Since the time of President Thomas Jefferson, and on through the presidents of the 20th century, the United States has talked about itself as the propagator, protector, and defender of democracy around the world. Yet America has never showed any qualms of forming military and political alliances with authoritarian regimes in Latin America, Europe, Asia, and Africa. The US justifies these international alliances on the basis that “not all dictatorships in the world are enemies of the United States, but all the United States’ enemies are dictatorships.” The US therefore adopted a two-track diplomacy: while working to spread democracy (directly or by means of international organizations and NGOs) the US has no issue in supporting autocratic governments when its interests are involved. How did US policy apply to the democratic transformation in the former Eastern bloc states in Europe on the eve of the collapse of the Berlin Wall in 1989 and subsequently, when American values and interests went hand in hand, and how did it then apply to the Arab Spring of 2011, when US values and interests were congruent in some cases and out of sync in others, according to the situation in each country and its strategic importance from America’s perspective? What are the results of these policies and what differences emerge from such a comparison of the Arab and East Europe cases.