Boumediene v. Bush, resolved by the U.S. Supreme Court in June of 2008, granted habeas corpus rights, at least for the time being, to the persons detained at Guantanamo Bay Naval Station. The majority partially based its ruling on the doctrine of the Insular Cases, first set forth in the 1901 decision in Downes v. Bidwell. Indeed, the court was unanimous that the plurality opinion of Justice Edward Douglass White in Downes is still the dominant interpretation of the Constitution’s Territorial Clause, abandoning the rule set forth in Dred Scott v. Sanford. This article provides historical context and analysis of the Insular Cases, that series of decisions on the power of the U.S. government over territory and people under the Territorial Clause and criticizes the majority’s use of it to justify the “situational” application of constitutional rights to subjects of United States law. The article also points out the fallacy that these situations are temporary and transitional given that most of the current territorial possessions have been continuously occupied since the end of the Spanish American War in 1898.