Anselm of Canterbury is the first Christian philosopher, perhaps the first philosopher, to offer a systematic analysis of libertarian freedom. His work prefigures that of Robert Kane, and looking at the two philosophers together is helpful in understanding and appreciating the work of each of them. In this paper I show how Anselm adopts a view of choice that foreshadows Kane's doctrine of 'plural voluntary control.' Kane proposes this doctrine as an attempt to answer the 'luck' problem. Alfred Mele criticizes this approach, arguing that, unless the agent's competing desires ultimately originate with the agent himself, he cannot be considered autonomous. It is true that on both Kane's and Anselm's analysis, agents have only a limited area of autonomy. However, an appreciation of the radical implications of this limited autonomy in Anselm's system shows that plural voluntary control gives the agent significant freedom.