In Latin America, recent processes of democratic backsliding have tested the robustness of the Inter-American democratic system (IADS). Based on theoretical frameworks of democracy promotion, hypotheses stemming from institutionalist and normative theories suffer from important limitations in explaining the liberal democracies' motivations to act in the face of anti-democratic threats. Analyzing the cases of democratic regression in Bolivia, Honduras, Nicaragua, and Venezuela, and the consequent responses from the Caribbean Community's (Caricom) liberal democracies vis-a-vis these autocracies, this article corroborates that democracy promotion responds to a materialistic-utilitarian hypothesis that prioritizes material cost-benefit calculations over democratic norms and institutions. The analysis reveals that the worrying but real prevalence of power politics over democratic principles challenges the solidity of the IADS.