Torquato Tasso was inspired to pen his Stanze per le lagrime di Maria Vergine santissima e di Gies. Cristo nostro (Rome, 1593) by a painting of the sorrowing Virgin belonging to Cardinal Cinzio Passeri Aldobrandini (1551–1610). A nephew of Pope Clement VIII by his sister, Cinzio took on the Aldobrandini name in a practice known as an “aggregation.” The publication of Tasso’s Lagrime allowed Cinzio to promote himself as a devout prelate favored by the pope, but it did not ensure his influence and a true “blood” nephew, Pietro Aldobrandini, successfully challenged his authority. This essay examines the status of the aggregated nephew, the painting that was Tasso’s inspiration, and the conception of sacred art presented in the introductory texts accompanying Tasso’s Lagrime. These lines of inquiry reveal the entwined histories of painting, poetry, and politics in the process of defining what was good sacred art in Counter-Reformation Rome.