This chapter notes that events in the Middle East posed major challenges for America’s supremacy in the 1990s. Iran was no longer in the American sphere as its ruler, Reza Pahlavi, had been overthrown in the Islamic Revolution (1978–1979). And the 1990 invasion of the tiny Gulf emirate, Kuwait, by the Iraqi regime of Saddam Hussain threatened the Western interests in the oil-rich Gulf region. These and other turbulent events elsewhere are analyzed in this chapter. The biggest crisis came after September 11, 2001, when Islamist militants linked to al Qaeda hijacked four passenger planes, crashing two aircraft into the Twin Towers of the World Trade Center in New York and one into the Defense Department just outside Washington. The fourth plane crashed in a field in Pennsylvania. President George W. Bush’s retaliation against the Taliban in Afghanistan, the base of al Qaeda and its leadership, the American invasion of Iraq and overthrow of the Saddam Hussain regime, and the “war on terror” are analyzed in this chapter.