The 1490s saw intense diplomatic activity between Francesco II Gonzaga, Marquis of Mantua (r. 1484–1519), and the Ottoman Sultan Bayezid II (r. 1481–1512). Envoys are often overlooked while attention is paid to the messages or goods that they delivered. This article, however, examines two important envoys in detail and argues that they were chosen for the specific military and technical skills that they possessed. Both envoys delivered armor to the Ottomans in defiance of a papal ban. The nature of the goods that were sent and the backgrounds of the envoys bring nuance to the notion of a uniformly adversarial relationship between the Italian city-states and the Ottomans.