The narrative of Winesburg, Ohio shifts back in time to the late nineteenth century to tell the story of Jesse Bentley, who owns a prosperous farm outside of Winesburg. Jesse and his four older brothers follow in the traditional footsteps of their family, who had been poor farmers in Northern Ohio for several generations. Jesse is the “odd sheep” of his family and leaves home at eighteen to become a scholar and minister. But after his brothers are all killed in the Civil War and his sick mother suddenly dies, Jesse returns home to help his father Tom Bentley on the farm.
By shifting the narrative to a bygone era, Anderson adds an additional layer to the rich narrative of Winesburg, Ohio. Jesse Bentley’s decision to leave home for intellectual and spiritual pursuits sets him apart from his brothers who are on a more pragmatic path of farm work and military service. The death of his brothers and mother forces Jesse to return to the family farm become the de facto head of household.
Jesse takes over the family farm and runs it with uncompromising authority, instilling fear in his farmhands and even letting his wife Katherine overwork herself to the point that she dies in childbirth. Jesse approaches his leadership role with religious fanaticism, ignoring his family to spend his days planning how he can cultivate the most successful farm in Ohio. He comes to view himself as an Old Testament figure and believes that he was chosen as a servant of God to do holy work.
In his newfound role as the overseer of the Bentley farm, Jesse takes on the persona of a traditional patriarch. His hyper-focus on the success of the farm causes him to neglect his familial duties as a son, husband, and father. Jesse’s vision of himself as a heroic biblical figure suggests a self-aggrandized belief that he can overcome his limitations as a mortal man to take control of his own destiny.
The narrator comments that modern men and women may find it hard to understand Jesse Bentley. Whereas men in Jesse’s era lived simple, pastoral lives centered around religion, those in the early twentieth century (when the other stories in Winesburg, Ohio take place) are influenced by industrialized urban culture. Jesse epitomizes this generational difference, focusing solely on God and interpreting every life event as a divine omen. On a walk in the countryside just before his wife gives birth, Jesse comes to the conclusion that he is “the true servant of God.” He believes that all of the other farmers in Ohio are “Philistines” and “enemies of God,” and that he deserves to take possession of their land. Jesse prays that his wife will give birth to a son named David who will help him fulfill his biblical prophecy of building a holy kingdom on Earth.
Whereas the characters in the contemporary storyline of the novel live in a more industrialized, interconnected world, men in Jesse’s time were not inundated with modern influences such as mass media and urbanized culture. Jesse is solely focused on his perceived role as a servant of God and what is under his immediate control. Ironically, Jesse’s conviction that other farmers in town are “enemies of God” contradicts most interpretations of Christianity which espouse the intrinsic worth of all human beings.