Later medieval theories of free choice differ fundamentally as to the importance they assign to deliberation. Some thinkers hold that the will's choices necessarily agree with the intellect's judgment, obtained by deliberation, of what is most worth choosing in a particular circumstance. They thus think that deliberation provides the object of choice. In addition, they take the control that is essential to free choice to be rooted in deliberation. Others object that deliberation cannot ground free choice since it is itself not originally in our control. They think that one can choose differently from what appears most choiceworthy upon deliberation, and so they deny that the object of choice is exclusively given by deliberation. This paper considers theories of the role of deliberation in free choice held by prominent thirteenth and early fourteenth-century thinkers. It will be shown that there are significant theoretical difficulties on both sides.