10 MOST BRILLIANT DOUBLE AGENT SPIES IN HISTORY

10 Most Brilliant Double Agent Spies in History
By Tayyub, Toptenz, 5 September 2014.

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, in fact it is 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 he is often mistrusted. He is lonely and he is devoted. He is 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 way back into 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 and CIA is training them.

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 the real life James Bond; handsome, cultured and confident. He was a very successful lawyer in Yugoslavia. He was very popular among ladies, they just 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 James 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 the name of the German officer (Johann Jebsen) who contacted Popov, 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 very 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 USA in 1941 by the Germans. They gave him a three-page questionnaire about US defense systems. His mission was to find answers of all those questions. Out of those three pages, one whole page consisted of detailed questions about defense systems of Pearl Harbour. Popov told 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 did not report to seniors. 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. She was not being paid!

Lew was a member of the elite of Richmond. Her social status came handy for doing some of the jobs. For instance, she was allowed in Libby Prison. She brought (seemingly) harmless material 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 Confederacy. After the war, Grant said that Van Lew was the most critical source of intelligence during the final two years of war.

When Richmond fell to Union forces, she was the first person to fly the US flag on her home. It was this action of hers which revealed which side she actually was on…and made her a villain among the local community. They hated her so much that neighbouring parents told their children that she was a witch.

When Ulysses Grant became the 18th president of USA, he appointed her as Postmaster of Richmond. She hired several African-Americans on her staff. Things were going all right 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 the 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. Nevertheless, 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 USA. 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, Oleg Penkovsky was abducted from a road in Moscow, charged with treason and executed. Peter Wright believes that he was not executed, but rather was 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 in this list, he wasn’t using his talent for anything good. He was robbing jewellery 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 supposed to serve only two years in Channel Islands, but police were making a case against him to serve another 14 years on 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 shined 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 parachute jumping. Germans assigned him the task to blow up de Havilland aircraft factory in Hatfield. A German bomber jet 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, Germans considered him a hero, a great hero who deserved Iron Cross, the highest civil military award of German army. Chapman remains the only British person to have received it.

By the way, Anna Chapman is not a descendant of Eddie Chapman.

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 to become a double agent for them, and he agreed. However, just being a double agent was not enough for him, he wanted to be a triple-agent!

The CIA had been running programs to make double agents. Humam al-Balawi seemed like an ideal candidate to be a double agent. He was an educated man, a medical doctor. He was likely to adapt modern moderate school of thought. Al-Balawi was sent to Afghanistan and assigned to report Al-Qaida’s activities. He did report enough to win 100% of 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 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 waiting for him, 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. Nonetheless, 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, 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 anything against the crown, yet, he was exactly that.

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 coffee house, 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 public led to decline of readers, and eventually ceasing of the business. The rest of his life was spent in deep poverty.

4. Arthur Owens

The only double agent who double-crossed both parties.

Arthur Owens, codenamed “Snow,” was a Welsh Nationalist and had little loyalty towards 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 services of Owens and asked him details of British fleet. He told them whatever he knew.

Later, he toured Munich, met with Abwehr’s officers and joined them officially. And why wouldn’t he, they were giving him what he desired the most, money and women. Especially, women. Young, gorgeous, attractive women. This was Owens’s weak point. However, while returning to UK, he had a crazy idea, the idea to 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 to feed false information to the Germans.

However, in 1941 the Germans called-in two British double agents, Owens and another guy named Charles Dicketts. They both went to Lisbon to meet Abwehr command. Dicketts was arrested, taken to Hamburg, interrogated and executed, yet, nothing happened against Owens. Hence, the British realized that Owens was not really working for the British, he was working for himself taking benefits from both sides. Then 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. British did buy him off and he spent the rest of his life quietly. However, his daughter Patricia Owens did become 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 90s. Ames is one of the first people to break a polygraph, and he did it more than once. He did it against 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 in parties and such silly temperamental mistakes made it crystal-clear that he was not going to be a legend…yet he did become so, but for the wrong reasons.

In huge debt and newly divorced, Ames needed to get some cash. The Embassy of 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 for them.

Over a period of time, Ames delivered pricelessly critical information to the Russians for US$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 beeped on the radar due to his lavish lifestyle that was way beyond the reach of a person with a US$60,000 salary. He was charged and now spends the rest of his life 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 is to MI6 what Aldrich Ames is to the CIA. The only difference is that the Kim Philby phenomenon is much bigger. Philby was the biggest mole in the West by the communist bloc. He was the pivotal figure of the famous Cambridge Five (ring of Soviet spies).

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 one is still a mystery. However, one thing is certain, which is that Philby was the central figure of everything.

Philby was hired for the secret service by none other than 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 he was doing a brilliant job for the British, but all this time he was also transferring information and messages to Soviets, during WWII and during his missions in Austria, Spain, Turkey, 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 such. In fact, his first wife, the love of his life left him because she thought he was sympathetic to ‘tyrant bloodsucking capitalists,’ little knowing 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, it would have made him feel that all 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 is the daddy to all spies. He is the one of the greatest con artists ever stood on earth. He is 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 tables were about to turn.

He knew he had a talent, a talent 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 impartial in the war. He contacted MI5 and US intelligence. Both declined him. They thought that a person, who cannot even farm chickens, could never be trusted with military secrets during a World War. They could not have been more wrong!

Undeterred with 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 did not have the resources to go London…he did not even speak English. So what did he do? He went to Lisbon, Portugal.

Garcia collected postcards of Big Ben and other monuments of London, and sent them to Germany. He started sending made up spying reports with a little help from radio news and newspapers. Of course, he also complained about London’s weather where he totally was. He was so convincing the Germany kept buying the stories.

Garcia studied a lot about the country where he had never been, whose language he did not speak, and yet he was supposedly spying in, sending information to the one of the greatest fascist dictators of all time. He continuously listened to the news, read maps, read travelogues and newspapers and anything 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 there were twenty-two more like these…all fake! Nonetheless, he did start to receive payments for all of the spies working under him.

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 knew nothing about them, nothing at all! 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 now. He delivered seemingly impressive, dramatic, but actually useless spy reports. The information was either: a little late, a little useless or a little already known. But he and his ring of 27 agents were working day and night and the Germans respected the efforts, courage and of course, their great work.

By June 1944, Garcia had become the one of the greatest German assets in the UK, or at least they thought so. It was Garcia who saved thousands of soldiers who landed on D-Day. Garcia sent detailed telegrams to Hitler himself that 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 are.

Now you would think that such telegrams must have revealed his identity, and the Germans must have hunted down and executed him. Dead wrong! 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 British army and US had deployed 11 Divisions, 150,000 men with tanks, air force and all the paraphernalia on the south of England. Actually, there were not 11 divisions, there were barely 7 divisions…and many of those tanks were blow-up balloons. Yes, balloons! It was a bluff. Garcia reported that these special divisions would launch the decisive strike, and since the divisions did not move, to not move as well. So Hitler remained at his positions and D-Day became a huge success.

In November 1944, about three months after the war, he received the Order of the British Empire from the Queen. To this day, he is the only person to have lied so much, right into Hitler’s face and lived 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 years celebration of D-Day, some veterans gathered on Omaha beach and there he was spotted. A soldier grabbed him by his hand and introduced to the crowd “the man who saved our lives.”

Top image: Juan Pujol Garcia. Credit: Salon.

[Source: Toptenz. Edited. Top image added.]