Though his assistant Caravaggio is better known today, at the turn of the seventeenth century Giuseppe Cesari, later known as the Cavaliere d'Arpino, enjoyed the patronage of pope and court, receiving major commissions throughout Rome. His position at the cusp between Mannerism and the Baroque is shown well in this drawing, where the elegance and grace of the sixteenth century are combined with the emotional and narrative clarity of the seventeenth.

Born in 1568 in Arpino, the hill town southeast of Rome, Cesari learned the art of painting from his father before travelling to the papal city in 1582. The fourteen-year-old artist assisted Niccolò Circignani, known as il Pomarancio, with his work on the final stages of the Vatican Loggie decoration and by the following year had received both a regular papal stipend and membership in the Accademia di San Luca. His star rose quickly, so that he soon gained the patronage of Cardinal Alessandro Farnese, for whom he painted frescoes in S. Lorenzo in Damaso. Under Pope Clement VIII Aldobrandini (pope 1592–1605) he was favored highly, in 1593 painting the ceiling of the Contarelli chapel in S. Luigi dei Francesi for which Caravaggio, his assistant at the time, later provided the side canvases, as well as the entire Olgiati chapel in S. Prassede. In 1599–1600 the artist was honored with the principato of the Accademia di San Luca and the papal knighthood that gave him the title of Cavaliere. The Pope's death in 1605 ended his favor at court, such that by 1607, when he was briefly imprisoned on a weapons charge,(1) Scipione Borghese, the new pope's nephew, seized his collection of 105 paintings.(2) Paul V was not entirely unreachable, however, restoring him to his previous commissions for Saint Peter's by 1608. Over the following decades—though taste was changing around him—Cesari continued to receive commissions from popes and cardinals and was twice more principe of the Accademia di San Luca (1615, 1629). He died a highly-respected and wealthy artist in 1640.

"[H]a in sé quella vaghezza che in un tratto rapisce l'occhio e diletta [He has the kind of charm that captures the eye and at the same time fills it with delight]."(3) Written in the early seventeeenth century, the critic Giulio Mancini's words about Cesari's paintings can be applied to the Crocker drawing as well: the composition's focus on the ring draws the viewer's attention, which is then informed by the expreience of pleasurable looking as it turns to figures and drapery. Stylistically the sheet fits best with drawings from the artist's early maturity, with typical parallel shading in drapery and background. It seems, however, that the composition may be related to another subject in which Cesari depicted the Child turned outwards, the Adoration of the Magi in the Aldobrandini chapel in S. Maria in Via of 1594/96. Though in the fresco the Child rests on the Virgin's knees rather than her lap, the turn of the latter's head, her bodice and her glance are nearly identical.

Bearing an inscription to the later seventeenth-century artist Pietro da Cortona, the drawing was first published in relation to Cesari in 1973.(4) It seems that the artist was not satisfied with his original composition, since nearly the entire current figure of Saint Catherine, with the exception of her hand, appears on a second sheet of paper carefully cut to the outline left by its predecessor, both being laid down to a third sheet. The artist was certainly responsible for the change since the shading lines are broken at the edge of the paper above, while they extend across the edge below.

In 1973, Herwarth Röttgen related the drawing to a Holy Family in the Prado which he has since given to Morazzone.(5) Four years later Moir placed the drawing near a panel of the Mystic Marriage in Apsley House of uncertain attribution.(6) The drawing itself being certainly from Cesari's hand, to this writer the relationship of the Virgin to the figure in the fresco in S. Maria in Via remains significant. It seems best to date the drawing near that work, between 1594 and 1596, rather than earlier as some authors have preferred.

William Breazeale, in William Breazeale, with Cara Denison, Stacey Sell, and Freyda Spira, A Pioneering Collection: Master Drawings from the Crocker Art Museum, exh. cat. Sacramento and tour, 2010