Mehmed II, Malatesta and Matteo De’ Pasti: a match of mutual benefit between the ‘Terrible Turk’ and a ‘Citizen of Hell’

AbstractIn 1461 the notorious Sigismondo Pandolfo Malatesta, Lord of Rimini, sent his court artist Matteo De’ Pasti to portray the Ottoman Sultan Mehmed II. The artist never reached his destination, being arrested as a spy by Venetian authorities in Crete. Despite the mission's failure it has as much to contribute to our understanding of Italian–Ottoman relations as other fruitful visits. Malatesta had selected Valturio's military treatise De re militari along with maps of Italy as gifts for the sultan. The treatise has been dismissed by many as having no practical use. However, this is to overlook the fact that it explained developments in Italian military architecture that would have been beneficial to the Ottomans. Furthermore, it will be argued that De’ Pasti's services could have extended beyond the production of portrait medals by bringing to light his experience as an inspector of fortifications. The gifts that were sent and the knowledge possessed by the loaned artist highlight the diversity of attitudes to be found within the Italian city‐states towards the ostensible enemy. In fact, the fractured political system of the Italian peninsula will be shown to have been fertile ground for the nurturing of this obliging friendship with the Ottomans.