Nobody knows spies like Ben Macintyre. With Double Cross, Agent Zigzag, and Operation Mincemeat, the London-based author established himself as the master chronicler of spooks and subterfuge, a biographer of the most eccentric personalities ever to dwell in the shadows of diplomacy. (Macintyre is also a regular dweller of our Best of the Month lists.) His latest, A Spy Among Friends, tackles the story of the man who may have been the most damaging double-agent in history: Kim Philby, Britain's top spy-hunter charged with catching Soviet moles, who all the while spilled deadly secrets to the Soviets themselves.
We couldn't think of anyone more qualified than Ben Macintyre to ask for history's most notorious double-crossers, and unsurprisingly (spoiler alert) Philby made the list.
History's Five Most Notorious Double-Agents
by Ben Macintyre
The FBI has coined an acronym to describe the motivations of the spy: MICE, which stands for Money, Ideology, Coercion and Ego. Some spies are inspired by simple greed; others by pure conviction. But the greatest spies of all are a driven by something that defies categorization: a love of espionage, an addiction to the thrill and danger of subterfuge, and a dedication to this most fickle of professions for its own sake. The most successful and notorious spies in history have all possessed this peculiar quality: they each fell in love with spying itself, and remained besotted, prepared to take the most appalling risks to remain one step ahead in the lethal espionage game. These are the most dangerous spies of all, because they cannot be controlled by money or blackmail, by appeals to their vanity or ideology. They do it for love of the game.
Chapman was a burglar, con man, and gangster in pre-war London, who happened to be in prison in Jersey when the Nazis invaded the Channel Islands. He struck a deal with the Germans to spy against Britain in exchange for his freedom. Trained at a spy school in occupied France, he was parachuted into Britain in 1942, and immediately defected to British intelligence. For the rest of the war, he spied for Britain, while pretending to spy for Germany. The British code-named him “Agent Zigzag,” because they could never be sure whose side he was on. The Germans never realized the game he was playing, and even awarded him the Iron Cross for services to the Third Reich. After the war, Chapman immediately returned to a professional life of crime.
Ian Fleming, the creator James Bond, considered the half-German and half-Russian Richard Sorge to have been “the most formidable spy in history.” A committed communist, Sorge spied for the Soviets in Japan at the start of the war, supplying vital military intelligence gleaned while ostensibly working as a journalist. He even informed Moscow that Japan was not planning to attack the USSR, which enabled the transfer of Soviet troops from the east to defend Moscow and changed the course of the war. Sorge was eventually betrayed, captured by the Japanese secret police, tortured into confessing, and hanged in November 1944. In 1964 he was recognized as a Hero of the Soviet Union.
Pujol was a Spanish chicken farmer, who managed to get himself recruited as a German spy at the start of the war while always intending to spy for the Allies. He is one of the very few spies in history who set out to become a double agent. Ensconced in a safe house in London, Pujol (codenamed Garbo, on account of his acting abilities) not only supplied reams of false information to the Germans, but invented no fewer than twenty-nine additional sub-agents, all of whom were entirely fictitious, and wholly deceptive. He was one-man band, with a huge, invented orchestra. Pujol was, in a way, a spy-novelist, creating an imaginary world and then luring his German spy-masters into the illusion that it was real. He played a pivotal role in the run-up to D-Day, successfully convincing the Germans that the invasion would come at Calais, and not Normandy, thus tying up thousands of German troops. After the war, he took on a false name, and vanished into obscurity.
Rose O’Neal Greenhow
Greenhow was not technically a double agent, since she only ever spied for one side (the Confederates during the Civil War), but she was undoubtedly America’s most successful woman spy. Socialite, diplomat and secret agent, she ran an extensive spy network in Washington, DC, during 1861, helped to bring about Union defeat in the First Battle of Bull Run. Betrayed and captured, she was imprisoned for five months and then deported to Richmond. Undaunted, she then represented the Confederacy on a diplomatic mission to France and Britain, and was drowned after her ship ran aground on the return journey. Greenhow was a ferocious ideologue, but a most effective spy: “Instead of loving the old flag of the stars and stripes, I see in it only the symbol of murder, plunder, oppression, and shame,” she said.
The notorious British spy and KGB agent was recruited to the communist cause in 1934, and went on to achieve something no other spy has managed: he got himself recruited by the enemy spy-organization, namely Britain’s Secret Intelligence Service, better known as MI6. By 1944 he had become head of the Soviet counter-intelligence section of MI6, responsible for attacking Soviet espionage around the world, exposing Russian spies and breaking up the USSR’s spy rings. In other words, he was in charge of hunting people like himself. Tipped as the future head of MI6, he used his position to extract a multitude of secrets from his friends in British and American intelligence, and did spectacular damage by betraying everything to Moscow. Hundreds, if not thousands, died as result of Philby’s betrayals, for which he never expressed a single word of remorse.
Philby was the most remarkable example of a spy acting, in the end, out of pure love for the game of espionage. Philby was a master spy, addicted to the thrill of betrayal, whose willingness to manipulate and double-cross his friends allowed him to survive uncaught for three decades, and then escape to Moscow to spend the rest of his days. Philby is the greatest double agent in history.