In many constitutional systems around the world, the powers of the executive branch are vast, ever-expanding, and elusive. This chapter draws on a number of examples, from “established” and “fragile” democratic contexts to develop a typology of the different functions that courts can play in checking executive power. It concludes that courts can be surprisingly successful in limiting the growth of even powerful executives. It finds that, as a strategy, courts are more likely to be successful when they focus on empowering other institutions that can serve as a counterweight to powerful presidents, rather than seeking to shoulder the entire burden of limiting executive power themselves. Through case studies the chapter explores the circumstances under which courts have sought to make the constitution matter by placing limits on executive power.