Before the white man can bear the burdens of empire, he first must be taught how to do it. Before the “new-caught, sullen peoples / half devil and half child” of Kipling’s famous poem can begin to govern themselves, they too must first be taught. The question remains, however, of how best they can become what they ought to be, for manhood is a state that must be achieved; it is not merely given. Two boys, roughly contemporaneous, are the case-studies in my examination of boyhood masculinity in the American Philippines from 1899-1930. The first—Manley Lawton—was the only son of an American war-hero. The second—Pit-a-pit—was born in the highlands of the northern Philippines among the Igorot who were described by the anthropologists and administrators of the new American colony as a "warlike people" of "savage headhunters" who were then "just emerging from lower barbarism." Born into the Anglo-Saxon race, the white boy is destined to rule the world; the brown boy’s fate is to follow—or so colonial ideology would want us to believe. And yet these two case-studies, I argue, demonstrate startling similarities that challenges the easy dichotomies that ascribe masculinity to the (white) colonizer and effeminacy to the colonized.