In 1989, Soviet Premier Mikhail Gorbachev, still struggling to reform the Soviet system after allowing in March the first free elections in the Soviet Union in seventy-two years, generally acceded to the defection of the Soviet satellites. Most dramatically, in November 1989, East Germany opened its border, and its citizens enthusiastically helped tear down the hated Berlin Wall, which had been erected in 1961 to halt the flow of East Germans to the West. In December 1989, Gorbachev declared that the Cold War was over. In early 1990, Kennan, now eighty-five and worried by Gorbachev's troubles in the Soviet Union, pleaded unsuccessfully for a more generous American policy toward the Soviets. Thus, as his 1947 prophecy of Soviet disintegration seemed close to coming true nearly a decade before the twentieth century ended, Kennan sought to devise ways of stopping that process because of the dangerous instability that might result. In early 1990 he also feared the de facto unification of Germany before other Europeans were prepared for that development, and urged in congressional testimony that "this dangerous situation which is developing has to be stopped in some way or other." The administration of George H. W. Bush, wary of taking the lead or significantly intervening in events, chose more cautious policies than Kennan had proposed. But in 1991, as the Soviet Union faced disintegration, President Bush, fearing the disorder there, actually counseled Ukraine (some 52 million people) not to leave the Soviet Union. But his words failed to halt the dissolution of the USSR. The Soviet Union formally dissolved in December 1991.
Containment—if understood primarily as an anti-Soviet policy—was clearly no longer relevant with the disintegration of the Soviet Union and the establishment of a number of states, and preeminently Russia, in place of the USSR. But among the challenges to Bush in his remaining thirteen months in office, to President Bill Clinton in his succeeding eight years (1993–2001), and to George W. Bush in his first year (2001) was to determine how much of the intrinsic anticommunism in the containment policy, as it had evolved between 1947 and 1991, was relevant in dealing with the very different communist regimes in Cuba, North Korea, and China. Up through 2001, all three U.S. administrations remained hostile to Cuba, and unwilling to open relations with Fidel Castro's government. All three American presidents continued to worry about North Korea, and instability on the Korean peninsula. For George H. W. Bush in 1989–1993 and Bill Clinton in 1993–2001, as well as the new George W. Bush presidency in 2001, generally the lure of trade with China, and frequently the belief that soft words were better than hard words in improving human rights policies, would guide the uneasy but often shifting American policy toward China.
At the same time, international "terrorism"—sometimes conducted by foreign groups nurtured initially by earlier American covert aid, under Presidents Carter and Reagan, when those secretly funded military groups were opposing Soviet policies—periodically plagued the Clinton administration and George W. Bush's early administration, too. Such challenges occurred in a rather new world. It was one in which the containment of communism was no longer generally a major issue and the quest for world order would often be defined broadly to mean capitalism, and sometimes democracy and human rights, in an international system in which there was only one superpower, the United States. In that post–Cold War world, terrorism was generally viewed as anathema to America and its values. But some critics, usually analysts on the left, suggested, sometimes uneasily, that terrorism unfortunately was rather similar, not infrequently, to the hidden side—the "liberation" side—that earlier containment policy, in various American administrations, had applied to help weaken communism abroad. Such an unsettling argument, suggesting similarities between some post–Cold War terrorism and some secret Cold War "liberation" policies under the CIA, departed greatly from dominant American, and Western, thinking. The dominant view denied that there were any meaningful similarities. That dominant view was perhaps best expressed by President George W. Bush and Secretary of State Colin Powell, as well as former Secretary of State Henry Kissinger, in September and October 2001, when they, among many outraged Americans, sharply condemned the terrorist attacks on the World Trade Center buildings in New York City and the Pentagon outside Washington, D.C., as assaults on the good by the forces of evil.