Democratic representation seems to be increasingly under stress in various established democracies, such as Greece, Spain, and the USA. Chile is also following this trend, but there are a number of particularities that make the Chilean case distinctive. After all, Chile is widely regarded as one of the most consolidated democratic regimes in Latin America and as having solid economic performance. However, citizens have shown decreasing levels of satisfaction with democracy and representative institutions, and are turning to protest and social mobilization to express their discontent. The paradox that Chile is facing today lies in the mismatch between the attitudes of voters and the overall performance of the regime. In explaining this intriguing puzzle, most of the literature has emphasized the legacy of institutional arrangements inherited from military rule. We argue that institutions are necessary but insufficient for explaining the increasing challenges that democratic representation faces. Thus, we also claim that it is necessary to consider not only the expansion of critical citizens and middle income earners, but also the repoliticization of inequalities.