Sometime between 1544 and 1550, Michelangelo gave two sculptures, the Rebellious Slave and the Dying Slave, to Roberto Strozzi, a fellow Florentine resident in Rome. Although the gift ostensibly signified gratitude for Strozzi’s hospitality during the artist’s convalescence from a grave illness, it had strong political undertones. Shortly after receiving this extraordinary present, Strozzi, most likely with Michelangelo’s consent, gave the sculptures away, presenting them to the King of France as part of an effort to persuade him to intervene on behalf of the Florentine Republic in its final struggle against Medici rule. Michelangelo’s loyalties, both personal and political, were simultaneously revealed and concealed in this act of calculated generosity. This article situates the gift within the context of Michelangelo’s habits of gift-giving, his networks of kinship, and the complicated politics of the 1530s and ’40s.