In 1966, as commercial jet-airline travel became more routine, the United States Supreme Court confirmed that the “freedom to travel throughout the United States has long been recognized as a basic right under the Constitution.”1 Recent federal security measures designed in response to the terrorism of September 11, 2001 complicate this freedom. Currently, the Transportation Security Administration (TSA) is implementing a comprehensive computerized profiling system called “Secure Flight.” Secure Flight is the next generation of the TSA’s existing “Computer Assisted Passenger Pre-Screening System” (CAPPS). CAPPS itself generated considerable privacy and civil liberty concerns, evoking references to an Orwellian society. The current aviation security environment marks a shift in the government’s approach to airline passengers’ rights. Governmental impulses to regulate and upgrade airline service through an “Airline Passengers’ Bill of Rights” (Ravich 2002) have ceded to security-related initiatives that implicate passengers’ Fourth Amendment privacy rights. This article surveys the constitutional concerns about the TSA’s initial CAPPS program and its subsequent reformulation. In doing so, this article confronts and offers a practical and legal juxtaposition of the ideal of a “right to be let alone” (Warren and Brandeis 1890) relative to the post- September 11 ultimatum of former American Airlines Chairman and CEO Robert L. Crandall (2002): “You want to travel on the airline system? You give up your privacy. You don’t want to give up your privacy? Don’t fly. Your privacy isn’t equal to the safety of the rest of us.”