Chapter 5 offers a new reading of Cuba’s most famous enslaved writer, Juan Francisco Manzano, who started publishing in 1821 and became legally free in 1836. While it engages with his well-known autobiography, the chapter focuses on his poetry. To the degree that slavery was justified through race, Manzano’s emergence as an author produced racial doubt among those who believed that poetry and literary skills were the exclusive domain of white people. At the same time, he explicitly disidentified from blackness, prompting many generations of critics to discuss how Black he was. As new generations return to his texts, the palimpsest of conflicting ideas about his Blackness or lack thereof keeps changing. The chapter examines some of these layers by focusing on the paradox of enslaved authorship – of a writer who built his authority on the basis of his deauthorization. Poems, the chapter shows, were Manzano’s most elaborate literary form of back talk, as they allowed him to evade the abolitionist pressure to write about slavery.