Blue blood, red agent? New book on alleged mole Duncan Lee ’35

When The Good Shepherd came out a few years ago, we watched the fictionalized story of how General William “Wild Bill” Donovan recruited Yale men to help create the forerunner to the CIA.

Now, a nonfiction book tells the story of one of those recruits: Duncan Chaplin Lee ’35, a top aide to Donovan—and, apparently, a Soviet spy.

In fact, Lee was “possibly the best-placed mole ever to infiltrate U.S. intelligence operations,” according to the publisher’s blurb for Mark Bradley’s A Very Principled Boy: The Life of Duncan Lee, Red Spy and Cold Warrior.

A Rhodes Scholar who studied law at Oxford and secretly became a communist, Lee returned to New Haven as a Sterling fellow at Yale Law School, according to his entry in the Class of 1935’s 25th reunion book. In 1939, he went to work for Donovan’s New York law firm.

Recruiting for the Office of Strategic Services—the nation’s new spy agency—“Donovan picked men for their backgrounds, favoring pedigreed blue bloods,” says a Wall Street Journal review of A Very Principled Boy. “Lee made the cut, following Donovan to the OSS and working his way up to chief of the Secret Intelligence Branch before the OSS disbanded in 1945.”

By that time, the Soviets had also recruited Lee. For nearly three years during the war, he passed along “sensitive information to his Soviet handlers, including the likely timeframe of the D-Day invasion and the names of OSS personnel under investigation for suspected communist affiliations,” the publisher’s summary says.

After the war, one of those handlers—Elizabeth Bentley—defected to the United States, confessed to the FBI, and named Lee as a source. But her accusations were hard to prove: fearing detection, Lee never provided documents and refused to let Bentley take notes, she told the FBI.

Later, Bentley testified before the House Un-American Activities Committee. So did Lee, who staunchly denied the allegations.

Lee’s former OSS colleagues “refused to believe that one of their leading officers, one who so embodied the OSS’s Ivy League WASP image, could have betrayed them,” write the authors of Venona, a Yale University Press book based on decrypted Soviet spy messages. “Similarly, much of the press treated Bentley’s charges about Duncan Lee as preposterous.”

Yet those very Venona files “would appear” to demonstrate that Lee was a Soviet agent, a US Senate commission on secrecy concluded.

Despite the zealous efforts of FBI director J. Edgar Hoover, Duncan Lee was never prosecuted. “It was [Bentley’s] word against his, and no jury would believe Bentley, an unstable witness who was also a professed former communist,” the Wall Street Journal notes. Adds the publisher’s summary: “He died a free but conflicted man” in 1988.

The Journal praises the book’s “straightforward narrative [that] refuses to sensationalize.” Quoting Bradley, a former CIA officer, the review says Lee’s life exemplifies “the morally shaded, highly compartmentalized black, white, and gray worlds that spies inhabit.”

And, you might add, the black-white-and-gray world that American history inhabits. Lee’s ancestors, after all, reportedly include two signers of the Declaration of Independence—and Confederate general Robert E. Lee.

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The Yale Alumni Magazine is published by Yale Alumni Publications Inc., an alumni-based nonprofit that is not run by Yale University. Its content does not necessarily reflect the views of the university administration.