By using the critical realist approach, this paper uncovers the root causes of Taiwan's massive outward investment in the 1987- present. As Taiwan's economy was highly integrated into the world trade system in this period, this paper takes the global commodity chains as the governing structure of the studied event. The entailed causal mechanisms, such as the post Fordism, economic globalization, and the deterioration of local productive environment are found the root causes that are responsible for the arising of the studied event. A lack of any of these makes the event hard to occur, and the arising of the event becomes inevitable with the influx of these forces. Unlike the empiricism (or mainstream economics) that focuses on facial examination by setting up event regularities among variables, this paper takes 'the why question' approach to explore the underlying governing structure and the ultimately generative forces of the studied event. The established theory is efficacious because, rather than been a formal one, it is a real analysis that centers on the real domain that is able to account for the major features of the studied event.