These three panels once formed an altarpiece. The largest, which shows the Virgin Mary holding the Christ Child, would have appeared at its centre. Saint Nicholas of Tolentino and a bishop saint would have stood on the left, with Saints Bartholomew and Monica on the right (the figures turn towards the Virgin and Child, making the intended position of the panels clear).

The presence of Saint Monica, mother of Saint Augustine, suggests that this altarpiece was made for an Augustinian foundation. This idea is further reinforced by the inclusion of Saint Nicholas, an Augustinian friar shown wearing the habit of the Order. Scholars have speculated that the three panels, which were among the first early Italian paintings to arrive at the National Gallery, came from the Florentine church of S. Spirito, but there is little evidence for this claim. Another possibility is that they came from the Tuscan hilltop town of Montepulciano, where they were recorded in a private collection in the early nineteenth century. It has also been said that they formed part of the same altarpiece as two others by Zanobi Machiavelli, but while their composition and gold backgrounds correspond, their shapes and sizes do not.

The pointed arch shape of the panels, which might have recalled architectural elements in the original church, is typical of Italian panel painting of the fourteenth and fifteenth centuries; examples in the National Gallery’s collection include the San Pier Maggiore Altarpiece, Baptism Altarpiece and Santa Maria Maggiore Altarpiece. So, too, is the decorated gold background. But by around 1470, when Zanobi Machiavelli painted this panel, both the shape and the gold background would have appeared slightly old-fashioned – they had been superseded by naturalistic landscape settings and rectangular picture fields. Pala altarpieces, where the Virgin and Child with saints are depicted on a single unified surface rather than on separate panels, had also become the norm. The fact that Machiavelli did otherwise paint pala altarpieces suggests that the unknown patron of this work demanded the pointed-arch, multi-panelled format.

It is possible that our altarpiece once had a large base that accommodated a predella, a tier of smaller pictures with scenes from the lives of the saints depicted above. Scholars have suggested that a small panel now in the Rijksmuseum, Amsterdam belongs to this altarpiece. It shows the thirteenth-century saint and mystic Nicholas of Tolentino rescuing a man condemned to death from the gallows. Canonised in 1446 by Pope Eugenius IV, Saint Nicholas became one of the most popular saints in Italy, as evidenced by the number of legends surrounding his virtuous life. His remains are enshrined in Tolentino, a small town near Macerata in the central Italian region of the Marche, but devotion to the saint went far beyond his hometown. It is Saint Nicholas who looks out at the viewer in the left-hand panel, and it is likely that the chapel this altarpiece once decorated was dedicated to him. The wooden framing elements that would have surrounded this panel to create a separate compartment are now lost, but they can be imagined on the basis of surviving examples.