From the time of Augustine to the late thirteenth century, leading Christian thinkers agreed that freedom requires the ability to make good choices, but not the ability to make bad ones. If freedom required the ability to sin, they reasoned, neither God nor the angels nor the blessed in heaven could be free. This essay examines the work of Peter Olivi, the first medieval philosopher known to reject the asymmetrical conception of freedom. Olivi argues that the ability to sin is (...) essential to creaturely freedom and remains even in heaven. While Anselm is the nominal target of Olivi’s arguments on this topic, they form part of a wider critique directed even more at Aquinas and his followers. Olivi faults them for misunderstanding the nature of the created will and for failing to provide a foundation for a particular kind of moral responsibility: personal merit. (shrink)