Wing Biddlebaum

Wing Biddlebaum, who was once known as Adolph Myers, is a reclusive, bald, and overweight man living in a small house on the outskirts of Winesburg, Ohio. Although he appears frail and elderly, he is only forty years old. His most notable feature is his hands, which are constantly in motion, making expressive gestures as he speaks. This habit earned him the nickname "Wing." In his youth, when he went by Adolph Myers, he was a schoolteacher in rural Pennsylvania. He was an excellent teacher who motivated his students and displayed affection by patting their shoulders and tousling their hair. However, a "half-witted boy" misinterpreted Myers's gestures as sexual advances, leading to Myers being driven out of town. Now, living alone in Winesburg under an assumed name, he avoids social interactions. Only with his friend George Willard does he feel comfortable enough to converse and attempt to inspire young men. He encourages George to pursue his dreams, but when he forgets himself and touches George's shoulders, Wing becomes frightened and flees.

Henry Bradford

Henry Bradford is a saloon owner in Pennsylvania and the father of one of Adolph Myers's students. Believing that Myers made inappropriate sexual advances toward his son, Bradford confronts Myers at school, attacking him with punches and kicks in the schoolyard.

Half-witted Boy

One of Adolph Myers's students is a "half-witted boy" who develops an infatuation with his teacher. The boy imagines sexual encounters with Myers and reports these fantasies as reality. His stories reinforce the "hidden, shadowy doubts" that the townspeople already harbored about the kind-hearted Adolph Myers.

Adolph Myers

See Wing Biddlebaum

George Willard

George Willard, the reporter for the Winesburg Eagle, is Wing Biddlebaum's only friend in the town where Wing has lived for twenty years. George occasionally visits Wing in the evenings, and as the story begins, Wing is pacing on his porch, hoping George will come by. In the past, they have taken walks together in town or through the countryside, with Wing encouraging George to chase his aspirations. George has noticed Wing's peculiar habit of alternately waving his hands and hiding them, but he refrains from asking out of respect for his friend.