Wherever there are rivalries, there are double agents. These rivalries can be between corporate houses, drug cartels, countries or even civilizations. For one side, double agents become heroes, but for the other side they are the worst type of traitors… rats!
Compared to any other job, double agents work in the most dangerous circumstances. This danger is what makes this job so thrilling, and so high paying. Yet not every double agent is after money. There are many who do it for the love of their country, or ideological reasons.
The character of a double agent is so exciting that it is often used in literature. However, in literature, money does not drive the character. Instead, it’s typically passion. One of the most brilliant double agent characters from modern literature is Severus Snape of the Harry Potter series. Author J.K. Rowling portrayed the perfect double agent. He remains in high risk and is often mistrusted. He’s lonely, and he’s devoted. He’s cunning, and he is complicated. But above all else, he gets the job done. Almost all brilliant double agents have these characteristics in common.
The history of double agents goes all the way back to ancient China, but their use rose to its highest level during WWII and the subsequent Cold War. Even today, double agents are playing a vital role in the war against terror, often trained by the CIA.
10. Dusan Popov
Charmed his way through peak ranks of Abwehr. Spied for full five years of WWII, did not get caught. Received Order of the British Empire.
Dusan Popov, codename “Tricycle,” was a real life James Bond: handsome, cultured, and confident. He was a very successful lawyer in Yugoslavia. Popov was popular among the ladies. They loved him, and he loved them back. He was a friend of Ian Fleming, so many people believe that he is one of the real life inspirations for Bond.
Despite speaking fluent German and having many German friends, he secretly hated Hitler. So when the Germans approached him to become a double agent for them, Popov immediately contacted MI6 and offered his services.
Obviously, British intelligence did not trust him immediately, but when he told them the name of the German officer (Johann Jebsen) who contacted him he won their trust, because the German officer was a double agent working for MI6. The British started to provide him carefully devised information, which he delivered to Abwehr and received promotions. In a few months, Germans started to consider him a valuable asset.
Tricycle became one of the key agents of British intelligence. He communicated via invisible ink, microdot codes, wireless, and various other techniques. He continued to work even when Germans caught his handler Jebsen.
Popov was sent to the USA in 1941 by the Germans. They gave him a three-page questionnaire about US defense systems. His mission was to find answers to all of those questions. Out of those three pages, one whole page consisted of detailed questions about the defense systems of Pearl Harbor. Popov said in a televised interview that he had contacted FBI chief J. Edgar Hoover and informed him about German interest in the Hawaiian island, but Hoover didn’t report it to his superiors. Why? That is still a mystery. Maybe the German-speaking, Yugoslavian playboy did not seem trustworthy.
9. Elizabeth Van Lew
Helped prisoners to escape Libby Prison. Commanded a spy ring. First person to fly Stars and Stripes in Richmond after Civil War.
Elizabeth Van Lew was a 43-year-old woman living with her widowed mother when the Civil War broke out. Lew was against slavery but she assumed the identity of a loyal Confederate. She realized her duties as soon as the war erupted, and she started working on the dangerous job out of pure patriotism — not for pay.
Lew was a member of the Richmond, Virginia elite, and her social status came in handy. For instance, she was allowed into Libby Prison. She brought (seemingly) harmless materials, such as food and clothing for the prisoners, but she also brought information and guidance to help them escape. She was naturally gifted for espionage. She transferred several critical intelligence reports to Ulysses S. Grant, the commanding general of Union army. These reports were sent inside hollowed eggs.
She did not work alone, but established a whole spy ring. In fact, she even managed to get one of her spies inside the White House of the Confederacy. After the war, Grant said that Van Lew was the most critical source of intelligence during the final two years of the conflict.
When Richmond fell to Union forces, she was the first person to fly the US flag on her home. It was this action that revealed which side she actually was on… and made her a villain among the local community. They hated her so much that neighboring parents told their children she was a witch.
When Grant became the 18th president of the United States, he appointed her as Postmaster of Richmond. She hired several African-Americans to her staff. Things were going alright, but then President Rutherford Hayes came to power and sacked her. She lived a poor life after that, although she received allowances from some of the ex-prisoners that she helped escape Libby Prison.
8. Oleg Penkovsky
Prevented a nuclear war.
Oleg Penkovsky, codename “Hero,” is the man who prevented the Cold War from turning into a hot one. He was a colonel for Soviet Military Intelligence, and he was the person who informed President John F. Kennedy that Soviet Russia was going to install an intercontinental missile system in Cuba. He also provided critical evidence proving that the Soviet arsenal was much less capable than what the CIA assumed. This important bit of information prevented a nuclear war between the USA and the Soviet Union.
Apart from this crucial matter, he did not provide any other intelligence to America. For this reason, Peter Wright, a scientist working for MI5, believes that Penkovsky was actually planted by the Soviets to prevent the war. According to CIA records, Penkovsky was abducted from a road in Moscow, charged with treason, and executed. Wright believes that he was not executed, but rather given an out-of-bounds post with a changed identity so that he would never be found by the Americans or the British. Wright believes this because there was no reason for Penkovsky to stay in Moscow when he knew he would get caught. He could have fled to the west.
7. Eddie Chapman
A criminal, turned German agent, turned British double agent. Only Englishman to receive Iron Cross.
Edward A. Chapman, codename “Zigzag,” was an explosives expert. Yet unlike some others on this list, he wasn’t using his talent for anything good; he was robbing jewelry shops. He was also a master of breaking locks.
In 1939, he was caught red-handed trying to rob a nightclub. Jersey police imprisoned him in Channel Islands. He was only supposed to serve two years, but police were making a case against him to serve another 14 in the mainland prison. However, fate had decided something else.
In 1940, the Nazi army occupied Channel Islands. They did not release prisoners but started researching for anybody useful. Of course, Chapman stood out. By the time his two year sentence was completed, he had become a German agent. They took him to Paris and further trained him in explosives, radio communication, and parachuting. Germans assigned him the task to blow up de Havilland aircraft factory in Hatfield. A German bomber carried him over England, and he jumped.
MI5 was aware of the German plans. They were decrypting German coded messages, so they knew where and when Chapman would land. Soon after he landed on the ground, he was hunted. During interrogation, he showed his intent to become a double agent. MI5 believed him, and decided to help him.
The British authorities designed one of the most brilliant deception operations of WWII — a faked sabotage of de Havilland factory. It worked. In fact, it worked so well that even some of the workers thought their factory had been destroyed.
When Chapman returned, the Germans considered him a hero who deserved the Iron Cross. Chapman remains the only British person to have received it.
6. Dr. Humam Khalil Al-Balawi
The triple agent who conducted the deadliest attack on the CIA in Afghanistan.
Not everyone who claims to be your friend is actually your friend, and the CIA learned this lesson the hard way. Humam al-Balawi was studying medicine in Istanbul, Turkey, when a local intelligence agency found him leaning towards extremists. He was captured, and the CIA took over his case. They offered him a chance to become a double agent for them, and he agreed. However, being just a double agent wasn’t enough for him. He wanted to be a triple-agent.
The CIA had been running programs to create double agents. Humam al-Balawi seemed like an ideal candidate. He was an educated man — a medical doctor. He was more likely to adapt modern moderate school of thought. Al-Balawi was sent to Afghanistan and assigned to report Al-Qaida’s activities. He reported enough to win the CIA’s confidence. When he achieved that, he did what he always meant to do.
One day, he announced that he had a very important bit of information about Ayman al-Zawahiri, the current No.1 of Al-Qaida. He said that he needed to convey the information only to superior officers, so he was called in to the CIA command office. Since he was late and senior CIA officials were anxiously awaiting his information, nobody bothered to check him for security precautions. He went straight in. Once inside the office, he blew himself up, killing seven CIA officers and two military officers. This was the deadliest strike on the CIA in more than 25 years.
5. James Rivington
Spied for George Washington, ran a British loyalist newspaper.
He was British born, but he was more of a US patriot than anyone else. He was James Rivington. In 1773, he started an impartial newspaper, The New York Gazetteer. Within a year, he turned into a ‘loyalist.’ By 1775, he managed to become the most hated media person among the patriots. In fact, the situation became so critical that on May 1775, members of the Sons of Liberty mobbed Rivington’s home and press, making him flee to England.
By 1777, Britain had fully occupied the city so he returned. This time he was officially the King’s Printer for New York. This made him the last person to be suspected of doing anything against the crown; yet, that was his precise plan.
He was a member of Culper’s Spy Ring. The initiator of that ring, Samuel Culper, Jr. (real name Robert Townsend) was Rivington’s silent partner in his coffeehouse, which was the last place to be suspected for anti-government activities. Under Rivington and Culper, the spy ring delivered critical information to General George Washington. Finally, in 1783 when New York was evacuated, Rivington remained in the city.
After 1783, he tried to continue with his publishing business, but he had played his double-agent role too well. People did not believe that he was on their side all along. The hatred from the public led to a decline of readers, and eventually the business ceased. The rest of his life was spent in deep poverty.
4. Arthur Owens
The only double agent who double-crossed both parties.
Arthur Owens, codename “Snow,” was a Welsh Nationalist and had little loyalty toward the UK. He was a naval engineer who made batteries for ships. Before the war, he was a contractor for both the British Royal Navy and the German Navy. When WWII seemed evident, Germans acquired the services of Owens and asked him details about British fleet. He told them whatever he knew.
Later, he toured to Munich, met with Abwehr’s officers, and officially joined them. And why wouldn’t he? They were giving him what he desired the most: money and women. Especially women — young, gorgeous women. This was Owens’ weak point. However, while returning to the UK, he had a crazy idea: he would become a double agent.
He contacted MI5 authorities, and they accepted him, making him the first double agent of WWII. Owens did remarkable things for the Allied forces. He disclosed a network of no less than 120 German spies working in the UK, which helped MI5 and MI6 feed false information to the Germans.
However, in 1941 the Germans called-in two British double agents: Owens, and another man named Charles Dicketts. They both went to Lisbon to meet Abwehr command. Dicketts was arrested, taken to Hamburg, interrogated and executed. Yet nothing happened to Owens. Hence, the British realized that Owens was not really working for the British — he was working for himself, taking benefits from both sides. MI5 imprisoned him in a hospital until the end of the war.
After the war, he demanded the British pay him a certain amount of money for his ‘wrongful’ arrest, or else he was going to publish his memoirs. The British did buy him off, and he spent the rest of his life quietly. His daughter Patricia Owens became a movie star, best known for 1958 movie The Fly.
3. Aldrich Ames
The man who beat the polygraph, twice!
Thanks to the media hype, Aldrich Ames became a household name in the US during the 1990s. Ames is one of the first people to break a polygraph, and he did it more than once. On top of that, he did it against perhaps the world’s best intelligence agency.
Ames was not a very promising agent when he was working in the CIA. Drinking problems, extramarital affairs, loud arguments at parties, and silly temperamental mistakes made it crystal-clear that he was not going to be an espionage legend. Yet somehow, he became exactly that… just for all the wrong reasons.
In huge debt and newly divorced, Ames needed to get some cash. The Embassy of the Soviet Union was willing to provide it. Fortunately for him, he was placed on the team assessing Soviet embassy officials as potential double agents. Instead of turning them into double agents, Ames became one himself.
Over a period of time, Ames delivered critical information to the Russians for $4.6 million. He also disclosed at least ten of the CIA’s sources in the KGB. All of them were executed. Eventually, the CIA caught him. He blipped on their radar due to his lavish lifestyle, which was way beyond the reach of a person with a $60,000 salary. He was charged, convicted, and is spending the rest of his days in prison.
2. Kim Philby of the Cambridge Five
The most brilliant Soviet spy of Cold War era. Receiver of the Order of the British Empire.
Kim Philby was to MI6 what Aldrich Ames was to the CIA. Philby was the Communists’ biggest mole in the West, and the pivotal figure of the famous Cambridge Five (a ring of Soviet spies).
The Cambridge Five was a group of (you guessed it) five spies who became Communists during their student years at Cambridge University. All five members worked in the British Secret Services. Four of those members have been located, while the fifth is still a mystery. However, one thing is certain: Philby was the central figure to everything within the group.
Philby was hired for the secret service by Guy Burgess, a Soviet double agent himself and a member of the Cambridge Five. Unlike Aldrich Ames, Philby was a huge success. He was working wholeheartedly and doing a brilliant job for the British, but the whole time he was also transferring information and messages to the Soviets, both during WWII and during his missions in Austria, Spain, Turkey, the USA, Lebanon, and of course, the UK.
For his sublime services, the government awarded him with the highest merit, The Order of the British Empire. It took eight years of investigation to realize that Philby was indeed a double agent, yet still he could not be captured. He was serving on a mission in Lebanon, from where he fled to Moscow and resided there as a national hero for the rest of his life.
He did not do all this for money, women, or anything like that. In fact, his first wife — the love of his life — left him because she thought he was sympathetic to ‘tyrant bloodsucking capitalists,’ unaware of how loyal he was to the hammer and sickle. He did all this for something he believed in: Communism. Perhaps it is a good thing that he died a year before the demise of his beloved socio-economic system. Otherwise, it would have broken his heart, making him realize that all of his sacrifices were in vain.
1. Juan Pujol Garcia
The only person in history to receive the highest civil military awards from both the Nazis and British.
He was one of the history’s most legendary spies, and one of the greatest con artists that ever walked the Earth. He was Juan Pujol Garcia, codename “Garbo.”
Unlike most fictional heroes who are born great, Garcia had a very humble beginning. By the age of 32, the Spaniard had failed in almost all walks of life: studies, business, and even his marriage was falling apart. He was a failure walking around in human form, but then the Second World War broke out and the tables were about to turn.
He knew he had a talent, one that could change the whole scene of the war. He was ready to match wits with the brightest minds of the Third Reich. However, he needed help from either the British or the US because Spain, his home country, had decided to stay (relatively) neutral in the war. He contacted MI5 and US intelligence. Both declined his offer. They thought that a person who’d failed at farming chickens would be useless with military secrets during the war. They couldn’t have been more wrong.
Undeterred by the rejection, Garcia turned to the Germans and made them believe that he was a true sympathizer of the fascist government. The Germans then assigned him to London. Garcia didn’t have the resources to go London, and he didn’t even speak English. So what did he do? He went to Lisbon, Portugal.
Garcia collected postcards of Big Ben and other famous London landmarks and sent them to Germany. He started sending made up spy reports, with a little help from radio news and newspapers. Of course, he also complained about London’s weather, since he was… ahem… totally there. He was so convincing that Germany kept buying the stories.
Garcia carefully studied the country where he’d never been and whose language he didn’t speak, where he was supposedly spying and gathering information for the Nazis. He continuously listened to the news, read maps, travelogues, and newspapers — along with anything else he could get his hands on — which described London.
He started with simpler things, such as reporting movements of troops. After gaining confidence, he took the game to a whole new level: he invented a spy ring. His network of spies included a British censor in the Ministry of Information, a Cabinet office clerk, an American soldier in Britain, a Dutch airline stewardess, a Welshman sympathetic to fascism, and 22 more like these… all fake. Yet somehow, he was so convincing that the Germans provided funds and resources for everyone in his “spy ring.”
Garcia was becoming immensely popular among Abwehr, so a British mole in the German secret service informed MI5 about this network of spies. The UK authorities nearly lost their minds. A ring of spies, working in the heart of England, and they had known nothing about them. This was the time when Garcia approached MI5 again. He told them everything. With astonished, amused, and impressed eyes, the British hired him.
Now, the best minds of British intelligence backed him, and he had all the resources he could need. There was no stopping him at this point. He delivered seemingly impressive, dramatic, but actually useless spy reports. The information was either a little late, a little useless, or already known. But he and his ring of 27 “agents” were working day and night, and the Germans respected their efforts and courage.
By June 1944, Garcia had become the one of the greatest German assets in the UK, or so they thought. It was Garcia who saved thousands of soldiers who landed on D-Day. He sent detailed telegrams to Hitler himself that the Normandy invasion was just a deception and the reserve German Panzer divisions must remain in Belgium. Those German tanks were already on the road to reach Normandy when orders came that they must stay where they were.
Now, you would think that such telegrams must have revealed his true identity and motives, and the Germans must have hunted down and executed him.
Nope. Instead, they awarded him with the Iron Cross for his valiant services to the Third Reich. This happened in July 1944, just a month after D-Day. Garcia managed to fool the Germans thanks to the deceptive measures taken by the Allied Forces. What happened was that the British and US had supposedly deployed 11 Divisions consisting of 150,000 men with tanks, the Air Force, and all the paraphernalia to the south of England. In reality, there weren’t 11 divisions — there were barely seven. Many of those “tanks” were blow-up balloons. It was a bluff. Garcia reported that these special divisions would launch the decisive strike. So, Hitler’s forces remained at their positions and D-Day became a huge Allied success.
In November 1944, about three months after the war, he received the Order of the British Empire from the Queen. It’s astonishing to consider someone could so convincingly lie and deceive a dictator as monstrous as Hitler, and live to tell the tale. He is also the only person in history to have received the highest civil military awards from both Germany and Britain.
In 1945, he staged his death, went to Venezuela, and opened a bookshop. He lived a low-profile life for another forty years. In 1984, on the 40 year celebration of D-Day, some veterans gathered on Omaha beach, and there he was. A soldier grabbed him by the hand, and introduced to the crowd as “the man who saved our lives.”
Tayyub is a learning documentary maker. Sometimes he writes for money. Say hi to him on Facebook, he loves making friends.