Jack O’Connell, who served as CIA Station Chief in Jordan between 1963 and 1971, was a unique and remarkable figure in the contemporary history of United States involvement in the Middle East. He established a closer personal relationship with King Hussein than any other foreigner before or since. Subsequently he went on to serve as the King's attorney-at-law in the United States and as his informal diplomatic adviser. This article explores O’Connell's role as CIA Station Chief, focusing in particular on his account of the events leading up to the outbreak of the 1967 war and of the covert diplomacy which followed it. It concludes that if O’Connell's claims are sustained, the United States must bear a greater share of responsibility for failing to prevent the outbreak of war and for the failure to secure a diplomatic settlement in its aftermath than has hitherto been acknowledged.