This paper examines Reverend Henry Harris Jessup’s Fifty-three Years in Syria, reading Jessup through the broader framework of tropes of Christian manhood to look at the ways Protestantism structured specifically gendered power relationships between Protestant missionaries like Jessup, and native Syrian men, and to locate how the cultural and social dimensions of Protestantism served to construct ideal manhood in 19th century Syria. These issues are discussed against the backdrop of an expansionary Protestant evangelical missionary movement driven by new conceptions of Christian manhood and budding American imperial interests in the Middle East during the early 20th century. The changes in local culture that accompanied Protestant conversion in the 19th and 20th century Middle East have been a prominent topic of scholarly focus recently. This work has established the influence of Protestant missionary women on local domestic life and conceptions of modernity through their engagement with native women. Less attention has been given to the nuances of the relationship between Protestant missionary and local men, and the ways Protestantism may have compelled native males into new ways of conceiving of themselves as men within their families, cultures and societies. Likewise, the linkages between missionary work and imperialism have been examined closely, particularly in studies of the British empire, while scholarship on the relationship between American Protestant missionaries and the emergence of American imperialism in the Middle East remains less developed. This paper argues that Jessup’s personal understanding of Christian manhood helped to shape gendered power structures and emerging notions of ideal manhood and modernity in turn of the century Syria. Jessup’s ideal manhood consisted of a sliding scale of qualities. Native men from different religious communities and walks of life could exhibit most of them or just a few, allowing Jessup to form respectful relationships with non-Christians, while reserving the ultimate embodiment of ideal manhood for white Protestant men and their native convert protégés. Jessup’s conception of ideal masculinity came to be broadly influential in Syrian society in the 20th century due to the Protestant role in constructing modernity through missionary educational institutions. Protestant models of modernity were lent authority by the growing presence of American power in the region, which allowed missionaries like Jessup to impose specific ideas about domesticity, intellectualism, and taste, on Syrian society, and to police modernity by including and excluding native men based on their adherence to an ideal standard of Christian manhood.