Of Luck and Debt (取り立て代行, Toritate Daikō, Lit. "Collection Agent") is the 45th substory in Yakuza Kiwami.
Plot
At night, after Kiryu drinks any three drinks at Shellac, he is asked to leave. When he returns, the bartender is worried over something. Kiryu can Ask What Happened to start the substory. (Choosing "Order the Usual" may cause a glitch.)
One of the regular customers has accrued a large tab, but the bartender is hesitant to collect due to the customer being a yakuza. Kiryu can ask Do you want me to collect the tab for you? with a glowing reaction from the bartender. The bartender gives Kiryu a Check for Tab and says he can keep half of the debt. He states the yakuza, Tanno, is at a secret casino.
At Rune Casino, Kiryu sees Tanno and approaches him. Tanno is waiting to win big to pay back his tab, but the odds are not in his favor, and he believes it is because he lost his Goddess of Children Amulet. Tanno agrees to agrees to pay if he gets an amulet.
With the amulet, Kiryu can choose to Hand It Over to Tanno. With the amulet in his possession again, Tanno feels lucky and goes back to playing.
Back at Shellac, Tanno states he will be betting on boxing matches now that his tab has been settled.