The 7 Craziest Moments in Espionage History

These real-life spy thrillers give the James Bond franchise a run for its money.

From government-orchestrated coups to brazen snatch-and-grabs to high-profile assassinations, espionage is a dirty business. Here, an in-depth look at some of the strangest, bloodiest and most decisive moments in the history of modern spycraft.

1. The Capture of Adolf Eichmann

Organization: Mossad

May 11, 1960

Photo: Associated Press

In 1956, Sylvia Hermann announced to her father Lothar, a Holocaust survivor who had moved his family to Argentina, that she had a new boyfriend. His name: Klaus Eichmann. It was the first clue to Nazi hunters that Hitler’s architect for his Final Solution, Adolf Eichmann, was living near Buenos Aires. Like hundreds of Nazis, Eichmann had fled there after World War II, taking the name Ricardo Klement. (His son Klaus was brazenly throwing around the old family name.)

It would take four more years — to track him as he moved and to identify him from old photos — but in 1960, some 30 undercover Israeli Mossad flew in to set a trap.

They parked two cars on Eichmann’s street in Buenos Aires, opened the hoods and tinkered with the engines. When Eichmann stepped off the bus from work, at 8PM, they leapt. “He let out a scream like a wild animal,” says Michael Bar-Zohar, a historian who wrote the 1970 Spies in the Promised Land, a biography of Mossad’s founder Isser Harrell, and other books on the intelligence agency.

The panicky spies shoved Eichmann in the lead car, put black-out goggles over his eyes, pushed him to the floor, put a gun to his side and told him he’d be killed if he moved, and then sped off to a nearby safe house. Getting him out of the country would be dangerous. On May 20th, they drugged Eichmann, dressed him as a injured El Al Airlines crew member, bandaged his head and drove to Ezeiza Airport. At the airfield security gate, the spies — also dressed as crew — acted drunk and told the guards their friend had suffered a fall. They then bundled the stumbling Eichmann into the first class section of a four-engine Bristol Britannia.

On taxiing, the tower suddenly ordered the plane to stop. “It was like in a movie, a tense four minutes,” says Bar-Zohan. “Then they got the green light.” The plane took off just before midnight, refueled in Dakar and landed the next day in Israel.

Eichmann’s trial — on 15 counts of crimes against the Jewish people, crimes against humanity, and war crimes — lasted eight months, with 99 Holocaust survivors testifying against him. Eichmann was eventually sentenced to death and hanged May 31, 1962, the only time Israel has ever used the death penalty.

2. The Assassination of Che Guevara

Organizations: CIA, Bolivian Army Rangers

October 9, 1967

Photo: MARC HUTTEN/AFP/Getty images

By the time CIA agent Felix Rodriguez found Ernesto “Che” Guevara in the mountains of Bolivia, where the Marxist rebel had gone to ignite a communist revolution, “he looked like a beggar,” says Rodriguez, “filthy dirty, with matted hair and strips of leather on his feet.” The U.S., fearful that Guevara was spreading communism in South America on behalf of his revolutionary comrade Fidel Castro, had sent in Rodriguez to capture the rebel. A Vietnam vet, Rodriguez helped covertly train a local Ranger battalion to fight Guevara’s 17-man guerilla army. On October 8, two hundred Rangers attacked their camp at the Yuro Ravine, killed several guerillas, shot Guevara in the right calf and captured him.

What followed was one of the biggest shit shows in covert ops history. The soldiers put Guevara in an old mud school house. They mocked him, and tried to steal his pipe. The CIA had ordered Rodriguez to keep Guevara alive, fearing that killing him would turn him into a martyr, and only further his mythic status among leftist thinkers. But a day after his capture, Rodriguez received a coded call with orders from Bolivia’s president: code 500 and 600 — the first referred to Guevara, the second an order for his execution.

Rodriguez delivered the news. “I came into the room, I stood right in front of him, and said, ‘Commander, I’m sorry, I tried my best,’” says Rodriguez. “He turned white like a sheet of paper and said, ‘It’s better this way. I should have never been captured alive.’” (Rodriguez had previously taken Guevara outside for one of the most notorious and tasteless selfies in history. In later years he would claim to be wearing Guevara’s Rolex.)

The execution order was passed down, refused by a lieutenant, and eventually given to a Sergeant Mario Teran. Teran steeled himself with beer until he was drunk. Guevara, who insisted on standing, even as Teran told him to sit, offered some goading last words: “Know this now, you are killing a man.” Teran gunned him down with his M23 Carbine. Soldiers cut off Guevara’s hands, as proof of his death, and buried him next to an airfield.

3. Project Fubelt, the CIA’s attempted coup in Chile

Organizations: CIA, Chilean Army Generals

October 17, 1970

Photo: Billhardt/ullstein bild via Getty Images

On September 15, 1970, President Richard Nixon called Richard Helms, his director of central intelligence, to the Oval Office to rage over the election of Chile’s new socialist president, Salvador Allende. Notes from the meeting state, “Nixon was furious.” He was convinced Allende would ensure the spread of Fidel Castro’s communist revolution to Latin America. Nixon hated the CIA. He believed its Ivy League spooks had helped Kennedy beat him in 1962. “He called them liberal Ivy League faggots to their faces,” says Kristian Gustafson, an expert on intelligence and security at Brunel University in London—whose research on the episode the CIA has posted on its own website—and co-editor of Intelligence Elsewhere: Spies and Espionage Outside the Anglosphere. With six weeks to go before Allende’s inauguration, Nixon ordered the CIA launch a coup to stop him. “The CIA knows it can’t be done,” says Gustafson. “But Nixon bullies them into it.”

The six CIA officers stationed in Chile scrambled to find disaffected army generals who could lead a coup. The plan: have the generals to kidnap the Army’s chief commander, General Rene Schneider, a constitutionalist who would have opposed any coup attempt, paving the way for a takeover of the military. To help with the plot, the CIA provided $50,000 in cash, a bag of tear gas and three submachine guns—delivered via diplomatic pouch. On October 22, Army General Roberto Viaux—who even the CIA considered unstable—and a small group of plotters accosted Schneider on his way to work. He pulled a pistol to defend himself and was shot dead. The murder shocked the public so much that it helped rally support for Allende’s constitutional right to assume power.

Undeterred, the CIA continued to funnel covert money to opposition newspapers, fund truck driver and shopkeeper strikes, and generally stoke civil and political mischief until the military and national police finally overthrew Allende in 1973. (He allegedly committed suicide in his palace.) The coup became a signal event in the history of the Cold War. The military established a junta, which the US recognized and supported as it consolidated its power. The brutal regime jailed, tortured and killed left-wing opponents and finally brought Allende’s Army chief, Augusto Pinochet, to supreme power in 1974.

4. Shi Was A He

Organization: Chinese government

Time: 1964-1982

Photo: Associated Press

Bernard Boursicot was a 20-year-old accountant assigned to the French Embassy in Beijing in 1964—a plum post for a wannabe diplomat. But his life was more Walter Mitty than James Bond. Sexually and politically naïve, he longed to be a man of consequence and mystery. So when he met Shi Pei Pu, a female Chinese opera singer, he began a sexual affair that lasted 19 years, only to later learn she was a spy—and a man.

During the affair, Pei Pu convinced Bouriscot she had given birth to a son (a mixed race child the Chinese government bought from a doctor). She pressured him to turn over secret documents—500 all told—to keep the Chinese government from persecuting her. The lovers were eventually arrested in Paris, in 1983. In custody, Pei Pu explained she had tricked Boursicot by always insisting on sex in the dark, and by hiding her genitals. The pair were sentenced to six years in prison, but served only a year before President of France Francois Mitterand pardoned them, in 1987, describing it as a “very silly” and unimportant case. The documents Bouriscot had leaked were of no real consequence.

“It remains one of the most important espionage cases not because of some geopolitical implication, but because of this riddle of deception and self delusion on Bouriscot’s part,” says playwright David Henry Hwang, whose 1988 play, M. Butterfly, chronicles the tale. “He had this fantasy about being a powerful spy in Asia, and that helped deceive him.” In later years, Bouriscot, who had at first tried to kill himself when the affair was revealed and splashed across the British tabloids, staring showing up at performances of the play. “He’ll announce himself in the theater,” says Hwang, “and people take him out to drinks.”

5. The Umbrella Murder

Organizations: KGB, Bulgarian Secret Police

September 7, 1978

Photo: Associated Press

The KGB has preferred poison as a means of political assassination ever since the 1920s. The reasons are simple and elegant: it dissolves in the body and it can be impossible to detect. It is also slow to act; an assassin can be miles away by the time the target dies.

Case in point, Georgi Markov. A Bulgarian dissident writer, he had defected to London in 1969 and had kept up a steady stream of sarcastic criticism against his old country’s president—and his Soviet puppet masters—on the BBC World Service. One day, while waiting on the Waterloo Bridge for a bus to take him to work, Markov felt a sharp sting on the back of his right thigh. He reached down to slap what he thought was a bug biting him, only to see a man pick up an umbrella, cross the street and hop into a taxi.

At work, a red mark appeared on his leg and the pain became unbearable. He managed to tell a colleague about the incident before developing a blistering fever that night. He died four days later, at age 49. Forensic pathologists found a platinum and iridium pellet, no bigger than a pin (0.07 inches), embedded in Markov’s leg. Two holes were drilled in it to release the poison, ricin. The assassin had shot the pellet from the umbrella into Markov’s leg. “The method of delivery was quite new at the time,” says Boris Volodarsky, a veteran of Russia’s GRU military intelligence service and author of The KGB’s Poison Factory. “Possibly someone watched James Bond and came up with the idea, who knows.” The killer has never been found. “We know why and how,” says Volodarsky, “not the who.”

6. Operation Wrath of God

Organization: Israeli Mossad

Time: 1972-1990s

Photo: The Sun

The 30-year-old woman in the apartment called herself Penelope. A British expat living in war-ravaged Beirut, she could often be found staring out her window on the busy Rue Verdun. On January 22, 1979, at exactly 3:35 PM, the scene below her window turned to chaos as a 100-pound car bomb exploded. It killed nine people, including the passenger of a Chevy station wagon—a Palestinian named Ali Hassan Salameh. Known as the Red Prince, Salameh was the notorious operations chief of Black September, the terror group whose raid on the 1972 Munich Olympics left 11 Israeli athletes dead and shocked the world.

Immediately after the massacre, the Mossad set out to methodically assassinate every terrorist associated with it. They killed one with an explosive-packed table in his own Paris apartment—a telephone call luring him to the table where the bomb went off; another killed on an exploding mattress in Cyprus; three others gunned down by assassins dressed as women. But the assassination of Salameh was a rare one, in which the Mossad used a female agent—and used her only once before she disappeared. Penelope’s real name was Erika Maria Chambers, an Anglo-Jew who had been scouted and trained by Mossad, and kept as a sleeper agent in Germany until she was activated for the hit.

“She spent weeks at the window, watching Salameh ride every day from work at the exact same time,” says Michael Bar-Zohar, the Israeli historian and Mossad expert. “She’s the one who personally triggered the bomb at just the right moment.” It was among the Mossad’s most notorious and carefully crafted hits. “It’s also a lesson for anyone in the terrorist business,” says Bar-Zohar. “You never take the same route twice.”

7. Operation Cyclone

Organizations: CIA, Pakistani Intelligence Service, Saudi Arabia

Time: 1979-1989

Photo: Wikimedia Commons

During the 1980s, the CIA gave $20 billion in covert aid to Afghan’s Mujahideen, the rag tag, cave-dwelling Islamists battling the Soviet invaders in Afghanistan. For the CIA, it was a naked attempt to deal a body blow to their foe and payback for Vietnam. A generation of CIA officers had come of age during the Vietnam War, where the Soviets supported the North and were often present during the interrogation of American POWs. “There was a personal element for the CIA coming to this fight, this idea that they wanted to respond in kind,” says Steve Coll, dean of Columbia Journalism School and Pulitzer Prize-winning author of Ghost Wars: The Secret History of the CIA, Afghanistan, and Bin Laden, from the Soviet Invasion to September 10, 2001. “The main project was to punish the Soviets.” With backing from Saudi Arabia and Pakistan’s Interservices Intelligence (ISI), the Mujahideen bloodied and demoralized the Soviet forces, killing 14,000 and sending another 50,000 home wounded and maimed over the course of the decade-long war.

During the conflict, the CIA pushed the ISI—who funneled American dollars north, after taking a cut for themselves, along with surface to air Stinger missiles—to train ever more radical Islamists, believing they would fight harder than moderate and secular Afghan guerillas. The Islamists undertook training in explosives and sabotage techniques, and attacked Soviet officers in what Coll notes in his book pushed the CIA itself, along with the Islamist resistance and ISI, “closer to the gray fields of assassination and terrorism.”

After the CIA turned its back on Afghanistan in 1989, the guerillas found a new patron in Osama bin Laden, who started channeling radical Islam against the U.S. in 1990. “There was this realization by the CIA toward the end, that the groups ISI favored had an anti-American agenda,” says Coll. “You had these radicals giving private sermons to the U.S. while wearing gold Rolexes that American tax payers had paid for.” During the 1990s, the CIA sought to buy back its Stinger missiles—fearing they would be used against commercial airliners. They secured about a dozen, at a cost of $80,000 apiece, says Coll.

The leftover missiles were a big concern when the U.S. invaded Afghanistan following the September 11th attacks, but by then, “the batteries on them had faded,” says Coll. “But it was probably one of the more significant issues of blowback from that operation.”

That, as well as training and arming a bunch of people who want to kill us, or who might eventually turn out own weapons against us.  “What lessons we learned from that war are still actively debated inside the CIA, in reference to Syria,” says Coll. “Should we arm the radicals who will fight like hell, or the more moderate groups?” There is also some evidence that the Afghan war and the U.S. support for the rebels, was a factor in the collapse of the Soviet Union. “It’s a rare example of a covert operation that achieved it’s objective,” says Coll, “but with a bit of an asterick, because it gave birth to al Qaeda.”

Photos by Everett Collection