Socioeconomic and political developments in Hong Kong always hang on a balance of contending interests as well as a skillful management of tensions and contradictions inherent in a delicate social system that promised to accommodate capitalism vs. socialism and authoritarian Beijing vs. liberal Hong Kong. Given that One Country, Two Systems (OCTS) was an outcome of a political compromise, it would be difficult to meet all the expectations of different parties. Indeed, there are gaps and missing pieces in OCTS. And there is unfinished business as well. This paper is an attempt to analyze the current impasse of Hong Kong society from a longer perspective and to unravel the tensions and contradictions in the OCTS design.