The Obama administration struggled throughout its first term to live up to its campaign promises to reverse the most objectionable of the Bush administration's counterterrorism policies and to govern by “rule of law” principles. It is clear that most of these policies continued with minimal changes, and some even expanded to include more controversial elements such as targeted killings. The most visible policy failure has been the inability to close the military prison at Guantanamo Bay. Efforts to accomplish this closure became entwined with two other unfulfilled campaign promises—rejection of the use of military commissions for prosecuting terrorist suspects and halting the practice of indefinite detention of uncharged suspects. In this article I analyze the impact of the role played by the rivalry for influence between White House political advisors and policy principals, on the one hand, and executive branch legal advisors, on the other, on the failure to roll back Bush's counterterrorism policies.