This dissertation explores the relationship between the compendios de castigos brought into Castilian during the last years of the reign of Fernando III and the first four years of Alfonso X’s rule and the socio-political milieu in which they were circulated. The first two works are canonical texts of Arabic adab, instructional works for the education and criticism of rulers, and the third work was written in Castilian and modeled on the style of adab literature. For each text, I analyze the formal aspects of the frametales within each collection, and I propose a new method for looking at the didactic content. I first examine the work of Calila e Dimna, which the infante don Alfonso ordered to be translated into Castilian in 1251. Apart from being the first work of prose literary fiction to be made in Castilian, the act of translating this work, I argue, was important for three main reasons: first, for crafting his royal image as a patron of wisdom; second, for laying the foundation for a new model of Castilian monarchy; and third, for changing the goals of conquest from strictly material gains to the acquisition of knowledge, wisdom, philosophy, and science.The second text I look at is the Sendebar, the translation project of Alfonso’s oldest sibling, the infante don Fadrique, who ordered the making of a Castilian version of the work in 1253. Following the same techniques of analysis as implemented in the study of Calila e Dimna, I propose a reception of Sendebar in the context of mid-thirteenth-century Castile that challenges the goals of Alfonso’s cultural program and undermines Alfonso’s attempts to further centralize authority under the king. Where Alfonso’s book seeks to legitimize the centralization of power under the wise monarch, Fadrique’s book offers an alternative perspective to that model by offering an example of the dangers of potential abuse from an unchecked authority.The final work studied was also made under the patronage of Alfonso X, most likely between 1255-58, and is titled the Libro de los doze sabios. I contend that the work as a whole also supports Alfonso’s cultural project of redefining the role of the king, crafting a new image for the monarchy in Castile, and re-writing the history of the conquest to make the acquisition of wisdom its primary goal. The application of my conclusions, regarding the process of meaning-making that is involved in these texts, to the socio-historical moment of the translation of Calila e Dimna and Sendebar and the creation of the Libro de los doze sabios, will allow a more nuanced understanding of the way the Alfonsine cultural campaign exercised its power and influence.