Legal and Writing Career
In 1887 in Cleveland, Chesnutt studied for and passed the bar exam. Chesnutt had learned stenography as a young man in North Carolina, and he established what became a lucrative legal stenography business.
Chesnutt also began writing stories, which were published by top-ranked national magazines. These included The Atlantic Monthly, which in August 1887 published his first short story, "The Goophered Grapevine." His first book was a collection of short stories entitled The Conjure Woman, published in 1899. These stories featured black characters who spoke in Southern dialect, as was popular in much southern literature at the time.
Chesnutt's stories were more complex than those of many of his contemporaries. He wrote about characters dealing with difficult issues of mixed race, "passing", illegitimacy, racial identities and social place throughout his career. The issues were especially pressing during the social volatility of Reconstruction and late 19th-century southern society. Whites in the South were trying to reestablish supremacy in social, economic and legal spheres. With their regaining of political dominance through paramilitary violence and suppression of black voting, they passed laws imposing legal racial segregation and a variety of Jim Crow rules that imposed second-class status on blacks. From 1890 to 1910, southern states passed new constitutions and laws that disfranchised most blacks and many poor whites from voting. At the same time, there was often distance and competition between families established as free before the war, especially if they were educated and property-owning, and the masses of illiterate freedmen making their way from slavery.
Chesnutt continued writing short stories. He also completed a biography of the abolitionist Frederick Douglass, who had escaped from slavery before the war and become renowned as a speaker and abolitionist.
He began to write novels that reflected his stronger sense of activism. His Marrow of Tradition was based on the Wilmington Massacre of 1898, when whites took over the city and threw out the elected biracial government. Eric Sundquist, in his book To Wake the Nations: Race in the Making of American Culture (1993), described the novel as "probably the most astute political-historical novel of its day", both in terms of recounting the massacre and reflecting the complicated social times in which Chesnutt wrote it. Chesnutt wrote several novels and appeared on the national lecture circuit, primarily in northern states.
Because his novels posed a more direct challenge to existing sociopolitical conditions, they were not as popular as his stories, which portrayed antebellum society. Among the era's literary writers, Chesnutt was well respected. For instance, in 1905, Chesnutt was invited to Mark Twain’s 70th birthday party in New York City. Although Chesnutt's stories met with critical acclaim, poor sales of his novels doomed his hopes of a self-supporting literary career. His last novel was published in 1905.
In 1906, his play Mrs. Darcy’s Daughter was produced, but it was also a commercial failure. Between 1906 and his death in 1932, Chesnutt wrote and published little, except for a few short stories and essays.
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