In my dissertation, I study a selection of little known Spanish and Cuban texts published during the Cuban War of Independence at the end of the 19th century. In this project, I provide a transatlantic approach of literary texts in various genres and subgenres, and political messages exchanged between Cuba and Spain, which have been neglected by scholars in the field. By analyzing the emergence of a colonial discourse in the works of novelists, politicians and thinkers who wrote about the Cuban-Spanish confrontation, I establish their ambiguous and frequently contradictory colonial messages. In doing so, this dissertation furthers our understanding of the complexities of the political moment as well as the interest and ideals that ignited the conflict. The study is of great relevance in view of the recent agreements between the United States and Cuba. The relations between the two countries are evolving in a way that was unthinkable at the beginning of the 20th century. Furthermore, secessionist feelings within the Spanish nation are reemerging and similar allegations and demands that brought Cuba to independence are in place. For all these reasons, it is necessary revisiting and comprehending the complex and, frequently contradictory, discourses that emerged in a moment, which was determinant for the development and future political attitudes of the three nations involved.