The Nutmeg Mata Hari



 The story of Elizabeth Bentley, Connecticut’s own Soviet Spy
Connecticut Yankee Elizabeth Terrill Bentley was a spy for the Soviet Union in the United States from 1938 until she defected in 1945.

Elizabeth Terrill Bentley was born to middle class, old line Episcopalian Yankee parents in New Milford, Connecticut.  The family had lineage but no money and moved frequently to find work.
She read a great deal and seemed to live almost exclusively in a fantasy world. Elizabeth attended East High School in Rochester and described herself as "lonely, withdrawn child". Which she mostly blamed on her mother, a member of the Women's Christian Temperance Union (WCTU).  “She was” Bentley wrote "very, very strict... who didn't allow me to befriend girls of my age who were drinking, smoking and visiting nightclubs."
In 1926, Bentley won a scholarship to Vassar College and according to Kathryn S. Olmsted: "The cloak of loneliness she had donned in high school still clung to her at Vassar. She was a tall girl - over five feet nine - with a large build, long neck, and a shy smile. She was growing into the kind of woman that some people would term 'somewhat attractive,' but more critical observers would call plain. At Vassar, Elizabeth seemed uncomfortable among her rich, prestige-conscious classmates."
One of Elizabeth's boyfriends, Harvey Matusow, as saying: "She used alcoholism to ease her pain, and she had a lot of pain. Matusow speculated that she was a "manic depressive".
"She lived the high life” Olmsted wrote “even though as a financial aid recipient she could not afford it. She borrowed money frequently from her friends and did not always repay it. Breaking the last of her parents' rules, she always drank to excess. Elizabeth would be an alcoholic throughout her life... Not surprisingly, considering her enthusiasm for spontaneous sex in the years before oral contraceptives, there were rumours that she had some illegal abortions." 
While on a fellowship trip to the University of Florence in Italy, she joined a local student Fascist group, the Gruppo Universitario Fascista but shortly afterwards began an affair with her anti-Fascist faculty advisor Mario Casella who brought her around to the left leaning Anti-Fascist pro-communist leanings.  By the time she returned to the United States both her parents had died of natural causes leaving her alone in the world
Bentley graduated from Vassar, class of 1930 with a degree in English, Italian, and French and then went on to graduate school at Columbia University. After graduation she took a job at the Italian Library of Information in New York City which was, essentially, fascist Italy's propaganda bureau in the United States. At one of the early CPUSA meetings Elizabeth Bentley met Juliet Poyntz who was using the name Juliet Glazer and also worked at the Italian Library of Information
Juliet Glazer was actually Juliet Stuart Poyntz, an American born, Moscow trained member of the Soviet secret police. Poyntz was born Juliet Stuart Points on November 25, 1886 in Omaha, Nebraska. She was a member of the Daughters of the American Revolution (DAR).
She earned degrees at Barnard College in 1907 where she was an outstanding and far above average student. From 1907 to 1909, Poyntz was "Special Agent for the U.S. Immigration Commission," working in Chicago, Milwaukee, Philadelphia, Utica, Lawrence Massachusetts, and other cities.
She joined the Socialist Party of America in 1909 while teaching at Barnard College. Six years later, in 1915, she became education director of the Worker's University of Local 25 of the International Ladies Garment Workers Union (ILGWU) and in 1926, ran for New York State Comptroller and later in 1928 for New York State Attorney General, both times on the Workers Party ticket.
Poyntz was a delegate to several consecutive American Communist Party conventions, and was a member of the Party’s Central Executive Committee, besides being on New York’s District Executive Committee but dropped out of the CPUSA in 1934 in order to work for the OGPU (Soviet military secret police, later the NKVD)
Whittaker Chambers recalled "Juliet Poyntz... had been a member of the first unit of the Communist Party which I joined in 1925. A heavy-set, dark, softly feminine woman, she was also a little absurdly imperious and mysterious as Communist bureaucrats often become, sagging self-consciously under the weight of so much secret authority and knowledge."
In 1936, Poyntz secretly travelled to Moscow to for spy training and witnessed the Great Purge instigated by Stalin. She returned to the US disillusioned and unwilling to continue spying for Russian intelligence.
On June 3, 1937, Poyntz disappeared after leaving the Women's Club in New York City. No trace of her was ever found. Carlo Tresca, a leading Italian-American anarchist, publicly accused the Soviets of kidnapping Poyntz in order to prevent her defection but it was later learned that she was writing a book which would expose the Communist movement in America.
She disappeared when her former lover, Shachno Epstein, the associate editor of the Communist Yiddish daily Morgen Freiheit and a NKVD intelligence agent lured Poyntz out for a walk in Central Park.
A biographer wrote that "They met at Columbus Circle and proceeded to walk through Central Park...Shachno took her by the arm and led her up a side path, where a large black limousine hugged the edge of the walk... Two men jumped out, grabbed Miss Poyntz, shoved her into the car and sped away.”
She was driven to the woods near the Roosevelt estate in Duchess County, and killed and buried her there. "The body was covered with lime and dirt. On top were placed dead leaves and branches which the three killers trampled down with their feet."
When American turncoat Chambers asked spy master Boris Bykov what had happened to Poyntz, Bykov replied coldly "Gone with the wind. Chambers wrote "She was living in a New York hotel. One evening she left her room with the light burning and a page of unfinished handwriting on the table. She was never seen again. The thought of this intensely feminine woman, coldly murdered by two men, sickened me in a physical way, because I could always see her in my mind's eye." As a result of her death, Chambers decided to stop working for the Communist Party of the United States.
However, before his own mysterious death, the soviet intelligence defector Walter Krivitsky suggested another motive for Poyntz murder. He said that while Poyntz was in Moscow, she became the lover of a Red Army Corps Commander named Vitovt Putna.
In August 1936 the NKVD arrested Putna and accused him of maintaining contacts with and taking instructions from Leon Trotsky. Under torture, Putna testified to the existence of a nation-wide center of Trotskyists, and to his involvement in a "parallel" military organization.
On June 11, 1937 a military tribunal condemned Putna and other high-ranking officers to death. The NKVD, according to Krivitsky, may have abducted Poytnz one week before the trial out of fear that she would defect once the execution of Putna became known, or simply because she was a known friend of the "enemy" Putna.
Poyntz recruited Bentley for the Soviet communists and convinced her to provide information about Italian Library of Information to her assigned contact and controller, a KGB officer named Jacob Golos, a Russian émigré and deep cover intelligence officer who had been a naturalized United States citizen since 1915.
Bentley claimed that Poyntz introduced her to a possible intelligence source named   "Smith" who seemed more interested in developing a sexual relationship with Bentley than anything else
 When Bentley rejected Smith’s advances he reported her to Poyntz who became worried that Bentley might turn her into the FBI. That night Poyntz went to Bentley’s apartment and denounced her as a "subversive" and said "Just remember one thing, if ever you meddle in my affairs again, I'll see that you're taken care of. You'll be put six feet under and you won't come back to do any more talking!"
Poyntz’ and Bentley’s assigned contact and controller was a stout man named Jacob Golos was born into a Jewish family in Dnipropetrovsk, Russia, on 24th April, 1889. He joined the Social Democratic Labor Party as a teen and in 1904 became active in the Bolsheviks and took part in the 1905 Russian Revolution.
In 1907 Golos was arrested for operating a clandestine Bolshevik printing house, found guilty and sentenced to eight years in prison in exile in Siberia. He somehow not only managed to escape he made his way to San Francisco in 1910 and found work as a printer, eventually bringing his sisters and  parents to America as well.
Golos showed up in New York City in 1912 where he was extremely active in the Russian Socialist Federation, the Socialist Party of America and raised money for the Bolshevik Party.
In September 1919, Golos joined Earl Browder and others in forming the Communist Party of the United States (CPUS). Within a few weeks it had 60,000 members. Two years later, in 1921, he was working as an organizer at the Communist Party in Chicago. The following year, the newly reorganized Bureau of Investigation (later renamed the Federal Bureau of Investigation) began to follow his activities.
In 1926 he returned to the Soviet Union and by the request of the American Communist party was returned to the United States in 1928 where he began building his intelligence network. Secret Soviet intelligence cables from Golos were called "our most reliable man in the US”
Using bribery to underpaid federal workers Golos developed a network of foreign consular officials and U.S. passport agency workers who supplied him with passports, naturalization documents and birth certificates belonging to persons who had long since died.
In 1934 Golos became the head of its Central Control Commission, meaning he was to ensure that all members of the Communist Party of the United States followed party policy as directed by Joseph Stalin.
By 1935, Golos was one of the Soviet Union's most important intelligence agents in the United States and was deeply involved in planning the assassination of Leon Trotsky in Mexico in 1940.
On October, 15 1938, she met Jacob Golos for the first time. Kathryn S. Olmsted described their first meeting "Like any good spy, Golos did not stand out in a crowd. A heavy-set, rather nondescript man in a bad suit and scuffed shoes, he did not make a favorable first impression on Elizabeth. At five feet two inches, he was seven inches shorter than the strapping young woman he hoped to use as a source. She eyed with disapproval his tattered felt hat and shabby car."
However, she gradually changed her mind about Golos: "He seemed intelligent and thoughtful. Soon she found herself telling him the story of her life, including her disappointing earlier contacts with the Soviet underground. As she warmed to him, he seemed to grow better looking. He was no longer short and squat but 'powerfully built'; he was not colorless but had 'startlingly blue' eyes that stared straight into hers... Though she was intimidated, she felt flattered by the attention that this powerful Communist was giving her."
She began doing some simple spy work for Golos while Golos trained in the art of espionage. Bentley, who didn’t know Golos true name had wrongly assumed that she was spying for the American Communist Party and no one else and Golos made it a point not to tell her otherwise.
At Golos's direction she took a secretarial job with Richard Waldo, a conservative businessman so she could spy on him and his contacts.  She also carried information, including copies of U.S. government documents, to other agents and couriers and “entertained” as she put it, men that Golos needed to get close to.
By 1938, Golos was Bentley’s lover (Despite the fact that Golos had a mistress, and a common-law wife and child back in Russia) and two years later he told her his true name and his status with Russian intelligence but only after the US Justice Department forced Golos to register as an agent of the Soviet government under the Foreign Agents Registration Act.
Golos travel agency, World Tourists in New York City, a front for Soviet spies was raided by the FBI who found documents showed that Earl Browder, the leader of the Communist Party of the United States, had travelled on a false passport and arrested Browder.
The Justice Department agreed to drop the investigation and the charges against Browder, if Golos pleaded guilty and Moscow, which needed to protect Browder forced him to cooperate. "I never thought” he told Bentley “that I would live to see the day when I would have to plead guilty in a bourgeois court."
On March 15, 1940, he appeared in court and was fined $500 fine and placed on four months’ probation and added to the Justice Departments watch list.
On January 18, 1941, the FBI were tailing an espionage suspect named Gaik Ovakimian. Unknown to them was that Ovakimian was the head of Soviet espionage in the United States from 1933 to 1941.
Agents watched Golos, whom they knew was a Soviet agent, meet Ovakimian on a Manhattan street. Over the next few weeks, the agents saw Golos meet Ovakimian several times, and even watched the two men exchange documents. The meetings brought on the full attention of the FBI’s top brass who were just becoming aware of the vast numbers of Soviet spies in the United States.
Based on his meetings with Ovakimian, FBI agents began sporadically tailing Golos and observed him going to the offices of the U.S. Service and Shipping Corporation, where Elizabeth worked, and an apartment at 58 Barrow Street, where she lived. It became apparent that Golos, although he kept a hotel room elsewhere, was living with Bentley and the agents noted that Bentley was probably a soviet spy as well.
With the Justice Department watching, Golos was unable to operate as a spy, Bentley willingly stepped into his place also running Golos front company the United States Service and Shipping Corporation. At that point Soviet Intelligence gave her the code name Umnitsa (meaning "wise girl") However, on May 23, 1941, the day Ovakimyan was arrested (and later deported) bureau agents began tailing her.
Her biographer wrote “Elizabeth grew terrified that she might be arrested at any time. She tried desperately to ensure that the tails never witnessed her meeting with important contacts. Very quickly, she developed an incredible number of ruses" for shaking a tail, including sneaking out of fire exits, abruptly changing direction, and boldly walking up to her pursuer and asking him for directions. Her tactics worked. The FBI found nothing interesting in her activities. The surveillance was stopped on August 20, 1941, after just a few months.’’
At that point Bentley learned that she was part of the Silvermaster group, a network of spies centered around master spy Nathan Gregory Silvermaster, one of the most important, of not the most important Soviet spies in the US.
Silvermaster worked with the Resettlement Administration and later with the Board of Economic Warfare and while he did not actively operate as a spy himself, he arranged for Communists sympathizers within the US government to pass information to him by way of Bentley.
"You are no longer an ordinary Communist” he told her “but a member of the underground. You must cut yourself off completely from all your old Communist friends." And that she must not think of herself as a traitor "the Party would not ask this sacrifice of you if it were not vitally important."
It was easy for Bentley not to see herself as a traitor largely because at the time the Soviet Union and the United States were allies against Hitler and most of the information she collected seemed to be about secret estimates of German military strength and so on.
In 1942, Golos would transfer a Communist cell of engineers headed by Julius Rosenberg into the direct contact with Soviet intelligence operatives in New York. Rosenberg would later pass information on the nuclear bomb to the Russians.
Bentley would testify in the Rosenberg trial and earlier her statement had led the FBI to Harry Gold who had been a courier for David Greenglass. At the trail she testified that Golos had met a tall, thin man with glasses one night who was named Julius although she was not sure that the Julius was Julius Rosenberg.
Despite all that Golos had done for the Soviets, Moscow was still upset over the arrested of named Gaik Ovakimian and essentially blamed the entire mess of Golos. As a slap, they replaced him as President of U.S. Service and Shipping Corporation with John Hazard Reynolds, a millionaire who put up $5,000 in capital in the beginning stages of the corporation and later poured another $15,000 into as well. Although Reynolds kept Bentley on as vice president of the company, she disliked him and recalled decades later   "His slightly arrogant manner and his accent said loudly Park Avenue, the Racket Club, and the Plaza."
All of it, the pressure from the FBI and the Russians, was taking its toll on Golos. Bentley wrote "His red hair was becoming grayer and sparser, his blue eyes seemed to have no more fire in them, and his face became habitually white and taut."
As Golos health began to deteriorate Bentley began to take over some of his duties including keeping order in the two groups her managed, the Silvermaster’s group and the Perlos group, both centered in Washington DC.
Bentley began travelling to DC to pick up documents from Nathan Silvermaster and his wife Helen who shared an apartment with another spy, Ludwig Ullman. Helen Silvermaster was suspicious of Bentley and assumed that she was an FBI agent.
Kathryn S. Olmsted wrote that "Every two weeks, Elizabeth would travel to Washington to pick up documents from the Silvermaster’s, collect their Party dues, and deliver Communist literature. Soon the flow of documents grew so large that Ullmann, an amateur photographer, set up a darkroom in their basement. Elizabeth usually collected at least two or three rolls of microfilmed secret documents, and one time received as many as forty. She would stuff all the film and documents into a knitting bag or other innocent feminine accessory, then take it back to New York on the train. The knitting bag soon bulged with critical documents from the U.S. government."
In 1943, Jacob Golos died of a heart attack. Bentley wrote "I knew now that Yasha was a dying man and that the end might come at any moment - it was only by some miracle of will power he was still alive."
On the morning of November 27, Bentley woke up hearing "horrible choking sounds" coming Golos. She tried to wake him from what appeared to be a heart attack but couldn’t. She it was too late. When the police arrived Bentley told them that she worked with the man and had just called in to see how he was because she knew he had been ill. She then rushed to Golos office and destroyed all the documents in the safe.
The end was near for Golos anyway. Just before his death Golos began to question the policies of Joseph Stalin "He said” Bentley wrote “he fought for Communism and now he was beginning to wonder." And the Soviets began to question Golos loyalty as well. In 1940Major Pavel Fitin, head of NKVD's foreign intelligence unit, reported to the Commissioner of Internal Affairs, that: "The American Trotskyite organization is the strongest in membership and financing among all the Trotskyite groupings." and that Golos, was not to be trusted: "since he knows a great deal about the station's work, I would consider it expedient to bring him to the Soviet Union and arrest him." Fitin proposed recalling Golos, but Golos, an American citizen, refused to return to Moscow.
At the urging of Earl Browder, head of the American Communist Party, Bentley officially took Golos place in the organization. Her new contact in Soviet intelligence was Iskhak Akhmerov, a spy who was working as a KGB operative without diplomatic cover.
Itzhak Akhmerov was born in Troitsk in 1901 and was recruited by Soviet intelligence directly out of college. In 1932 he served as an undercover agent in Turkey. And was moved to China in 1934 before being sent to the United States where he posed as a foreign student named Michael Green. He was actually the New York station chief, a high position in the Soviet Intelligence network.
In 1936 he began living with Helen Lowry, the niece of Earl Browder, the leader of the American Communist Party. Helen was quickly put to work as a courier between legal and illegal stations while maintaining a Washington residence where Akhmerov met his sources.
Moscow didn’t trust Bentley because she was an American and because they knew that she suffered from bouts of depression and was a heavy, life-long drinker who missed work at U.S. Service and Shipping and who seemed to be drinking even more after the death of Golos. Moscow ordered Akhmerov to have Bentley’s contacts report directly to him.
Akhmerov reported back to Moscow that “(Bentley) is a rather complicated and controversial character.... she knows perfectly well that she is working for us. She, as a rule, carries out my instructions gladly and reports everything about our people to me. However, her behavior changes when I ask her to organize a meeting with (Silvermaster) for me or to connect some of the (American) probationers with our operative. She becomes an absolutely different person and... Claims that she is not our operative that she works for (Browder) ... Sometimes, by her remarks, I can feel that at heart, she doesn't like us (i.e., Russians). She is inclined to distinguish us from compatriots (i.e., American Communists) and bitterly notices only our professional interest in different questions. She says that all of us personally care little about Americans that the USSR is the only country we love and work for. I tried to explain that she is mistaken.”
With the backing and encouragement of American Communist Party leader Earl Bowder, Bentley believed that an American intermediary was best to handle American sources. She also had a lifelong dislike for being told what to do and knew that if Moscow took control of her group she would be left her with no meaningful role so she initially ignored the Kremlin’s orders and even expanded her spy network which came to be known as the "Perlo group", with contacts in the War Production Board, the United States Senate and the Treasury Department.
Soviet controller Iskhak Akhmerov said that Victor Perlo was his most important agent or at least he was until Perlo divorced his wife in 1943 and fell into a bitter dispute over the custody of the daughter.
In April 1944 Mrs. Perlo sent a letter to President Franklin D. Roosevelt naming her husband and several members of his group as Soviet spies. The FBO investigated but did nothing.  Writer Kathryn S. Olmsted wrote that "Possibly, the men of the FBI discounted the tale of an unstable, vengeful ex-wife. Or perhaps the tale of Russian espionage did not seem so sinister in 1944, when the brave Soviet allies were battling the Nazis. In any event, Katherine Perlo failed in her quest to destroy her ex-husband, and Elizabeth Bentley survived to spy another day."
Bentley now had control of the Perlo group but she hated her overseer, Anatoly Gorsky who had taken over Jacob Golos role. Bentley described him "as a short, fattish man in his mid-thirties, with blond hair pushed straight back and glasses that failed to mask a pair of shrewd, cold eyes." She added that there was something about him that made "shivers run up and down your spine."
Bentley claimed that Gorsky, who saw Bentley as a self-obsessed neurotic, a child who was to be manipulated, sexually harassed her saying that he stared at her like "a trader about to decide whether to buy a horse" and said, suggestively, "I like you personally; I think we could work very well together."
However, Gorsky complained to Moscow that Bentley was making sexual advances towards him: "In a meeting with Gorsky where they exchanged Christmas presents, Bentley informed her Russian colleague that he reminded her of Jacob Golos. It was difficult for a young and lonely woman to live without a man, she told him, noting that she thought more and more often about having a family. A flustered Gorsky, plainly hoping to avoid entanglement, immediately cabled Moscow stating that it was urgent to find a husband for Bentley."
Eventually, Gorsky discovered that Bentley was involved with a man, Peter Heller, who they suspected was a FBI agent. He wrote t Moscow that "Bentley is a serious and dangerous burden for us here. She should be taken home (to the Soviet Union), but how to do it, frankly speaking, I don't know since she won't go illegally."
In early June 1944, Akhmerov took over Bentley’s group and that move is what she would later describe as the event that turned her against Communism. "I discovered then that Earl Browder was just a puppet, that somebody pulled the strings in Moscow," she said. Later in the year Bentley was ordered to give up all of her remaining sources and to leave her position as vice president of U.S. Service and Shipping. On November 27, 1944, Gorsky sent a memo about the possibility of another agent, Joseph Katz, killing Bentley.
In 1945 she began an affair whom she suspected was either an FBI or a Soviet agent sent to spy on her. When she told her Soviet contact what was happening, Moscow started to pressure her to move to the Soviet Union which Bentley assumed would end in her execution at the hands of the KGB.
By that time Akhmerov had returned to the Soviet Union and became deputy chief of the KGB's illegal intelligence section working openly under the rank of full of colonel. He died in Russia in 1976.
The US government was already on the hunt for spies in the government. Secretary of State James E Byrnes began a purge of the State Department firing anyone suspected of being pro-Soviet and the FBI began investigations of State Department officials that included background checks, wiretaps, and direct surveillance. That began in October of 1945.  In November of 1945, Elizabeth Bentley, then 37 years old, was vacationing in Old Lyme on the Connecticut River. She drove into New Haven and walked into the FBI offices and told the agent on duty, Edward Coady, about the U.S. Service and Shipping Corporation and how it was used to send information to the Soviet Union.
What may have prompted the visit to the FBI was her meeting in September with Anatoly Gorsky, her latest NKGB controller. Bentley arrived at the meeting drunk and willing to fight. She called Gorsky and his fellow Russian agents gangsters, and obliquely threatened to become an informer. When she sobered up she realized that her tirade put her life in danger. And it did. Gorsky reported the meeting to Moscow and recommended that they "get rid of her" but Moscow turned him down.
A second factor in turning herself into the FBI was that Louis Budenz, editor of the national communist newspaper and one of Bentley's sources, had defected to the West and if he was talking, she had no proof that he was, he knew her name and a basic outline of her espionage activities. The walls were closing in on her and she made her final decision to defect on November 6, 1945.
Bentley had approached the FBI twice before (August and October 1945) and hinted at her involvement in espionage but the agents, including the field agent in New Haven   that saw her as a "psychopath rambling on."
The field agent wrote up the minutes of the meeting with Bentley and passed it along to the espionage section of the New York office, who called Bentley in for a follow up interview.
Debriefing interviews began on November 7, 1945, with Bentley implicating almost 150 Americans, including 37 federal employees, as spies for the Soviet Union. Most of those that she named were already on the FBI’s suspect list making the FBI sure her story was genuine. In all she gave the FBI the names of more than eighty Americans who were spying for the Soviets.
The day after the interview FBI Director J. Edgar Hoover, sent a message to President Harry S. Truman confirming that an espionage ring was operating in the United States government.
Robert J. Lamphere, a senior FBI agent who handled Bentley noted that "The problem was that Bentley had nothing to backstop her stories - no documents, no microfilm, not even a gift of Russian origin which might have been traced. So very little in the way of prosecutions could be mounted, based on her recollections. Privately, some of us were exasperated and thought we knew what could and should have been done with Bentley. I believe that very early the FBI could have forced things by moving in aggressively and interviewing everyone connected with her; in this way we might have gotten some of them to break, or to contradict one another's stories. We also could have obtained warrants and searched the Silvermaster home and the apartments of the Perlo group for evidence. No such actions were taken at the time.... That spring of 1946, after the Bentley affair's initial phase, we in the New York office's Soviet Espionage squad felt frustrated: we were near and yet so far. (Russian defector) Igor Gouzenko and Bentley had shown that Russians were operating all around us, but we were unable to counter their efforts."
J. Edgar Hoover’s plan was to keep Bentley's (Who now had the code name Gregory) defection a secret and for her to work her way back into the Soviet spy circles to get evidence against dozens of spies. But Hoover advised Sir William Stephenson, head of British Security Coordination for the Western hemisphere, of Bentley's defection and inform him that Bentley had said a former member of his staff at the British Security Coordination, a Mr. Cedric Belfrage, was a spy. Stephenson notified British Secret Intelligence Service's and the new boss of counter-espionage against the Soviet Union unit Kim Philby.
Philby was a double agent who would defect to Russia in 1963. Philby alerted Moscow to Bentley’s defection and Moscow immediately shut down all contact with Bentley's organization just as the FBI was beginning surveillance of them. Once again Bentley's NKGB contact Gorsky once again recommended to Moscow that she be killed to silence her but again Moscow rejected the idea.
Another problem was that after losing her job with the U.S. Service and Shipping Corporation Bentley was broke and, in August of 1946, after what the FBI called "an exceptionally severe night of drinking" she took an overdose of phenobarbital.
The FBI needed Bentley and with the help of a FBI lawyer, Thomas J. Donegan, she was successful in taking legal action against the U.S. Service and Shipping Corporation and she was awarded a year's salary in severance. However that breach of secrecy around Bentley's defection foiled a year-long attempt by the FBI to have her act as a double agent and the FBI surveillance of the agents Bentley had named turned up no evidence that could be used to prosecute them.
Some 250 FBI agents were assigned to the Bentley case, following up the leads she had provided and, through phone tap, surveillance and mail openings, investigating people she had named.
On 15th April, 1947, a small army of FBI agents (A total of 200 agents were assigned to following up on the information Bentley provided) descended on the homes and businesses of twelve of the names provided by Bentley. Their properties were searched and they were interrogated over a period of several weeks but all of them refused to confess. It soon became apparent that the evidence provided by Bentley (As well as by other who defected back the US Side including Louis Budenz, Whittaker Chambers and Hede Massing) was not enough to get convictions.
On August, 3 1948, Whittaker Chambers appeared before the House of Un-American Activities Committee and testified that he had been a member of the Communist Party and a paid functionary of that party but left after the signing of the Nazi-Soviet Pact in August 1939. He also Bentley’s role in the Communist infiltration of the American government.
She converted to Roman Catholicism by Bishop Fulton Sheen in 1948 and lectured on the Communist threat by Catholic groups for a standard fee of $3,500. At the same time, she also started charging the FBI for consultations on how the Soviet’s spied in the US. 
In the late 1940s to early 1950s, the highly secret Venona project succeeded in decrypting wartime cables sent between Soviet intelligence agents and Moscow and Bentley was referred to in many of those cabals by the codename she told to the FBI. For FBI director Hoover and the handful of army intelligence personnel who were privy to the information, the cabals were definitive corroboration of Bentley's story.
The problem was that the Venona project was so secret the US Government was unwilling to expose to almost anyone beyond a need to know basis. (Including President’s Roosevelt and Truman who were unaware of the Venona project.)
After naming one of her operatives, William Remington, to the FBI, she mentioned Remington again on the radio version of Meet the Press. Remington immediately sued Bentley, NBC, and the show for libel. But Bentley was telling the truth, Remington was a spy who had caused serious damages to the United States,
William Remington was an economist, he also worked for the National Resources Planning Board the Office of Price Administration of the Office for Emergency Management and during the war worked for the War Production Board.
A friend of his later related to the FBI "(Remington) and his wife, Ann, longed to reestablish contact with the Party in Washington, but they knew that open membership would hurt Bill's career. As a solution some Party friends introduced them to a mysterious, redheaded man with an Eastern European accent."
The man they introduced him to was Jacob Golos and he passed him onto Bentley.
From 1943 through 1945, Bentley met Remington on a regular basis, where he handed over classified information on aircraft production and testing to the D-Day invasions. "He was one of the most frightened people with whom I have ever had to deal". She told the FBI.
Eventually Remington refused to meet Bentley and openly joined pro-Communist organizations in the hope that he would lessen his value as a spy. Bentley responded by saying Remington was "a small boy trying to avoid moving the lawn or cleaning out the furnace when he would much rather go fishing." And she advised Golos to drop him but Golos argued that they remained in contact as other powerful members of the network might be able to "push him into a really good position."
The Remington law suit was settled out of court when NBC decided that the cost of the investigation outweighed the cost of the case, and they settled with Remington for $9,000 (Remington had asked for $100,000 in damages).
Bentley was furious over the settlement and turned over information gathered by NBC’s private detectives to the HUAC and the FBI arrested him for espionage. Remington's trial began in January 1951 with the infamous Roy Cohn on the prosecution's team and the main witness against him was his former wife, Ann Remington.
Cohn later said "Elizabeth Bentley later supplied a wealth of detail about Remington's involvement with her and the espionage conspiracy. Remington's defense was that he had never handled any classified material, hence could not have given any to Miss Bentley. But she remembered all the facts about the rubber-from-garbage invention. We had searched through the archives and discovered the files on the process. We also found the aircraft schedules, which were set up exactly as she said, and inter office memos and tables of personnel which proved Remington had access to both these items. We also discovered Remington's application for a naval commission in which he specifically pointed out that he was, in his present position with the Commerce Department, entrusted with secret military information involving airplanes, armaments, radar, and the Manhattan Project (the atomic bomb)."
On 18th May, 1950, Elizabeth Bentley testified before the grand jury that Remington was a communist. When he stopped spying we "hated to let him go." The grand jury now decided to indict Remington for committing perjury.
By that time Bentley was drinking heavily and her lover, Harvey Matusow, was worried about the impression she would make in court. She was, he said, upset at her "frivolous treatment" in the press. "She didn't understand the hostility... She never got to the point where she could handle it."
She also complained about the way she had been treated by the FBI: "She felt that she'd been used and abused."  Bentley told her friend, Ruth Matthews that she "should step out in front of a car and settle everything."
Kathryn S. Olmsted, the author of Red Spy Queen wrote that during the trail Bentley "Once again, though, despite her emotional problems outside of court, Elizabeth performed well on the stand. As usual, she was somewhat snappish and impatient under cross-examination... But like his predecessors, Jack Minton (Remington's new attorney) could not shake her self-confidence. She again succeeded in creating the illusion of a calm, controlled, and even patronizing witness, a Sunday school teacher somehow dropped into the middle of an espionage trial."
In all eleven witnesses claimed they knew Remington was a communist. Remington was convicted after a seven-week trial and given a five year sentence, the maximum for perjury. The sentence was reduced to a three-year term.
On November 22, 1954, two of Remington's fellow inmates George McCoy and Lewis Cagle, Jr., attacked Remington in his cell at Lewisburg Penitentiary. According to Kathryn S. Olmsted: "William Remington attracted the attention of a group of young thugs in the cell across the hall. They despised this young man of education and privilege who had inexplicably turned on his country and become a 'damn Communist' and a 'traitor.' One morning, as Remington slept, they crept into his room and slugged him repeatedly with a brickbat. The handsome Ivy Leaguer died two days later. He was thirty-seven years old."
After the trail, Bentley took a post teaching political science at the College of the Sacred Heart in Grand Coteau in Louisiana. Harvey Matusow, recalled: "She felt like her life could be put together again." She lived in the grounds of the college and gave anti-Communist lectures in the surrounding areas and earned a reputation as a good teacher. However when she learned Remington’s murder she fell into a deep depression.
One of the other people Bentley exposed was Harry Dexter White, a senior Treasury Department official. White belonged to one of the two spy rings Bentley managed, the Washington circle. Besides White the circle included Laughlin Currie, an administrative assistant and economic affairs advisor in the Roosevelt White House, William Henry Taylor, a midlevel government economists, Duncan Lee, Office of Strategic Services (OSS later renamed the CIA) and Abe Brothman, a private sector chemist who worked on defense projects. All of them either denied her charges or pleaded the 5th Amendment. Several of them even claimed that she was paranoid and mentally unstable. However White, Currie and three other mentioned by Bentley as spies were confirmed by Whittaker Chambers seven years before in 1939.
White, she told a Senate subcommittee in 1953, had passed US currency treasury printing plates in occupied Germany to the Soviet Union, which in turn used them to print millions of dollars that were being used in war ravaged Europe. The result was that Europe black market exploded giving rise to organized crime in Allied occupied western Germany and causing serious inflation. The cost to the US was estimated to be, in 1946 value, a half a billion dollars. White, who already had heart disease, died of a heart attack a few days after his testimony before HUAC where he denied the charges.
Her personal life became increasingly out of control, she drank heavily which led to several severe car accidents and she became involved with a man who beat her severely. Her FBI handlers to worry that she was "bordering on some mental pitfall". But the bureau was amazed that while on the witness stand Bentley was calm and professional and highly respected by the prosecutors.
In 1951, she still faced with money problems. The FBI did what they could and pressured United States Service and Shipping Corporation to give Bentley a year's salary as severance pay.  Still unhappy, Bentley began a self- promotion plan, giving her story to a reporter from the New York Journal-American in which she portrayed herself as a naïve and otherwise innocent woman who has been corrupted by liberal professors at college and by Golos.
Bentley began writing her biography. The final work, Out of Bondage, was serialized in McCall's Magazine in June 1951. But instead making her money the backlash on the book added to her woes. Large groups of Americans boycotted the work because they either objected to a turn coat making a living off of selling out her country and other complained that it glorified treason. A great many of the reviews were hostile and very negative and the book sold poorly.
In January 1957, while working at the Cathedral School of St Mary in Long Island, a photograph Bentley appeared next to the review of the movie The FBI Story. Her students saw the photo, parent complained and she was fired.
She eventually managed to buy a house in Connecticut, (but had to sell it soon afterwards to pay her bills). She took a series of teaching jobs but left almost all of them under some sort of dark cloud. She was out of work until the fall of 1959 when she was hired by the Long Lane School in Middletown Connecticut, a reform school for girls.
She gradually began to suffer from depression and paranoia, convinced that the KGB was planning to kill her and make it look like an accident. She drank too much and was probably an alcoholic.  She suffered a near complete breakdown when, in the early 1950s, the IRS began to haunt her for back taxes. It was all made worse when Harvey Matusow, a communist turned informer, accused Bentley of fabricating information because “she had run out of things to testify about”  Bentley was livid. She pressed the FBI to find witnesses to back her stories up and they did. Matusow was sent to federal prison for perjury for five years.
Her private life was empty. She had no friends and rarely went out. In 1963, at age 55, she began to have constant pains in her stomach. An examination showed that she was riddled with advanced cancer.
She died from complications from the surgery on December 3, 1963, at Grace-New Haven Hospital in New Haven. Bentley was buried near her relatives in New Milford. The funeral was sparsely attended. The press paid little attention to her passing and her memory eventually slipped away into obscurity.