Shinpachi has a sudden meeting with an old friend who has joined a gang to get tougher.
Gintoki, Shinpachi and Kagura work in a convenience store in place of Hasegawa Taizou, who had to run off town for the day. As he works, Shinpachi catches someone that tries to steal hair styling gel. The thief turns out to be one of Shinpachi's childhood friends, Takaya Hachibei. Despite his attitude, Shinpachi lets him go and not turn him in. Takaya doesn't show any gratitude and arrogantly says that he will probably come back again to steal, only to get a straight answer from Shinpachi that he will stop him again. A flashback is shown of Takaya getting beaten by some kids, with Shinpachi and his sister, Otae, coming to the rescue. Takaya comments on how Shinpachi always came to save him but after "that incident", in which Shinpachi "betrayed" him, he stopped considering him a friend. Before he departs, Takaya informs Shinpachi that he has joined a gang, the Bulldogs, and he is now stronger than before. Back in the store, Shinpachi's sister comes to visit the group and Shinpachi asks her if she remembers Takaya, with Otae responding negatively. She then encourages Shinpachi to help his friend that is in his greatest need. Takaya is shown getting beaten again by his gang members, as he failed to steal the special hair styling gels. They tie him to a motor bike and drag him along the road, when suddenly Shinpachi appears and knocks the driver down with his wooden sword, demanding that they let Takaya get off the gang. A moment before the fight starts, Gintoki, Kagura and Otae come to aid. The gang's boss is informed of the incident and joins the scene. He agrees to let Takaya go, as long as the gang manages to complete the ceremony, which everyone that is about to leave the gang has to complete. The ceremony involves a race to the edge of the town. Little do they know that this ceremony serves as a punishment to those that betray the gang, so the Bulldogs try to kill the four heroes during the whole race. Soon, Gintoki and Kagura riding the same scooter fall down because of some thrown moisturizer in the road. However, Otae and Shinpachi continue to race along with the boss and one of his minions, who are riding a horse. As Otae grabs the boss and takes off his wig, she faints, so now Shinpachi has to control the motorbike. Kagura and Gintoki soon catch up. At the end, Shinpachi and the gang's boss have a fair race to the finish line. Shinpachi loses control of his bike at some point, so he collides with the boss' horse. The two contestants continue to race on foot. Ultimately, Shinpachi wins the race, after the boss tripped, and manages to free Takaya from the Bulldogs.
- Otae and Kagura call Takaya "Takachinko" and "Takachinpo". "Chinko" and "Chinpo" mean penis in Japanese.
- In the manga, the finish line of the race was at the terminal, whilst in the anime it was at the edge of the town where the highway ends.