The Basic Law of Hong Kong proposes the eventual election of the legislature and chief executive by some form of universal suffrage. Achieving this requires consensus between the political branches in Hong Kong and the legislative body of the People‘s Republic of China. Although not a formal requirement, any democratisation efforts will also need buy-in from Hong Kong residents to function effectively. Increasingly the views of all do not converge on how and when these constitutional aspirations should be realized. This paper identifies design problems in the Basic Law that have led to this political deadlock. The article will then look at the role of the courts in moving the democratic transition of Hong Kong forward, focusing on the need to reconstitutionalize political debate on electoral issues. This article evaluates possible reasons for the largely unsuccessful use of the courts thus far and proposes alternative litigation strategies for better results.