Recent attention to presidential action recognizes the legal and constitutional questions surrounding the controversial use of many of these powers. Yet, scholarly research on executive policymaking tends to ignore the role of the courts, instead focusing on presidential–congressional relations. I develop a formal theory of the president’s decision to issue a signing statement in the face of constraints from the Supreme Court. The model produces several novel predictions. First, I predict that the president is more likely to issue a signing statement when he is ideologically aligned with the Court. Second, contrary to previous literature, the president is more likely to issue a statement when his preferences are also aligned with Congress. Finally, when reviewing legislation that is constitutionally challenged, I predict that the Court is more likely to rule in favor of the president’s position when he has issued a signing statement.