This dissertation examines the overlooked commercial relationships that linked Chinese communism to international capitalism from the early days of the Pacific War to the aftermath of the Great Leap Forward. By exploring the diversity and continuity of these relationships, this dissertation challenges the stark themes of socialist solidarity and capitalist hostility that frame much of the literature on communist China’s international experience under Mao. Instead, what emerges is an adaptive mode of CCP engagement with capitalism that transcended the Cold War ideological divide. Understanding the larger historical significance of this engagement requires thinking about these commercial transactions as more than the transfer of goods, services, and currencies. Business deals also served as sites for the exchange of ideas, habits, and beliefs, and as venues where individuals, institutions, and the logics that guided them underwent subtle but lasting transformations. These latent influences lie at the heart of this dissertation, which is as much a political, diplomatic, social, and cultural history of communist China in the world during the mid-twentieth century as it is an international history of Chinese communist business and trade. These findings contribute to several veins of historical scholarship. They advance debate over the significance of ideology to Cold War international relations by tracing how CCP foreign-policy ideas transformed through sustained contact with foreign capitalists. The project brings Mao's China into the field of transnational history by moving beyond high politics to explore working-level ties between the CCP and foreign firms, smuggling rings, and other nongovernmental organizations. Finally, this dissertation reorients the study of capitalism in China by challenging the longstanding presumption that "liberation" in 1949 marked China’s withdrawal from global capitalism. As the dissertation shows, China’s ties to capitalism transformed under Mao, but never broke off entirely. The dissertation draws from a variety of sources not typically associated with scholarship on Mao’s China. In addition to fresh documents produced by Chinese officials at the central, provincial, and municipal levels, the project also draws from advertisements, corporate statements, ship manifests, and other materials from commercial and state archives in China, Hong Kong, the United States, Japan, and Great Britain.