This chapter analyzes Black writing from the leadup to the Civil War to the end of the nineteenth century, works that shored up the literate voice long denied to enslaved people, and explores how the pre-emancipation essay served to determine freedom. The century’s standout Black orator, Frederick Douglass, became a print phenomenon, advancing a strong first-person voice that spoke for the conscience of the nation. However, it was left to younger writers to tackle the meaning of freedom at a time when emancipation seemed like a hollow promise. The works of activist journalist Ida B. Wells highlight the synergy between investigative reporting and essay writing during the period. The chapter concludes by comparing the prose works of two towering figures: Booker T. Washington and W. E. B. Du Bois. The ideological split in their views on civil rights is registered in their different writing styles, with Washington stressing action and advocacy and Du Bois embracing introspection and contemplation. Between them, these figures register the suite of oratorical, journalistic, and literary resources that will be bequeathed to twentieth-century practitioners of the African American essay.