Enoch Robinson is a childish man who seems crazy. He grew up on a farm near Winesburg, and he used to want to be an artist. When he was twenty-one he went to live in New York City, where he remained for fifteen years. There, he made friends who were artists, and they came to visit him in his little rented room. They talked of the composition of his pictures, but he felt they did not understand the art. Then, he stopped letting them come visit and instead invented people to keep him company in his room, people he could better control. Eventually, he married an art student, but that, too did not work out because of his egotism. He wanted people who exactly suited his needs, rather than real people, so he left his wife and two children, returned to his room, and continued imagining people. Finally, a young woman started visiting him again, and he tried to make her understand about his people, but she realized he was crazy and ran away. He ran after her and tried to explain, but he ended up swearing at her, instead. When she left, she took all the life and imagined people out of his room. He returned to Winesburg to live out his life alone and defeated.
The big city, with all its promise, could not give Enoch Robinson what he wanted. It is a lonely place, where he fails to establish connections with people. Instead, he populates his own village within the city. This does not make him an artist; it makes him immature because he cannot interact with other people. While people go away to the city to find something bigger or better than they can get in Winesburg, they are left with shattered dreams when they fail to make a connection with others.