At the beginning of the 1280s, two books were published in Castile. One was written by the Castilian King Alfonso X, the other by the Jewish author Rabbi Isaac Ibn Sahula. Alfonso X’s illuminated book of stories and songs, the Cántigas de Santa Maria, portrayed the miracles of the Virgin Mary and was dedicated to her. It was written over a period of three decades and completed in the year 1284. Isaac Ibn Sahula’s Hebrew book of fables, Meshal Haqadmoni, was written in 1281, and the stories in it are accompanied by illuminations with captions written by the author. This paper examines the possible connections between Alfonso’s book and Ibn Sahula’s, with an emphasis on the Jewish-Christian polemic in thirteenth-century Castile. The main focus will be on the historical and cultural context in which the books were written, through a discussion of one of Meshal Haqadmoni’s fables against the background of contemporary Christian literature. The sense of persecution in the Meshal Haqadmoni stories may derive from the attitude of Christian society toward the Jews. From the point of view of the Christian public, the King’s attitude toward the Jews are expressed in his book, despite the fact that Alfonso X is considered a tolerant king who was benevolent toward the Jews. Most scholars studied the Cántigas de Santa Maria in search of an answer to the question of whether or not the book and its author were expressing an anti-Jewish attitude. Examination of the book reveals that the anti-Jewish stance is consistent, and while King Alfonso himself may have treated the Jews fairly, his book conveys an anti-Jewish message to his audience. In Meshal Haqadmoni we find a possible response to this message.