The article examines the American political efforts to bring about an agreement between Israel and Egypt between 1967 and 1969 and analyses the reasons for their failure. But it does not focus exclusively on the Americans; it also outlines the alternatives for Egyptian action during the period in question and looks at the political and military steps taken by Egypt's president, Gamal Abdel Nasser, vis-à-vis Israel and the United States. The main conclusion is that despite Egypt's dependence on the Soviet Union for economic aid and the rebuilding of the decimated Egyptian army, Nasser knew that the only route to a political process to regain Sinai ran through the United States. His diplomatic efforts were all derived from this insight. At the same time, the Egyptian president's attempts to exploit American pressure to his benefit, as he had done in 1957, was undercut by his overestimation of his bargaining chips, a mistake that was one factor in the collapse of the efforts to reach a diplomatic agreement in the region.