The question of whether constitutional law can protect, consolidate, and advance democracy has been considered extensively in multiple jurisdictions. The issue has not yet been considered in the context of one of the most problematic contemporary democratic transitions: Hong Kong’s, from an externally governed colonial outpost to a self-governed suffrage-based special administrative region of the People’s Republic of China. The Basic Law of Hong Kong proposes the eventual election of the Legislative Council and Chief Executive of Hong Kong by some form of universal suffrage. These provisions are at the core of the ‘democratic constitution’ of Hong Kong. Achieving this goal requires consensus between the executive in Hong Kong, members of the Legislative Council in Hong Kong, and the legislative body of the People’s Republic of China. Although not a formal constitutional requirement, any democratization efforts will also require popular buy-in from Hong Kong residents in order to function effectively. However, it is increasingly clear that the views of all concerned do not converge on how and when these constitutional aspirations should be realized. In addition, all parties have started moving outside of this constitutional framework when deliberating issues of political reform. This article looks at the problems in the constitutional design of the Hong Kong Special Administrative Region that have resulted in this political deadlock. The article will then look at one solution to mitigate the effect of these design issues and to move forward again on the issue of reform: ‘litigating’ the democratic constitution in the courts. The article discusses the advantages of the courts in the process: primarily the capacity of the courts to reconstitutionalize political debate on electoral issues. This article evaluates the largely unsuccessful use of the courts thus far by Hong Kong residents to correct and advance political reform. It considers possible reasons for the high failure rate in courts and proposes alternative litigation strategies that can better utilize the position of the courts to re-orient all parties to the Basic Law.