In this contemporary retrieval of the Christian doctrine of original sin oriented toward an apocalyptic perspective, we pursue a deeper understanding of this doctrine that is built upon a rigorous and critical retrieval of the ideas of Karl Rahner and René Girard. Their diverse insights reveal the historicity of sin in a remarkable way. They show not only that the universality of original sin is grounded upon the fact that sin happened at the beginning of human history, but also that the concrete historical effects of our decisions continue to have a deleterious influence upon the exercise of human freedom, such that all of our decisions are codetermined by a prior history of guilt and distorted desire. Sin truly has a history, and our concrete actions are the means by which this history makes progress toward our death and self-annihilation. At the same time, from within human history the truth of the Gospel struggles against the escalation of sin and works to bring human history out of the meaninglessness of evil and toward realizing and revealing the deeper meaning of the world in view of the eschatological future. Rather than reducing the truth of original sin to a simple formula, we proceed by showing the complex and profound interrelation of several different theological aspects. Guided by Rahner and Girard and in conversation with contemporary viewpoints, we explore issues of human evolution, history, freedom, desire, and the ways in which society and culture incline us toward sin. We then constructively expand upon these ideas. Linking Rahner’s theology with Girard’s apocalyptic perspective, we illustrate the ways in which sin continues to make progress in our world: by infiltrating and distorting our naturally-good desires, aesthetic systems, societal institutions, and even our very biological nature. These reflections are ultimately directed toward combining a deeper appreciation of divine grace with a revitalized Christian ethic of striving toward justice even in the face of escalating violence. By our actions for a better world, we hope for the transcendent and apocalyptic victory of divine love over original sin.