Twilight

Synopsis
Jiraiya arrives in Tsunade's office and tells the Hokage that he has managed to locate Pain, the leader of the Akatsuki. Tsunade decides to mobilise an attack unit until Jiraiya reminds her that they should not be haste, and offers to discuss the situation over a drink. Elsewhere, the Eight Man Squad follow Kiba's sense of smell towards Sasuke, who is sleeping off his injuries. Karin, who was sent to fetch supplies, sense the chakra of both the shinobi and their ninken and warns Sasuke. Sasuke orders Hebi to move out, claiming that the sheer number of forces would indicate that it is a Konoha unit and not the Akatsuki, as the latter move in two-man teams. As Sasuke and Suigetsu head out, Karin asks Jūgo to tie pieces of Sasuke's clothing to birds in order to disperse his scent, making it harder for the ninken to track him.

Over a bottle of sake, Jiraiya tells Tsunade that Pain lives in Amegakure, an isolated hidden village wedged between the Lands of Earth, Wind and Fire, a place often used as a battleground by the three countries, thus creating numerous refugees. Jiraiya tells Tsunade that due to the isolated nature of the village, many nations do not know that a civil war transpired within Ame and that one half of the village is run by Pain himself. Tsunade worries over Jiraiya going alone, as she deems that Pain must be strong in order to be the leader of formidably powerful individuals that are members of the Akatsuki; Jiraiya, however, reminds her that he is one of the Three Legendary Sannin and that he is more than capable of going alone. Tsunade reminds Jiraiya how their sensei, the Third Hokage, had wanted Jiraiya to succeed him as the Fourth only for Jiraiya to refuse, and how Jiraiya felt despair after being unable to prevent Orochimaru's decline into darkness, hence why he had monitored his old teammate's activities for years. Jiraiya replies spitefully that he does not need to worry about that no more and Tsunade muses on how she never thought Orochimaru would die. Jiraiya recalls the past all three shared, how Tsunade went from a flat-chested girl to a woman with a full bosom, and how they've both grown old despite Tsunade holding all the memories of her loved ones inside of her ample bosom, causing Tsunade to blush.

In the woods, Kiba tells the group that Sasuke's scent has dispersed, causing Naruto to use his Multiple Shadow Clone Technique in an attempt to spread out and find Sasuke. He ends up finding Itachi, who tells Naruto that he merely wishes to talk. When Naruto refuses to listen and attempts to attack him, Itachi uses his Demonic Illusion: Mirage Crow to place him within a genjutsu. As the genjutsu fades, Itachi leaves; the rest of the team find Naruto shortly after, who hides his encounter from them.

Meanwhile, Sasuke manages to reach one of the Akatsuki hideouts that Jūgo had found, telling Hebi to stay outside while he checks it out. Back in Konoha, Jiraiya is prepared to leave when Tsunade tells Jiraiya to summon her if things get bad. Jiraiya reminds Tsunade that she cannot leave the village as she is Hokage, only for Tsunade to retort that Kakashi could succeed her and eventually Naruto as well. Jiraiya laughs at Tsunade's high hopes for Naruto, knowing that her hope comes from the fact that he shares the same dream as her brother and lover and is the only one of the three who did not die. Tsunade retorts that Jiraiya has the very same expectations for Naruto, having taught him the Rasengan. Jiraiya explains that he only did it for nostalgic purposes as Naruto reminds him of his student Minato Namikaze, who became the Fourth Hokage. Tsunade muses how Naruto reminds her of his father Minato due to their looks, but that his personality is more akin to his mother Kushina Uzumaki, a kunoichi from Uzushiogakure. Jiraiya reveals that while he never had children, he thinks of Minato as a son he could be proud of, and Naruto as his grandson by extension.

Jiraiya decides the time for his departure has arrived, and Tsunade tearfully tells him to return back to her safely, as she does not wish to lose him. Jiraiya asks whether she would cry for him and seems as if he was about to confess love for her, only to laugh it off as Tsunade blushes. Due to her bad luck at winning, he tells her to gamble everything on his death so that her bad luck may keep him safe. As he sets off, he reminds her to be wary of Root, which she acknowledges. Jiraiya then leaves the village as Tsunade watches, tears streaming down her face.

Trivia

 * Tsunade tells Jiraiya that out of everyone in the village, she views Kakashi and Naruto as her future successors. Kakashi eventually does become the Sixth Hokage while Naruto succeeds the two as the Seventh.
 * Naruto's parents are revealed to be Minato Namikaze and Kushina Uzumaki, the former being Konoha's Fourth Hokage.
 * The manga did not depict Tsunade crying as she watched Jiraiya leave the village as shown in this episode.

Credits
Crepúsculo Zmierzch