Hasegawa is tired of being a Madao, so together with Gintoki, they bet on horse races. After many failures, Hasegawa tells him of his effort to leave the "Madao Spiral", an unfortunate turn of events that happened since he gained the nickname. Together with Gintoki Madao decides to try one last time, betting on the horse Justaway. In the middle of the race, Gintoki tells him that he bet on another horse and after a head-on head race between Justaway and Gin's horse Cheap Impact, it seemed at first that Justaway won but then it got disqualified and Cheap Impact won instead. But by that time Gin has already shredded his ticket into pieces and neither of them won.
Tired of his Madao life, Hasegawa and Gintoki head to the Horse Races to try their luck. A pundit in the field of Horse racing, Hasegawa gives Gintoki a rundown of how to pick a horse through thorough analysis. The didactic nature of Hasegawa annoys Gintoki so he chooses a horse based on the date. In the end, they both lose their bets. Not allowing their respective losses to get to them, they try several more times and still lose.
On top of the horse race building the two lament over their losses. Hasegawa then realizes that his Madao lifestyle began after he met Gintoki. A series of flashbacks are played which show how Hasegawa meets Gintoki and his major fall from grace in becoming a Madao. Gintoki, however, claims that despite their gambling losses together they always try and again. On the other hand, Hasegawa spirits aren't raised. He then explains that his wife Hatsu's is the following day. Furthermore, his love for her and her inspiration is what kept him going. However, it's noted that when Hasegawa involves himself with Gintoki all of his efforts have turned sour, but Gintoki instantly denies it. From time to time Hasegawa still talks with Hatsu on the phone and the last time he saw her was after his court battle. Sequentially after it, Hasegawa unintentionally uses a move known as the "Hasegawa Buster" on her. Still, he wants to get her a present, but due to his Madao spiral that's impossible. Thankful for Gintoki's presence, Hasegawa tells Gintoki that he can leave as he doesn't want to drag him along with him. Gintoki though refuses to leave him and the two try their luck again. Which of course fails leaving them left with nothing but their underwear and a handful of change.
With his last bit of change, Hasegawa bets on one last horse race. Internally, Hasegawa hopes that the horse he bet on Justaway wins for Hatsu's sake. Amid the race, it's revealed that Gintoki didn't bet on the same horse but one called Cheap Impact. Gintoki's bet on the ideology that the "Main Character" always wins. Because of Hasegawa's Madao title, his bad luck spiral will perpetuate his losing streak forever. In the end, Justaway wins the race but is then disqualified due to it going out of bounds to block a fellow racer's path. As such, it's then announced that Cheap Impact won the race. Although Gintoki the race he shredded his ticket already. Scorn by his loss, Gintoki then finds out that Hasegawa left a suicide not behind.
- Sakata Gintoki
- Hasegawa Taizou
- Shimura Shinpachi
- Kagura (flashback)
- Prince Hata (flashback)
- Jii (flashback)
- Hasegawa Hatsu (Mentioned)