In the fourteenth century, the salvific and Eucharistic meanings of the Man of Sorrows accrued a political dimension that harnessed the figure’s potency for the state. Two of the most powerful rulers of the third quarter of the century used the humble and abased figure of Christ in their sacred art to legitimize and sanctify their sovereignty, shaping their own public images as terrestrial representatives of Christ’s heavenly reign. Examined here are relevant works of art commissioned by Charles IV, King of Bohemia and Holy Roman Emperor, and his court, and the Livre de sacre of Charles V Valois of France. That the two Charleses, uncle and nephew, collected holy relics to express both deep piety and their royal prerogatives, and together exchanged confidences in three personal meetings point to the likelihood that their trusting relationship established a new connotation for the Man of Sorrows which marked royal authority.