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This dissertation explores the transregional impacts of the 1949 Chinese communist revolution on diasporic Chinese students and scholars in Cold War Asia and Asian America. It argues that higher education was a key site of contestation in the U.S.-China Cold War tensions of the 1950s, where American efforts to contain and isolate communist China produced a series of educational experiments and initiatives to school a new generation of diasporic Chinese youth as Free Asians. At the same time, new Asia-based educational institutions relied heavily on the initiative of diasporic Chinese elites on both sides of the Pacific -- including Hong Kong and U.S.-based refugee intellectuals, wealthy Chinese merchants in the Straits Settlements -- who were important but overlooked protagonists in shaping the cultural Cold War in Asia. As American anticommunism encountered diasporic Chinese energies, they collectively produced new higher educational institutions outside the PRC, forming a transpacific Cold War educational infrastructure in the 1950s. Overlooked in histories of the post-1949 PRC, which stresses the impact of its socialist campaigns, and histories of the Chinese minorities in postwar Southeast Asia and Asian America, which stress localization and equal citizenship, I argue instead that this educational activism of the 1950s was a region-making project which also shaped the nature of American cultural diplomacy in Cold War Asia, and the dynamics of decolonization in the late colonial British empire in Hong Kong and Southeast Asia. Beginning with the Chinese communist revolution of 1949 and concluding with the founding of the Chinese University of Hong Kong (1963) and the reorganization of Singapore's Nanyang (South Seas) University in 1965, this dissertation demonstrates how debates over diasporic Chinese students, scholars, and the provision of Chinese higher education in the diaspora were core to U.S.-China geopolitical rivalries in the early Cold War, even as the diverse goals of students and scholars themselves never fully aligned with superpower agendas. The first two chapters introduce American efforts to aid the stranded Chinese students/scholars in the U.S. and Hong Kong, demonstrating how American humanitarianism was entangled with broader efforts to retain and re-orient these Free Chinese toward Free Asian goals in the Cold War. The next four chapters focus on the ethnic Chinese-majority British colonies of Hong Kong and Singapore as central sites of contestation, as local efforts to discourage students from traveling to China gave rise to a series of educational experiments to "educate the overseas Chinese," culminating in the founding of two Chinese universities in Hong Kong and Singapore as educational hubs for the diaspora. While neither university ultimately catered to the educational needs of all ethnic Chinese youth around the globe, they reflect how ruptured Cold War mobilities produced new sites of reconnection, particularly intellectual circulations and mobilities between diasporic Chinese in Cold War Asia and Asian America. This history of schooling Free Asia thus provides an important context to subsequent debates over a global Chinese diaspora vis-a-vis the Chinese state, Asian and Asian-American connections, and Sino-American rivalries in an era where global higher education is once again a battleground of great powers. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]