Chapter 4 examines Naipaul’s engagement with the legacy of slavery beginning with The Loss of El Dorado (1969), a remarkable example of a novelistic rendition of historical events based on Naipaul’s reading of nightmarish primary documents relating to the colonization of the West Indies and littoral Latin America. What surfaced in the creative history that he wrote is a narrative of failures and failed, egotistical heroes, and administrators who, living out their own fantasies, saw nothing aberrant in their treatment of the slaves they traumatized and condemned, and the Indians they dispossessed and then killed off. Before The Loss of El Dorado, Naipaul had written his first travel book, The Middle Passage (1962), also discussed in this chapter. Naipaul returns to the theme twenty-five years later in A Way in the World (1994). The chapter examines the disturbing novel Guerrillas (1975), a dark book about fantasy-driven Black Power enthusiasts and, given the historical connections between Spanish and English slavery, a work on the American South, A Turn in the South (1989). The chapter makes the case that to Naipaul nations fail when they do not fully come to terms with their history.