Captivity and ransoming were part and parcel of diplomacy and naval warfare in early modern Mediterranean. This presentation will deal with agents who conducted cross-confessional negotiations for the exchange and release of war captives in the second half of the sixteenth century. Relying on hitherto unexamined documentation from Archivo General de Simancas (Spain) and Archivio di Stato di Venezia (Italy), it will specifically focus on the career of a Mediterranean go-between par excellence, the Albanian Bartolomeo Brutti, an interpreter (dragoman) at Venetian embassy, a power broker engaged in Ottoman factional politics, a secret agent at Habsburg employ, and a ransom agent who went back and forth between Ottoman Empire, Papal States, and the Habsburgs, powers which, at the lack of open diplomatic channels, were forced to rely on intermediaries with necessary political connections in both halves of the Mare Nostrum. The son of a Dalmatian cavalry captain in Venetian service and the founder of the Brutti dynasty who would become one of the key Periot dynasties who produced several dragomans for European embassies in the following centuries, Brutti had an exceptional career which took a rather radical turn in the 1580s when he reached the higher echelons of power Moldavia and Poland. His outstanding career that unsettles many of the historians’ schematic paradigms reveals hitherto unrevealed facets of Ottoman factional politics, Ottoman-Habsburg rivalry and Mediterranean-wide diplomatic networks. By focusing on the negotiations Brutti undertook for the exchange of war captives between Constantinople, Ragusa, Naples and Rome, this presentation will demonstrate how diplomacy, espionage and ransoming converged and how “trans-imperial” go-betweens, who weaved dense networks of patronage across empires, played a crucial role in mediating political, cultural, religious, and linguistic boundaries in sixteenth-century Mediterranean.