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Hawaiian by birth, white by race, and American by parental and educational design, the children of nineteenth-century American missionaries in Hawai‘i occupied an ambiguous place in Hawaiian culture. More tenuous was the relationship between these children and the United States where many attended college before returning to the Hawaiian Islands. The supposed acculturation of white missionary children in Hawai‘i to American cultural, political and religious institutions was never complete, nor was their membership in Hawaiian society uncontested. The tenuous roles these children played in both societies influenced the trajectories of each nation in surprising ways. Similarly, the children’s cultural experiences shaped their views of religion, race and world affairs. This complicated, bicultural childhood inspired the missionary children to participate in revolution in Hawai‘i and accept U.S. annexation of the islands, even while attempting to keep the Hawaiian nation free from outside influence. This dissertation examines the competing parental, cultural and educational interests affecting the hundreds of white children born and raised in the Hawaiian Islands during the nineteenth century and assesses the children’s impact upon nineteenth-century U.S. foreign policy, including the particular influences of missionary sons Samuel Chapman Armstrong, Sanford Ballard Dole and John Thomas Gulick.