The purpose of this dissertation was to study the narrative discourse of three Cuban novelists who produced their works from 1902 to 1933, using a typology that reveals a picaresque view of Cuban society. Focusing on La conjura and La manigua sentimental by Jesús Castellanos (1879-1912), Las honradas and Las impuras by Miguel de Carrión (1875-1929), and Generales y doctores and Juan Criollo by Carlos Loveira (1882-1928), this dissertation identified and defined picaresque traits and elements in the characterization, contrasting main and secondary, male and female characters, at all social levels. The study considered the theories of the Spanish picaresque novel proposed by Antonio Maravall, Américo Castro, Claudio Guillén, Marcel Bataillon, and other critics, in order to delineate a model of traditional picaresque behavior, which was then applied to the analysis of each character. Sociopolitical and cultural conditions, as well as the psychology of the Cuban collective as presented by the authors, were also analyzed to pinpoint similarities and differences between the traditional Golden Age rogue and the characters created by the authors. Critics who have studied the influence of the Spanish picaresque genre on the Latin American novel make no reference to any of the authors or novels included in this study. Key analyses, however, identified the presence of characters that use picaresque modes of behavior as a means to manipulate the structures of power in order to survive and as a futile attempt to achieve their ends within a socioeconomic context that is undergoing a significant transition. Castellanos’ characters use their picaresque behavior mainly to attain a higher social status. Carrión concentrates on picaresque behavior in women as a means to manipulate the dominant male society, while Loveira’s picaresque characters are mainly interested in securing a position of political power.