This medal is generally considered to be the first portrait medal of the Italian Renaissance. Though there are a few early prototypes of a medallic form, it was this and the further works of Pisanello which begot followers for the new art form of the portrait medal. The medal is believed to have been created in 1438 or 1439, when John VIII Palaeologus was in Ferrara to attend a council convened by Pope Eugenius IV.

John VIII was the penultimate Byzantine emperor who had been trying in vain to gather assistance in Europe for his fight against the Turks, and a constant issue was a union of the Roman Catholic and Greek Orthodox churches. Eugenius IV convened a council to address problems of the Church, and the issue of a union between the Roman and Greek churches was to also be discussed. John VIII was invited to attend and, after many delays, arrived with his delegation in Venice in February of 1438.

After postponing the start to allow for the arrival of various other European representatives, the council opened in Ferrara on October 8, 1438. Soon after, an outbreak of the plague in Ferrara caused the council to move to Florence in February of 1439. In the end, John VIII did not receive the assistance that he so desperately needed, and upon his return to Constantinople he faced riots by his own subjects who found the idea of reconciliation of the two churches unacceptable.

At the time of the council, Pisanello, already a famous painter, was working in Ferrara for Leonello d'Este. A number of surviving drawings from his hand show his interest in the exotic appearance of the Byzantine delegation. It is during this time, when both John VIII and Pisanello were in Ferrara, that the medal is believed to have been conceived and created. The reverse design, with the emperor on horseback with a bow and quiver, shows him partaking in two of his favorite activities of riding and hunting, of which he spent considerable time partaking in while in Ferrara. The image of him praying before a wayside cross evokes the purpose of his visit to Ferrara.

The medal, while significant for its place in art history as the first proper portrait medal, also contains several interesting points in the designs. On the obverse, the exotic dress and appearance of the emperor is clearly shown, with his impressive hat occupying nearly half of the vertical space for the portrait. On the reverse, the page on horseback is shown with noticeable foreshortening and, intriguingly, the horse's left ear is penetrating through the border. The artist's signature, in both Latin and Greek, proudly proclaims him as a painter.