Targeted assassinations using drones raise questions not only of legality and morality but also of efficacy and prudence. The martyrdom of drone targets and the anger at the civilian casualties that drone attacks cause might arouse more militant activity than the assassinations prevent. And terrorists themselves might someday use drones. Shane illuminates these issues by examining U.S. President Barack Obama’s decision to approve the killing of a U.S. citizen in Yemen, Anwar al-Awlaki, whom U.S. intelligence suspected of having ties to al Qaeda. Shane suggests an intriguing parallel in Obama’s and Awlaki’s trajectories. Although Obama ultimately embraced targeting killing, he came to office wishing to build bridges with Muslim countries and troubled by how his predecessor had conducted the “war on terror.” For most of his life, Awlaki had seemed comfortable in the United States, and his initial response to the 9/11 attacks had been moderate. He became an unusually influential extremist preacher only after he fled the United States for Yemen on learning that the FBI had uncovered embarrassing details about his personal life while investigating his suspected connections to terrorists. Although clearly unhappy with Obama’s decision to authorize the assassination, Shane recognizes how difficult it would have been for the U.S. president to eschew one of the few means available for dealing directly with terrorist threats.