Portrait of a Man with a Medal of Cosimo the Elder

[2] The medal appears to be the same as one possibly designed by Donatello and cast in 1465, an example of which is in the collection of the Victoria and Albert Museum in London, England, called "Cosimo de' Medici as Pater Patriae".

Writing in 1900, art historian George Noble Plunkett colorfully identified whom he believed the youth portrayed: one realizes painfully that this is the Piero who has left an indelible stain on the Medici family by his betrayal of Florence.

The small covetous eyes, the ignoble nose, the pursed animal mouth, with only the restraint of selfishness on it, the very manner in which he holds up the memorial of his house's founder, as though it were his badge of honor!

[9] Frederick Hartt suggested it might be Lorenzo di Pierfrancesco de' Medici (Il Popolano, 1463–1503), whose two certain portraits, both profiles on medals, vary considerably, though one resembles this.

[10] The appearance at an auction in 1982, from the Thomas Merton collection, of a rarely seen painting by Botticelli of a Portrait of a Young Man Holding a Roundel identified (with no real evidence) as Giovanni il Popolano in a similar pose, holding up a round medallion cut from a much older painting (albeit of a bearded saint, not Cosimo), has led to speculation that this might be a companion piece, and thus that the young man in this portrait is possibly his brother, Lorenzo di Pierfrancesco de' Medici.

Detail of Botticelli's supposed self-portrait in Adoration of the Magi