This paper engages the theological anthropologies of Karl Rahner and James Alison in order to develop two mutually clarifying perspectives concerning original sin and the nature of conversion. It begins by considering the value and limitations of Alison's use of the Resurrection, as well as his Girardian reading of history, as lenses through which to understand the self, original sin, and conversion. Rahner's transcendental anthropology, because of its similar assumption regarding the priority of the Resurrection for understanding the self, provides an effective instrument for evaluating Alison's project. I conclude that Rahner's transcendental perspective from within the “order of being” represents a necessary compliment to the Alisonian viewpoint, which remains exclusively within the “order of discovery” and thereby limits rather than enhances persons' capacity to experience grace. I ultimately propose, however, that further investigation of Alison's work and its usefulness for illustrating the psychological, ethical, and socio-political aspects of conversion constitutes a worthy theological task within contemporary Christian culture.