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Wing Biddlebaum, a fat little old man, lives an isolated life in a small frame house outside Winesburg, a small, provincial Ohio town. Beset by troubling doubts, he does not think of himself as a part of the life of the town where he has lived for twenty years. In fact, only with George Willard, the young son of the proprietor of the New Willard House, does Wing have anything close to a friendship, and only in George’s presence does Wing lose some of his timidity. On this single day of the story’s action, Wing hopes that George will spend the evening with him. George never appears, and most of the story’s action occurs not in the present but in flashbacks.

During an earlier meeting between the two men, Wing became “wholly inspired” and told the younger man that he cared too much about the opinions of others, and should shut his ears to the roaring of other people’s voices and begin to dream. Wing “raised the hands to caress the boy and then a look of horror swept over his face.”

After Wing flees this scene, George thinks Wing’s hands have something to do with his fear of him and everyone. Here begins a major flashback, “the story of the hands. Perhaps our talking of them will arouse the poet who will tell the hidden wonder story of the influence for which the hands were but fluttering pennants of promise.”

Wing had an earlier existence as Adolph Myers, a twenty-year-old school teacher in rural Pennsylvania. Adolph Myers was much loved by the boys of his school, for he was meant by nature to teach young people. His voice and his hands were both expressive. “He was one of those men in whom the force that creates life is diffused, not centralized. Under the caress of his hands, doubt and disbelief went out of the minds of the boys and they began also to dream.” Then tragedy struck. One of the boys became enamored of Wing, dreamed unspeakable things, and spoke them to others. The hysteria against Adolph grew quickly. Henry Bradford, a saloon keeper, called Adolph out from the schoolhouse and beat and kicked him, and a mob drove Adolph out of town that night. Wing moved to Winesburg to stay with an old aunt, and lived with her until she died. He was ill for a year after the incident in Pennsylvania and has worked since as a day laborer in the fields around Winesburg.

Back in the present time of the story, in its final paragraph, Wing walks up and down the veranda of his house, prepares and eats a simple meal, washes his dishes, and then gets ready for bed. “A few stray white bread crumbs lay on the cleanly washed floor by the table; putting the lamp upon a low stool he began to pick up the crumbs, carrying them to his mouth one by one with unbelievable rapidity.” He looks like a priest engaged in a church service. The sad, lonely figure of Wing Biddlebaum is transformed in this last image into a transcendent spiritual being.

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