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Niccolò Piccinino (1386-1444) was among the most accomplished condottieri (mercenary soldiers) who were hired by the contending city-states, principalities, and foreign invaders in Italy in the fourteenth and fifteenth centuries. He was extremely short, as indicates his name, the "tiny one." He worked primarily for the duke of Milan, Filippo Maria Visconti, who in 1439 adopted Piccinino.
During the years 1439 to 1442, Pisanello traveled in northern Italy, and it was in this period that he came into contact with Filippo Maria Visconti, Niccolò Piccinino, Francesco Sforza, and Gianfrancesco Gonzaga. Portrait drawings of the first two survive, as do medals of all four. In each case, it seems likely that the artist had access to his subjects and drew them from life, translating these drawings into the more permanent and distributable medium of bronze.
In the drawing, Piccinino is represented in civilian dress, as he would undoubtedly have appeared when he sat for the artist, but that changed into armour for the medal, the latter communicating to a wider audience the subject's profession as a renowned soldier. Pisanello's innovative use of black chalk enabled him to endow the features of his sitter with a delicately modeled, relieflike quality that could serve equally for a painting or a medal.
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