While we have no research to back this up, espionage would have easily been one of the most dangerous occupations one could have chosen during the Cold War. Regardless, countless espionage operatives worked on both sides of the Iron Curtain, driven by ideology, cash, or a bit of both. These notable Cold War spies regularly took up high-stakes, Hollywood-esque jobs that eventually led to their imprisonment and execution.
10. Raymond Mawby
Raymond Mawby was a British Member of Parliament who died in 1990, earlier working as an assistant paymaster general and junior minister. According to a BBC investigation, this was the time when he was also working as a spy for the Czechoslovakian security service for over a decade, from 1960 to 1971.
Throughout his tenure as an operative, Mawby supplied sensitive political information to communist spies during Czechoslovakia’s communist era, including a hand-drawn floor plan of the prime minister’s Commons office, details about parliamentary committees, and a confidential parliamentary investigation into another Conservative Party politician.
Allegedly operating under the codename ‘Laval’, Mawby’s relationship with the Czech spy service began in 1960, when he was approached at a cocktail party and convinced to provide political gossip in exchange for cash payments – exactly £100 for every exchange of information he provided. He continued to assist the foreign intelligence agency even after his promotion to junior minister in 1963. As per the report, this relationship came to an end in November, 1971.
9. Micha? Goleniewski
Micha? Goleniewski was a high-ranking officer in Poland’s intelligence service. He was also a KGB operative, though he’d later turn into one of the West’s most valuable double agents during the Cold War.
Goleniewski began his political career by collaborating with the Nazis during the Second World War. He would soon become a high-ranking counterintelligence officer for the Polish intelligence, followed by his stint as a KGB operative supplying information about the Polish intelligence to his handlers back in the Soviet Union.
In April 1958, Goleniewski voluntarily defected to the United States, and for the next 33 months or so, he’d smuggle a large amount of top-secret Soviet and Warsaw bloc military and espionage secrets to the West, including details that exposed 1,693 communists working across western intelligence and government departments.
8. Otto von Bolschwing
Otto von Bolschwing was an early recruit to the Nazi Party, rising through its ranks to become Heinrich Himmler’s deputy in the Reich Main Security Office, where he mainly focused on the supposed ‘Jewish problem’. In 1937, he designed terror tactics to drive Jews out of Germany and rob them as they left. Bolschwing’s radicalism led him to support the anti-Semitic Iron Guard in Romania, even attempting a coup against the German-allied government. He continued to climb the Nazi hierarchy even after his detention, as he was soon hired as Adolf Eichmann’s deputy and oversaw the logistics of the Holocaust.
After the war, Bolschwing escaped to American-occupied Austria and worked with exiled Iron Guard members, before he was recruited by the CIA under the code name ‘Agent Unrest’. His Nazi background was overlooked due to his espionage value against the Soviet Union. Eventually, Bolschwing would work as a CIA asset with valuable connections in Austria and Eastern Europe, supporting the larger US intelligence effort during the Cold War until 1953.
7. Gunvor Galtung Haavik
Gunvor Galtung Haavik was a Norwegian Foreign Ministry clerk and an agent of the Soviet Union for over 27 years. Her career began during the Second World War, when she worked as a nurse and interpreter for Soviet prisoners held by the Nazis, where she fell in love with a Russian prisoner of war. When the soldier’s safety was threatened by the Nazis, the KGB promised protection in exchange for Haavik’s cooperation. By the time Norway joined NATO in 1949, she had already signed a spy contract with the Soviets for future operations
Over time, there were suspicions that Soviet diplomats were too well-informed about Norway’s classified positions on various matters, especially regarding its European Community membership. Haavik was eventually identified by Norwegian counterintelligence during her meeting with a KGB operative, A.K. Printsipalov, leading to her arrest in 1977. While she confessed to her espionage activities against Norway and other western nations, Haavik died before her trial due to heart failure.
6. Oleg Vladimirovich Penkovsky
Often called one of the West’s most valuable double agents during the Cold War, Oleg Vladimirovich Penkovsky began his espionage career in the Soviet Red Army in 1937, later working as an artillery officer against the Nazi invasion during the Second World War. By 1949, he had moved to the Soviet Army Intelligence Directorate (GRU) and attended the Military Diplomatic Academy, before being hired as an intelligence officer in Moscow. By 1960, he had risen to the rank of colonel in the GRU.
By April 1961, however, Penkovsky had turned against the Soviet system, offering his services to British intelligence through a British businessman named Greville M. Wynne. Over the course of the next year and a half, he secretly provided British and US intelligence agencies with over 5,000 photographs of classified military, political, and economic documents from the Soviet union. The information he supplied decisively revealed the limited long-range missile capabilities of the Soviet Army during the Cuban missile crisis of 1962.
5. Elizabeth Bentley
Born in Connecticut, Elizabeth Bentley was well-educated, with degrees in the humanities at Vassar College and Columbia University. In 1935, she joined the American League against War and Fascism due to her exposure to fascism in Italy, followed by her relatively-brief stint as a member of the US Communist Party.
Bentley’s espionage career began when she was recruited by a coworker, Juliet Stuart Poyntz, at the Italian Information Library. She collected information on fascist activity and later worked as a secretary with Juliet Stuart Poyntz – a Russian-born American involved in espionage through a Soviet-backed travel agency.
When Golos died in 1943, however, Bentley grew disillusioned with the Communist Party, resulting in her turning to the FBI as a double agent. Bentley’s testimonies would eventually lead to the conviction of 11 Communist party leaders.
4. Adolf Tolkachev
Adolf Tolkachev was a Soviet engineer who turned into one of the most important CIA assets during the Cold War. His work began in 1978 in Moscow, and involved leaking top-secret information about Soviet radar technology, avionics, and cruise missiles. He soon became known as the ‘Billion Dollar Spy’ for saving the United States an estimated $2 billion in weapons research and development costs.
Operating right under the eyes of the KGB, Tolkachev engaged in 21 meetings with CIA officers on the streets of Moscow throughout his two-decades-long career. A big part of his job was smuggling documents out of his military laboratory – usually concealed within his overcoat – and photographing them in secret. According to declassified documents, Tolkachev was motivated to work against the Soviet Union due to his family’s plight during Stalin’s Great Terror era.
3. Hede Massing
Hede Massing was born in Vienna in 1900 to a Polish father and Austrian mother. She joined the Communist Party around 1920 and married Gerhart Eisler, a prominent member of the German Communist Party. Between 1933 and 1937, Massing served as a Soviet espionage agent in the United States. In her later years, however, she went against the Soviet Union – particularly the communist movement under Stalin – and turned into a staunch anti-communist.
In 1949, Hede Massing played an important role in the Alger Hiss espionage trial, testifying that Hiss had been working with the Soviet Union against the interests of the United States. Although her testimony had some inconsistencies, it directly contributed to Hiss’s conviction for perjury in 1950.
2. Philip Agee
Born in 1935, Philip Agee was a former CIA officer-turned-whistleblower. Agee’s transformation came during a chaotic period in American history, marked by the Vietnam War, Watergate scandal, and a growing popular disillusionment with US foreign policy. He finally left the CIA in 1969 after twelve years of service, primarily motivated by the agency’s perceived role in undermining democracy to serve American interests abroad.
In 1975, Agee published his book Inside the Company: CIA Diary – an unprecedented work that revealed the extent of CIA’s covert operations in Latin America. Unlike other whistleblowers before him, Agee exposed the identities of CIA officers, agents, and assets working in the field. Despite criticism, Agee continued to undermine the CIA operations and US policies he deemed objectionable.
1. Aleksandr Dmitrievich Ogorodnik
Born in 1939, Aleksandr Dmitrievich Ogorodnik was a Soviet diplomat-turned-CIA spy at the height of the Cold War. While he was initially thought to be an unlikely candidate for western espionage, Ogorodnik was eventually recruited by the Colombian intelligence agency and the CIA, operating under the codename TRIGON, or Trianon.
Ogorodnik worked as a valuable spy due to his high level of access to secret diplomatic cables within the Soviet Foreign Ministry in Moscow, which he photographed and transmitted to the CIA. He even requested a suicide pill, or the L-pill, as a contingency plan. While we don’t know exactly why he turned into a double agent, it might have had something to do with his continued financial problems, or his deep-seated discontent for the Soviet bureaucratic system.
Ogorodnik’s career and life came to an end when he was apprehended by the KGB in Moscow. Instead of capture, he opted for the L-pill and ended his life, leaving many unanswered questions about the extent of his espionage and counter-espionage activities. Till today, Ogorodnik remains one of the most important double agents of the Cold War, particularly due to his involvement with coded numbers transmissions called numbers stations.