A narrative artist of exquisite sensibilities, Daddi was among the most important Florentine artists of the first half of the fourteenth century. His vision was shaped by Giotto, with whom he may have trained, and his paintings combine a clarity of structure associated with fresco painting with the jewel-like color and refined execution of a miniaturist. In the 1330s and 1340s his busy workshop produced numerous portable altarpieces for private devotion. Although these can be somewhat repetitive, his work from the 1320s is of an unfailingly high order.

This picture—one wing of a diptych that doubtless included a companion painting of the Virgin and child, now lost—is one of Daddi's earliest and most Giottesque efforts and is especially notable for the restrained expressiveness and nobility of its figures. The mournful attitudes of the Virgin and Saint John, seated on the ground in positions of humility, derive from figures of captives on Roman sarcophagi. (Interestingly enough, similar expressive gestures were explored contemporaneously by Simone Martini in Siena.) Although the figures of Christ and the lamenting angels have suffered from abrasion, the picture is of great beauty and is crucial for understanding the mainsprings of Daddi's art.