This paper analyzes the crucial, albeit at times difficult, relationship between Washington and the last Shah of Iran, Mohammed Reza Shah Pahlavi. From the early 1950s to the late 1970s, Tehran’s fundamental contribution to America’s policy of global containment of the Soviet Union emerges as the central element of U.S. policy. Despite the mismanagement of Iranian internal affairs and the domestic problems which persisted throughout the decades, the American leaders constantly sought to secure a tight and positive relationship with the Shah. The events leading to the 1979 revolution and Washington’s countermeasures are assessed within this context, pointing to America’s erroneous perceptions and misjudgments of the local reality which resulted from a still rigidly Soviet-centric worldview. Finally, the paper indirectly tackles with the difficult question of what, if any, are the lessons and implications of this complex history for the future of U.S.-Iranian relations.