Soviet spies called her “umnitsa,” or clever girl. The FBI called her “Gregory” and the Bureau’s early cables described her as “he.” The tabloids, when they got a hold of her story, called her the Red Spy Queen, and for a time during the Communist witch hunts of the 1940s and ’50s, no person on earth was more despised by the American Left than Connecticut-born, Vassar-educated Elizabeth Bentley.

She was portrayed as a drunk, a slut, and you can be sure names were used for her that nobody would print in those days, even in counterintelligence memos. Toward the end of her life and career as an FBI source, as she grew increasingly hard up for money and impatient with the agents handling her case—all of them men annoyed by her demands—they frequently resorted to the same explanation in their internal communications. As one of her biographers wrote with appropriate irony, “According to the FBI, Elizabeth Bentley had the longest menopause in recorded history.”

When looking at her story, one is always tempted to write, as many have, “Had Elizabeth Bentley been a man...” But had she been anyone other than the woman she was she would not have had the combination of smarts, guts, a romantic sense of adventure and sheer desperation that led her to do what she did.

“ The first FBI agent she talked to in New York thought she might be a psychopath. ”

Even Bentley’s sympathetic, scholarly biographer, Kathryn Olmsted, presents her as a “sad and lonely girl,” tall, big boned and rather plain, who wound up looking for love in all the wrong places, including the Communist Party and the Soviet espionage apparatus variously known in those years as the NKVD and NKGB. But that’s also the way Bentley eventually pictured herself in a potboiler memoir she hoped would appeal to housewives who read the serialized story in McCall’s Magazine in 1951.

“She decided to portray herself as a sort of Communist June Cleaver,” writes Olmsted, alluding to the mom in the popular TV series, Leave It To Beaver, which premiered a few years later. As even Bentley eventually admitted, the memoir was basically fiction, and it did much to destroy her credibility as a public penitent, a spy who’d seen the light and gave important testimony in the most highly publicized hearings and trials of what’s now called the McCarthy Era.

As the CIA’s review of Olmsted’s book points out, Bentley attained “a celebrity status second only to Whittaker Chambers in the tribe of ex-communist witnesses.” But Chambers was glorified by the American right. President Ronald Reagan gave him a posthumous medal, and his farm in Maryland is designated a National Historic Landmark. Bentley was largely erased from the nation’s memory.

There was one moment, however, before the public had ever heard her name, when Elizabeth Bentley was absolutely brilliant and, we now know, remarkably precise and accurate.

It was toward the end of 1945, nearly two years after she lost her Soviet spymaster lover and inherited his extensive networks, and a year after NKVD apparatchiks from Moscow took those agents away from her. She had been spooked by a chance encounter in a bar with a man claiming—as a pickup line—that he was a U.S. government “investigator,” and she was increasingly fearful that Stalin’s men would terminate her life as well as her employment. So she went to the FBI. And she began to talk.

The full length Bentley confession in November 1945 was a rambling Rosetta Stone that not only exposed scores of Soviet agents and their operations but provided detailed information vital to the decryption of Soviet cable traffic in the super-secret Venona project.

Although Bentley is best remembered for two bits of thin hearsay used to help convict State Department official Alger Hiss for perjury and Julius Rosenberg for espionage, those are only a few sentences at the very end of 107 pages, seemingly included as afterthoughts, and by themselves far from conclusive. The rest is a granular spy saga filled with extraordinary first-hand detail about Soviet operations in the United States from the late 1930s through the end of World War II.

As the CIA noted in 2003, “The espionage campaign in which Bentley participated has to rank as one of the most formidable conspiracies ever launched on American soil.”

In the years since, important moles and spies have been uncovered in different operations, but there probably was no other offensive of such scope until Moscow’s intelligence services turned their “active measures” on the United States before and during the 2016 U.S. elections.

In the late 1940s, for at least a couple of years, Bentley’s betrayal of the Soviets led them to shut down operations almost entirely. At the same time, she opened the door to the hysteria of McCarthyism.

Yet at first—not least because she was a woman—Bentley had trouble making the Federal Bureau of Investigation pay attention.

FROM ALLIES TO ENEMIES

When Bentley first walked into the FBI field office in New Haven, Connecticut, in August 1945 and started to hint tentatively at the story she had to tell, the Feds didn’t know what to make of her. They opened a file on the guy with the “investigator” pickup line in the bar.

World War II had just ended and the Soviets had been America’s allies. FBI Director J. Edgar Hoover might worry about the Reds, and Whittaker Chambers, among other Communist defectors, had passed on some information about members of the Communist Party infiltrating the U.S. government, but their information seemed to be out of date. As long as the war went on against the Germans and Japanese, the Soviet threat did not seem a priority.

So Bentley’s initial rather cautious revelations in August might have continued to gather dust in the Feds’ files if hundreds of miles away at the Soviet embassy in Ottawa a disgruntled code clerk had not decided to defect at almost the same time.

Igor Gouzenko, too, initially met with skepticism. But within weeks the information he provided was sending shock waves through the highest levels of Canadian, British, and U.S. counterintelligence operations as evidence grew of Stalin’s vast espionage operations.

Now that the war was over, there was this sudden and very unsettling revelation that “Uncle Joe” had systematically targeted his allies, their nuclear technologies, their intelligence operations, their diplomacy, their economic policies. Anywhere his agents could penetrate, they did, and now it seemed that was almost everywhere.

Suddenly in October the FBI was in a mood to interview Bentley again, this time at the field office in New York, but she was coy, testing the waters, trying to figure out how much the Feds knew about her already, or not, and gauging how best to stay out of jail.

She worried that one of her prominent contacts in the Communist Party of the USA had just announced publicly his renunciation of communism and his embrace of Catholicism under the tutelage of a celebrity priest. That made him an instant celebrity himself and a dangerous rat. So Bentley was careful. But her elusive dialogue did not serve her well with the agent interviewing her, who was treading water until his imminent retirement. He thought she might be a psychopath.

What she was at that moment, in fact, before her fame and infamy, was an adventurer, a survivor, and an encyclopedia of Soviet espionage in the United States.

THE LOVERS

Elizabeth Bentley was born in 1908 in the Connecticut village of New Milford on the Housatonic River near the New York border. But she grew up on the move with family as her father constantly changed jobs. She finished high school in Rochester, New York, where he worked at a department store and her mother taught eighth grade. Maybe they were the strict moralizers that she later claimed—he had been a campaigner for Prohibition. But Elizabeth, an only child, was coming of age in the Roaring Twenties, and when she got a scholarship to Vassar, she soon had a chance to witness and perhaps to taste whatever fruits had been forbidden by her parents.

Bentley’s classmates would remember her as something of a wallflower. Certainly the job she took when she graduated from Vassar with a degree in romance languages was not one likely to enhance her social life. She went to teach at Foxcroft School in the heart of the Virginia hunt country, a kind of secular equestrian convent where the redoubtable head mistress, “Miss Charlotte,” had the girls ride competitively during the day and sleep on screen porches at night even in the depths of winter. After two years at Foxcroft, she quit. Her mother had died and then her father; she was 25, orphaned, and ready to cut loose.

Bentley had made several brief trips to Europe, including the Italian university town of Perugia, and now she took off for Italy again, this time to do graduate studies at the University of Florence. There she finally felt the kind of liberation she’d been looking for, drinking and fucking to a fare-the-well. But she was living the Roaring Twenties in the rather more judgmental Depression Thirties, and scandalous stories went around. At a New Year’s Eve party in Florence she supposedly challenged the other women there to “pull down your pants and have your partner take you right here on the floor.”

“ "Pull down your pants and have your partner take you right here on the floor" ” — Elizabeth Bentley at a New Year's Party in Italy

No, June Cleaver never said anything like that. But then June Cleaver never flirted with fascism either, and while in Italy, Bentley was doing what a lot of Romans did. She at first embraced the idea that Benito Mussolini was the savior of his country, and fascism the wave of the future. But one of her lovers, a professor 20 years her senior who was on a secret police “watch list,” turned her against Il Duce. He also had an assistant write her thesis for her.

When Bentley returned to the United States the Depression was at its height, the poverty in the streets appalling, and the idyllic promise of Communism as an answer to the suffering of the people appealed to her just as it did to many others in her generation, especially among the intelligentsia. Whatever else one might say, Communism also was the most militant force opposed to the fascism and Nazism spreading across Europe—and it advocated equality of the sexes. Bentley felt at home among the cadres she knew, and she joined the Party.

In 1938, when she had taken a job working undercover at Mussolini’s propaganda office in New York, she was introduced to a man called “Timmy,” and would only learn gradually that this Russian immigré 18 years her senior had as fine a Bolshevik pedigree as could be had. Born Jacob Raisin, he had joined the revolutionaries long before they took power, and had paid for his radicalism with years in the Czar’s Siberian prison camps. He escaped, made his way to the United States, where his parents had already established themselves, and then returned to Russia to rejoin the Bolshevik revolution in 1920. There it appears he became an operative of the Cheka and then the OGPU, predecessors of the NKVD and KGB.

By the mid-1920s, Jacob Raisin had changed his last name to Golos, meaning “voice.” He was helping to build the Communist Party in America and, by the 1930s operating as an independent-minded Soviet spymaster who jealously guarded his networks not only from the FBI, but from Stalin’s espionage apparatchiks. (Wisely, during the Soviet purges of the 1930s Golos refused to be recalled to Moscow.)

Bentley worked for Golos undercover, and then as a courier meeting with various members of his networks. She also fell in love with him, but he was suffering from arteriosclerosis and in declining health. By the time he died of a heart attack on Thanksgiving Day 1943, he had passed his most important networks on to her. And Stalin’s men moved in on them. They wanted those agents for themselves, in the hands of professional Russians answering directly to Moscow Center.

THE CONFESSION

Throughout 1944, Bentley met with a succession of case officers—”Bill,” “Jack,” and “Al”—all of whom tried to cajole and pressure her to pass on Golos' agents now deeply embedded in various important government agencies, including the Treasury Department and, importantly, the Organization of Strategic Services, predecessor of the CIA.

Bentley refused repeatedly, but by the end of 1944, finally, she surrendered to the pressure from her handlers. The one part of her job that she tried to keep through most of the following year was an administrative one at a travel agency and shipping company dealing with the Soviets. Golos had set up the operations as genuine business concerns and also as covers for espionage activities. They were important to her emotionally as well as financially.

In September 1945 as the Soviets rightly perceived they would soon be viewed by the West as enemies, Bentley had a disastrous meeting with “Al,” a top intelligence officer. Unbeknownst to her, his real name was Anatoly Gorsky. He had managed the “Cambridge Five” in Britain, including the uber-mole Kim Philby, and had supervised the vital Soviet penetration of British work on the atomic bomb. Al told Bentley he thought there could be a war, as people began to say, with “the damn Russians,” and it was imperative to change the rather casual way things had been done under Golos and Bentley.

That day she had been to a celebratory lunch with the head of the shipping company and she had downed “several dry martinis.” She was, by her own admission, drunk, and she’d never really liked Al, whom she described to the FBI as about 5'5" and 175-180 pounds, with "dark blond hair combed straight back, blue-gray eyes, irregular front teeth, and sensuous lips."

Al had hit on her once, or she on him—they told conflicting stories—but whatever the fact of the matter, she'd been insulted. And now he was ordering her to quit her job and lie low. Eventually, Al said, the Soviets might set her up in a little business, perhaps a hat shop or dress shop or another sort of travel agency, maybe in Baltimore, maybe on the West Coast. After a few months she’d be brought back on line to handle four or five agents. Or maybe she could go teach at the Russian school in Washington.

“ "I told him that I was an American and could not be kicked around." ” — Elizebeth Bentley to her Soviet case officer

Bentley was no fool. Al was firing her. And drunk as she was, she was furious. She categorically refused, and told Al “in plain words,” as she recalled, “what I thought of him and the rest of the Russians, and further, told him that I was an American and could not be kicked around.”

It didn’t take Bentley long after that to realize she might have sealed her fate with an organization that did not hesitate to liquidate those who betrayed it. And she was right to worry. Subsequent scholarship has revealed Gorsky sent a cable back to Moscow Center saying he’d read her remarks as hints she would go to the Feds. And he was coldly analytical: “Judging by her behavior, she hasn’t betrayed us yet, but we can’t rely on her. Unfortunately she knows too much about us.” Thus “only one remedy is left—the most drastic one—to get rid of her.”

Moscow Center was not so sure. For once, male condescension worked in Bentley’s favor. Gorsky’s boss in Russia suggested paternalistically that all the lady needed was a shoulder to cry on and a little money.

So it was that the day after she had talked to the bored soon-to-retire FBI agent who thought she might be a psychopath, Bentley met with Al again. And this time he gave her an envelope with $2,000 in it—a very considerable sum in those days—which he said came with no strings attached.

“ Only one remedy is left—the most drastic one—to get rid of her. ” — 'Al,' Elizabeth Bentley's Soviet case officer

In the weeks that followed, Bentley hesitated. The FBI was now calling with sudden and increased insistence, but she wouldn’t answer, until one day, after a fight with an American Communist Party official about the finances of the shipping company, she realized that chapter of her life was coming to an end, and the risk of a very final sort of termination was growing every day.

On November 6, 1945, the FBI called and she answered. And two days later the serious interviews began. All day long on November 8, 10, 12, 15, 17, 18, 19, 20, 21, 22, 24, 26, 28, and 29 she talked until, on November 30, 1945, she signed that statement that was 107 single-spaced pages.

But Benchley had little or no documentary evidence to back up her story. It was her word against those she accused, and in the months and years to come, when the men she named denied her allegations, they often won their court cases, or never came to trial at all.

Many also gained the sympathy of a public appalled by the excesses of McCarthyism and put off by Bentley’s notorious personal life as well as the lies and exaggerations she perpetrated as she tried to cash in on her newfound fame.

THE VENONA VINDICATION

Not until 50 years later when the decoded Soviet message traffic from the Venona project finally was released to the public did scholars determine that, indeed, almost everything she told the FBI as first-hand knowledge in that vast deposition was true, at least to the best of her recollection—and her recollection was phenomenal.

As John Earl Haynes and Harvey Klehr wrote in their 1999 book Venona: Decoding Soviet Espionage in America, “Bentley had been in love with Jacob Golos and had sustained a great loss when he died in late 1943. She had then thrown herself into continuing his work. But by the end of 1944 the KGB had taken that away. In 1945 it further urged her to give up the U.S. Service and Shipping Corporation, the only thing she had left of her life with Golos. Her morale hit rock bottom. By the late summer of 1945 she was convinced that the FBI was closing in. It was not, but her fear of arrest and her disillusionment led her to defect. The KGB had pushed Bentley out because it wanted a more secure system. What it got by doing so was the exposure and neutralization of the very networks it was trying to protect.”

“ The FBI agents responded that "they knew she was a 'slut,' but that she could be telling the truth about other things. ”

“The real Elizabeth Bentley had been a strong woman who defied limits, laws, and traditions,” writes Kathryn Olmsted at the conclusion of her 2002 biography, Red Spy Queen. “She deceived and manipulated the NKGB, the most brutal and murderous secret police agency in the world, and lived to tell the tale.”

She also forced an increasingly reluctant J. Edgar Hoover to support her. “The FBI always had to balance its desire to promote her conservative political message with its distaste for her liberal standards of behavior,” writes Olmsted. “Once, an angry witness denounced Elizabeth to the bureau as a lying slut. The FBI agents responded that ‘they knew she was a “slut,” but that she could be telling the truth about other things.’”

Bentley eventually embraced Catholicism, but had trouble keeping jobs as a teacher at Catholic institutions. Her final employment was at a reform school for girls in Connecticut, keeping a low profile, she said, to “build up good citizens” and “contribute to a better America.”

Bentley died of cancer in 1963 at the age of 55. Time gave her two sentences in its “Milestones” section. In a final insult to a woman widely viewed as completely discredited, the magazine identified the former Red Spy Queen as little more than a “frumpy New Englander” who went astray.