A young news reporter begins his news story on an older man with a chronic illness who lives in the town. The older man's name is Winkelburg and he is known for all of the misfortunes that have occurred to him. Winkelburg is a tall, thin man who has lost his family, money, and health. The news reporter writes about how Winkelburg always seems to appear at unexpected times and the general public avoids him, in fear misfortunes will follow them in his presence. However, the news reporter was drawn to Winkelburg's story because of these misfortunes. The news reporter finds Winkelburg very intelligent, despite what he has gone through. Winkelburg talks about his life in an interview with the news reporter. Winkelburg explains that he is dying and is in chronic pain. The older man recounts a time he attempted to go to a hospital, while in extreme pain, because he would rather die in a hospital than alone in a room. However, when Winkelburg arrived at the hospital, the interns made fun of him and the doctor absently handed him a prescription and told him to walk home, despite Winkelburg's pain levels. Winkelburg believes this encounter occurred because society has no place for those who are poor and in pain. Winkelburg sends a letter a week later to the newsreporter, saying that the hospital denied the story that they refused Winkelburg from the hospital. Many philanthropists had reached out to the older man, willing to pay for the medical fees and hospitals were willingly letting him in. Winkelburg thanks the news reporter for releasing his story. However, soon after, all of the hospitals throw Winkelburg out. He was admitted by an older couple to stay with them, but they threw him out too. Winkelburg explains that this occurred because, despite his ailments, he smiled often. People believed his smile meant he was faking his illness and threw him out. Winkelburg explains to the news reporter that he is a grateful man and that his smile was not sardonic, as the people believed it to be. Six months later, Winkelburg sends more letters to the news reporter. Many people of the city believe Winkelburg will die soon, but the older man is persistent in getting a hold of the news reporter again. The two get back together to talk and the news reporter fears that Winkelburg is going to beg him for money. Winkelburg does not and says he has more stories to tell. Winkelburg instead asks the news reporter to continue writing news stories about him. However, the news reporter finds Winkelburg's incessant begging annoying and begins to believe that Winkelburg's stories are not true. After this, the news reporter refuses to see Winkelburg and tells his staff to tell the older man that he is constantly out of office. Eventually, Winkelburg sends a letter to the news reporter simply asking for company amidst his loneliness. The news reporter refuses and claims that Winkelburg is faking is ailments. In the Christmas season, the news reporter goes to a well-known charity woman and asks her to go care and give gifts to Winkelburg, feeling guilty about rejecting him. However, when the charity woman goes to visit Winkelburg's home, she finds the older man dead. The charity woman returns to tell the news reporter about what happened. The charity woman explains that she feels immense guilt and wishes she would've gone to visit Winkelburg sooner. The news reporter also feels guilty about it and often thinks that they will run into Winkelburg again someday on the street. Yet, the news reporter also thinks of Winkelburg's smile and about how he is better off dead.