Chapter 4 examines the nature of the extra-hemispheric threats to the national and geostrategic interests of the United States in the Caribbean Basin, primarily during the Cold War, from the perspective of the United States policymakers. In the aftermath of the Second World War, the Soviet Union challenged the liberal world order, exemplified by democratic principles as well as open economies and markets, under the tutelage/stewardship of the United States and endorsing its values. The United States faced another ideological threat (communism) from the European continent, as the Soviet Union sought influence in the third world by stimulating or exploiting local/regional conflicts. To the apprehension of U.S. policymakers, Soviet involvement in the conflicts in the Caribbean Basin in the 1970s and 1980s, whether directly or through surrogates, suggested that it was pursuing a deliberate strategy to project power in an area that fell within the U.S. sphere of influence. Accordingly, the chapter highlights the role of the Monroe Doctrine in the firmer U.S. management of inter-American relations, undergirded by a strategic question – the power controlling the Latin American/Caribbean trade routes and Sea Lines of Communication.