A recluse, the politically brilliant, autocratic ruler of Milan was hideously fat, walked with difficulty, and had poor eyesight, but he knew Pisanello would manage to minimize these defects and is said to have wanted no one else to portray him. Pisanello lit the figure from the back, thereby softening the appearance of his "deformed, frightening face and large restless eyes" (Pope Pius II). Often thought to be a preparatory study for the duke’s medal (cat. no. 95), this sheet may, instead, be one of the artist’s earliest independent portrait drawings. The narrow format clearly relates to Pisanello’s painted portrait of Leonello d’Este (cat. no. 70).