Cold War and CIA
In 1950 the head of the CIA's Office of Policy Coordination (OPC), Frank Wisner, recruited Roosevelt. Assigned to Egypt, Roosevelt impressed his colleagues with Project FF, which encouraged the Free Officers Movement to carry out a coup d'état in 1952, and Roosevelt developed close CIA links to the new leader, Gamal Abdel Nasser.
The historian Hugh Wilford attempts to describe Roosevelt's motivations and views underpinning his intelligence efforts and states:
[Roosevelt Jr.] had this notion of America forming an alliance with the Arab countries as they emerged from under the sway of Britain and France. He was very concerned with backing Arab nationalists in the region. He saw that as the best way of keeping it within the American orbit, as the Cold War was gathering momentum....
The views of the CIA Arabists were not in isolation: Wilford notes that the "Eisenhower administration [including Secretary of State John Foster Dulles, was] initially quite sympathetic towards... Roosevelt's Arabist agenda" and willing to oppose Middle Eastern régimes seen "as backing the Soviet Union rather than the U.S.". Ultimately, the emergence of American public support for Israel and the administration's evolving framework to respond to its principal Cold War adversary, the Soviet Union, would lead to failure of the Arabist agenda of Roosevelt and his colleagues. In discussing Roosevelt's role, Wilford describes him as being among "the most important intelligence officers of their generation in the Middle East."
Roosevelt played a highly important role in Operation Ajax (the 1953 coup d'état) in Iran as the ground operational planner, especially in getting the Shah to issue the firmans, or decrees, dismissing Mossadegh. He established networks of Anglophiles and sympathizers in Iran, who were willing to take part in various aspects of the coup. The tactics aided in dividing and dissolving Mossadegh's political power-base within the National Front, the Tudeh, and the clerics. However, the first attempt at the coup on 15 August 1953 failed, likely because Mossadegh had learned of his impending overthrow. Although the CIA telegraphed Roosevelt to flee Iran immediately, he began work on a second coup and circulated a false account that Mossadegh attempted to seize the throne and bribed Iranian agents. The second coup, a few days later, proved successful and hence was adapted as a model for use in other Third World countries during the Cold War. Eisenhower secretly awarded Roosevelt the National Security Medal in 1954 for his work. In 2014, the National Security Archive released telegrams and accounts of the CIA operation, many of which are revealing as to the part he played in the operation.
Roosevelt, 26 years after the Mossadeq coup, wrote a book about how he and the CIA had carried out the operation, Countercoup. According to him, he had slipped across the border under his CIA cover as "James Lochridge" on July 19, 1953.
Roosevelt submitted his Countercoup manuscript to the CIA for pre-publication approval. The agency proposed various alterations, and in the perspective of a CIA reviewer, "Roosevelt has reflected quite faithfully the changes that we suggested to him. This has become, therefore, essentially a work of fiction." The conclusion allowed the release of the book; a catalog of the actual changes made during the review is available.
A former senior adviser to the Obama administration and Council on Foreign Relations Iran expert, Ray Takeyh, wrote in 2014 that "Contrary to Roosevelt's account [in Countercoup], the documentary record reveals that the Eisenhower administration was hardly in control and was in fact surprised by the way events played out." William Blum wrote that Roosevelt had provided no evidence for his claim that a communist takeover in Iran was imminent but rather "mere assertions of the thesis which are stated over and over." Abbas Milani wrote, "Roosevelt's memoir inflated his own and, in turn, America's centrality to the coup. He tells the story with the relish of a John le Carré knock-off.... Eisenhower, for one, considered reports like this to be the stuff of 'dime novels.'"
After Iran, Roosevelt became assistant deputy director of the Directorate of Plans.
Dulles asked Roosevelt to lead the CIA-sponsored 1954 coup in Guatemala, which deposed the government of Jacobo Árbenz. Roosevelt refused: "AJAX had succeeded, he believed, chiefly because the CIA's aims were shared by large numbers of Iranians, and it was obvious that the same condition did not obtain among Guatemalans." Noting that Árbenz's resignation had been forced largely by rumors "that a full-scale U.S. invasion was imminent," Roosevelt later remarked, "We had our will in Guatemala, [but] it wasn't really accomplished by clandestine means."
Roosevelt left the CIA in 1958 to work for American oil and defense firms. He often visited former operatives and the Shah in Iran.