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The Virgin is portrayed sitting in a flowery meadow, against a background of young athletes (probably to be interpreted as allegoric of ascetic virtues); towering above her are the monochrome figures of John the Baptist and two prophets. The figurative references contained in this painting are extremely varied and sophisticated. There are references to Piero della Francesca's descendants of Adam (the young man in the background), to archeological elements, as well as tributes to Flemish painting (the monochromes in the upper part); and, above all, there is an explicit reference to Leonardo and his followers in the flowery meadow in the foreground, in the toned down colours, in the careful attention paid to chiaroscuro values.
The work has many unique details, beginning with the shape: the tondo, the traditional round shape favoured for religious paintings destined for private residences and the magistrates of the Florentine Republic, is framed with a false frame in carved stone adorned with the figures of two prophets intent upon their writing and, in the centre, the bust of St John the Baptist. The monochromatic tones of the frame serve to enhance the vibrancy of the image of the Madonna, humbly seated on the ground in a natural setting surrounded by the ruins of ancient monuments and absorbed in the care of the baby Jesus, whose nudity emphasizes his human nature. The figures clustered in the background are also nude; the significance of this is unclear, although one interpretation could be the representation of mankind before the time of the Law of Moses and the coming of Christ; similar 'ignudi', or nude figures can be seen in the background of the Holy Family by Michelangelo, also housed at the Uffizi.
The iconographic complexity of the work, as well as the unusual layout, seem to suggest a cultured, refined and avant-garde client. Originating from the Medici villa of Castello, according to Vasari the painting was carried out for Lorenzo de' Medici; this is most likely not Lorenzo the Magnificent but rather his cousin, Lorenzo di Pierfrancesco. There can be no doubt that the learned symbolism and the allegorical references the painting contains would have been fully appreciated by the Medici Court, whose religious ideals in those years were founded on highly intellectual and philosophical studies, deeply imbued with Platonism and Classicism.
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