In September 1947, on the day the Central Intelligence Agency was formally established in Washington, D.C., two of Teddy Roosevelt’s grandsons, Archie and Kim, drove from Beirut across the Lebanese mountains into Damascus to meet a fellow spy named Miles Copeland. Archie, 29, was the CIA’s first station chief in Beirut; Copeland, 31, was its man in Damascus. Kim (or Kermit Jr., whose namesake and father had roared around the Middle East like T.E. Lawrence during World War I) would, by 1949 at age 33, head the CIA’s covert operations in the region. For now he was traveling, nominally, as a private citizen, working on a book based on his posting to Cairo during World War II for the Office of Strategic Services, the precursor to the CIA.

In two years, Copeland would help engineer the first military coup in the Arab world: the 1949 bloodless putsch by Colonel Husni al-Za’im in Syria. To what degree is a matter of debate, including Copeland’s own boasts, and then retractions, in subsequent memoirs. Archie would try and fail to engineer another military overthrow in Syria in 1957, after a series of coups and countercoups in Damascus (Za’im only lasted a few months before he was overthrown and executed by rival officers). But the 1947 meeting, like the men’s CIA years in the Middle East during the Truman and Eisenhower administrations, was a mix of business and pleasure. As Copeland later wrote, after Archie and Kim arrived in Damascus, they set out “on a tour of Crusader castles and off-the-beaten-path places.”

While Kim directed operations from Washington and made periodic trips to Cairo, Beirut, and Tehran, Archie and Copeland built a nascent American spy network by speaking Arabic and knowing the culture (Archie spoke 16 languages), working their charm and connections, and, occasionally, making things up. “What’s the difference between my fabricating reports and your letting your agents do it?” Copeland, an Alabama college dropout and self-regarded “Tennessee riverboat gambler,” told an accusing Archie. “At least mine makes sense.”

This was the life of a few elite American Middle East specialists and spies in the early days of the Cold War: intrigue and a self-possessed sense of adventure in a region emerging from European colonialism and into, they insisted, a more magnanimous American orbit of what historian Hugh Wilford has called “disinterested benevolence.” If only it had happened that way.

America’s Great Game: The CIA’s Secret Arabists and the Shaping of the Modern Middle East is about the moment, from the late 1940s to the late 1950s, when the United States was the region’s upstart, rather than its hegemon. Wilford’s book—a three-part biography of the two Roosevelts and Copeland—underscores the high hopes but ultimate flaws and fallacies in the Americans’ meddling. He focuses on Kim, Archie, and other spies’ patrician, East Coast roots, including their Groton and Harvard upbringings, to explain their sense of entitlement and responsibility. (Copeland described his Beirut counterpart as “a member in good standing of what passes for nobility in America.”) They spoke of a new era even as they fomented anti-democratic coups, coddled military strongmen, and sought to turn former British or French wards into anti-Soviet satellites though bribes, “crypto-diplomacy,” and secret meetings in the middle of the night (often behind the back of the local ambassador and the State Department).