Al-Qaeda’s attacks on the United States on September 11 2001 affected America’s policy toward one region of the world-the Greater Middle East-more significantly than any other. In response to the attacks, the United States carried out two military operations-Operation Enduring Freedom in the fall of 2001 and Operation Iraqi Freedom in the spring of 2003-designed to eliminate the existing regimes in Afghanistan (the al-Qaeda-harboring Taliban) and Iraq (President Saddam Hussein’s repressive Baathists) and lay the foundation for the development of enduring liberal democratic institutions in those states and in the broader Arab and Muslim Greater Middle East. In addition to the daunting challenges in implementing that strategy on the ground in Afghanistan and Iraq-challenges that have grown ever more evident in US-led nation/state-building efforts in each of those contexts-the George W. Bush administration’s grand strategy to transform the Greater Middle East involves a delicate balancing act given the existence of a string of long-standing American alliances with authoritarian governments in the region. Understandably, those governments are reluctant to support US efforts to promote democratization generally and freedom of political expression specifically because such developments would likely undermine their own control over their populations.