In this article, I explore how risk transformed from being understood as a property of groups to being understood as a property of individuals by examining the history of public and private insurance in the United States. Rather than locate changes in how risk is managed in our society in the “great risk shift” that occurred with the emergence of neoliberalism, I suggest the individualization of risk in recent decades is only the latest instantiation of a recurrent conflict between security and freedom that has marked the evolution of capitalism. Seen from this longer historical perspective, the “personal responsibility revolution” appears not as the handiwork of neoliberal policymakers but, rather, as the unintended result of social movements that contested discriminatory practices in insurance markets. Thus, paradoxically, my account suggests that struggles against discrimination seeded the individualization of risk that is now the hallmark of neoliberal capitalism.