The People’s Republic of China is one of the strongest and most durable authoritarian regimes in the world, and it has historically been remarkably successful in controlling the flow of information and ideas within its country. In recent years, however, the regime has come to understand that a successful capitalist-style economy requires greater freedom of ideas and information. These facts create a puzzle. Can the regime both “liberalize” the economy and simultaneously maintain political control? This dissertation examines the evolution of the Chinese news media in the context of these contradictory pressures. I argue media liberalization is the result of global economic pressures and the endogenous transformation created by contradictory political and economic logics. How do we understand the various pathways and mechanisms of gradual change? I find that media liberalization in China mirrors that of a complex adaptive system, characterized by emergent agent strategies, multiple levels of selection and the simultaneous existence of self-reinforcing and self-undermining institutional change. The “dictators dilemma” of economic liberalization without formal changes in institutional control, gives rise to competing constellations of commercial interests, some of which re-enforce political control and some of which promote more aggressive professional journalism.