There is a story, probably apocryphal, that Franklin Roosevelt, when informed that Whittaker Chambers had named Alger and Donald Hiss as Soviet agents, responded by derisively dismissing the possibility that two products of Harvard Law School and elite East Coast law firms could possibly betray their country. British spies like Donald MacLean similarly avoided suspicion because of their establishment bona fides.

One of the prime beneficiaries of such a blinkered view of what attracted men of privilege to communism was Duncan Chaplin Lee, a son of missionaries, descendant of one of the most storied families in America, Rhodes scholar, Army officer—and Soviet spy. From the moment he began working in the Office of Strategic Services (OSS) during World War II, he cooperated with Soviet intelligence, even as he moved up the bureaucratic ladder and earned a promotion to lieutenant colonel in the Army. Had Lee not been exposed by Elizabeth Bentley in 1945, he likely would have been chosen for a high-ranking position in America’s postwar intelligence service. And even though his career never fully recovered, his influential friends, who were reluctant to believe the charges, enabled him to begin a second career as an anti-Communist cold warrior.

Duncan Lee’s improbable story is well-told in this new biography by Mark A. Bradley, a former CIA officer, who has diligently mined the many new sources on Soviet espionage that have become available in the past two decades. Bradley was also able to persuade the Lee family to give him access to an extraordinary cache of letters demonstrating Duncan’s conversion to communism during his sojourn at Oxford. While some parts of Lee’s story remain a mystery (since he never acknowledged or explained his espionage), Bradley has provided a fascinating account of one man’s treachery and the toll it took.

Descended from Richard Henry Lee, a signer of the Declaration of Independence, and numbering Robert E. Lee among his collateral relatives, Duncan Lee could trace his maternal lineage to the Mayflower. His father was an Episcopal missionary who spent decades in China. Upon returning to America, Edmund Lee became headmaster of a failing girls’ school in Virginia and transformed Chatham Hall into one of the premier boarding schools in the country.

Duncan was born in China in 1913 and lived abroad, except for one year, until 1927. Imbued with his parents’ message that their family mission involved the performance of good works, he attended Yale on a scholarship during the Depression, amassed a distinguished academic and extracurricular record, and, in 1935, earned a Rhodes scholarship to read jurisprudence at Oxford.

Lee was radicalized in England. A thriving Communist movement at Oxford and the onset of the Spanish Civil War provided the impetus; but Lee’s burgeoning romance with Isabella “Ishbel” Gibbs, a “strong-willed and intellectually confident” daughter of a Scottish civil servant in India who was a strident and passionate radical, completed the process. Not long after meeting her, Lee was writing to his parents about his disillusionment with God and capitalism.

In the summer of 1937, at the height of Stalin’s purges, Duncan and Ishbel traveled to the Soviet Union and were besotted. Lee informed his frantic parents that there was no middle ground between Hitler and Stalin, and that he and Ishbel were planning to join the underground British Communist party. He finally agreed to wait until they were financially independent, but his romances with both communism and Ishbel precipitated his mother’s nervous breakdown.

While studying at Yale in preparation for a legal career, Lee and his wife threw themselves into Communist activity, prompting their landlady to report them to the local FBI office. They formally joined the Communist Party USA in 1939, just before Duncan began work on Wall Street at a firm headed by future OSS director William Donovan.

By the time Lee joined his boss at the OSS, in the spring of 1942, Mary Price had already recruited him for Soviet intelligence. (Lee had worked on a Communist front aiding Chinese war victims with Price’s sister.) He sailed through a perfunctory security check, and, once assigned to the OSS secretariat, he had access to virtually all reports coming to Donovan. A delighted Jacob Golos, who supervised more than a dozen Communist spies in government agencies, boasted to Moscow: “He wants to work with us and provide us with any information he can get.”

Despite his enthusiasm for betraying his country, Lee maintained a well-honed sense of self-preservation. He refused to smuggle out any documents and would instead memorize information that he would repeat to Price and, later, Elizabeth Bentley. He demanded that neither of them write anything down until he had left their meetings. Even as Moscow pressed him for more information or documents, he spied at his own pace and on his own terms. Nothing would tie him directly to espionage. His one major violation of tradecraft was his decision to sleep with both Price and Bentley. His affair with Price, who hoped he would marry her, led to tensions with his wife and contributed to Price’s breakdown and withdrawal from espionage.

Even with those safeguards, however, Lee was an exceptionally frightened spy. By December 1943, he had lost his nerve. Petrified of being exposed, fearful that J. Edgar Hoover would like nothing better than to arrest a Soviet spy in his archrival Donovan’s OSS, and obsessed with the idea that he would be executed for espionage, Lee broke appointments with his Soviet contacts, forcing Bentley to persuade Ishbel to urge him to continue spying.

His precautions served him well, though. After Bentley went to the FBI in November 1945, the NKVD shut down its American networks (Kim Philby, the British liaison with American intelligence, warned Moscow), and Duncan Lee’s espionage career was over. Despite constant surveillance, the FBI would never uncover any evidence against him. He left the government in January 1946.

Unlike many others accused of being spies by Elizabeth Bentley, Lee never relied on the Fifth Amendment when called before congressional committees. He admitted to meeting her frequently and even to having dinner with Jacob Golos, but he insisted they had all been innocent social occasions, and he attributed Bentley’s charges to resentment because he and Ishbel had distanced themselves from an odd, emotionally needy woman whom they had briefly befriended.

Because of the Venona decryptions, the FBI knew that Lee was lying, but it was stymied by the absence of evidence that could be used in court. Several times the Bureau thought that Lee might break and confess; during one interview, he trembled so much that he was unable to hold a cigarette. But he stuck to his story. Bentley herself was a problematic witness, and Venona remained top-secret. For years, the FBI tried to tie Lee to either the American Communist party or to the Soviet Union and failed.

The government was able to complicate his life, however. Ishbel had never become an American citizen, and after the Lees moved to Bermuda for business reasons, she couldn’t return to the United States. For a time, Britain expelled Duncan from Bermuda as an undesirable alien, and the U.S. State Department denied him a passport. The couple finally divorced, and both remarried, with Lee eventually settling in Toronto after years of well-compensated service as a vice president of the insurance giant AIG, a position provided for him by his wealthy and well-connected friends.

The strangest part of the story Bradley tells involves Lee’s activities in the late 1940s, after he joined the Washington law firm headed by Thomas Corcoran, FDR’s legendary fixer. With General Claire Chennault of Flying Tigers fame, Corcoran and his law partner William Youngman set up a private airline to assist Chiang Kaishek in his civil war with the Chinese Communists. Lee worked closely with the CIA, which later bought the airline and renamed it Air America, and he was even instrumental in keeping a fleet of planes out of the hands of Mao’s forces. Lee, Bradley notes, “successfully remade himself from one of the Kremlin’s best-placed spies inside US intelligence into a Cold Warrior,” speculating that it allowed him “to dry-clean his conscience.”

To the end of his life, Lee refused to admit that he had been a Soviet spy: His children were stunned to learn the truth when Russian and American archives were finally opened. Privately, Lee must have deeply rued his decision to spy for the Soviet Union; he became a heavy drinker and, late in life, lamented that his once-promising career had derailed. Yet Lee never admitted the damage he had done, not only to his own career, but also to the country that he betrayed.

Harvey Klehr, the Andrew W. Mellon professor of politics and history at Emory, is the coauthor, most recently, of Spies: The Rise and Fall of the KGB in America.

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