This chapter surveys the career of Charles Chesnutt, first by focusing on his strategic, self-conscious efforts to enter what he called the literary world. It looks at Chesnutt’s rise in the literary world through publication with Houghton Mifflin and the critical acclaim of William Dean Howells, then his downfall after The Marrow of Tradition led to his being marked as a propagandist. It analyzes his short story “Baxter’s Procrustes” for its satirical insight into the paradoxes of contemporary literary value. It charts his final years when he was recognized by Harlem Renaissance writers as “the first Negro novelist,” even as he struggled to publish new work during that period, making him a sacrifical precursor for the Harlem Renaissance writers with whom he could only partially identify.