This article revisits the nature of American expansionism in the Progressive Era. It contends that the figure of Evelyn Baring, the first Earl of Cromer, and the British “Veiled Protectorate” over Egypt shaped the internal American retention debate regarding the Philippines in terms directly compatible with the political dichotomy between liberal advocacy of “self-government” and conservative calls for “good government” that lay at the heart of British imperial policy. It further argues that prior British imperial experience and political thought were consistently rhetorically privileged by American administrators within the trans-imperial marketplace of ideas surrounding colonial governance. In doing so, it builds on previous transnational and comparative scholarship on U.S. imperialism of this period, typified by the work of Paul A. Kramer and Frank Schumacher. It rejects renewed exceptionalist attempts to artificially isolate American colonial state-building via Jeremi Suri’s “Nation-Building” paradigm and the “American Umpire” concept recently advanced by Elizabeth Cobbs Hoffman.