This chapter discusses the collapse of the Soviet Union and the United States’ stance regarding the question of Baltic independence. During the long Cold War years, Washington pursued a policy of non-recognition regarding the three Baltic states. As such, the Balts were perceived as “heroic little people” who opposed Soviet rule. However, when Vilnius first sought to break away from direct Soviet rule, the US hesitated. With all the goodwill towards the Estonians, Latvians, and Lithuanians, President George H. W. Bush wanted to play it safe, without upsetting Gorbachev’s reformist agenda. Caught between these two competing pulls, Bush attempted to walk a tightrope until it became untenable. After Washington reestablished official relations with the Baltic countries, there was little to suggest that these ties could one day mature into a formalized security alliance. Curiously, though, the US Department of Defense had begun to draw a larger blueprint for America’s security role in the post-Cold War era. As part of the plans, the Pentagon had gamed out a scenario in which it defended Lithuania against a Russian military incursion. The material that follows recounts how American-Baltic ties evolved during a pivotal moment, namely the dissolution of the Soviet Union.