A cryptic portrait, Alessandro de’ Medici, painted circa 1534 by Pontormo, hangs in Philadelphia (Fig. 4.1).1 If the sitter is, as is generally accepted, the illegitimate son of Giulio de’ Medici, later Pope Clement VII (1478-1534; 1523-1534), then Alessandro (1511/12-1537; first duke of Florence, 1532-1537), dressed in black, here mourns the death of his father, who died in September of that same year. From the start, this is an unusual portrait insofar as it represents a man mourning another man; such representations are rare in the early modern period.2 Also curious, infrared reflectography reveals a provocative pentimento – the absent presence of a second male figure in what has been loosely identified as a background window or open doorway to the right of Alessandro’s head.3 The identity of the enigmatic ‘repressed figure’ remains elusive, though the male figure – and his erasure – may be related to the ambiguous situation at Palazzo Pazzi, which then served as the Cybo/Malaspina residence, where Pontormo is thought to have painted the portrait and where Alessandro conducted his political – and personal – affairs.4