Chaebol is a very contentious word in Korea, both practically and theoretically. Chaebols serve as genes, deeply imprinted on the structural characteristics and historical origins of all sectors, including politics, society, and culture, as well as the economy and business management in South Korea. The assessment of Chaebols is largely expressed using one of three metaphors: angels, demons, or necessary evils in South Korea’s political economy. The democratization in 1987 and the 1997 Asian economic crisis served as dual pressures that triggered economic reform and resulted in extensive institutional change and Chaebol reform. Under the pressures of globalization and democratization, the country’s developmental state and Chaebols are all going through the process of reform and evolution. The sustainability and future of Chaebols will depend on how innovative they are in the global market and how much they can enhance social trust in South Korea.