Gai takes Sasuke promising to take care of him. He asks Jiraiya to get Tsunade back and Naruto replied that they are definitely going to bring her back. Gai says that he likes kids with guts so he left Naruto with a suit exactly like Lee's and Gai's. Naruto became excited about the suit while Jiraiya was just plain annoyed hoping that Naruto never ever puts it on. At least not in his presence.
Naruto and Jiraiya are on their way to find Tsunade. During their walk, Naruto thinks about their encounter with the Akatsuki. He distinctly remembers the thing that Jiraiya said. Jiraiya said that the Akatsuki are after Naruto after all. Naruto stopped walking and asks Jiraiya why they are after him and he says that they are not after Naruto, they are after the Nine-Tailed Demon Fox.
Meanwhile, Tsunade and Shizune arrived at a gambling spot. Shizune is scared because the wages are so high. Tsunade and Shizune enter the room and ask the dealer to convert all her money into chips. One of the players asks the dealer who the person is and his reply was that she is called the legendary sucker.
Naruto asks Jiraiya how long it would take before they could find Tsunade but Jiraiya doesn't really know. Tsunade changes her appearance using a jutsu so it's hard to know what she looks like. Then Jiraiya says that they will use their travel time training Naruto. Naruto drops his backpack and takes out the uniform Gai gave him but Jiraiya says not to put it on.
Naruto and Jiraiya arrives in the city just as the festival started. Naruto tries to run off and have fun with the money he saved up from his ninja missions when Jiraiya takes it to "save" him from the three things ninjas should look out for: alcohol, women, and money.
Naruto proceeds to have fun. He played games and bought a mask. He wore it and trips. Out of Jiraiya's backpack is his checkbook. Naruto looks at it and sees a lot of zeros. With the rest of his money Naruto buys some food for Jiraiya when he discovers Jiraiya with some prostitutes drinking alcohol. Jiraiya used up all of Naruto's cash!
Naruto is outraged with Jiraiya and tries to attack him when the squid (meant for Jiraiya) springs out of his hand onto a suit of another customer who wants an outrageous sum of money to pay for the damage to his suit.
Jiraiya uses a controlled form of chakra in his hand (looks like a chakra ball) and directs it towards the man lower chest blowing him out of the building.
The show ends with Jiraiya trying to teach Naruto how to use the technique he used against the man.