Taxation is a big part of the larger puzzle behind income and wealth inequality in Latin America, largely considered to be the most unequal region in the world. This dissertation asks why some Latin American countries are more capable of collecting tax revenue than others, and what are some of the main impediments to tax reforms in the region. The dissertation is organized around three main empirical studies, each contributing to specific literatures in the social sciences. First, a cross-national time series analysis of 17 Latin American countries since the 1990s identifies some of the main social and political drivers of variation in levels and structure of tax revenue in the region. Second, qualitative hand-coding analysis of roll-call congressional debates over two different tax reforms in Brazil and Argentina identifies and classifies the rhetorical strategies employed by both proponents and opponents of tax reforms. And third, analysis of rich data collected from more than 50 in-depth elite interviews with Argentinian agrarian producers who mobilized against a tax increase in 2008 describes the different pathways business actors take when they decide to engage in street protests, and the patterns in which they maintain their anti-tax business activism after this initial mobilization.