This chapter situates Chesnutt’s writing within a tradition of black classicism as political engagement and historical critique extending from the antebellum period to the twentieth century and beyond. Reading Chesnutt as a figure at the crossroads of multiple historical times and cultural forms, the chapter examines his manipulation of multiple mythic traditions into a cohesive and unsettling vision of history as unfinished business. In the novel The Marrow of Tradition and the late short story “The Marked Tree,” Chesnutt echoes a nineteenth-century tradition that included David Walker, Henry Highland Garnet, and writers and editors for antebellum black newspapers, while at the same time anticipating a later anti-imperial discourse generated by writers such as Richard Wright and Toni Morrison. Chesnutt provides a fulcrum for a collective African American literary history that has emerged as a prophetic counterpoint to the prevailing historical consciousness in America.