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This paper examines how ideological variations within populism lead to dissimilar experiences in democratization of some Latin American countries. While the impact of populism on democratization is mostly associated with the Left and anti-neoliberal rally, this relationship has shown itself through the Right and neoliberal policies as well. It is widely agreed that populism is inimical to democracy, be it Leftist or Rightist. However, which type of populism is more detrimental to democracy is a question of debate. In this paper, we attempt to solve this puzzle through an analysis of four cases of two Rightist populist regimes (Argentina under Carlos Menem and Peru under Alberto Fujimori) and two Leftist populist regimes (Venezuela under Hugo Chavez and Bolivia under Evo Morales). We examine the conditions under which different ideological orientations within populism produce political change. By looking at these cases, we offer a mechanism that demonstrates Rightist populism is more detrimental to democracy than Leftist populism. We argue that Rightist populism through neo-liberal policies successfully isolates citizens from politics and leaves a little room for participation at the deeper level of society on one hand. On the other, Leftist populism at least provides a larger segment of society with social policies that enable citizens to create opportunity spaces at the local level. As a result, through participation this kind of public opportunities at the locale, which promote the inclusion of the underrepresented and the underdog, creates more solid roots for democracy at a nationwide level in the long term.