Chapter 6 compares the work of the enslaved poet Ambrosio Echemendía with that of several free authors of African descent, including Juana Pastor (often considered the first woman poet in Cuba), Plácido (Gabriel de la Concepción Valdés, probably the most popular Cuban writer of the century), and África Céspedes (one of the collaborators of Minerva (1888–1889), the first periodical by Black women). Black Cuban writing, the chapter argues, does not begin with Juan Francisco Manzano or Plácido, as most scholars have generally assumed; neither of them reclaimed Blackness in their texts. It makes more sense to argue that it begins with the poetry collection that Echemendía published in 1865 – the first book published in Cuba in which an author self-fashioned as racially stigmatized and questioned this stigma. Through this panoramic view, the chapter traces how a long history of public disidentifications with blackness began to make room for a distinctively Black literature – one that foregrounded and problematized racialized subject positions.