This work examines when, and under what conditions, the president seeks to accomplish his policy goals through his interactions with the United States. While there is a wealth of literature that explores how other actors seek to influence the courts, there is little work that systematically explores when and how presidents try to influence the courts. I argue that the president’s decision to take action, and the degree of action he takes, is a function of his level of interest or commitment in achieving policy change and the likelihood that policy change would occur without his intervention. This project moves beyond simply assuming presidents want to influence the judiciary to proposing a novel theoretical framework for when they are mostly likely to do so, in what manner, and the potential costs that presidents must weigh in deciding whether to act.