This article tracks the trend of Hong Kong people's confidence in the idea of "one country, two systems" and identifies various factors affecting its level. It also examines newspaper coverage of "one country, two systems" over the past 20 years and how it is related to people's confidence level. Five variables, namely trust in the SAR government, the government's performance, societal appraisal, press freedom, and confidence in China's and Hong Kong' s future are found to be related to people's confidence in and newspapers' coverage of "one country, two systems." Newspapers have used various approaches to frame the situation over the past two decades. When there was more news coverage, there seemed to be less confidence. The oxymoronic nature of "one country, two systems" is explicated in the context of Hong Kong.