While “Marxian,” Mao’s thought came from a wide variety of sources, notably from his cultural roots and from his life-long study of classical Chinese philosophy, which in many aspects registers a striking affinity with the postmodernist movement of the West in the late 20th century. Mao’s Chinese Marxism can be interpreted as a break-away from traditional Marxism, a political-economic-philosophical metanarrative, which is culturally Eurocentric and epistemologically logocentric—formulated along the line of rationalistic thinking that can be traced back through the Enlightenment all the way to Plato’s idealism. Postmodernism “abandons absolute standards, universal categories, and grand theories in favor of local, contextualized, and pragmatic conceptual strategies” (Seidman, 1994: 207). This article has no intention to declare Mao as a complete postmodernist, but the obvious would have to be pointed out: i.e., Mao’s notion of integrating Marxism into the specific situation of China is clearly in favor of what Seidman has called “local, contextualized, and pragmatic conceptual strategies,” which explains why the Chinese revolution, essentially an agrarian revolution, led by him had turned out to be a success story. This article will be centering around two basic themes: one is to trace Mao’s thought to ancient Chinese philosophy, which differs radically from its Western counterpart but contains ideas and thoughts strongly echoed by postmodernist thinkers in the West; the other is to look closely at some of the key concepts in Mao’s philosophy in connection with postmodernism, along with his strong anti-metaphysical stance, to explore how it was possible for him to create conceptual leeway for launching his own philosophical, and political, break-through.