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In the summer of 1901, the United States government began a project of colonial education in the Philippines, sending close to one thousand teachers to the newly-acquired colony. These teachers, called “Thomasites,” were part of a wider justification of empire, which was intimately linked with notions of manly duty, masculine endeavor, and the innate superiority of whiteness. However, all of the American teachers headed for the Philippines, male and female, black and white, engaged with the idea of strenuous living and imperial duty, viewing themselves as personally adventurous, as well as integral members of the imperial project. More so than any other group, these teachers were positioned between the colonial administration and the Filipino people. It was the teachers who were often responsible for implementing colonial policies on the ground and for representing American government and values to Filipinos. Their position as imperial mediators allowed the teachers to create roles for themselves that would not have been possible at home, which both complemented and challenged official visions of empire. Examining these teachers’ negotiations with American officials and Filipinos illuminates the gulf between official policies and the day to day functioning of empire, demonstrating how the implementation of empire on the ground often deviated from the expectations of the colonial state. Rather than construing their experiences as expressions of maternalism – which many scholars argue was the linchpin of women’s Progressive Era politics – white female teachers in the Philippines constructed identities as adventurers, imperial officials and professionals. African American teachers, on the other hand, used their positions within empire to disrupt the linking of civilization and modernity with whiteness. Black teachers argued that their racial sympathy with the Filipino people made them most fit to be benevolent colonizers, and linked racial oppression in the United States to the imperial mission in the Philippines. This dissertation examines how notions of race, gender, and national identity colored quotidian colonial interactions. I argue that these interactions nuance the narrative of American empire and provide deeper understanding of the processes of colonization.