This chapter examines Chile’s remarkable developmental trajectory and highlights achievements in economic growth, poverty reduction, and social indicators such as life expectancy and access to clean water. It does so considering that, despite these successes, widespread public dissatisfaction still erupted. It presents this as a paradox of progress that reveals that even a nation that can excel across any and all developmental metrics can still face profound discontent. Its main argument is that while inequality remains a relevant factor for explaining unrest, it was neither the sole nor the dominant driver. Instead, it proposes that inequality interacted with other critical dynamics that moderated its effects or complemented it as a source of frustration. Specifically, the chapter explores three alternative variables, namely, a pervasive sense of economic vulnerability, a perception of systemic inequality in institutional and societal treatment, and a frustration with perceived slowness and inequity in the delivery of the economic model’s benefits. It also proposes a reason as to why this unlikely version took precedence as a theoretical explanation. All together, this chapter provides a comprehensive understanding of the crisis, challenging the oversimplified narrative of inequality and reframing the discussion in a manner that is more consistent with retrospective evaluations.