A commonplace of modern feminist scholarship holds that fifteenth-century Italian humanists regarded the figure of the articulate women with hostility and suspicion. This position is insufficiently nuanced: while it may have been true to some extent in republican contexts, it was emphatically not the case in the secular princely courts, where women's capacity for eloquence was frequently a subject of praise. Humanistic attitudes toward female eloquence are examined here with special reference to Ercole de’ Roberti's representation of the classical heroine Portia in oratorical guise in his Portia and Brutus, painted at the court of Ferrara in the late 1480s or early ’90s. The article contextualizes Roberti's painting with regard to its classical literary sources, to contemporary practices of female oratory, and to the cultural and social self-positioning of the work's probable patron, Duchess Eleonora d'Aragona.