Doctor Reefy is an old man who was once affluent and well-known in Winesburg. In his younger days, Reefy married a beautiful, wealthy girl who had been left a farm after the death of her parents. The townspeople of Winesburg questioned why the girl would marry the doctor, and a year after the marriage she died.
Doctor Reefy is established as a character who is judged and perceived as mysterious by other people in Winesburg, as they wonder why a wealthy and beautiful young girl would settle down with a much older man.
Forgotten by the town of Winesburg in the wake of his wife’s death, Doctor Reefy now leads a lonely, solitary existence in his empty office above the Paris Dry Goods Company store. Reefy has a disheveled appearance, having worn the same threadbare suit for ten years. He is obsessed with thinking up and rejecting ideas, relentlessly scribbling “truths” onto scraps of paper that he balls up into his jacket pockets.
The death of his young wife has a profound effect on Reefy, who has since lost all sense of purpose and now spends his days isolated in his office. In lieu of meaningful relationships, Reefy is possessed by intellectualism and obsessively records his thoughts in attempts to work out philosophical truths. Similar to the writer’s ideas about truth in “The Book of the Grotesque,” principles arise in the doctor’s mind, consume him, then fade away. This habit leaves Reefy lost and empty rather than leading him to any meaningful conclusions.
The narrator likens Doctor Reefy to the delicious, sweet twisted apples that are rejected by the pickers in Winesburg’s orchards. The enormous knuckles of Reefy’s hands are also similar to the gnarled, twisted apples. When Reefy was forty-five, the woman he married first came to see him because she had gotten pregnant by one of the suitors who pursued her after her parents died and left her a sizable inheritance. She quickly fell in love with Reefy and they were married after she had a miscarriage. Throughout that winter, Doctor Reefy read her the thoughts he wrote down and kept stuffed in his pockets, and the following spring she died.
Much like the overlooked twisted apples in Winesburg’s orchard, Reefy’s knuckles reflect his deceptively sweet inner nature. The fact that Reefy shared his philosophical musings with his wife before she died further emphasizes Anderson’s ongoing argument that an outward search for meaning cannot save people from the reality of their human limitations.