The binary categories of “left” and “right” that have structured Western political discourse since the French National Assembly of 1789 are undergoing a profound semantic crisis. This paper systematically engages with the philosophical diagnosis offered by Brazilian thinker Luiz Felipe Pondé, contextualizing it within the broader scholarship on populism, class voting, and identity politics. We argue that the contemporary Left’s migration from class-based politics toward an academic-driven program of identity and cultural recognitions has generated a representational vacuum among lower-income populations—a vacuum increasingly occupied by right-wing and populist movements. Drawing on Pondé’s critical framework, empirical evidence from the 2024 United States presidential election, comparative Western European data, and postcolonial Brazilian political sociology, we trace the genealogy of the left–right divide from its praxeological origins in the états généraux through its twentieth-century semantic degradation and twenty-first-century reconfiguration. We examine how the dynamics of cancel culture, the institutionalization of progressive discourse within universities and media ecosystems, and the displacement of economic solidarity by symbolic politics have collectively alienated the working class. The paper further analyzes the conservative valorization of family structures among economically precarious groups, the epistemological roots of moral paternalism on the Left, and the philosophical tradition of conservatism as distinct from reactionary politics. We conclude that the exhaustion of the classical dichotomy demands a reconceptualization of political representation—one that moves beyond semantic tribalism toward a substantive engagement with the material conditions of ordinary life.