In the center of this picture is Saint Augustine, who was a bishop in the 4th century and was born in present-day Algeria, which was then under Roman domination. Saint Augustine wrote "Confessions"—memoirs that recount his conversion to Christianity, from which the episode depicted by Niccolò di Pietro is derived.
The saint is shown playing chess with his friend Alypius while the Christian Ponticianus entertains them with episodes from the life of Saint Anthony. The two players interrupt their game to devote their attention to his fascinating story. We are thus invited to witness a moment in the saint’s conversion, rather than a simple game of chess.
This work was part of a predella (a kind of frieze) at the bottom of the retable in the Augustinian church of Pesaro, which was renovated around 1413. This predella consisted of other small panels now housed in French, Italian and American museums. It was probably surmounted by larger panels depicting saints.
The painter arranged his characters in an architectural space formed of converging lines that give the illusion of depth. However, the chessboard is viewed from a different angle and the characters look out of proportion to the decor because Niccolò di Pietro painted this work at the turn of the Middle Ages and the Renaissance, when notions of perspective were not yet fully developed.