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This paper examines the spread of American pubic schooling into western Oregon following the acquisition of the region by the United States in 1846. Focusing on the second half of the nineteenth century, I analyze the public and private writings of early American school promoters in the region, reconstructing early debates surrounding the creation of public educational institutions in Eugene, Grants Pass, Medford, Oregon City, Portland, and Salem. Contrary to the prevailing historiographical wisdom, I argue that the spread of public education into the region was not simply the product of Yankee migrants attempting to recreate familiar institutions on a distant frontier, but calculated and contested attempts to encourage real estate development by luring eastern migrants and capital.