Elizabeth Bentley

Elizabeth Bentley

Long before talk of Russian hacking dominated the headlines, Connecticut’s Elizabeth Bentley was at the heart of a different type of espionage scandal...

On an unusually chilly summer day in August 1945, Elizabeth Bentley walked into the New Haven field office of the FBI.

Nazi Germany had been defeated a few months earlier and the uneasy wartime alliance between the U.S. and the Soviet Union was over. And thanks in part to Bentley — a Soviet spy turned double agent — the Cold War was about to start in earnest. The information she would provide FBI agents would directly fuel the anti-Communist witch hunts spearheaded by Joseph McCarthy, temporarily stop Soviet espionage activity in the U.S. and lead to convictions in two of the most famous spying cases in U.S. history — the Rosenbergs and Alger Hiss.

In the months and years after that meeting with the FBI, Bentley would emerge as the poster girl of early Cold War espionage. She had a list of ex-lovers longer than a Hollywood screenwriter would dare invent and her life story reads like a real-world version of FX’s show The Americans. Newspapers described the Connecticut woman-turned-Soviet spy as “a shapely blonde” in a “form-fitting black dress.”

In reality, Bentley was “a large-boned, self-confident brunette with a sharp nose and receding chin,” and her life contained more gloom than glamour, writes Kathryn S. Olmsted, author of

Red Spy Queen, the definitive biography of Bentley. “Above all, she was an intensely lonely woman searching for love and acceptance,” Olmsted writes.

Born in New Milford in 1908 to middle-class Republican parents, Bentley received her undergraduate degree from Vassar College and her master’s degree in languages from Columbia University. She got her first brush with international politics in 1933 when she won a fellowship to the University of Florence. In Italy, she briefly joined the fascist student movement before being persuaded against the cause by Mario Casella, her academic adviser and one of several Italian lovers.

Returning to New York in 1934, Bentley was now fiercely anti-fascist and gravitated to communism, officially joining the Communist Party in 1935. She volunteered to spy on fascist Italy’s New York City propaganda agency, where she got a job. She engaged in increasingly brazen espionage activities over the next few years. In 1938, she met Jacob Golos, an important Soviet agent who controlled a network of Communist Party members who worked for New Deal agencies and spied on the U.S. government for him. Golos became Bentley’s handler and lover.

Bentley helped Golos communicate with his sources, serving as a courier and making regular trips from New York to Washington. It was through Bentley that the Soviets received intelligence from the Silvermaster group, an infamous spy ring centered around Nathan Gregory Silvermaster, an economist with the U.S. War Production Board. Silvermaster would transport sensitive microfilm documents to Bentley every few weeks.

In 1943, Bolos died of a heart attack and Bentley took over his spy network. But the work was not the same without Bolos. Bentley had long been prone to bouts of depression and alcoholism, and she slipped into both following Bolos’ death.

When her new Soviet handler wanted her to provide the names of her spy contacts, she resisted. In 1945, she began an affair with a man she came to suspect was either an FBI or Soviet agent sent to spy on her. Her fears increased after she launched into a drunken tirade against her new handler. She began fearing for her life.

It was at this time that she walked into the New Haven field office in her home state of Connecticut. She defected shortly afterward, and by the end of 1945 had given the FBI more than 50 names. However, the Soviet Union quickly learned of her defection through Kim Philby, a high-ranking member of Britain’s MI6, who was in reality a double agent working for the Soviets.

With word of Bentley’s defection out, all illegal activity among the spy ring she had once run ceased, and intense FBI surveillance of those whose names Bentley had provided turned up nothing.

FBI Director J. Edgar Hoover verified Bentley’s story through the top-secret Venona project, which intercepted and decoded Soviet transmissions.

But information obtained through Venona couldn’t be used in court because the project was deemed too valuable to publicize. Unable to prosecute the suspected spies, Hoover gave Bentley’s story to members of Congress with the understanding that they would launch congressional inquiries and generate enough bad publicity for those on the list that their careers in the U.S. would be over and value as spies eradicated.

In 1948, Bentley appeared before the House Un-American Activities Committee, helping to begin what would grow into a communist witch hunt. In the 1950s, Bentley testified at several congressional hearings and criminal trials, including the trial of Julius and Ethel Rosenberg, and wrote a memoir, Out of Bondage. In her memoir she exaggerated her story, a practice she increased as her life went on, causing some to mistakenly dismiss her as a liar.

In the late 1950s, she largely faded into obscurity. Bentley returned to Connecticut, where she worked as a teacher, first in Hartford and then in Middletown, teaching English at the Long Lane School for Girls, a state correctional institution. She taught there for the final five years of her life, and lived in nearby Middlefield. Bentley died on Dec. 3, 1963, from abdominal cancer at Grace-New Haven Hospital. She was 55. But in those 55 years, the woman from quiet New Milford had been at the center of the espionage between the world’s two superpowers, and, for better or for worse, had changed the world.

The senior writer at Connecticut Magazine, Erik is the co-author of Penguin Random House’s “The Good Vices” and author of “Buzzed” and “Gillette Castle.” He is also an adjunct professor at WCSU’s MFA Program and Quinnipiac University