Ethiopia’s soft diplomatic history with the United States goes back to the dawn of the twentieth century when King Menelik in 1905 responded favorably to the overtures by the United States for official relations between the two countries when Ethiopia was the only independent country in Africa. The purpose of this paper is to highlight the benchmarks of a successful engagement that had lasted for over seventy years only to suffer reversals from critical events both internal and external. A brief historical analysis will be rendered to highlight the role of the United States in the modernization of Ethiopia and how that virtuous soft-power diplomacy was destroyed by cold war calculations for détente with the Soviet Union ignoring the geopolitical reality in the Horn that eventually spelled disaster for Ethiopia. One of the friendliest official relations that the U.S. has had with an African country in the twentieth century became a casualty when U.S. foreign policy failed to match the challenges in the Horn of Africa in the early 1970s, giving way to a brutal military regime aided and abated by some highly educated Marxists many of whom went to school in some of the best institutions of higher learning in the U.S. and Europe