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This article analyzes the ambiguities of Bolivarianism on democracy. Led by Hugo Chávez, Bolivarianism was an ideology and a strategy of regime transformation and democratization. Its populist language identified internal and external enemies such as US imperialism and elites that served US interests. This meant that the complexity of national and international politics was simplified in these countries to a struggle between two antagonistic camps: neoliberalism vs. the socialism of the twenty-first century; bourgeois-liberal democracy against real democracy; and US led Pan-Americanism vs. Latin Americanism. Bolivarian leaders made clear that clean elections were the only source of democratic legitimacy, and they were at the forefront of the opposition to the military coup d'état of 2009 in Honduras for example. While promoting elections as the only tool to elect and remove leaders, Bolivarian leaders simultaneously undermined democracy from within by concentrating power in the hands of the president, packing the courts with cronies, and using the legal system to punish critics. The paper unravels how Chávez diffused his model of regime transformation, and how Bolivarian leaders learned from his successes.