Different regimes face distinct political challenges and develop unique measures to manage political crises. Mainland China, Hong Kong and Taiwan have different political systems: China is an authoritarian one party state practicing “democratic dictatorship”; Taiwan is a democracy that entrenches human rights protection and the separation of powers; Hong Kong, as an SAR of China, is a consultative democracy, with entrenched rule of law and judicial independence. It is a free, tolerant, and orderly society struggling for democracy. Between 2013-15 all three experienced similar crises – large scale public protests that were lengthy and highly political, challenging the respective political system. Yet the ways in which law was used and the extent to which the respective leaders have been punished contrasted among the three places, reflecting the differences in regime. This paper explores how courts in different systems treat political challengers, and the implications of those decisions.