This is probably the portrait of the ‘fattore’ (estate manager) Jacopo Cennini first described by Giorgio Vasari in his ‘vite’ of the artist Franciabigio (1568). Documents support the existence of a Jacopo Cennini, who was from a large and respectable Florentine family, and managed the small Fiesole villa and estate of Pierfrancesco di Lorenzo de’ Medici the Younger (1487-1525).

The attributes in this portrait appear to refer straightforwardly to the sitter’s stewardship of an estate. He is shown at half-length, poised as though interrupted midway through writing in a ledger raised on a book rest; he holds a quill pen in his right hand and an ink pot in his left, and rests his right elbow on the stone parapet that runs the width of the composition. A bunch of keys are prominently displayed hanging over his right wrist, symbols of a trusted servant, and on the wall behind him are two garden hooks; a pruning hook and a bill-hook. His outfit is a simple lilac-grey coat over a plain white shirt, with a charcoal-grey hat covering his long grey hair. The Medici arms (five red palle, one blue) are visible on the parapet.

To the right of the ledger are two laurel shoots. These may be the casual results of pruning, or they may hold greater significance as symbols of the truncation and renewal of the branches of the Medicean family. By 1523 the legitimate line descending from Lorenzo di Piero, ‘il Magnifico’, had died out and Pierfrancesco of the younger branch had a good claim to be head of the family. However, Cardinal Giulio de’ Medici, later Clement VII, supported the illegitimate Alessandro and Ippolito. The two laurel-shoots may be intended to refer to this situation; one is upright, while the other (Pierfrancesco’s) is down, and virtually eclipsed under the ledger.

Inscribed on the pruning hook, upside down, the artist’s monogram (‘FRAC’); on the left page of the ledger, ‘MDXXIII’; on the right page, ‘…flore…/ogi adi 20…/…si girolamo….’