Naruto trains hard to master the rasengan and not to lose his bet with Tsunade. He practiced relentlessly all night, never making it back to the inn. This is brought to his attention by his mentor Jiraiya, who woke up hungover after his and Tsunade’s encounter in the liquor store the previous night. At this time, Tsunade wanders the streets of the city, contemplating her next move. She recalls Orochimaru’s proposal, Shizune’s words, and Jiraiya’s offer to become the new Hokage; she remembers her brother and the lover she lost. She even peeks into Naruto’s training ground, where the boy, at the time, was lying exhausted from his earlier efforts.
Meanwhile, Orochimaru and Kabuto discuss what decision Tsunade might make. If she refuses, Orochimaru will have to force her to cooperate, citing Kabuto’s presence with him. However, he believes that Tsunade will agree to the deal herself, as he knows her very well.
The sixth night arrives, which means that Tsunade has to voice her decision to Orochimaru the next day. Jiraiya notices that Tsunade is too hesitant, and suggests that Orochimaru should have offered her something really important. Jiraiya decides to have another talk with Tsunade and they meet again at the liquor store. While Jiraiya is out of sight, Tsunade slips something into the bottle and begins to observe her companion. Jiraiya fills his bottle and drinks the contents.
Meanwhile, Shizune decides to check on Naruto and is horrified by the devastation at his training site.