Upon graduation he entered the clergy and rose rapidly through the ranks. His first appointment was as dean of Santiago in 1415 or 1416, a post that he seems to have regarded with a certain amount of fondness, as in his will he bequeathed two hundred florins to the chapter of Santiago. By 1420 he was serving as dean of Segovia. He also enjoyed the favor of King Juan II at the Castilian court, where he served as a respected royal adviser from 1419. Operating as a politician as well as a theologian, Cartagena was never far removed from the political intrigue that fueled the dynastic disputes of fifteenth-century Castile.
Unlike his father, Cartagena was a peripatetic prelate whose career was characterized as much by extensive travel as by literary productivity. His first diplomatic missions were to the neighboring state of Portugal. He visited the court of King João I on several occasions between 1421 and 1431. The purpose of these missions was to finalize and ratify a peace treaty between Castile and Portugal that had been stipulated in truces agreed upon in 1411. As Abdón Salazar observes in his 1976 study of Cartagena's diplomatic missions to Portugal, Castile had good reasons to postpone signing a treaty with Portugal because of Castilian claims to the Canary Islands, which were strategically important for the purposes of Atlantic seaborne exploration.
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