Jiraiya

was one of Konohagakure's Sannin. Famed as a hermit and pervert of stupendous skill, Jiraiya travelled the world in search of knowledge that would help his friends, the various novels he wrote, and, posthumously, the world in its entirety – knowledge that would be passed on to his godson and final student, Naruto Uzumaki.

Background
After he graduated from Konoha's Ninja Academy, Jiraiya was teamed with Orochimaru and Tsunade under the leadership of Hiruzen Sarutobi. Hiruzen gave them a bell test for the team's first exercise, during which Jiraiya repeatedly fell for Hiruzen's tricks, and for failing to acquire a bell, he was tied to a stump as punishment. Hiruzen encouraged Jiraiya to be more like Orochimaru, but Jiraiya countered that his Transparent Escape Technique was a fair testament to his skills, as he could spy on bathing women without getting caught: Hiruzen offered to accompany him to see if this was true. Jiraiya had a certain interest in Tsunade from their first meeting, and when her breasts developed, she became a frequent target of his peepings. She nearly killed him when she caught him on one occasion, forcing him to be more discreet about his interests.

Jiraiya at some point discovered Mount Myōboku, the residence of the toads; in the anime, he was brought there when he tried to summon a toad without first having a contract with them. Fukasaku trained Jiraiya in their ways, most prominently senjutsu. While he was at Mount Myōboku, the Great Toad Sage made a prediction about Jiraiya: that he would travel the world and during that time meet the Child of the Prophecy, a student who would grow up to either save or destroy the world depending upon how Jiraiya taught them. When he returned to Konoha and began training a team of his own, Jiraiya started to suspect that one student, Minato Namikaze, might be the Child of the Prophecy because of his natural genius. As such, he took Minato as his disciple and taught him many of his skills; Minato would eventually teach Jiraiya the same.

Although their team under Hiruzen's leadership had disbanded, Jiraiya, Orochimaru, and Tsunade continued fighting together during the Second Shinobi World War. During one such fight in Amegakure, they were the only three to survive an encounter with Hanzō, for which accomplishment Hanzō dubbed them Konoha's "Legendary Sannin". After the battle, three war orphans approached them and asked to be taught ninjutsu. Jiraiya, guilty for his involvement in the war, decided to stay in Ame for a time in order to look after them. Shortly after he joined them, he discovered that one of the orphans, Nagato, possessed the Rinnegan, once used by the Sage of the Six Paths to save the world. Jiraiya decided that Nagato was the Child of the Prophecy, and as such agreed to teach the orphans ninjutsu so that he might guide Nagato towards the world's salvation.

Nagato was a kind child, torn between his desire to not hurt others and his wish to protect Yahiko and Konan. Jiraiya comforted Nagato that it was enough to want to protect people one holds to be important, as the world is plagued with seemingly endless conflict. Nagato decided that it was possible to end the constant bloodshed and, though he didn't know how, that he would someday find the path to peace. Jiraiya was inspired by Nagato's words and started writing what would become The Tale of the Utterly Gutsy Shinobi. After three years of training the orphans, Jiraiya decided they were ready to forge out on their own and he returned to Konoha; he left them a finished copy of Gutsy Shinobi, dedicated to Nagato. News of the orphans' deeds would reach him from time to time, but eventually he heard that they'd all died.

Gutsy Shinobi did not sell well when it was released. Minato - selected as Konoha's Fourth Hokage after Jiraiya refused the position - enjoyed the book, finding the main character very much like Jiraiya. He decided to name his and Kushina Uzumaki's then-unborn son "Naruto" after the main character, hoping that their Naruto would be just as determined as the character (and thus its author). Jiraiya tried to convince them not to since that would make him Naruto's godfather, but Minato and Kushina insisted this was a good thing. Minato died during the Nine-Tailed Demon Fox's Attack, giving his life to seal the Nine-Tails into the newborn Naruto; as one of his last acts, Minato sent Jiraiya Gerotora, on whose stomach he wrote the key to Naruto's seal. Jiraiya guessed that Minato wanted him to help Naruto gain control of the Nine-Tails' power, though he couldn't guess what that power would be needed for.

Although Orochimaru had always been his better, someone that Hiruzen pointed to as an example for Jiraiya to live up to, Jiraiya considered Orochimaru to be one of his closest friends. For this reason, when Orochimaru eventually defected from Konoha, Jiraiya pursued him and tried to convince him to return. Orochimaru refused and attacked Jiraiya in order to secure his escape. For a time, Jiraiya tried to find a deeper meaning in Orochimaru's betrayal, something that, if changed, would bring Orochimaru back. He could ultimately come up with nothing. From that point onward, Jiraiya started following Orochimaru's movements as well as those of Akatsuki, an organisation which Orochimaru eventually joined. His investigations often took him away from the village, preventing Jiraiya from becoming Fifth Hokage like Hiruzen wanted him to.

Personality
Jiraiya was generally light-hearted and gregarious, making jokes at his own expense and giving a mirthful laugh about it afterwards. In his interactions with others, he liked to pretend to be smug or selfish, upsetting them so that he could further rile them up with his humour. Even when entering combat he did not miss an opportunity to be flashy and over-the-top, striking kabuki poses and giving dramatic self-introductions; these intros were often interrupted in some way, and Jiraiya was quick to express his annoyance at whoever was responsible. Friends and foes alike were fond of Jiraiya for his eccentricities, admiring that somebody so seemingly irreverent could in actuality be an extremely competent shinobi: he was deeply loyal to Konoha despite how often he is away from it, not hesitating to threaten to kill Tsunade if she betrayed the village, despite their long history. Jiraiya felt that his personality quirks render him incapable of being Hokage, as he either lacked the responsibility for the position or he had, through his past infractions and failures, proven unworthy of such an honour.

Jiraiya was a self-proclaimed super-pervert with no equal. His favourite hobby was spying on women while they bathe, a passion he flaunted openly and in fact took pride in because of how infrequently he was caught. Despite this, Jiraiya disliked it when Naruto Uzumaki referred to him as the in front of others. With the "research" from his peepings, Jiraiya wrote a series of adult novels called Icha Icha. The novels were based on his personal experiences in love - particularly his rejections by Tsunade - retold in a comical way. The books were wildly popular, giving his chequebook a balance that is "filled with zeroes"; this fact did not stop him from taking Naruto's money when he got the chance and spending it on alcohol and women. In the anime, Naruto ghost-writes an Icha Icha book without anybody noticing, suggesting that either Naruto can write like an adult, or that Jiraiya's writing abilities were no better than a child's. Tsunade suspected it was the latter, as she notes that a report Jiraiya wrote when he was younger was poorly written and accompanied by crude crayon illustrations.

Jiraiya's perversion has backfired on him a number of times. When he first meets Naruto, he has no interest in training him. Naruto convinces him to change his mind by using the Sexy Technique, which Jiraiya so strongly approves of that he asks Naruto to continue to use it for the duration of their training. Itachi Uchiha and Kisame of Akatsuki later hypnotise an attractive woman to lure Jiraiya away from Naruto so that they can try to capture him; though it works at first, Jiraiya quickly realises that women aren't usually attracted to him, allowing him to return to Naruto in time to rescue him. When he was younger, he spied on Tsunade while she was bathing and, when she caught him, she broke both of his arms, six of his ribs, and ruptured a number of organs as punishment. Ever since, he's used greater discretion in expressing his interests in Tsunade, careful to make his advances come off only as playful. Jiraiya considers his inability to win Tsunade's heart to be one of the greatest failures of his life.

Jiraiya in fact regreted a number of things in his life. He believed the world was plagued with violence and long wanted to find a way of bring peace to it, but was never been able to come up with a way to do so. He never had children of his own, for which reason he thought of Minato Namikaze as his son and, by extension, thought of Naruto as his grandson. Jiraiya stated simply that to be happy was not his fate; Tsunade doubted he believed his own words. He did, however, have great faith in the next generation, Naruto in particular, believing that Naruto would be able to create and enjoy the world that Jiraiya could only dream of. When he dies, Jiraiya decided that, despite his numerous failures, the successes of his time with Naruto made everything worthwhile.

Appearance
Jiraiya was a rather tall man in adulthood with fair skin. He had a wart on the left side of his nose and waist-length, spiky white hair that he usually ties back into a pony tail, with two shoulder-length bangs framing his face. There were red lines under his eyes which extended further down his face as he got older, going all the way to the bottom by the time he was an adult. His usual attire consisted of a green short shirt kimono and matching pants, under which he wore mesh armour that is visible at his wrists and ankles. He also wore hand guards, a black belt, traditional Japanese wooden sandals, and a red haori with two yellow circles on each side. He often carried a large scroll on his back, and had a tattoo on his left palm, and he wore a horned forehead protector with the kanji for, which denoted his affiliation with Mount Myōboku.

Abilities
Like his fellow students of the Third Hokage, Jiraiya is an exceptionally talented shinobi. It wasn't until the Second Shinobi World War that their skills became widely known; dubbed by Hanzō as the Sannin, the strongest of their generation. He was offered the position of Hokage three times, and would have been offered it a fourth time had he lived longer. Itachi Uchiha and Kisame Hoshigaki of Akatsuki prefer to avoid a fight with Jiraiya as Itachi estimating that both he and Kisame would be killed, even with more aid. During his long career as a ninja, Jiraiya has had only two near-death experiences, once by fellow Sannin, Tsunade, and once by Naruto Uzumaki in a Nine-Tails' version 2 form (though both came from people he cares for with the latter he focused more on containing rather than defeating). Though he finally dies against Nagato, Nagato believes Jiraiya would have won had he known the secret of the Six Paths of Pain;, which Tobi feels is a major testament to the Sannin's abilities.

Chakra and Physical Prowess
Jiraiya has chakra reserves large enough to summon Gamabunta and chakra potent enough to use senjutsu. Jiraiya also was masterful with his chakra control, able to perform two Rasengan at the same time, or even carve a message just using his chakra despite it being disrupted. He also taught Naruto how to break genjutsu using chakra control. The manga shows little of his physical prowess other than being able to fling Naruto several metres with a single finger tap. In the anime, he is shown lifting and throwing large boulders as well as kicking away some of the Giant Multi-Headed Dogs.

Jiraiya was also remarkably durable, able to withstand a lot of damage before going down. He could survive a full on kick from Might Guy with barely a scratch, and even attacks from summons as big as Gamabunta, such as the Giant Ox couldn't even inflict damage on him despite their huge size and mass. Due to this durability he's only been brought to the brink of death twice: against Naruto Uzumaki's Four-Tailed Form and Tsunade's monster strength, and even Nagato had a difficult time inflicting lethal damage on his old master using the Six Paths of Pain.

Ninjutsu
Jiraiya is a ninjutsu master, who is famous as the because of his affinity for the toads of Mount Myōboku. This affinity most commonly manifests as summoning toads, either to fight alongside him in battle or simply summoning a toad's œsophagus to coat the area and restrict any movements within that area. Other toad-based skills include spitting oil from his mouth, hiding himself within a target's shadow to control their actions undetected, or using toads to infiltrate sensitive areas.

Jiraiya is well-versed in fūinjutsu, as he deduces the workings of Naruto's Eight Trigrams Sealing Style within moments of seeing the seal's design. He also quickly notices the seal is being restricted, and as such removes the restriction. He can create seals for others that they can use to suppress the chakra of those who have been applied with Jiraiya's seal. He also displays a certain skill for barrier ninjutsu, erecting barriers to either detect all movements within a wide radius or toad-themed barriers for him to take shelter in.

Jiraiya's natures include Fire, Earth, Water, and Wind, as well as Yin and Yang Release. He most often uses fire, typically to ignite his own or one of his toad's oil. With Earth Release: Swamp of the Underworld, he can create a swamp beneath a target to trap them. He is able to grow and manipulate his hair, either to bind and destroy targets or to surround him as a defense, injuring any who try to contact him. Minato Namikaze taught him the Rasengan - the highest form of shape transformation - but Jiraiya is most proud of his Transparent Escape Technique, which he uses to spy on women while they bathe.

Senjutsu
Jiraiya was taught how to use senjutsu by Fukasaku, which he can use to increase his speed, durability, and physical strength. He can also use it to empower his other ninjutsu, such as the Ultra-Big Ball Rasengan. Before he can gain these benefits, Jiraiya must enter Sage Mode, which he does not have mastery of. This causes his Sage Mode form to make him more toad-like in appearance, such as warts and webbed hands and feet; although his frog-like legs enable him to jump better, he dislikes the overall appearance because he believes women will find it unattractive. Using Sage Mode requires his supply of natural energy be constantly replenished, something that is difficult to do while in combat. For this reason, Jiraiya summons Fukasaku and Shima and fuses them to his body, having them gather natural energy for him. As an added bonus, Fukasaku and Shima can combine attacks with Jiraiya's, as with the Sage Art: Goemon, or they can perform justu that he can't, as with genjutsu.

Intelligence
Despite what his personality might suggest, Jiraiya is actually very shrewd in the field. His specialty is intelligence gathering, having a spy network that runs throughout the Five Great Shinobi Countries that he can use to gain information about a particular person or group to be used to his or his allies' advantage. In combat, this translates to a keen perceptiveness; Jiraiya observes all of the opponents' various actions, forms a theory about the how and why, and uses that theory to try and capitalise in the battle. His memory is apparently very good, as he, while dying, is able to craft a coded message using the page numbers of Icha Icha Tactics, with the first word on each page serving as his message.

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.

Konoha Crush
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.

Sunagakure Support Mission
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.

Tenchi Bridge Reconnaissance Mission
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.

Three-Tails' Appearance
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.

Itachi Pursuit 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.

The other five Pains quickly surround Jiraiya when he returns to the battlefield, but he's able to confirm his theory: each of the Pains is somebody he met during his travels. Before he can communicate this to Fukasaku, his throat is crushed and he is stabbed by the Pains' black receivers. As his life starts to fade, Jiraiya reflects on his failures: his failure to win the heart of Tsunade; his failure to redeem Orochimaru; his failure to protect Minato or the Third Hokage; and now his failure to have a meaningful death. His thoughts turn to Naruto, who Jiraiya knows wouldn't submit to failure like this and would keep fighting for as long as he could. Jiraiya decides that he, as Naruto's teacher, should demonstrate the same resolve. As such, he forces himself back to consciousness and uses the last of his energy to etch a coded message into Fukasaku's back.

Despite Pain's attempt to stop him, Fukasaku is able to escape to Konoha. Jiraiya, meanwhile, is thrown into the sea by Pain's attack and starts sinking into its depths. Jiraiya spends his final moments continuing to think about Naruto, and decides that it is he, not Nagato, who is the Child of the Prophecy. Jiraiya is confident the world is in good hands if Naruto is to be its salvation. Satisfied with how this final chapter of his life has turned out, Jiraiya officially ends what he titles the Tale of Jiraiya the Gallant. Before he dies, Jiraiya decides that the sequel should be called the Tale of Naruto Uzumaki, and smiles at how good the title is.

Legacy
Deciphering Jiraiya's dying message becomes Konoha's top priority, though Jiraiya's code is not recognisable to the Konoha Cryptanalysis Team. Only Naruto, one of the people closest to Jiraiya, is able to identify the code's key: Icha Icha Tactics. By taking the first word on each page that Jiraiya specifies, they produce the message, "the real one isn't among them." It isn't until the examination of the Animal Path and the interrogation of the Ame ninja are completed that Jiraiya's message makes sense: the Six Paths of Pain are controlled remotely by a main intelligence, Nagato. Pain's Assault on Konoha is already underway by the time this is figured out, but Naruto, after defeating all six Pains, is able to use the information to find and meet with Nagato.

Naruto is very depressed when he first learns of Jiraiya's death and tries blaming it on Tsunade since she let him fight Pain alone. It eventually occurs to Naruto that Jiraiya, by fighting Pain, has bought him time for his own fight with Pain; he uses this time to learn senjutsu which, in combination with what Fukasaku is able to report about Pain's abilities, allows him to defeat the Six Paths of Pain. When he meets Nagato, Naruto wants to take vengeance for Jiraiya's death, but he decides instead to forgive Nagato, thereby ending the cycle of hatred that the main character of Jiraiya's book, The Tale of the Utterly Gutsy Shinobi, spoke against. Nagato realises that this same idea that Naruto got from Jiraiya, Jiraiya in turn got from him, and that his actions in Akatsuki therefore contradict both himself and Jiraiya. He gives his life to revive those killed during his attack on Konoha, the only atonement he can offer. Nagato later observes that if Jiraiya's was the first story in a trilogy and Naruto's will be the last, his own is the better-forgotten middle volume.

After observing Naruto's confrontation with Nagato, the Great Toad Sage discovers that his prophecy was somewhat incorrect: Jiraiya would not train the Child of the Prophecy, he would train the Children of the Prophecy, Nagato and Naruto, both of whose actions steer the world towards peace because of Jiraiya's influence. Obito Uchiha, after plunging the world into the Fourth Shinobi World War, blames the actions of Naruto and Nagato for the failure of his Eye of the Moon Plan; because Jiraiya was their teacher, Obito decides that, in a sense, it was Jiraiya who defeated him in the end. For Jiraiya's influence, Naruto creates a memorial to him in the woods near Konoha after Pain's Assault ends. The memorial itself is a rock with the kanji for carved into it; Naruto also leaves a copy of Gutsy Shinobi and "never-dying flowers of hope" given to him by Konan.

Tsunade is just as sad as Naruto when she finds out about Jiraiya's death, and it provides her with yet another reason to keep Konoha safe from Pain, so that his sacrifice isn't wasted. She is rendered comatose in her effort to protect the villagers, at which point the Fire Daimyō voices his regrets that Jiraiya, being dead, cannot replace Tsunade as Sixth Hokage. When the Fourth Shinobi World War starts, Kabuto Yakushi expresses interest in reincarnating Jiraiya to have him fight for Akatsuki, but unfortunately is unable to reach him as his body rests in the lower depths of the sea. Orochimaru, his death having been misreported, reemerges during the war with a reformed outlook. Tsunade argues that this change in him might have saved Jiraiya had it happened sooner, but Orochimaru believes it was better for Jiraiya to die as he was rather than risk him changing because of Orochimaru's change.

Naruto Shippūden the Movie: Bonds
When Naruto is about to go on a mission, Jiraiya has Sakura Haruno deliver a package to him. In the package is a charm, which activates when Naruto enters a version 2 form and suppresses the Nine-Tails' influence. When, at the end of the mission, Naruto and Amaru almost fall to their deaths, Jiraiya arrives and saves them with Gamabunta.

Naruto Shippūden the Movie: The Will of Fire
When the world begins mobilising for a Fourth Shinobi World War, Jiraiya saves the Fifth Kazekage from an attack by Hiruko's forces. He tells the Kazekage that he believes Naruto can stop Hiruko and avert the war, but he allows the Kazekage to come to his own conclusion. Naruto does indeed defeat Hiruko; afterwards, he and Tsunade discuss how old they've gotten, as evidenced by Naruto's rapid growth.

Naruto Shippūden the Movie: The Lost Tower
Twenty years in the past, Jiraiya takes Minato Namikaze aside and shows him that he's finally learned to use the Rasengan. Minato is unfazed and leaves with a simple congratulations, much to Jiraiya's confusion.

Road to Ninja: Naruto the Movie
The Jiraiya of the Genjutsu World died trying to procure the Red Moon Scroll, which the Great Toad Sage foretold would help defeat the Masked Man.

Video Games
Jiraiya in the video games often gains extra abilities, such as being able to use his elongate his hair in various ways, as well as his taijutsu's motions being theatrical in appearance, reminiscent of a kabukimono.

Creation and Conception
Masashi Kishimoto originally planned to draw Jiraiya with a different design and with a different style of hair. He also intended for Jiraiya to summon toads that were of a similar size to humans. However, this idea was deemed a failure. During an interview, he commented that, of the student-teacher relationships in Naruto, Jiraiya and Naruto's is the one he likes the most. At the 2015 New York City Comic Con, Kishimoto also said that Jiraiya was his favourite character after Naruto.

Trivia

 * Jiraiya and the other Sannin are named after the characters in the Japanese folktale Jiraiya Goketsu Monogatari; Jiraiya references the story before his death. The Jiraiya of that story excels in toad magic.
 * , roughly translated can mean "I came", whereas from the derived story the name holds the meaning "Young Thunder" or "Young Lightning".
 * Jiraiya's autograph is featured in the real version of The Tale of the Utterly Gutsy Shinobi.
 * In the Live Spectacle Naruto, the role of Jiraiya was played by Yoshiaki Umegaki.
 * Jiraiya is given no rank in the manga or its databooks, but the anime classifies him as a jōnin.
 * Studio Pierrot's Settei sheets of Jiraiya show that he was 153 cm when he was part of Hiruzen's genin team. They also show that his sandals add 7 cm on to his height.
 * According to the databook(s):
 * Jiraiya's hobby was sneaking a peek into a Women's Bathing House.
 * Jiraiya wished to fight Naruto Uzumaki.
 * His favourite food was garlic pickled with Japanese basil and karaage-fried chicken, while his least favourites were kiwifruit and gratin.
 * Jiraiya completed 1,839 official missions in total: 58 D-rank, 345 C-rank, 684 B-rank, 614 A-rank, 138 S-rank. With this rating of mission completion by Jiraiya, he has the most completed missions of all characters in the entire Naruto series.
 * Jiraiya's favourite phrase was.
 * Jiraiya shares the same blood type with his former team-mates, Tsunade and Orochimaru, as well as his former apprentices, Naruto Uzumaki and Minato Namikaze.
 * Jiraiya is tied with Itachi Uchiha as having the highest stats total in the databook.
 * Jiraiya's last words are based off of a Japanese proverb:.

Quotes

 * (To Tsunade) "Yo! I'm Jiraiya! You can send me the love letter later!"
 * (To Nagato) "When people get hurt, they learn to hate… when people hurt others, they become hated and racked with guilt. But knowing that pain allows people to be kind. Pain allows people to grow… and how you grow is up to you."
 * (To Naruto) "I'm not a pervert… I'm a super pervert!"
 * (To Orochimaru) "You're wrong, that's not what makes a shinobi. You never did get it, a real ninja is one who endures no matter what gets thrown at him… Let me explain something to you, there is only one thing that matters if you are a shinobi, and it isn't the number of techniques you possess. All you do need, is the guts to never give up."
 * (To Naruto) "Even I can tell that hatred is spreading. I wanted to do something about it … but I don't know what … but I believe… that someday the day will come when people truly understand one another!! If I can't find the answer, it will be up to you to do it!!"
 * (To Tsunade) "Now my job is to help the next generation, and set a good example for them. And for that I'll gladly lay down my life, and I'll be smiling the whole time. It's what makes us old guys cool, you see."
 * (To Tsunade) "A person who feels nothing at the death of those close to him is no different than a butcher."
 * (To Naruto) "Never go back on your word… and never give up. That's your ninja way… and as your mentor… I have no business whining! Because… the student's ninja way should be the master's too! Isn't that so, Naruto?!"
 * (Last words) "There, that ending… was a little better. The frog at the bottom of the well drifts off into the great ocean. Heh heh… yep… pretty damn honourable… pretty damn honourable… I guess it's time to put down my pen. Right… I need a title for the next book… let's see… Ah, got it… The Tale of Naruto Uzumaki… perfect."