Spies work in deception, and double agents are the masters of this. They work with both sides, before screwing over one to help the other. Some double agents are patriotic, or idealistic, and try to dupe the side their morally against. Other double agents simply work for money, or women, whichever they prefer. This is a list of the 10 most intelligent double agents in history.

The Real James Bond: Dusan Popov

Dusan Popov was a spy, womaniser, and one of the main inspirations for the character James Bond. He infiltrated the Abwehr, and began sending them disinformation. He had important connections in the business world in both France, and the UK. Because of this he was considered a great asset by the Germans. While he was spying, he was famous for womanising, and even seduced a famous French celebrity, Simone Simon. He was awarded both the Iron Cross, and the Order of The British Empire. He helped to attempt to trick the Nazis that the allied invasion of Europe would take place in Calais not Normandy, diverting thousands of German troops. The British codenamed him Tricycle, because he was in charge of three double agents.

William Sebold

Sebold visited Germany in 1939, and was coerced into becoming a spy for the Nazis by high ranking German officers. He informed the FBI when he could, and became a double agent for them. He went on to recruit 33 agents for the Nazis, and then had them all arrested in 1941. They were sentenced to a total of 300 years in prison.

Eddie Chapman

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Eddie Chapman had a spotty past as a criminal, who used multiple aliases in his crimes. But he managed to infiltrate the Abwehr, and then became a double agent for the British. He was given the codename zigzag due to his strange life story. While acting as a spy he had two fiancées, one in France, and a woman in Germany, who turned out to actually be an undercover Norwegian spy . He abandoned both of them after the war ended, and married his old English girlfriend Betty Farmer. The Norwegian spy he was with, was arrested for dating a German officer (Eddie Chapman), and since Eddie fled, she could never prove she was innocent.

Elizabeth Van Lew

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Van Lew spent her time building up a large spy ring for the United States during the Civil War. She started off simply treating injured soldiers, and was eventually allowed to bring in food and other items to Union soldiers who had been imprisoned there. She cleverly took advantage of this to pass on information and tools which would allow them to escape from their prisons. She also got information from the prisoners, which she passed on to Union commanders. Her spy ring was known as “Richmond Underground”. She managed to provide her side with priceless information.

Oleg Penkovsky

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Oleg Penkovsky was a Soviet colonel who turned spy, and began informing the British and American governments about Soviet activities. It’s controversial whether Penkovsky was actually a spy for the British or not, or if he was a triple agent. He provided the west with information about the Soviet military, and told them that their nuclear arsenal was much less impressive than they thought. It was claimed by an MI5 scientist that he was simply misleading them into believing the Soviets were less advanced than they really were. Penkovsky is one of the most controversial double agents in history.

Triple Agent Dr. Humam

On 30th December 2009, CIA agents welcomed islamist loyalist Dr Humam Khalil Abu-Mulal al-Balawi, into their base with open arms, and a warm welcome, just as they were ordered to. They believed him to be a double agent working for them, when secretly he was carrying a bomb into their base, which he intended on setting off. He easily got past the security in Camp Chapman, and waited for the right moment. When he was in the vicinity of seven CIA officers and two employees, he detonated the bomb, killing all of them, along with himself. It was the worst attack against the CIA in 25 years, and he claims he did it out of revenge.

James Rivington

James Rivington was a journalist who wrote articles for the a loyalist paper called Rivington’s Gazette, during the American Revolutionary War. He is believed to have been a part of the Culper Ring. A collusion of spies formed by Major Benjamin Tallmadge, under the orders of George Washington himself. The goal of the group was to send secret messages to Washington. Although he worked for the British he was secretly providing Washington with information. His messages were written on the covers of books, and delivered to the American camp, by people who had no idea the books contained hidden messages.

Agent SNOW

Real name Arthur Owens, was a Welsh double agent, who provided MI5 with information on the Abwehr, the German secret intelligence agency. Owens ran a company that made batteries for ships, and because of his job he had regular contact with both German the German Navy, and the British. He began working for the SIS in 1936, providing them with information. In 1938 he was contacted by the Germans, who offered him money, for information. But he was mainly incentivised by the attractive women they provided him with. He regretted doing this and so told the SIS, and provided them with information again. His wife, whom he was separated from, outed him as a double agent to both the Germans and the British. After war broke out between the two countries, he went to the Special Branch to offer his services but instead they sent him to prison. But, then they changed their minds and began using him as a double agent again, sending fake messages to the Germans. He was their first double agent in the war, and helped the British catch more than 120 German spies hiding in the UK.

Aldrich Ames

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Ames was an American spy, who turned his back on his country, and became a double agent for the Soviet Union. He was the single most devastating mole in US history, and compromised more CIA assets than anyone in history, until Robert Hanssen that is. He originally contacted the Soviets in order to simply pay off his debts, asking for only $50,000. But he was walking down a slippery slope, and once he had started he couldn’t stop, even when he was no longer in debt. The information he first gave them was info he considered valueless, but he soon began providing with more damaging information. He sold out agents in the FBI and CIA, who were spying on the Soviets, by doing this he made a lot of money, and protected himself from people who could potentially catch him.


Juan Pujol Garcia

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When Garcia managed to dupe the Nazis, and gain both the highest possible civil military awards from both the Nazis, and the British, he became the greatest double agent in history. Garcia got into contact with the Germans and claimed he wanted to be a spy. After putting on a convincing act, they ordered him to go to London, and provide them with information. He chose, instead, to go to Lisbon Portugal. There he would send postcards of English monuments, while writing bogus information on the back. The Germans believed every word of his made up stories, and even considered him one of their greatest spies. His stories had incredibly detailed plots, and involved more than 27 characters. He then went to the British secret service to inform them of his trickery. They hired him, and he continued to trick the Germans. His false information was significant in defeating Hitler, and saved thousands of lives.

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