Political intrigue and espionage are nothing new. But in the days before high-tech spy gear, the work of spies looked far different than it does today. The lives of 15th- and 16th-century spies were filled with intrigue, backstabbing, and bizarre machinations, though, because the human race has not changed all that much.

10 William Parry

During the reign of Elizabeth I, being a Catholic was a dangerous thing. Many Catholics fled to the continent, and William Parry was sent to spy on them. He sent regular reports back to London, telling his queen who was harmless and who might be plotting against her from the relative safety of Paris.

His troubles began in 1580 when he was put on trial for allegedly assaulting a moneylender. The queen pardoned him from execution, but he was unable to sustain the lifestyle to which he had become accustomed. By 1583, he had decided to play both sides and wrote to a Roman cardinal of his intentions to serve the Catholic Church.

It was not a wise life choice. In 1585, Parry was hanged, drawn, and quartered for his part in a plot to kill the queen.

9 Isabella Hoppringle

Isabella Hoppringle was the 16th-century prioress of the convent at Coldstream, which sat on the border between England and Scotland. At the same time that she relied on the Scots to keep her convent safe, she was writing letters to agents of Henry VIII reporting on the Scottish army.

Her favored position with Scotland’s queen, Margaret, meant that Isabella was often in Glasgow and Stirling and that she was witness to troops being mustered and equipped. In 1523, the Lords of Council decided that the punishment for talking to the English would be the death penalty, and word had gotten out about the prioress’s messages. It was only when Margaret interceded that the lords called off an attack on the convent and made it clear that Isabella was safe only for as long as she was loyal.

Isabella—and her successor, Janet Hoppringle—continued their work for the English.

8 George Eliot

There were few things that got the attention of the Tudor monarchs faster than writing a book called Ten Reasons (to be a Catholic), which Jesuit priest Edmund Campion did in 1581.

The Earl of Leicester sent George Eliot, a known con artist, after the priest. Eliot was desperate to avoid a sentence for murder when he agreed to spy on the priest, collect the needed evidence, and ultimately arrest him. Eliot ingratiated himself into an Oxfordshire parish to keep an eye on the rogue priest, finally fetching the local magistrate to oversee the arrests.

Campion managed to hide until the owner of the house at which he was staying requested that he give a sermon in the middle of the night. He finished the sermon, but the members of the household had gathered to hear it and woke those who were looking for them. The priest was ultimately hanged, drawn, and quartered.

7 Bertrandon de la Broquiere

In 1432, Frenchman Bertrandon de la Broquiere embarked on a year-long espionage mission to Palestine for the Duke of Burgundy and was tasked with gathering any military information that would assist in mounting a Crusade against the Turks.

Bertrandon wrote that the Turks were disciplined but lacking in arms, and in retrospect, it seems as though he erred on the side of optimism. He also wrote of the helpful nature of those who cared for him while he was sick and painted many of the people he met as selfless humanitarians in spite of their different religions.

His story was an incredible one, filled with near misses, traveling in disguise, and even joining a Muslim caravan to Bursa. In the end, he optimistically reported back in favor of a victorious Crusade for the Christians, but no Crusade happened as a result of his intel.

6 Petrus Alamire

Petrus Alamire is not his real name. The pun on musical notes (A-la-mi-re) was given to a spy working for Henry VIII—a spy who also made a career as a musician and scribe.

Alamire was Bavarian, and his workshop produced some of the most beautifully illuminated manuscripts of the early 16th century. They were often gifted to members of the royal courts of Europe, who would then send for the mastermind who had created them. With unprecedented access to royal houses, Alamire collected intel that he passed on to other royals whom he wanted to keep indebted to him.

Alamire supplied a massive amount of information to Henry VIII, his biggest client, on the movement of Richard de la Pole, the last Yorkist with any claim to the throne. But Alamire was also passing information to Pole and never returned to the English court after his betrayal was uncovered.

5 Francis Walsingham

Francis Walsingham, well traveled and fluent in Italian and French, was the spymaster for Elizabeth I for 22 years. Walsingham had more than 50 agents working in Turkey and other countries across Europe, but Elizabeth’s biggest threat was not far from home.

Walsingham and his spies spent much of their careers gathering evidence of plots to overthrow Elizabeth and replace her with Mary, Queen of Scots. Even after the conspirators in the so-called Babington plot were hanged, drawn, and quartered, Elizabeth still refused to sign Mary’s death warrant.

She finally signed on February 1, 1587. Walsingham oversaw Mary’s execution, the burning of her clothing, and the encasing of her body in lead (to ensure there would be no relics circulating). He also established a school for the spies under his control, where they were taught things like reading and writing coded messages.

4 Antony Standen

Antony Standen (aka “Pompeo Pellegrini”) was one of Francis Walsingham’s many spies. Based in Italy, Standen reported on the movements of the Spanish Armada, although he was living in exile because of his Catholic beliefs.

Moving from England to Scotland to France and finally landing in Tuscany, Standen was fortunate enough to get friendly with Tuscany’s ambassador to Spain. In 1587, Standen was officially on Walsingham’s payroll and began passing him regular information that ultimately allowed Sir Francis Drake to move on the Spanish fleet while at Cadiz.

Standen’s information helped to cripple the Spanish fleet. But by the time he finally returned to England in 1593, Walsingham was dead and Standen’s service was overlooked. Later, he attempted to help the Catholic Church regain a foothold in England and found himself in the Tower of London.

3 William Herle

In 1571, Philip II of Spain and Pope Pius V were in league with a Florentine banker named Roberto Ridolfi in an attempt to depose Elizabeth in favor of Mary. Ridolfi’s messenger, Charles Bailly, was arrested and sent to Marshalsea Prison. There, he met another prisoner, William Herle, who had been serving as a spy for Elizabeth I since around 1559.

Herle had been arrested for piracy in 1570 (and 1567) and was planted in Marshalsea to extract information from Bailly. After Bailly was put in isolation, Herle stepped in as a questionable, shady character who could get certain things accomplished.

Bailly began passing letters to his counterparts on the outside through Herle, who obligingly passed them along after he had copied them for his own employers. The unraveling of the plot changed the dynamic of the political spectrum in England and abroad.

2 William Stafford

To try to convince Elizabeth I to sign Mary’s death warrant, Francis Walsingham used all sorts of methods, including devising plots against Elizabeth’s life.

William Stafford, the younger brother of England’s French ambassador, was completely Walsingham’s man. In 1587, Stafford came forward with a bizarre assassination plot that he had uncovered. France’s ambassador, Chateauneuf, and his secretary had reportedly recruited Stafford to plant gunpowder under the queen’s bed to kill her.

Eventually, the French ambassador and his secretary were cleared of the accusations, and Walsingham concluded that Stafford had been using his position to extort money. Even so, Stafford remained in Walsingham’s service. It remained unclear if Walsingham was behind the whole setup or if Stafford had decided to give Elizabeth another reason to be wary of assassination attempts.

1 Madame de Sauve And The Flying Squadron

According to the memoirs of Pierre de Bourdeille, Catherine de’ Medici kept 86 (or 300) ladies-in-waiting to lure the men of the court into their beds to extract top secret information. Catherine then used the information from her “Flying Squadron” to secure her own position and that of her family.

The most notorious of these women was Charlotte de Beaune, Madame de Sauve. Catherine’s daughter, Marguerite, wrote extensively about Charlotte’s wooing of both Marguerite’s husband and her brother. Marguerite claimed that her mother had pitted the two men against each other with a maneuvering temptress in the middle, but the truth of Catherine’s manipulations of the men and women in her court is rather cloudy.

It probably won’t come as a surprise that script writers, directors, producers and even actors take some creative liberties recreating real life scenarios in the name of art (or rather, entertainment).

On this list Tony and Jonna Mendez, former CIA agents and Chiefs of Disguise, Jack Barsky, former KGB Agent turned American Intelligence, Peter Earnest, the founding executive director of the International Spy Museum and 35 year CIA veteran and William Colby, former Director of Central Intelligence, review some popular movie scenes that are more art than accurate.

10 Nazi Spies and Their Espionage Plots In America

10 Quick change

In this scene from Mission Impossible III, unlikely hero, Ethan Hawkes, uses the quick change methodology to disguise his identity. And he does it well, seamlessly transitioning into a cassock and posing as a priest.

According to Jonna Mendez, however, disguising an agent as a religious figure, media or peace corps is off limits. These vulnerable vocations need to be protected from the scrutiny they might be subjected to if they were suspected of harboring agents.

Believe it or not, one of the movie quick changes Jonna approves of happens in Teenage Mutant Ninja Turtles when April goes from librarian-type to naughty school girl while moving through a crowd; the bigger the crowd the more forgiving they are and the easier it is to change your appearance with small tweaks and layering.^[1]

9 Gadgets

If there’s one thing we all look forward to when a James Bond film is released it’s to see the crazy and clever gadgets Q has dreamed up in his workshop. The clip above shows the “gadget room” in the movie Kingsman and according to Dr Vince Houghton, most of them are either fictional or behind the times.

During his career as an intelligence officer, Jack Barsky mostly made use of everyday ordinary items. He recalls passing messages in film cannisters and finding a passport and money hidden in a rusty oil can.

Pens are a popular spy movie gadget and although, in real life, they aren’t necessarily used as weapons, Jonna Mendez does remember instances where a pen was used to secrete a camera and even an L-pill (lethal pill used by agents who are captured and choose to commit suicide rather than be subjected to torture). And yes, sadly, L-pills are entirely real and have been used in several instances.^[2]

8 What not to wear

When you think of the Matrix costumes, most likely you think leather and PVC. Who could forget Neo’s full-length leather jacket or Trinity’s PVC catsuit?

What do our real-life spies think of their outfits, though?

“I’ve never met a KGB officer in a leather jacket,” Jack Barsky, former KGB. “The whole point of being a spy is that you don’t want to look like one.”

To William Colby, former Director of Central Intelligence or America’s top spy, a real spy has to be ”a gray man who has a hard time catching the eye of a waiter in a restaurant.”

And Jonna Mendez agrees. When reviewing a clip from Avengers 1998 in which Uma Thurman sports yet another PVC catsuit, Jonna asks why they are so popular in movies… And then answers her own question with “because women look so good in them. At least Hollywood women do.” Most real agents, men and women, she continues, would not be caught dead in them.^[3]

7 Masks

The Mission Impossible franchise is well-known for its mind blowing masks – which, according to our experts, are a result of CGI and clever camera angles rather than latex. Because although real life masks can change a lot about a person’s face including gender and ethnicity, not even the Chief of Disguise at the CIA can guarantee animation. Masks are also additive; this means you can, for example, add bulk to a small nose, but you can’t hide a big nose with a small one.

During his tenure at the CIA, Tony Mendez made masks and disguises to allow CIA officers to slip past the watchful eyes of the KGB, meet foreign agents and collect secrets cached in dead drops without being detected by counterspies. He even helped a black CIA officer meet an Asian diplomat in a city under martial law and Soviet surveillance. He asked a Hollywood makeup artist he knew to send him some masks and transformed the case officer and the envoy into Caucasian gentlemen. They met undeterred by roadblocks and checkpoints.^[4]

6 Self-defense

When reviewing this clip from Iron Man 2, Jack Barsky remarks that although he was greatly impressed with the acting, the Black Widow’s self-defense techniques were considerably more aggressive than anything he was ever trained in. Which says a lot considering he used to work for the KGB!

Jack continues by explaining that although agents are trained in self-defense in case they find themselves in a dark alley confronted by an unsavory character who wishes to harm them (which seems likely due to the nature of the job), most agents are not as proficient in hand to hand combat as Hollywood would have you believe. Their purpose, after all, is to fly under the radar and gather intelligence rather than drawing attention to themselves by starting a fist fight.^[5]

Top 10 Famous Spies

5 Cultural customs

In this scene from Inglourious Basterds, the British soldier gives himself away by counting incorrectly on his hand. Europeans start with the thumb. Within a split second the German soldier realizes the man is European.

Jonna Mendez remarks that it is incumbent on the spy to learn not only the language but also the customs, mannerisms and procedures of the country/area within which they operate. “And sometimes,” she says, “once you’ve outed yourself there is no way out and you have to live with the consequences.”^[6]

4 Crowds

Following on from the example above, blending into the crowd is the safest way for a spy to “disappear”. But even doing little things differently to those around you can help those on the lookout spot you. During this scene from Casino Royale, the man in the crowd is called out for having his hand to his ear, touching his earpiece.

Jonna Mendez’ team at the CIA came up with a no hands/body harness-type system to prevent exactly this. She also made it her life’s work to understand how fashion influences people’s conclusion about those around them in order to help her colleagues and other agents “blend in”.

Uniforms are also often used to help agents blend in, and although the CIA doesn’t have stores of uniforms, they can arrange pretty much anything.^[7]

3 Documents

We all know this scene from Bourne Identity or any other spy movie – identity documents stored in a safe place just waiting for the right person to find and use them.

In reality, though, these kinds of documents are far too valuable to leave lying around just “in case” someone needs them. According to our experts, aliases are specifically created for specific agents and are very closely controlled by intelligence agencies. Putting together alternate identities is painstaking and meticulous.

Together with identity documents and passports, agents are also provided with pocket litter—those little pieces of paper, pictures and random stuffs we all collect in our purses or billfolds. They work hand in hand with the all-important cover story, which is also the next entry.^[8]

2 Cover story

“Spies are people too,” says Jack Barsky. To help them do their jobs, they need believable back stories. Something they can identify with and talk about spontaneously and believably, either as an individual or as a group.

Argo is the real-life story of how Tony Mendez helped to create the escape plan, the false identities and the brilliant disguises that let six Americans escape revolutionary Tehran, where they had been held hostage, in 1980.

The movie, starring Ben Affleck as Tony Mendez, won the Oscar for Best Picture in 2013 and both Tony and Jonna Mendez were heavily involved in the making of it. The cover story, a Hollywood location scouting team, had to be something that Tony and his team could easily talk about.^[9]

1 Sexpionage

The movie Red Sparrow is based upon the book of the same name by Jason Matthews, a former CIA operative, and explores the idea of the seduction methodology which is mostly associated with Germans (males called Romeos) and Russians (females called Swallows).

All of our experts agree that the art of seduction does play a role in espionage today and that it’s not that far-fetched to think the Americans use it too.

“I think sexpionage, that’s reality. I’d be surprised if there are any major intelligence services that aren’t in some way recruiting women to do dirty work,” says Jack Barsky.

But, unlike the one in the movie, it’s highly unlikely the CIA has a school of seduction.

At least, that’s what Jonna Mendez says…^[10]

10 Rogue Spies In History

Spies. Secret agents. Experts of espionage. These exciting and elusive characters have been sparking intrigue in the hearts of us average citizens since James Bond appeared on the big screen in a cloud of mystery and a jet-black tuxedo. Stories of heroic feats accomplished by these agents of intelligence spread like wildfire, and nothing excites us more than a dangerous mission or a daring escape.

Unfortunately, modern spy mania has been focused primarily on the furtive actions of male spies, leaving some incredibly fierce female spies high and dry. Well, it’s time for these hard-core women to enter the spotlight. Here are 10 of the most notorious female spies in history.

10 Belle Boyd

“Southern Belle” Boyd would not have considered herself a spy. However, she was essential to many of the South’s victories during the US Civil War. She gathered information about Union forces through covert means and passed it along to aid the Confederacy.

It was 1861, and the war was just beginning. At the time, Boyd was a resident of Martinsburg, Virginia. She was eager to join the efforts of the South against the North, so she got involved with the Confederacy’s fundraising efforts. However, she knew that she could do more. When Union soldiers occupied her town in 1861, she saw her chance.

Boyd took advantage of her status and conversational abilities to become close to some of the Union soldiers. Covertly, she gathered as much information as she could while maintaining her seemingly innocent persona. She would then relay this information to Confederate officers, even if it meant sneaking through enemy lines to tell General Stonewall Jackson about the opposition’s plan to burn the town’s bridges.^[1]

However, recon is not all that Belle was famous for. One day, during the Union occupation of Martinsburg, a Union soldier attempted to raise a flag over the home of Boyd and her mother. After Boyd denied the men access to her home, one rowdy soldier attempted to force his way into the residence. He did not make it very far. Belle pulled out a gun and shot the man dead. Pretty hard-core, right?

9 Melita Norwood

Melita Norwood was sweet and seemingly innocuous. A secretary at the British Non-Ferrous Metals Research Association (aka “the BNF”) in the 1930s, she was responsible for things such as organizing appointments and handling files. Nothing too serious.

Wondering where the spy part comes in? Here it is.

The BNF was actually a cover organization for the Tube Alloys project—Britain’s nuclear weapons program. Though she lived and worked in Britain, Norwood was a Russian at heart, identifying with the Communist ideologies of the Soviet government. This sympathetic attitude eventually got her involved in the KGB. When they gave her an opportunity to help them out, she accepted.

Acting under the code name “Hola,” Norwood was directed to stick around the BNF facilities after closing and covertly remove files from the safes. She would then copy these files and give them to KGB handlers at her house (unknown to her husband). Much of this information was used to advance Russian nuclear technology.^[2]

Following the discovery of her espionage efforts years later, Norwood was asked to reveal the identities of her Russian accomplices. She refused, claiming memory loss as the reason that she could not recall any of their names.

8 Christine Granville

Christine Granville was a beauty queen-turned-spy. Prior to her involvement in World War II, she was a model. At the start of the war, Granville became a messenger in Nazi-occupied countries in Europe. Her job was to carry messages through Poland, delivering them to various Allied forces without detection.

This proved to be a dangerous responsibility. Granville became famous for rescuing soldiers from execution, escaping gunfire, parachuting, sewing knives into the hems of her skirts, fabricating elaborate stories to get out of tight spots, and charming guards and guard dogs alike. One story tells of how she escaped Nazi police forces by biting her tongue and pretending she was dying of tuberculosis.

Granville also used her beauty as an asset, charming various lovers throughout her lengthy career in espionage. She quickly found the eyes of Winston Churchill, who would later make her a member of his personal espionage unit under the code name “Willing” (a hint at Granville’s sexy and exciting personality).

It is even rumored that Granville was the inspiration behind the female lead in the James Bond novel Casino Royale. Alas, Christine was murdered by a crazy ex-lover in London toward the end of her career.^[3]

7 Noor Inayat Khan

The first female radio operator and the first British-Indian spy. Yes, you read that right. Noor Inayat Khan was a groundbreaking woman. She was hired by the “Prosper” resistance movement in Paris during World War II under the code name “Madeleine.”

The movement’s leaders initially questioned whether Khan could get the job done, but their fears were quickly allayed. While many other members of the resistance were arrested, Khan avoided capture time and time again, frequently relocating and remaining in constant communication with London.

Unfortunately, Khan’s long and successful career as a spy ended when she was exposed by a local Frenchwoman who discovered her identity. Khan was quickly arrested by the Gestapo, who used her personal documents of secret signals and codes to trick London into sending new agents. The Gestapo then captured these agents as well.^[4]

After an attempted escape, Khan was placed in solitary confinement and tortured for information. However, she refused to reveal anything, eventually dying at the hands of the Nazi police. What a woman.

6 Mata Hari

Mata Hari was a spy disguised as an exotic Asian dancer. Cool, right?

She was famous for touring Europe, performing a series of strip shows in which she would make up elaborate stories about her youth. To some audiences, she was born in a sacred Indian temple. To others, she was taught to dance by Indian priestesses.

Mata Hari’s seductive nature and boisterous personality gave her the perfect cover for espionage. Thus, at the outbreak of World War I, she became a messenger and courier for the Allies’ opposition.

Mata Hari was famous for making lovers out of high-ranking military officials from different countries, allegedly coaxing them to reveal details about weapons and strikes. She would relay these details to the opposition, resulting in the deaths of thousands of people. However, some people have speculated in the 21st century that her effectiveness as a spy was overstated. Or that she may not have been a spy at all.

During her lifetime, Mata Hari was also suspected of being a double agent. But before her status could be revealed, she was discovered by the Allies and sentenced to death. A French firing squad killed her outside Paris in 1917—a dramatic end to a dramatic career.^[5]

5 Virginia Hall

Virginia Hall, an American spy with the British Special Operations Executive, was as tough as they come. She also worked for the American Office of Strategic Services during World War II and later for the CIA.

While on a hunting trip in Turkey, Hall lost her leg to a gun accident. After her leg was amputated, she named its wooden replacement “Cuthbert.”

She led networks of agents in various tasks throughout her career, rescued prisoners of war, and recruited hundreds of spies to work against the Nazis (who referred to her as the “limping lady”). Using her wit to remain one step ahead of the Nazis at all times, Hall served as an infuriating roadblock to many of their operations.^[6]

Hall became the only civilian woman to receive the Distinguished Service Cross.

4 Nancy Wake

Nancy Wake was not your average journalist. After a childhood in poverty (mostly in Australia), she worked as a journalist and then rose to become a hostess in high-society France by marrying a wealthy French industrialist. Wake saw the destruction and abuse caused by the Nazis firsthand, and she longed to do something about it.

She joined the French Resistance at the beginning of World War II, quickly becoming a heroine of the movement. Her successes included establishing communication between the British military and the French Resistance, saving Allied lives by secretly escorting them through France to Spain, and collecting and storing weapons for the advance of the Allies.

She was often credited with executing German spies, and it is even rumored that Wake once killed a German soldier with her bare hands. These daring feats gained her the nickname the “White Mouse.” For try as they might, the Nazis could never get their hands on her.^[7]

3 Anna Chapman

Three words: Crazy. Russian. Spy.

Anna Chapman is one of the more famous modern spies. Part of a spy ring devoted to Russia, she spent years in the United States while attempting to glean information of any kind that might be useful to the Russian government.

She was popularly accused of attempting to seduce the NSA whistle-blower Edward Snowden in an effort to keep him in Russia for questioning. Chapman hoped to marry him, lock him in Russia, and snatch American secrets from his brain. Intense, right?

But get this: Chapman was also a famous model. She would often use her status to learn covert information and gain access to government secrets. In 2010, she was finally arrested in New York City and deported after pleading guilty to conspiracy charges.^[8]

A model who is also a spy? A spy who is also a model? Seems legit.

2 Josephine Baker

Josephine Baker is just straight-up cool. Most famous for being both a singer and a dancer, she became wildly popular in the 1920s. Baker was into all things exotic—performing songs, dances, and even comedic skits wearing nothing but a feather skirt. As you might assume, she quickly became one of Europe’s most popular and highly paid performers, eventually even going on Broadway.

However, most people don’t know that Baker was also a spy.^[9] She worked for the French Resistance during World War II, smuggling messages by hiding them in her sheet music and sometimes even in her underwear. For her work, Baker received French military honors.

1 Ana Montes

Ana Montes, a famous spy for the Cuban government, began working for the US with the Defense Intelligence Agency in 1985. She was often referred to as an expert on all things Cuba. As she openly disagreed with US foreign policy, it was not long before Cuban officials reached out to Montes and persuaded her to do some work for them.

She was the perfect woman for the job. Not only did Montes have access to government secrets (specifically the Afghanistan invasion), she also possessed a photographic memory. This made it easy for her to memorize documents and encrypted files and recite them to her handlers later.

When her colleagues grew suspicious, Montes agreed to take a polygraph test to prove her allegiance to the US. She passed. She would go on working covertly for the Cuban government for a few more years until the FBI was able to build up a substantial case against her. In 2002, she pleaded guilty to spying and received a 25-year prison sentence.^[10] Her tentative release date is 2023.

Female spy enthusiast.

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.