Abstract: The exploration of the possibility and theoretical validity of the third concept of liberty, be it framed on the basis of Berlin’s conceptualization or not, has become an important theme in contemporary political philosophy. This essay first discusses the debate around the negative liberty and the value of liberty from the perspective of internal and external problems of liberty. It interprets Rawls’ theory of basic liberties as the integration of internality and externality. Then with an investigation of two critiques of liberty as non-domination, the essay argues that the value pluralism remains a challenge of republicanism and serves as a platform on which republican liberty theory is to be rebuilt. The essay also introduces the distinction between the atomic and molecular levels and illustrates its incremental and enlightening implications for the exploration of the third concept of liberty. Based on the aforementioned arguments, the essay further analyzes various views and responses around Habermas’ “private autonomy and public autonomy as the co-originality” and the conception of high-level political autonomy in contemporary political philosophy. It clarifies the deeper tensions developed by the exploration of the third concept of liberty and concludes that the theoretical motivation of such an exploration is the political philosophical pursuit of the ideal of transparency.