Latin America is often viewed as a region that suffers from insufficient taxation, but that idea is only partially true. In some countries, such as Chile, Guatemala, and Mexico, taxation is indeed relatively light. However, in others, such as Argentina, Brazil, and Uruguay, it is much heavier. This chapter argues that a key reason behind that variance involves the impact of historical episodes of state-led redistribution, especially ones that threaten private property. Where such episodes were most extensive, they created barriers to future taxation by mobilizing strong, enduring political coalitions devoted to limiting state economic intervention. Consequently, countries where such episodes occurred tend, ceteris paribus, to have more liberal development models, including not only lighter taxation but also lower social spending, freer trade, and a more restricted role for public enterprises. The argument is illustrated through a comparison of Brazil and Chile. Until the 1970s, both countries were highly statist and had heavy tax burdens. However, major redistributive reforms in Chile prompted a powerful conservative backlash that put the country on a long-term path of limited state intervention. In Brazil, in contrast, no such episode occurred, and the state continued to play a crucial role in the economy.