The magisterial portrait medal of Bramante stands out among artists’ medals of the Renaissance for its compelling portrayal of the architect shown in advanced age and in heroic nudity, complemented on the reverse by Lady Architecture and a distant view of New Saint Peter’s basilica. The medal represents the first example of an artist laying claim to his own work on a medal, previously the exclusive prerogative of the patron. This study reveals the personal nature of the medal’s iconographic program by introducing a classical source for the portrait and identifying the imagery and inscriptions with Bramante’s elevation by Pope Julius II as keeper of the papal seal.