Naim Cotran (c.1877-1961) was born in the northern coastal city of Acre, Palestine, at that time under Ottoman rule. He began his education at the Syrian Protestant College in Beirut. In 1899, he traveled to Baltimore to continue his medical training at the University of Maryland. Naim returned to Palestine to become one of Acre’s first registered medical doctors. During World War I, he served as a medical official in Omdurman, Sudan, with the Anglo-Egyptian Army. On his return to Palestine, then under British rule (1918-1948), his in-laws gifted Naim an enslaved woman named Sa‘da. Naim and his young wife Aniseh manumitted Sa‘da, but she lived and died with them as their domestic servant. Eight miles northeast of Acre, in a village called Nahr al-Nabi‘a, Naim owned about twenty hectares of land. During the war of 1948, his children and grandchildren took refuge in Lebanon and Egypt. Naim and Aniseh stayed on the land, in an attempt to hold on to Palestine’s shrinking remains. They lost that battle in 1951 and became refugees who lived the last years of their lives in Lebanon. Naim, was my great-grandfather. By sheer coincidence, I encountered Naim in ways that inspired new questions about history and the lived present. On a hot summer day in June 2016, I stumbled upon family papers that I did not know existed. Through his long-forgotten records and photographs, Naim invited me to move beyond the territorial and conceptual confines of Palestine. In the early twentieth century, this vulnerable but determined figure posed for a photograph in Omdurman. With his elaborate moustache, he sat crossed-legged and authoritative, donning the signature pith helmet of the British imperial official. Two Sudanese men stood dutifully at his side. That young man could not have imagined that the British officials he emulated would be the source of his own dispossession. Clearly, Naim believed himself to be culturally and racially superior. His civilizational logic shattered in the wake of dispossession in 1948, but how did it initially take shape and what can it teach us? In this paper, I take up my great-grandfather’s invitation and travel with him to Sudan. Through a focus on Greater Syrians in the Anglo-Egyptian army, I explore the racial hierarchies that made it possible for men like Naim to “pass” as a colonial official. In doing so, I pose questions about subjectivity and historical narration.