Around 1519, Raphael painted a portrait of his friend Baldassare Castiglione, author of the influential Book of the Courtier (1528). This portrait was later reproduced by Rubens, who may have seen the painting by Raphael, or a copy of it, during his Italian sojourn. Tracing the tensions between Rubens’ “copy,” Raphael’s portrait, and Castiglione’s book, this essay explores how Rubens’ painting problematizes the notion of visual translation in early modern Europe. I argue that his version is not merely a portrait of one person, but a conflation of four presences: the ideal courtly figure; the writer-courtier Castiglione; and the two court artists Raphael and Rubens. Ultimately, the painting represents a paradigm of collaboration and rivalry that underpins the process of translation, one involving multiple hands, works, and techniques, and thus defying the label “copy.”