Pisanello, who was a painter as well as a medalist, is generally credited with having invented the Renaissance medal form, as well as having brought it to its highest potential. He made several medals of the Marquess of Ferrara, this one being for the occasion of Leonello's marriage to Maria of Aragon in 1444. The composition of the reverse side alludes to their marriage, with Leonello (in the guise of a lion; his name means "little lion") being taught to sing by Cupid, who here represents matrimonial love. The artist has dated this reverse composition (MCCCCXLIIII, or 1444) on the pillar in the background, and has signed it OPVS PISANI PICTORIS ("the work of Pisano the Painter").
The inscription across the field and around the bottom of the obverse, LEONELLVS MARCHIO ESTENSIS D(ominus) FERRARIE REGII ET MUTINE, identifies Leonello as Marquess of Este and Lord of Ferrara, Reggio, and Modena. The truncated inscription around the top, GE R AR, is an abbreviation of GENER REGIS ARAGONUM, identifying him (through his marriage) as the son-in-law of King Alfonso V of Aragon, ruler of Naples; Leonello's marriage to Maria brought him a bride who increased his prestige by associating him with the powerful Neapolitan court.