This paper contributes to the recent turn to democracy by anticolonial political theory by theorizing the paradox of dependent democracy. While theorists have recovered thinkers that consider the corrupting effects of capitalism over postcolonial representative democracy or the need by postcolonial citizens to be vigilant toward foreign states and institutions, they have not delved into postcolonial capitalism and its reproduction, the way it shapes and limits postcolonial democracy, and how these factors are mediated by the dependent state. As such, they provide a political story about democracy untethered from the specific relations of production and the role of the state in mediating foreign and domestic capitalist interests. I draw on Marxist dependency theorists Ruy Mauro Marini and Vania Bambirra to conceptualize both the mode of dependent capitalist reproduction through super-exploitation and the role of the counterinsurgent states in the U.S. and Latin America in fending off democratic challenges to these arrangements. As such, radically democratic demands and revolutionary advances that may be considered promising politically, instead prompt the undoing of these projects, by unleashing counterinsurgent forces that interrupt democratic politics and establish authoritarian regimes. This is because their demands for emancipation are at the same time claims against the use of their resources by industrialized countries, which the latter reject violently. This sets up the paradox of dependent democracy: the attempt to appropriate the common wealth, by prompting violent repression, turns the emancipatory moment of appropriation into a moment of loss.