In May of 2009, President Obama said in a speech on national security that the political and constitutional challenges surrounding the ongoing detention of individuals held at the U.S. Naval Base at Guantanamo Bay, Cuba, would be one of the toughest issues his administration would face. This episode explores the constitutional authority of the President, Congress, and the Courts in this area of law through an analysis of the constitutional disputes in the cases of Hamdan v. Rumsfeld (2006) and Boumediene v. Bush (2008).