Leading grand processions through the towns of northern Italy in the late fifteenth century, the Franciscan friar Bernardino da Feltre brandished a banner emblazoned with the image of the Man of Sorrows, often called the Imago pietatis. His remarkable dual objective was to found and finance a civic lending bank or Monte di Pietà to help the working poor. Nowadays the designation "Monte di Pietà" seemingly embraces a tension: banking on the one hand and the redemptive body of Christ on the other. Or to put it differently, the need for capital in this world and the promise of Christian salvation in the next. Our article seeks to explain the apparent paradox of the Man of Sorrows as a fitting symbol for the Monte and to clarify Bernardino's role in adopting the image as an organizational logo. We explore these questions in the light of the history of the Man of Sorrows in the Veneto during the fourteenth and fifteenth centuries, and against the political strategies of the Observant Friars generally and Bernardino in particular.