This book analyzes the work of iconic Chilean author Alberto Blest Gana (1830–1920) through the lens of Machiavelli and Cervantes. Transatlantic in scope, it uses literary studies and cultural history to delve into Chile’s emergence as a nation and to illustrate a set of conflicts among the political parties and social classes in the early days of independence, the 1830s and 1850s. With a focus on Martín Rivas: Novela de costumbres politico-sociales [Martin Rivas: A Novel of Socio-Political Manners] (1862), El ideal de un calavera [The Ideal of a Rogue/Libertine] (1863), and Durante la Reconquista [During the Re-Conquest] (1897), this study examines the political and social exchanges and the place of social order in a critical period in Chile’s national development. Blest Gana’s three novels vividly depict the whys and hows of Chile’s early political struggles, dramatically underscoring the painfully real and very deep disagreements about the nation’s early direction and sense of identity, and showing how political and cultural antagonisms resulted from social hierarchies. For some, patria was synonymous with order itself; order needed to be established and maintained no matter how severe the measures. The book is informed by a desire to use early narrative expressions of Chile’s national identity to illuminate the political and cultural heritage of the twentieth century, especially the disruptions that occurred during the government and ultimate ousting of Salvador Allende Gossens (1908–1973), president of Chile from 1970 to 1973. In Blest Gana’s three texts, the enmities among Chileans reveal a fundamental and ongoing social, political and cultural disunity. This crack in the national foundation accounts in part for what erupted during the government of Allende, an idealist and a quixotic individual who believed in socialism via democracy and fought for equality in society. Betrayed from all sides, Allende was violently removed from power by a military junta led by Augusto Pinochet Ugarte (1915–2006), who ruled from 1973 to 1990. Under Pinochet’s dictatorship, books and print materials were scrutinized and censored in a way that was not unlike the period when Cervantes published the first and second parts of Don Quijote. Martín Rivas, however, continued to be read in schools, but mostly as a love story, with its political commentary effectively concealed.