This chapter provides a systematic exploration of the European Court of Human Rights’s (ECHR's) decisions in cases involving the structure of the democratic process. These “law of democracy” cases pose some of the most conceptually difficult and politically charged cases even for domestic courts, let alone for a supranational court tasked with enforcing democratic rights across the diverse ways the member states have structured and institutionalized their democratic systems. In the ECHR’s doctrinal terms, the legal question is how much of a “margin of appreciation” the Court should recognize for the member states to interpret and apply democratic rights in differing ways across their different systems of democracy. Focusing on the Court’s decisions regarding regulation of political advertising, access to the vote, and the spending of money to influence electoral outcomes, the chapter concludes that the Court in recent decades has recurringly entered into these areas with bold initial decisions, only to be forced to back down in response to the powerful political backlash such interventions have spawned, particularly in certain member states. This pattern suggests that a supranational court has trouble mobilizing the political legitimacy required to sustain acceptance of its decisions involving such morally powerful issues.