The two brothers were born as children of an Orthodox Christian Armenian subject from Bursa at the beginning of the seventeenth century. One of the brothers converted to Islam and took on the name of Hasan, climbed the echelons of the Ottoman administrative system and achieved the post of Istanbul Customs Officer, which he held from 1646 to 1656. In that capacity, Hasan Agha was among the victims of the so-called Çınar incident of 1656, a major soldiers’ rebellion that targeted financially powerful individuals in the Ottoman government. His brother Anton, on the other hand, remained a Christian and occupied the posts of customs officer in Izmir and Bursa. After the Çınar incident, he escaped to Livorno, converted to Catholicism, and through his close connections with the Medici family, became gonfalonier [standard-bearer], elected as the head of the administrative city council. The case of these two brothers, whose careers crossed multiple religious and geographical divides, provides a multifaceted case study to historians working on the early modern Mediterranean. The central question of this paper concerns the framework of the shifting identities of these family members. The two brothers made and remade their identities in order to flourish across a variety of contexts, including the Ottoman Muslim elite, Armenian diaspora communities, and the pan-Mediterranean mercantile networks of Livorno. This paper reveals the porous borders of the early modern Mediterranean not only in terms of cultural identities but also with regard to the notion of citizenship by addressing the archival documents from Ottoman and Italian archives.