The marble funeral monument to the organist Antonio Squarcialupi was sculpted by Benedetto da Maiano (and/or his workshop) around 1490, to a commission by Lorenzo the Magnificent, who also wrote the epitaph. Squarcialupi (Florence, 27 March 1416 – 6 July 1480) was one of the most important musicians and composers of his time, and also as organist of the Cathedral, remained closely linked to the Medici family throughout his life. This monument is actually a cenotaph, since Squarcialupi was buried in the Church of San Lorenzo, the so-called “Medici Basilica”. The monument, originally erected under the organs of the Sacristy of the Canons, was conceived as an ideal counterpart to that of Giotto, in the first arch of the right nave. Both of these monuments were part of the Lorenzan project to develop the Cathedral as a pantheon of Florentine glories: a political manifesto narrating the cultural supremacy of Florence. The design - with the portrait busts of the deceased inside a tondo and a large rectangular panel with epitaph in Latin capitals – takes up the invention of the earlier funerary monument of Brunelleschi, by Buggiano; the series would then be resumed and completed in the 19th century with the monuments to Arnolfo and De Fabris.

Squarcialupi is depicted slightly younger than he would have appeared at death, but his features are distinctive and certainly reflect his real appearance. The organist is imagined in the clothing of his time, in a rigid frontal pose and with a serene face: as if he were in contemplation, forever under the organs that he had played for almost his entire life. The monument was removed from its original position in 1495, at the time of the expulsion of the Medici, and then reassembled in the nave in 1512