage so that, together, they can stop whatever Orochimaru is planning against Konoha. Jiraiya is unwilling to get involved. In order to teach Naruto how to take advantage of the Nine-Tails' large chakra reserves, Jiraiya teaches Naruto the Summoning Technique, expecting him to use the Nine-Tails to summon bigger and bigger toads. Naruto is not only unable to tap into the Nine-Tails' chakra, but makes poor use of his own chakra, only managing to summon tadpoles. From talking to Naruto about his previous uses of the Nine-Tails, Jiraiya gathers that he needs to be in a life-or-death situation in order to instinctively draw on the Nine-Tails. When, after a month, Naruto is still only summoning tadpoles, Jiraiya puts Naruto in a life-or-death situation: he throws him into a ravine. Jiraiya is impressed when Naruto summons Gamabunta to save himself, but decides to return to his "research" before Gamabunta notices him. Chūnin Exams Orochimaru launches an invasion of Konoha, using snakes to break through the village's defences and destroy its infrastructure. Jiraiya stops them with Summoning: Food Cart Destroyer Technique, crushing the snakes with Gamahiro. He then seeks out the Third Hokage to lend assistance in his fight with Orochimaru, but by the time he arrives the Third is dead and Orochimaru has fled. Jiraiya does not attend the Third's funeral a few days later, instead visiting the Third Training Ground and crying over memories of the Third. Search for Tsunade Jiraiya is approached by the Konoha Council, who inform him that, due to the dire straits the villages has been left in following the invasion of Konoha, the Land of Fire's daimyō has already approved Jiraiya's selection as Fifth Hokage. Jiraiya declines, but offers to find Tsunade to have her take the position, which the councillors agree with. Jiraiya asks to be allowed to take Naruto with him; as he explains it to Naruto's teacher, Kakashi Hatake, the organisation called Akatsuki has been collecting tailed beasts like Naruto's Nine-Tails. Jiraiya plans to look after Naruto and further teach him to exploit the Nine-Tails' powers. He doesn't share any of this with Naruto, who therefore doesn't see much reason to accompany Jiraiya on his search for Tsunade. Jiraiya offers to teach him a jutsu stronger than Sasuke Uchiha's Chidori, which instantly wins Naruto's interest. After leaving Konoha, Jiraiya and Naruto stop in Shukuba Town. While they check into a room to rest in, an attractive woman starts flirting with Jiraiya; Jiraiya sends Naruto to their room while he and the woman spend time together. It quickly occurs to him, however, that women are not usually drawn to him, at which point he realises that the woman is under the influence of a genjutsu so that she could be used to lure Jiraiya away from Naruto. He returns to Naruto and finds him about to be captured by Akatsuki's Itachi Uchiha and Kisame Hoshigaki; Sasuke is also there, wishing to fight Itachi. Itachi and Kisame decide to flee rather than fight Jiraiya, which he tries to stop with his Toad Mouth Bind, but this fails. Jiraiya collects a sample of the Amaterasu flames that Itachi used to escape and returns to Naruto and Sasuke, at which point he is attacked by Might Guy. Guy apologises for attacking Jiraiya, explaining that he didn't get a good look because he was trying to avoid Itachi's Sharingan. Jiraiya asks Guy to go back to Konoha with Sasuke, who has been rendered unconscious by Itachi's Sharingan. Guy informs him and Naruto that the same thing happened to Kakashi, and that only Tsunade may be able to cure them; to that end, he asks that they be sure to find her. Afterwards, Jiraiya explains to Naruto why Akatsuki is after him. Naruto decides that he'll need to become stronger so that he can better face them next time, which Jiraiya decides to help with by teaching him the Rasengan. As they travel around the country trying to track Tsunade's location, Jiraiya instructs Naruto in the Rasengan's usage, providing him training aids where needed. Although Naruto relies on some unconventional workarounds and his developments often interrupt Jiraiya's rest, he masters the first two of Rasengan's three learning steps. Jiraiya and Naruto eventually learn that Tsunade is in Tanzaku Quarters. When they arrive at where she's supposed to be, however, she isn't there. What's more, there's evidence that Orochimaru has been there. They find a place to eat to decide what to do next, only to find Tsunade there with her attendant, Shizune. Tsunade is surprised to see Jiraiya, having just met Orochimaru, though she refuses to say anything about the nature of their meeting. Jiraiya informs her that Konoha would like her to become the Fifth Hokage; Tsunade is surprised - having thought Orochimaru was lying when he said he killed the Third Hokage - as is Naruto, who didn't realise Tsunade was being offered the Hokage position. Tsunade refuses to offer, ridiculing those who've been held the title, including the Third and Fourth Hokage, and dismissing the job as fitting only for fools. Naruto, who has his own dreams of being Hokage, is enraged and tries to attack Tsunade. Jiraiya holds him back, but Tsunade agrees to fight with him. Tsunade easily defeats Naruto, but not before he tries to use his imperfect Rasengan. She berates Jiraiya for teaching Naruto the Rasengan at all, declaring it cruel to let someone as untalented as him believe he can master something so complicated. Naruto makes a bet with her that he can master the Rasengan in a week and goes off to start training. Jiraiya invites Tsunade to drinks afterwards and guesses that Tsunade's bet with Naruto has something to do with the offer Orochimaru made her. He doesn't ask for details about the offer, but he promises to personally kill her if she does anything to endanger Konoha. She claims not to care about the village, so Jiraiya remarks how similar Naruto is to Tsunade's dead brother, Nawaki, who treasured Konoha. He invites her out to drinks again the night before the bet expires, planning to ask her more about what Orochimaru wants, but she's able to drug his drink without him noticing. When Jiraiya wakes up the next morning he has difficulty moving and using his chakra. He goes looking for Tsunade, but can only find Naruto and Shizune. He notices Kabuto Yakushi watching them, so asks Shizune what Tsunade's deal with Orochimaru is. Shizune reveals that, in exchange for healing the damage to Orochimaru's arms caused by the Third Hokage, Orochimaru will revive Nawaki and also Tsunade's dead lover, Dan Katō. As they try to find Tsunade in order to stop her from helping Orochimaru, Jiraiya worries that he may actually need to follow through on his promise to kill her. When they locate her, however, they find that she is already trying to kill Orochimaru. Jiraiya instructs Shizune to help deal with Kabuto while he fights Orochimaru by himself. He asks Tsunade to give him an antidote for the drug she gave him, but Kabuto has been able to trigger her fear of blood, rendering her unable to do anything. Jiraiya's inability to control his chakra and Orochimaru's inability to use his arms means they can't do much against each other. Jiraiya is able to create a Swamp of the Underworld, but it is too shallow to defeat Orochimaru's snake, only managing to stop it from moving. Nevertheless, Orochimaru is confident that Jiraiya will lose, proven by his "wasting" time with Naruto. He contrasts Naruto with Sasuke: Sasuke is an Uchiha, naturally gifted and capable of learning every ninjutsu; Naruto is mediocre, struggling to learn even one ninjutsu and thus failing to live up to the title of shinobi. Jiraiya rebuts: a shinobi is not someone who can learn all ninjutsu, but rather someone who refuses to give up. They watch as Naruto uses a completed Rasengan to defeat Kabuto, which Orochimaru decides is a problem. He goes to kill Naruto, parrying Jiraiya's attempt to stop him. Tsunade is able to protect Naruto and overcomes her phobia so that she can return to the fight. She summons Katsuyu to fight Orochimaru's Manda, with Jiraiya joining in by summoning Gamabunta. After they save Katsuyu from Manda, Jiraiya and Gambunta attack Manda with Fire Release: Toad Oil Flame Bullet. Manda avoids it and attacks them from behind, but they are saved by Tsunade, who defeats both him and Orochimaru. Orochimaru escapes with Kabuto; before he leaves, he warns that he has other ways of fixing his arms. Tsunade heals Jiraiya's broken bones, restores his chakra, and, having accepted the Hokage position, returns with him and Naruto to Konoha. Sasuke Recovery Mission When they get back to Konoha, Jiraiya has Tsunade heal the mental damage done to Sasuke and Kakashi, as well as ask her to look at Rock Lee on behalf of Guy. Naruto goes around the village to visit his friends, with Jiraiya secretly watching him. Naruto gets into a fight with Sasuke shortly after Tsunade heals him, which Kakashi interrupts in time to stop them from using their Chidori and Rasengan against each other. Kakashi notices Jiraiya and asks him if it was a good idea to teach Naruto the Rasengan; Jiraiya asks the same about teaching Sasuke the Chidori. Jiraiya admits to being surprised that Naruto would use the Rasengan against a friend and asks about his relationship with Sasuke. Kakashi explains that Sasuke is a rival that Naruto wants to live up to, just as Jiraiya once did with Orochimaru. Now understanding things, Jiraiya decides to speak with Naruto about it. Sasuke ends up defecting to Orochimaru and Naruto ends up in the Konoha Hospital in his failed attempt to stop him. Jiraiya visits him there and informs Naruto that he's going to take him away from Konoha for three years of training; both Akatsuki and Orochimaru will be unable to move forward with their plans for three years, meaning this is the perfect opportunity to prepare Naruto for the next time he faces them. Naruto declines, believing it's essential that he go after Sasuke immediately. Jiraiya tries to convince him to give up on Sasuke, drawing on his own experience with Orochimaru and pointing to Naruto's contemporary condition as proof that Sasuke no longer considers him a friend. These facts, coupled with the many more important challenges Naruto must face someday, causes Jiraiya to conclude that going after Sasuke would be foolish. Naruto replies simply that he'd rather be a fool. Jiraiya is satisfied by this and tells Naruto to be ready to go once he's discharged from the hospital. Land of Rice Fields Investigation Mission In the anime, Jiraiya takes Naruto and Sakura Haruno to the Land of Rice Fields to see if they can learn anything about where Orochimaru has Sasuke. They aren't able to locate him, but they are able to free the Fūma clan from Orochimaru's control. When they return to Konoha, Jiraiya asks Tsunade to keep Naruto busy until he returns from some investigations he needs to do, fearing Naruto may go after Sasuke by himself if he isn't kept preoccupied. As happens at the end of the Sasuke Recovery Mission in the manga, Jiraiya picks up Naruto at Ramen Ichiraku to take him away for three years of training. Gutsy Master and Student: The Training In the anime, shortly after leaving Konoha, they discuss the fact that Naruto will need to learn how to counter genjutsu if he hopes to be a match against Sasuke the next time they meet. Jiraiya summons Gamariki to help him practice dispelling genjutsu, but Naruto struggles with it and his chakra keeps hitting Gamariki, who doesn't appreciate it. Jiraiya takes Naruto to the Genjutsu Tree Village to try a different approach, but they discover the village has been taken over by Kandachi. They free the villagers and then attack Kandachi, who Naruto defeats with his newly-created Big Ball Rasengan. As they leave afterwards, Jiraiya is pleased by how similar Naruto is to Minato Namikaze and hugs him, which Naruto is bothered by. In Naruto's Footsteps: The Friends' Paths Two years into their training, Naruto's control of the Nine-Tails' chakra has improved significantly. Jiraiya tries to give him more access to the Nine-Tails' power and uses Gerotora to weaken Naruto's Eight Trigrams Sealing Style. This causes Naruto to enter a version 2 form with four tails; not in control of his body, Naruto attacks Jiraiya and nearly kills him before he manages to suppress the Nine-Tails. Naruto has no memory of what happened and Jiraiya doesn't tell him, instead shifting Naruto's training to other pursuits, including keeping his anger in check so that the Nine-Tails won't flare up again. Kazekage Rescue Mission Jiraiya returns Naruto to Konoha after two-and-a-half years. Kakashi greets them when they arrive and Naruto gives him a copy of Icha Icha Tactics, which Jiraiya wrote during their time together. He entrusts Naruto to Kakashi's care, warning that Akatsuki will likely be making a move soon; he sends the same warning to Sunagakure, whose Kazekage is a jinchūriki like Naruto. Jiraiya leaves Konoha to start investigating Akatsuki, but returns shortly afterwards to inform Tsunade that the Kazekage has been captured. She already knows this and is about to send Naruto and his team to Suna to lend assistance. He warns Naruto to keep his temper and to not use "that technique". He also tells Kakashi to keep an eye on Naruto, giving him a seal that can be used to suppress the Nine-Tails if Naruto starts losing control of it. When the Kazekage is successfully rescued, Jiraiya and Tsunade meet with Kakashi to discuss Naruto's display of the Nine-Tails' power during the mission, a sign of his worsening control. Jiraiya explains his own experience with Naruto's version 2 form and his observations about how Naruto's transformations work. Because Naruto can be as much a risk to himself as he is to others in these states, they task Yamato with keeping him in check. In the anime, Jiraiya returns to Konoha to congratulate Naruto on defeating Akatsuki's Kakuzu. Because Kakashi is about to take Team 8 on a mission to investigate one of Orochimaru's bases, Jiraiya distracts Naruto from this potential opportunity to find Sasuke by taking him to Yugakure for training. Because Naruto doesn't have any long-range jutsu in his repertoire, Jiraiya recommends that he use cooperation ninjutsu, synchronising with his toad summons to make up for this deficiency. He has Naruto try to perform the Water Release: Water Gun with Gamariki, but their personalises clash, preventing them from cooperating. Naruto instead summons Gamatatsu, with whom he's able to synchronise with Gamakichi's guidance. Jiraiya applauds Naruto's progress, but is called away to look into news on Akatsuki before he can see Naruto's training completed. He leaves Naruto to finish the training himself, though, before he goes, he convinces Tsunade to let Naruto help on Team 8's mission. Jiraiya visits Tsunade and reports rumours that Orochimaru has been killed by Sasuke. They share these rumours with Naruto and Sakura Haruno, who suspect that Sasuke is making moves against his brother, Itachi Uchiha of Akatsuki. Naruto proposes that they try to locate Itachi so that they can, in turn, find Sasuke. An Eight Man Squad is organised for this purpose, which, in the anime, Jiraiya and Tsunade see off as they leave Konoha. Tale of Jiraiya the Gallant While the Eight Man Squad is still on their mission, Jiraiya visits Tsunade with news that he's discovered the location of Akatsuki's leader, though he refuses to go into more detail until she meets him for drinks. While having saké, Jiraiya shares news of Amegakure's ongoing civil war, which the Akatsuki leader is rumoured to be behind. Because Amegakure is in a delicate political situation, Jiraiya must infiltrate the village by himself to confirm before Konoha can take direct action. Tsunade feels guilty for always relying on him to do dangerous work like this and offers to "help him if he needs it. He reminds her that she, the Hokage, can't just leave the village, but she replies that Naruto will inevitably replace her anyway. While they discuss Naruto, Jiraiya reflects that, because he thought of Minato as a son, being with Naruto feels like being with his grandson. Jiraiya departs, but warns Tsunade about Danzō Shimura before he goes. Jiraiya is able to successfully infiltrate Amegakure and quickly captures two Ame-nin, Ryūsui and Yūdachi. He tries using tickle torture to get them to reveal information about Pain, but it's only after using the Turning into a Frog Technique on Yūdachi that Ryūsui is forthcoming: Pain is the mysterious leader and god-figure of Ame, who brought the rebelling faction to victory in the civil war by personally killing Ame's former leader, Hanzō. Jiraiya is unsettled by news that Pain killed Hanzō, having assumed from his own past encounter with Hanzō that he was unbeatable. He takes a precaution by removing Gerotora from his body and instructing him to go to Naruto if anything happens to him. Gerotora warns him against this, feeling Naruto is unprepared for full access to the Nine-Tails' power. Jiraiya shares his suspicions that Madara Uchiha is somehow moving behind the scenes which, if true, would mean Naruto will need to master the Nine-Tails sooner rather than later. Jiraiya has one of his toads take Yūdachi to Konoha to be interrogated by Ibiki Morino while he controls Ryūsui in order to further explore Ame. He is quickly discovered and confronted by Pain's "angel", who Jiraiya recognises as Konan, one of the orphans he trained decades ago. Jiraiya is surprised to see her and guesses that Pain must also be one of the orphans, though she refuses to confirm and instead attacks him. He quickly captures her, but Pain rescues her and sends her away. Although Jiraiya does not recognise the body, Jiraiya assumes that Pain is Nagato because of his Rinnegan. Jiraiya expresses his disappointment that Nagato has turned away from his once-righteous path towards peace by leading a criminal organisation like Akatsuki. Pain asserts that, as a god, his plan to liberate the world through destruction is the definition of righteousness. Deciding that he must stop Pain before the world is destroyed, Jiraiya summons Gamaken to fight Pain while he prepares to enter Sage Mode. Pain counters with his own various summons and nothing else, which Jiraiya finds odd considering the huge arsenal of ninjutsu Nagato learned during their time together. Despite the constant attacks by Pain's summons, Jiraiya is able to enter Sage Mode with help from Fukasaku and Shima. Both are surprised that Jiraiya would call on him, so he informs them that Pain is the apparent Child of the Prophecy; they immediately understand, seeking out and destroying the chameleon Pain is hiding in. Pain responds by summoning two more bodies, each with their own Rinnegan and neither of which Jiraiya recognises. Though confused by this, Jiraiya, Fukasaku, and Shima team up with Sage Art: Goemon. One of the Pains (the Preta Path) absorbs their Sage Art: Goemon as well as Jiraiya's followup Ultra-Big Ball Rasengan, but Jiraiya succeeds in blinding another Pain (the Human Path). He tries to attack this blinded Pain from behind, but it mysteriously blocks him. Fukasaku notices that one of the other Pains saw him attacking the blind one and guesses that they share vision. Outmatched, they decide to retreat so that they can discuss tactics; they decide that their only hope is to split up the Pains and fight them one at a time, something they likely won't be able to do accomplish without genjutsu. Since Jiraiya isn't good with genjutsu, Fukasaku and Shima ready their Toad Confrontation Singing, which draws the Pains to their location. Jiraiya holds them off while the genjutsu is prepared: he obscures the Preta Path's sight; he binds the Human Path to the wall; he attacks the first Pain, the Animal Path, uninhibited until the genjutsu is finally cast. While the Pains are caught, Jiraiya stabs them with Stone Swords and believes they, and by extension Nagato, are dead. As he leaves, Pain's Asura Path attacks him from behind, severing his arm. The full Six Paths of Pain - with the three he defeated restored by the Naraka Path - face Jiraiya. He recognises the Deva Path as Yahiko, causing him to question his assumption that Pain is Nagato. When asked, Pain assures him that Yahiko is dead, then attacks to kill Jiraiya as well. After a prolonged battle, Jiraiya retreats into his Barrier: Toad Gourd Prison. The Animal Path follows him, but he's able to capture it. From looking at the Animal Path up close, Jiraiya realises that he met it once before years ago. Jiraiya, remembering the Great Toad Sage's prediction that Jiraiya would travel the world, starts to suspect why he knows the Animal Path. Fukasaku and Shima recommend he return to Konoha to report what he's discovered, but he refuses, believing this is the best chance to figure out who Pain is. He has Shima deliver the Animal Path to Konoha while he and Fukasaku confront Pain again.
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