The politics of trade after the Cold War has transformed United States foreign policy. In fact, given the surge of interest in free trade agreements (FTAs) and the far-reaching political and economic repercussions of globalization, this thesis argues that the post-Cold War period, reinforced by the September 11, 2001, terrorist attacks, constitute a critical juncture in the history of U.S. international economic policy and trade diplomacy. The U.S. began to seek FTAs after 1989 as a way to maintain its strategic influence in international relations and counterbalance the formation of trading blocs such as the European Union (EU). Yet, despite its hegemony, the U.S. has succeeded in negotiating and implementing relatively few FTAs. Addressing this paradox, this dissertation seeks to answer two basic questions: First, why does the U.S. have relatively few FTAs compared to other economically powerful countries belonging to the Organization for Economic Development and Cooperation (OECD)? Second, why has the U.S. taken longer to negotiate and conclude certain FTAs over others? These questions will be examined by analyzing the evolution of interest group coalitions and the persistent conflict surrounding FTAs and international trade in general since the end of the Cold War. To further this analysis, the dissertation will study the influence of interest groups, bureaucratic politics, and the role of institutions, as well as the interaction among state and civil society actors, on the politics of trade. The dissertation will focus on the immediate aftermath of the Cold War period, which set the tone for current U.S. trade policy, and will examine the negotiations leading to the agreements signed with Jordan, Singapore, and Chile.