This article assesses the complex career of Najeeb Saleeby (1870–1935): a Lebanese Protestant physician who became naturalized as a US citizen while serving the American colonial occupation of the Philippines. Saleeby was valued as a cultural intermediary whose facility with Arabic and Islam empowered his rise as the foremost American expert on the Muslim Moros of the southern Islands of Mindanao and Sulu. Saleeby’s story dramatizes the political advancement possible for an educated “Syrian” who aligned his mission with the American “duty” of teaching self-government to the Filipinos. However, his own background as a migrant from Asia and his sympathy for Moro history and culture raised unfair suspicions about his ultimate allegiance. Dr. Saleeby never settled in the United States but dedicated his whole career to the welfare of the Filipino peoples through his medical profession, his post-colonial advocacy for bilingual education, and his criticism of how imperialism compromised American democracy.