This article explores the American role in the Syrian political scene in Cairo toward the end of World War I and in its immediate aftermath. It challenges the absence of the United States and of American actors as primary players in much of the historical writing on the Middle East in this period. It illuminates a neglected episode of regional American diplomacy, argues that the United States was not relegated to the periphery in local debates surrounding the dismemberment of Ottoman Syria, and emphasizes the broader uncertainties that characterized the competition for Mandate territories in the Middle East prior to 1920. In doing so, it takes a close look at the long-forgotten reports of William Yale, the U.S. State Department's “Special Agent” in Cairo in late 1917, and situates them within evolving trends in Syrian-Arab politics. Yale, who surfaced in Egypt after serving with Standard Oil in Palestine, was the key Arabic-speaking American “on the spot” and proved to be an astute if imperfect observer of the diversity of Syrian national sentiment. A survey of his reports allows for a new perspective on Cairo's Syrians and their pragmatic and ideological turn toward the United States as World War I unfolded. Alienated from Britain and France, they looked increasingly to the United States, and the appeal of a postwar American trusteeship over Syria gained currency among émigré intellectuals and aspiring powerbrokers.