The present drawing was executed by Spada for Claudia de'Medici (1604-1648), who first married Francesco Ubaldo della Rovere (1605-1625) and then, after the murder of the latter, Archduke Leopold V of Austria (1586-1632). This drawing was probably drawn while Spada was accompanying his master Lorenzo Lippi to Innsbruck, where Lippi was employed by the Archduke (P. Dearborn Massar, 'Valerio Spada, Seventeenth-Century Florentine Calligrapher and Draughtsman', Master Drawings, 1981, p. 252). While in Innsbruck Lippi wrote a parody of Tasso's Gerusalemme Liberata called Il Malmantile Racquisito. In this long poem Lippi devoted a few verses to Spada and described his appreciation of good wine.
Spada was a writer, a draughtsman and a professor of calligraphy to the young Cosimo III and later to his son. His draughtsmanship shows the influence of Stefano della Bella.