4 Cold War Double Agents Who Could Outfox James Bond

Photo credit: PAUL J. RICHARDS/AFP via Getty Images

The best-known spy of all time is James Bond — a fictional British secret service agent developed during the height of the Cold War. Although James Bond is a fictional spy, there were many real-life men and women who worked as double and sometimes triple agents, who obtained highly classified secret information for a country that was not even their own.

Here are the top four double agents active in the Cold War who could probably outwit James Bond.

Sean Connery on the set of James Bond
Sean Connery, who played the original James Bond on the set of Goldfinger, 1964. (Photo Credit: Bettmann/ Getty Images)

1. Oleg Penkovsky

Oleg Penjovsky was a senior Soviet military intelligence officer who played a major role in the Cuban Missile Crisis in October of 1962. Because of the quality of information he passed on, he was one of the West’s most valuable double agents.

After serving in World War II, Penkovsky was transferred from the regular Soviet army to the Soviet Army Intelligence (GRU) in 1949. After attending the Military Diplomatic Academy (1949–1953), he became an intelligence officer primarily stationed in Moscow.

By 1960, Penkovsky had become a colonel in the GRU and deputy chief of the foreign section of the State Committee for the Coordination of Scientific Research, where he was responsible for collecting scientific and technical intel on the United States, England, and other Western countries.

Oleg Penkovsky
Portrait of Oleg Penkovsky (Photo Credit: Wikimedia Commons)

However, while Penkovsky was rising through the Soviet ranks he was increasingly feeling disappointed with the Soviet political system. Because of these feelings, he offered his services to British Intelligence through the British businessman Greville M. Wynne in April of 1961. Wynne would become Penkovsky’s main channel of communication, as he often visited the USSR on “trade matters.”

Between April 1961 and October 1962, Penkovsky inflicted enormous damage on the Soviet Union. He succeeded in transferring to the West 111 Minox films with 5,500 top-secret military documents, totaling 7,650 pages, as well as revealing the identities of hundreds of Soviet agents in the West.

Notes against Oleg Penkovsky
The spying material — codes, notebooks, instructions for using them and radio casting procedure — which was used by Oleg Penkovsky. (Photo Credit: Bettmann/ Getty Images)

Penkovsky’s technical information proved to be invaluable during the Cuban Missile Crisis in 1962. Penkovsky gave the West information on the relatively weak capabilities in Soviet long-range missiles, as well as documents that highlighted that the Soviet Union was not prepared for a war in the area.

These documents had a major impact on President Kennedy’s decisions during the historical event. However, Penkovsky’s luck ran out right at the height of the Cuban Missile Crisis, as he was arrested on October 22, 1962, once the Soviets had realized that highly classified information had been leaked to the West.

On May 16, 1963, Penkovsky was executed for treason. However, his story has finally been made into a Hollywood movie. The Courier starring Benedict Cumberbatch and Merab Ninidze as Oleg Penkovsky was released in the spring of 2021.

Merab Ninidze and Benedict Cumberbatch in The Courier
Merab Nindize (left) and Benedict Cumberbatch (right) in The Courier. (Photo Credit: MovieStillsDB)

2. Aldrich (Rick) Ames

Alrich (Rick) Ames maybe would not receive the Hollywood treatment as he was an American double agent during the Cold War, trading American secrets to the Russians in return for large sums of money. He betrayed at least 12 of the best Soviet agents working for the United States during the 1980s.

Rick Ames was a lifelong employee of the CIA, first starting his career there in 1962. From 1975 to 1985, he was promoted in the CIA to increasingly sensitive posts, eventually being elevated to chief of the Soviet Branch of the Counterintelligence Division. His job was recruiting foreign agents to the CIA.

Young Aldrich Ames
Photo of a young Aldrich Ames. (Photo Credit: Jeffrey Markowitz/Sygma via Getty Images)

In 1985, Ames sold a Soviet Embassy official the names of two KGB officers secretly working for the FBI. For this betrayal, he received a paycheck of $50,000. In September of 1985, the KGB set aside $2 million for Ames to continue to spy and pass along information to the Soviet government — a deal that Ames could not refuse.

He continued spying for the KGB for nearly nine years — at first in Rome where he was stationed from 1986–1989 and then from inside CIA headquarters in Langley, Virginia.

When he returned to Washington, he began passing classified information to the Soviets in the form of “dead drops,” which were prearranged hiding places where he would leave these documents to be picked up later by KGB officers from the USSR Embassy. Because of his actions, the Soviet Union arrested dozens of agents and executed at least 10 people.

US mailbox
Ames would supposedly leave a chalk mark on a mailbox to indicate he needed to get in contact with his Soviet contacts. (Photo Credit: Jeffrey Markowitz/Sygma via Getty Images)

However, the CIA grew suspicious when many of their informants were being ordered back to Moscow. By 1990, they were certain there was a mole in the agency, but they were unsure of who it was.

Suspicion had been growing around Ames in the previous years as he was able to enjoy a lavish lifestyle that was out of his pay grade with the CIA. In 1993, the CIA began surveillance on Ames and discovered documents that linked him to the KGB. On February 24, 1994, he was arrested at his home in Arlington, Virginia.

Ames is currently serving a life sentence for his espionage during the Cold War. Although Hollywood wouldn’t make a movie on his life (the best he’s going to get is the 1998 TV movie about him), perhaps the Russian cinema would consider it.

Aldrich Ames, 1994.
Aldrich Ames after his arrest in 1994. (Photo Credit: Mark Wilson/ Getty Images)

3. Robert Hanssen

Robert Hanssen is another American who traded U.S. secrets to the Russians from 1979 to 2001. The U.S. Department of Justice has called Hanssen’s espionage “possibly the worst intelligence disaster in U.S. history.”

Hanssen became a special agent for the FBI in January 1976. In 1979, Hanssen anonymously delivered a package to the GRU. This package contained information that revealed the name of an FBI mole in the GRU. For the next two years, Hanssen gave out similar information to the GRU and made about $20,000 from the information he passed on.

Richard Hanssen Photograph
Portrait of Richard Hanssen. (Photo Credit: FBI / Getty Images )

In 1985, Hanssen officially became a spy for the KGB. He delivered documents and computer files on U.S. intelligence and counterintelligence activity both within America and the Soviet Union.

The information he passed on to the Soviet Union revealed a number of different double agents that were planed in the Soviet intelligence system. During this time he was paid more than $500,000 in cash and jewelry.

In 1991, he stopped selling secrets to the KGB, partly because of the collapse of the Soviet Union, but also because the FBI believed there to be a mole in their midsts.

ID and Business Card Information of Richard Hanssen
The identification and business card of former FBI agent Robert Hanssen are seen inside a display case at the FBI Academy in Quantico, Virginia. (Photo credit: PAUL J. RICHARDS/AFP via Getty Images)

However, when Hanssen became chief of the FBI’s National Security Threat List Unit in 1992, he once again approached the GRU, whom he had not been in contact with for the previous 10 months.

However, the official he approached did not recognize him, and the Russians filed an official protest with the State Department, believing Hanssen to be a triple agent. This investigation was dropped, and by 1995, Hanssen had been reassigned as a liaison between the FBI and the Department of State’s Office of Foreign Missions, where he worked almost completely unsupervised.

Courtroom drawing of Richard Hanssen
A courtroom drawing done during Richard Hanssen’s 2001 trial. (Photo credit: MANNY CENETA/AFP via Getty Images)

In 1999, Hanssen once again renewed contact with the SVR (which replaced the KGB after the collapse of the Soviet Union). Eventually, in February 2001, he was arrested while he was dropping American secret information off at a designated dead drop.

He pleaded guilty for all of his espionage activities done for Moscow since 1979, but was able to avoid the death penalty by agreeing to participate in extensive debriefing with government agents. He is, however, serving a life sentence in prison without the chance of parole.

4. Dmitri Polyakov

Dimitri Polyakov was a Russian double agent who became one of America’s most valuable spies during the Cold War. For nearly 25 years, Polyakov served as a trusted resource for the United States passing on Soviet Secrets until he was abruptly called back to Moscow in 1980.

CIA agents weren’t sure what had happened to him and began to wonder if Polyakov was a double agent turned triple agent, feeding the United States false tips and misinformation.

Cold War double agent Dmitri Polyakov
Dmitri Polyakov, Public Domain

Polyakov was a decorated artillery officer in the Second World War, recognized for his bravery. After the war, he was recruited by the GRU. As he rose through the ranks of the GRU, he became increasingly disillusioned with Communist parties and sought to undermine the USSR from within.

At the height of the Cold War, the GRU had agents stationed all over the world to learn everything possible about Americans and American life. During Polyakov’s second assignment to New York from 1959 to 1961, he approached FBI counterintelligence agents and offered up his services as an informant.

For the next 25 years, Polyakov was America’s most important informant. He passed along important documents ranging from Soviet intelligence related to the Vietnam War to monthly Soviet military strategy reports to lists of Soviet military technology that the Soviets wanted to obtain from the West.

Throughout his time as a double agent for the United States, he passed along enough secret Soviet information to fill 25 deep file drawers at CIA headquarters.

Polyakov risked his life to pass along Soviet information to America. In Moscow, he stole the supplies directly from the GRU stockroom and passed along information in hollowed-out rocks that were picked up by American officials.

To signal to his handlers, he would take the tram past the U.S. embassy in Moscow and activate a miniature “burst” transmitter hidden in his pocket. During trips abroad, he passed along information directly to U.S. agents through his fishing rod, which had a secret compartment for information.

A view of the US Embassy in Russia in Novinsky Boulevard
U.S. embassy in Moscow. (Photo Credit: Anton Novoderezhkin\TASS via Getty Images)

His information helped the U.S. in both diplomacy and technological innovations during the Cold War. For instance, he provided the United States with evidence of a growing rift between the Soviet Union and China. This information and the knowledge of these tensions played a crucial role in Richard Nixon’s decision to open diplomatic relations with China in 1972.

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In 1980, Polyakov was suddenly called back to Moscow where he suddenly retired, cut all ties with American intelligence, and disappeared entirely. This unsettled the American intelligence community. Some insisted he had in actuality retired, while others argued he had been executed for his espionage activities.

However, it came to light that Polyakov had been arrested by the KGB in 1986 and had been sentenced to death for treason and executed in 1988. For America, Polyakov was a hero, but for Russia, he was a traitor.