For years, the most distinguished Florentine noblemen, scholars, and artists assembled at the Marchese Valori's country villa outside Florence every summer. There Filippo Baldinucci displayed his considerable amateur artistic talents. "[A]lmost every day he was condemned to make a portrait from life of one of his gentlemen companions, in black and red chalk, choosing by lots each day the one to be portrayed," wrote his son.
Baldinucci drew his friends' portraits, all in roughly the same format, and gave them to his renowned host, who hung them in his villa. After Valori's death, the collection remained intact, becoming part of the Uffizi Gallery's collection in 1866. Baldinucci also made duplicates for his own collection. These duplicate drawings, unbound from the book in which he collected them, were dispersed at London sales in the 1760s. Scholars are uncertain about the identity of this sitter. The verso displays an accidental offset from another portrait drawing, most likely by Baldinucci, which suggests that this drawing probably came from his book of duplicates. The residue of a tinted edge along the right side of the paper and traces of stitch holes at the left also demonstrate that the sheet was once part of a sketchbook or album.