Upon China’s reentry into the world economy, investments in countries with a substantial ethnic Chinese population, such as in Southeast Asia, were among the first steps taken in an international business environment. Conversely, ethnic Chinese businesspeople from Southeast Asia were among the first who took their business to China in the 1990s. The ethnic Chinese in Southeast Asia soon realized their potential to act as a bridge between China and their respective countries of residence. The question is how ethnic Chinese networks reflect economic integration into the Chinese dominated regional market, and shape the particular variety of Chinese capitalism across Southeast Asia? This chapter draws on literature on ethnic Chinese business communities in the Straits region comprising of Singapore, and parts of Malaysia and Indonesia. These three ethnic Chinese communities can be identified in terms of a common origin, a shared but diverse migration history, colonial legacy and “diasporic” condition. Based on a comparative literature review, this chapter argues that a comparative analysis of the historical dimensions of ethnic Chinese capitalism in Southeast Asian countries is vital to understand diverging perceptions and relations that ethnic Chinese businesses in the Straits maintain with China.