Over a century has passed since the United States Supreme Court decided a series of cases, known as the “Insular Cases,” that limited the applicability of constitutional rights in Puerto Rico and other overseas territories and allowed the United States to hold them indefinitely as subordinated possessions without the promise of representation or statehood. Essays in this volume, which originated in a Harvard Law School conference, reconsider the Insular Cases. Leading legal authorities examine the history and legacy of the cases, which are tinged with outdated notions of race and empire, and explore possible solutions for the dilemmas they created. Reconsidering the Insular Cases is particularly timely in light of the latest referendum in Puerto Rico expressing widespread dissatisfaction with its current form of governance, and litigation by American Samoans challenging their unequal citizenship status. This book gives voice to a neglected aspect of U.S. history and constitutional law and provides a rich context for rethinking notions of sovereignty, citizenship, race, and place, as well as the roles of law and politics in shaping them.