[1] He married three times, choosing his wives for political and economic convenience, and worked to match his children with partners associated with royalty.

As these titles follow the Aragonese nobiliary traditions, they were of little interest to the Castilian author, to the point that he never used them in his writings or correspondence, and they have only been associated to him by a handful of scholars.

Juan Manuel was trained in arts such as equestrianism, hunting, and fencing, and in addition learned Latin, history, law, and theology.

In 1304 he was entrusted by the queen mother, Doña María de Molina, to conduct political negotiations with James II of Aragon on behalf of her son, Ferdinand IV, then under age.

The diplomacy was successful and Juan Manuel's marriage to James II's daughter, Constance, added to his prestige.

This reconciliation was not complete until 1340, when Juan Manuel and Alfonso allied against the Muslims in the Battle of Río Salado, taking the city of Algeciras.

After these events, Juan Manuel left political life and retired to Castillo de Garcimuñoz, where he spent his last years focused on literature.

Following the path of his uncle, Alfonso X of Castile, Juan Manuel wrote in Castilian, a peculiarity in times when Latin was the official language for educated writing.

While his writings were directed largely to a literate class, it was nonetheless his assumption that they would be read aloud, as was common during the Middle Ages.

While his work is often classified under the general Medieval rubric of "the education of princes" it also begins to approach the Machiavellianism which is more characteristic of the Renaissance, by virtue of its dedication to the astute art of governing.