The monk looks to the left and is holding a red book with both hands. The painting is now in the Frick Collection. Originally, the painting was one section of the Polytych of Saint Augustine completed by Piero della Francesca between 1460 and 1470. The polytych was commissioned from della Francesco in 1454 by Angelo di Giovanni di Simone d’Angelo in 1454. The polytych was for the high altar of the Saint Agostino church in Borgo Sansepolcro, which was della Francesca’s home town. The commission was to fulfil a wish of the patron’s late brother, Simone, and his wife, Giovanna, and was for the spiritual assistance of Simone, Giovanna, and their forebears.
The commission was for a polytych consisting of four lateral panels and a central panel as a lower register with five smaller sections above the main panels as an upper register. The polytych is now dissembled. However, based on structural, pictorial, and thematic unity, a possible reconstruction of the polytych beginning from left to right is as follows. On the extreme left of the lower register is Saint Augustine (132 cm x 56.5 cm), currently in Museo de Arte Antiga, Lisbon. Above Saint Augustine is the depiction of an Augustinian nun holding an unfurled scroll (38.74 cm x 27.94 cm). The nun was acquired by the Frick Collection in 1950. To the right of Saint Augustine is a panel depicting Saint Michael the Archangel (133 cm x 59.5 cm), now in the National Gallery, London.
The smaller panel about Saint Michael has been lost. The central large panel has also been lost, but a Nineteenth Century description indicates that is a Madonna and Child. Above the central larger panel is a depiction of the crucifixion (37.47 cm x 41.12 cm) now at the Frick Collection. To the immediate right of the central panel is a portrayal of Saint John the Evangelist (131.5 cm x 57.8 cm), now in the Frick Collection. To the right of Saint John is Saint Nicholas of Tolentino (136 cm x 59 cm) now in Milan at Museo Poldi Pezzoli.
The Augustinian monk sits above Saint Nicholas. The lateral placement of the Augustinian nun and monk to the left and right, respectively, makes hierarchical sense as they are less significant than the central crucifixion. The nun to the left and the monk to the right allows both figures to face inward toward the central panel. Their attributes, a scroll for the nun and a book for the monk, provide a scholarly framing to the polytych, which fittingly proclaims the Augustinian focus on science and learning. Overall, the polytych demonstrates the mathematical rationality characteristic of the humanist early Renaissance. Although perspective is shown in the other panels, the Augustinian monk has a flat background that gives the figure an otherworldly and timeless presence.