This paper examines the complexity of identity and loyalty of a family of non-Muslim intermediaries and translators, historically known as ‘dragomans,’ in the service of the British embassy in the early to mid 19th century. It focuses on the Pisanis, a Latin, or Catholic family of Italian origin who were among the family dynasties of dragomans employed by foreign embassies, and prominent members in the Levantine community of Istanbul. They maintained this position not only through their diplomatic work at the embassy, but also through intermarriage with other important members of that community, and their attachment and activity in the Catholic churches in the district of Pera. Yet, some members of this family did not identify themselves as being wholly or partially Levantine, Ottoman, or European. Their sense of ‘self,’ therefore, contrasts with our present analytical categories of non-Muslim residents in the Ottoman Empire, including geopolitical (Levantine and European), in-betweenness (Ottoman born, but viewed as Levantine because of their heritage), and foreign vs. local (European vs. Ottoman), to list a few. By focusing on the Pisanis, this paper has two aims. The first is to provide a glimpse into how members of this family legitimized their own sense of self, found in consular records from the British National Archives and the Prime Ministry Ottoman Archives. Their identity claims can be linked to their positions as dragomans in the British embassy, and the diplomatic protection and benefits that they received through the Capitulatory agreement between the British and the Ottomans. The second is to consider how their own self-fashioning may have had an impact on their work as important intermediaries between the British and the Ottomans, calling into question the uncertainty of loyalty, an all too important requisite for employees of foreign embassies, and handlers of information between the British and the Ottomans. Doing so, tells a story through the perspective of ‘history from below,’ and suggests a refined understanding of the category of ‘identity’ of non-Muslims born in the Ottoman Empire, and their activity in the diplomatic community of Istanbul.