A great deal of scholarly attention has been focused on the role of the Catholic Church in leading the fight against authoritarianism in Latin America and elsewhere. However, there has been relatively less attention paid to how confrontational church strategies have changed over time. Focusing on the contemporary case of the Cuban Catholic Church, I use evidence gathered from extensive fieldwork in Cuba to create a new set of definitions that distinguishes between strategies of direct and indirect confrontation, and in so doing offer a new framework for comparative theory about religion and contentious politics. I build a new paradigm for comparing confrontational church strategies by articulating new definitions and offering a theory about what conditions and factors lead to the adoption of certain confrontational strategies. Placing the Cuban Church in comparative analysis with the national churches of Brazil, Chile, Nicaragua, Poland, and Venezuela, I argue that a combination of regime type, institutional church reforms, and the world-historical time period during which the church began its contentious activities have a direct influence on the church's choice of confrontational strategy. This dissertation constitutes a comprehensive examination of the Cuban Catholic Church based on original research conducted in Cuba, a case for which few political scientists have devoted rigorous academic attention, especially for comparative study. The arguments and evidence presented here demonstrate not only the importance of the institutional independence of the Cuban Catholic Church and its innovative confrontational strategy for the development of dissident movements in Cuba, but how vital the church and its laity will be in the building of democratic institutions and a democratic political culture should Cuba transition toward democracy in the near future.