Portia dell'Anguillara Cesi and Margherita della Somaglia Peretti were both wealthy heiresses in late sixteenth-century Rome, and each was the patron of a fine altarpiece for the Capuchin church of San Bonaventura. Although women were widely recognized as patrons in the period, the patronage of these two paintings, which show the Virgin, saints, and the portrait of a young boy, has always been assigned to their husbands, Paolo Emilio Cesi and Michele Peretti, because the works have been related to the patrilinear, agnatic image of the early modern family, i.e., fathers and sons. Instead, the works express a bilinear, cognatic image of the family, indicating legal, economic, and affective ties between mothers and sons. Portia dell'Anguillara's will of 1587 further elucidates aspects of the bilinear family structure.