The proposed essay is meant to portray the late history of the Ottoman Empire through the eyes of Cassandra Karatheodore. Raised by powerful Christian bureaucrats in the Muslim dynasty’s service, and married to a similar such bureaucrat, Alexandros Karatheodore, Cassandra became a behind—the—scenes witness to the turbulence of nineteenth century Ottoman diplomacy. Feeling always an observer, but never herself a protagonist, she accepted with growing resentment her role in the empire’s hierarchy. This essay will follow her transformation from Cassandra Mousourou to Cassandra Karatheodore through an examination of her personal correspondence with her lover and future husband; and by reference to the stormy history of the empire from mid-century reforms to the revolution of 1908. While Alexandros Pasha represented the Ottomans everywhere from Paris to Berlin and from Samos to Crete, his wife remained unwilling guardian of their household back in Istanbul. His worries and anxieties mirrored diplomatic tumults and challenges against the state. Her gloominess and irritation were profoundly personal reflections of an ambitious nature left behind. In this respect, the personal correspondence of the Karatheodore couple constitutes an intimate glance at the empire’s non-Muslim elite, echoing a world of fin-de-siècle privilege brought down by its own contradictions.