As a response to commercial competition among the Italian states and changing patterns in trade in the sixteenth century, the Medici dukes created an exceptional free port, Livorno, which not only became the principal entrepot of long-distance commerce connecting northwestern Europe, Italy and the Levant, but also hosted people coming from diverse ethnic and religious backgrounds. Although from the beginning of the seventeenth century, the attitude of the grand duchy toward the Ottoman Empire grew increasingly confrontational, Livorno offered opportunities to many merchants from the Ottoman Empire to set up a new life. Often coming from mixed cultural backgrounds, fluent in multiple languages and possessing complex personal identities, these merchants deserve sustained analysis for their contribution to building cultural bridges between East and West. The life of Ottoman Armenian merchant Antonio (Anton) Bogos, known also as Çelebi (1604-1674) makes a perfect case study in this regard. Born in Bursa to an Orthodox Ottoman Armenian family, Bogos Çelebi worked in Izmir and Bursa as customs officer until his brother Hasan Agha, Customs Officer of Istanbul, was killed during the Çınar incident in 1656. Bogos Çelebi, who fled to Livorno, became a Catholic and started a new life as a Tuscan citizen. His flexibility and adaptability enabled him to establish links with influential figures such as members of the Medici family and to take active roles in the city’s administration. His ‘oriental’ way of dressing, his command of Ottoman Turkish and Italian, and his extensive mercantile networks made him an important intermediary between merchants from the Levant and the Tuscan authorities. Moreover, his Ottoman-style palace functioned as a significant meeting point for Levantine merchants and migrants from the Ottoman Empire and generated a dense network for the transfer of knowledge and circulation of information. Building upon extensive research based on archival and visual documents in Florence, Livorno and Pisa, this paper reconstructs Bogos Çelebi’s life, his networks, and activities in Livorno in the late seventeenth century, while shedding light on his strategies for survival and social advancement.