Throughout history, spies have used sex, seduction, and emotional manipulation to achieve their shadowy aims. In this three-part anthology, Vanessa Kirby joins espionage authors Henry Schlesinger and Michael Smith to uncover the real stories behind some of history's most explosive honeytrap operations. In Part III, Michael and Henry share the real spy story behind one of history's most famous murders. When Ramón Mercader attacked Marxist revolutionary Leon Trotsky at his home in Mexico, the evidence suggested a crime of passion. In reality, it was the culmination of a long and intricate honeypot operation by Stalin's secret service. Could you get close enough to kill?
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True Spies Sexpionage, Part III: The Lover, the Ax, and Leon Trotsky

NARRATOR: Welcome to True Spies. Week by week, mission by mission, you’ll hear the true stories behind the world’s greatest espionage operations. You’ll meet the people who navigate this secret world. What do they know? What are their skills? And what would you do in their position? I’m Vanessa Kirby, and this is True Spies Sexpionage, Part III: The Lover, the Ax, and Leon Trotsky. It’s the spring of 1940 - the 24th of May. Dawn is breaking in the historic Mexico City neighborhood of Coyoacán. In bed beside his wife, Leon Trotsky - the great Marxist revolutionary - stirs to the sound of fireworks. A national holiday, perhaps? But the noises seem too close. Getting closer. And then the world explodes. The attackers are inside the building. 

MICHAEL SMITH: Initially, the NKVD sent in a group of armed assassins and they attacked Trotsky's villa. 

NARRATOR: And with a final crash, they’re upon him.

HENRY SCHLESINGER: They opened fire in Trotsky's bedroom. 

NARRATOR: Bullets kick up clouds of plaster, and the air buzzes with splinters of wood. Incendiary grenades turn the humble villa into a furnace. 

HENRY SCHLESINGER: He hid under the bed and miraculously wasn't hit. 

NARRATOR: In the next room, they hear their grandson cry out in pain. Later, they’ll learn that he’s been shot in the toe. Somehow, that’s the only serious injury sustained during the raid.

HENRY SCHLESINGER: Trotsky survived the attack, machine gun, and bomb attack.

NARRATOR: Eventually, the men retreat. Shaken, the family emerges from their hiding places. Leon Trotsky is under no illusions as to who is behind the assault.

MICHAEL SMITH: Stalin was determined to have him killed. He had been the main rival.

NARRATOR: It could only be the NKVD, Stalin’s intelligence service - the forerunners of the KGB. Soon, they will know that the attempt on Trotsky’s life has failed. But if at first you don’t succeed, try and try again.

HENRY SCHLESINGER: When the first one failed, they upgraded the second operation to an assassination plot. 

NARRATOR: Welcome to the third and final installment of the inaugural True Spies anthology. In these episodes, we’ve entered the glamorous and often-deadly world of honeypots: spies who use sex appeal to achieve their aims. We’ve met the seductresses of Israel’s Mossad on the prowl for military secrets in the 60s, and partied with Russian spy Anna Chapman in the nightclubs of New York and London. Now, join espionage journalists Henry Schlesinger and Michael Smith for the true story of an audacious honeypot operation that targeted one of the towering political figures of the early 20th century - and worked. 

HENRY SCHLESINGER: It was actually a very sophisticated assassination attempt with a lot of people involved. 

NARRATOR: This is Henry.

HENRY SCHLESINGER: Leon Trotsky was a revolutionary and was in direct conflict with Stalin following the death of Lenin. 

NARRATOR: Born in 1879, Leon Trotsky started life in modern-day Ukraine. He joined up with Marxist revolutionaries in his teens and later became one of the driving forces within the Russian Revolution which deposed Russia’s ruling family in 1917.

MICHAEL SMITH: Trotsky was a tremendous figure within the Bolshevik Revolution.

NARRATOR: And this is Michael Smith.

 MICHAEL SMITH: He was essentially the foreign minister, Commissar for Foreign Affairs initially, and then he's in charge of the Armed Forces. 

NARRATOR: But, during the 1920s, an ideological rift between Trotsky and Josef Stalin led to the former’s exile from the USSR. Forbidden to return to his motherland, he bounced around Europe and the Near East before eventually settling in Mexico.

MICHAEL SMITH: He set up the Fourth International, which is a rival to the Komintern, which is the way in which Stalin controlled communist parties around the world. 

NARRATOR: Needless to say, the idea of a competing communist power-player did not go down well in Moscow.

MICHAEL SMITH: In 1936, there were a series of show trials of people who were alleged to be Trotsky's supporters. And they were forced to make admissions. And one of the admissions was that they wanted Stalin dead and they were sentenced to death. 

NARRATOR: Trotsky himself was sentenced to death in absentia - a  sentence that Stalin and the NKVD would stop at nothing to carry out.

HENRY SCHLESINGER: Stalin was paranoid that he would come back and do a counterrevolution and displace him, and he became obsessed with Trotsky. 

NARRATOR: Trotsky arrived in Mexico in 1937. By then, his fame - or infamy, depending on who you ask - had spread worldwide. 

MICHAEL SMITH: Trotsky is in Mexico, and he's surrounded by people who are great fans of his, American communists. And he is in many ways, probably a much more glamorous figure than Stalin, and totemic really, to communists abroad.

NARRATOR: Three years after his arrival in Central America, it’s one of these American hangers-on who enables the first attempt on his life by the NKVD.

HENRY SCHLESINGER: They recruited a New York guy, Robert Sheldon Harte, who led a gang of marauders dressed like Mexican policemen and government and soldiers.

NARRATOR: Robert Sheldon Harte was one of Trotsky’s assistants on the Coacoán estate. During the raid on the 24th of May, 1940 - where Trotsky and his wife were attacked in their sleep - he disappeared.

MICHAEL SMITH: And he’s later found murdered. 

HENRY SCHLESINGER: Harte left with the marauders and was later killed by them. He believed that the marauders were coming in to destroy Trotsky's library, not Trotsky.

NARRATOR: Clearly, the NKVD had decided that Harte was not to be trusted, despite his assistance. Trotsky, on the other hand, was unwilling to think ill of one of his acolytes.

HENRY SCHLESINGER: Couldn't believe that he was betrayed by him. Actually put up a plot in his memory.

NARRATOR: In direct contrast to the paranoid Stalin, Trotsky was almost improbably trusting.

HENRY SCHLESINGER: He refused to have visitors searched because he believed it was impolite.

NARRATOR: By some miracle, he had survived the first attempt on his life in Mexico. But everyone’s luck has limits. When their first operation failed, the NKVD reverted to their backup plan. A honeypot operation that was initially supposed to give Stalin eyes and ears inside Trotsky’s compound. 

MICHAEL SMITH: You have this very long-term view being taken. It's not going to be: "Just send someone in and get it done now." It's going to be done very carefully. 

NARRATOR: After May 1940, an extra element was added to the plot - the death of Leon Trotsky. That operation began in 1938, two years prior to the first attempt on Trotsky’s life. It took place on two continents and featured a varied cast of characters. We’ll meet them more-or-less in order. The first is Pavel Sudoplatov, a senior NKVD official who Stalin has entrusted with Trotsky’s removal from the mortal coil. He’s the man who will orchestrate the botched hit in May 1940. And, as well as trying to kill him, he’ll simultaneously mastermind the plot to infiltrate Trotsky’s inner circle. To that end, Sudoplatov reaches out to a colleague in America. His name is Leonid Eitingon.

NARRATOR: By day, Eitingon masqueraded as a legitimate businessman working out of Brooklyn, New York.

HENRY SCHLESINGER: Import-export. But no one, including the woman who wrote the family history, ever recalls him importing or exporting anything. And I was unable to find any kind of business address for him. So probably that was just a very light cover. And he was working for the NKVD. And he's maintaining contact. He's running an organization that includes the moles within Trotsky's organization. 

NARRATOR: The Socialist Workers Party, a Trotskyist political movement in the USA which included a number of Trotsky’s entourage. 

MICHAEL SMITH: Prior to the Second World War, there was a lot of communism in America. As far as the Soviet Union was concerned, the main enemy was the UK. And the authorities were not keen on communism at all, but it existed as a legal party. 

NARRATOR: It’s through his moles in the SWP that Eitingon will place an agent inside Trotsky’s Mexican estate.

HENRY SCHLESINGER: Trotsky's organization was rife with spies. So Eitingon reaches down into it and finds a woman who's plain, who's unattached and perfect. Her sister worked for Trotsky. Right. Sylvia Ageloff. 

NARRATOR: Sylvia Ageloff is a social worker, and a committed Trotskyist. Hers is not to be the hand that pulls the trigger. No, unbeknownst to her, Ageloff’s role is to be a stepping stone into Trotsky’s inner sanctum.

HENRY SCHLESINGER: She was very plain and very withdrawn. She wasn't anybody you would look twice at on the street.

NARRATOR: In many ways, the perfect target for a honeytrap. Those who are overlooked by others are often the most susceptible to honeytraps. Everyone likes a little bit of attention. For another example of an operation in this mold, check out Episode 87 of True Spies - Stalin’s Romeo Spy. Luckily, Leonid Eitingon knows just the match for Sylvia Ageloff. Meet Ramon Mercader, a Romeo spy par excellence.

MICHAEL SMITH: His mother was a communist, and he'd grown up believing very strongly in communism. And he was Spanish, so he was in Spain during the Spanish Civil War and worked with the Communists during the Spanish Civil War, and he was then recruited by the NKVD as an agent.

NARRATOR: Eitingon first met Ramon Mercader, and his mother, Caridad, during the Spanish Civil War - a bloody three-year conflict in which left-wing and right-wing factions battled for control of the country. The NKVD was an active player behind the scenes, and the Mercaders, like Eitingon, were aligned with the Stalinist cause. Ramon Mercader had combat experience and had trained in spycraft in the Soviet Union during the conflict.

HENRY SCHLESINGER: And he's a good-looking guy.

NARRATOR: That’s important, too. And when you know more about Eitingon’s connection to the Mercader family, it’s even easier to see why Ramon would have seemed like the obvious choice for the operation against Trotsky.

HENRY SCHLESINGER: So Eitingon, he's a father figure to Mercader. He's a boyfriend to Caridad. Right, he's Caridad's lover, her boyfriend, whatever you want to call it, and he's worshiped by Mercader, Ramon, which makes his job of recruiting Ramon easier. I mean, how much easier does it get than having the mother help in the recruitment effort? 

NARRATOR: Did Eitingon use his relationship with Caridad to persuade her to give her son to the cause? Did a honeytrap beget a honey-trapper? Well, that’s unlikely. Ramon’s mother was a die-hard communist and probably wouldn’t have needed much persuading to offer up Ramon when the call came. Sometimes, in a world where manipulation is as natural as breathing, it’s easy to forget that people do act on principle, as well as lust, money, ego, and coercion. By the time the decision to use Ramon was made, in 1938, the 25-year-old was studying at The Sorbonne, Frances’ most prestigious university. When Eitingon comes calling, he’s eager to help his NKVD father figure. Before the operation can begin, Leonid Eitingon needs to maneuver his stepping stone, Sylvia Ageloff, into Mercader’s path. Their meeting has to appear natural - completely unplanned. Ageloff has to be made to believe that she’s simply stumbled across the good-looking Spaniard.

HENRY SCHLESINGER: They take her out of her natural environment of New York. They recruit another woman to invite her to Paris. 

NARRATOR: That’s Ruby Weil. She’s a journalist and Socialist Workers Party member who secretly reports to Eitingon - a Stalinist in Trotskyist clothing. Initially, the two women aren’t close. But Ruby begins spending more time with Sylvia. For Sylvia, a quiet, somewhat reserved character, the attention feels good. So when Ruby invites her on a trip to Paris to attend a conference of the Fourth International, Trotsky’s political organization, she’s thrilled.

HENRY SCHLESINGER: So Ageloff arrives with her friend Ruby Weil, who's an AP photo editor, but also a member of the Socialist Workers Party. 

NARRATOR: Ruby wastes no time in introducing Sylvia to Ramon Mercader, who is in Paris under a false identity.

HENRY SCHLESINGER: He's this Belgian playboy. He's working under the name Jacques Mornard. He's already well known in the neighborhood where he lives. He doesn't speak French with a Belgian accent. That's a problem for him. But everyone seems to overlook it. 

NARRATOR: ‘Jacques Mornard’ is, ostensibly, the son of a Belgian diplomat - which might go some way to explaining his wandering accent. It’s certainly a more feasible explanation than being a Spanish spy for Soviet Russia.

HENRY SCHLESINGER: And they arrive for this conference and Mercader romances them for 10 days, and on the last day, slept with Ageloff. Weil plays a key role. She allays any doubts that Ageloff might have about this tall, dark, handsome stranger, and kind of pushes Ageloff toward him. 

NARRATOR: A year later, Ramon Mercader pitches up in Brooklyn to be with Sylvia. Except now, he’s using another alias. Sylvia and Ramon resume their affair in New York. And in October of 1939, the NKVD made its move. Ramon Mercader heads south of the border.

HENRY SCHLESINGER: Mercader says that he has a business deal he has to do in Mexico. 

NARRATOR: In early 1940, Sylvia, besotted, follows her lover south. They set up home together. Sylvia is already acquainted with Trotsky and his family through her sister - another Socialist Workers Party die-hard - and she renews that relationship in Mexico. She takes a job volunteering with the great man as one of his secretaries. Initially, Ramon keeps his distance. 

HENRY SCHLESINGER: He doesn't attempt to go into the compound. He pretends to be apolitical. 

NARRATOR: The NKVD is willing to play the long game. Ramon takes Sylvia to and from work each day. While he waits to collect her, he slowly begins to earn the trust of Trotsky’s orbiters.

HENRY SCHLESINGER: [He] makes friends with all of the guards, and loans his fancy car to them for several weeks. He has smoke breaks with them, so he becomes a familiar face among the security. 

NARRATOR: Unbeknownst to Sylvia, Ramon has been joined in Mexico by his mother, Caridad, and her lover, Leonid Eitingon - the mastermind behind the honeytrap.

HENRY SCHLESINGER: And they're staying at a motel safe house.

NARRATOR: Later, under interrogation, Sylvia Ageloff would recall noticing Ramon writing encoded letters, presumably to Eitingon. Perhaps her affection for him caused her to overlook this behavior. Another school of thought has it that Sylvia was not the innocent she would later claim to be. But for now, we’ll stick with the official narrative. In time, Ramon Mercader - albeit under an alias - became a familiar face on Trotsky’s estate.

HENRY SCHLESINGER: He's worked his way into the compound and he's become friends with Trotsky. He brings gifts to Trotsky and his wife and son. He becomes a trusted figure.

NARRATOR: It’s during this period in early 1940, before the May raid, that Trotsky receives an unexpected letter.

HENRY SCHLESINGER: While this is going on, interestingly enough, a Soviet defector, Alexander Orlov, writes two letters, one to Trotsky and one to his wife, warning of an assassination attempt, and then tries to contact them by phone. 

NARRATOR: Ironically, Trotsky - who is usually trusting to a fault - refuses to heed the defector.

HENRY SCHLESINGER: Trotsky believes it's a provocation. It's a Soviet provocation and ignores the warnings.

NARRATOR: You can understand why. Up until Alexander Orlov’s defection in 1938, he had been one of Stalin’s chief witch hunters, arresting and executing Trotskyists. When Stalin’s paranoia trained itself on him, he fled to Canada. If you were Trotsky, why would you assume Orlov was contacting you?

HENRY SCHLESINGER: To stir distrust within his small circle in Mexico. 

NARRATOR: After more than a decade in exile from the Soviet Union, Trotsky needed to trust those closest to him. This was a fact that the NKVD happily used to their advantage.

HENRY SCHLESINGER: Orlov finally gives up, and he's got his own problems. His daughter is ill, terminally ill and he's on the run from both the FBI and the KGB at that point. 

NARRATOR: As we know, on the 24th of May, 1940, Trotsky realized that Orlov’s warnings were legitimate. A trusted member of his security team, an American called Robert Sheldon Harte, appears to give an NKVD hit-squad access to the villa. Harte is murdered for his trouble, and Trotsky, never believing in his guilt, mourns him as a friend, leaving a gap wide open for another young, male acolyte to step into. Ramon begins to grow close to the revolutionary whose guard is still down.

MICHAEL SMITH: The way that he insinuated himself into the household certainly made use of Trotsky's naivety in that sense.

NARRATOR: After the failure of the May raid, Leonid Eitingon is instructed to retool his infiltration plan into an assassination. Fortunately, Ramon Mercader - a trained killer and war veteran - is perfectly placed to do the deed. The trio - Ramon, his mother, and Eitingon - begin to put a plan together. First, they needed to assess the estate’s vulnerabilities.

HENRY SCHLESINGER: They had increased security, so the door had to be opened by one of the guards remotely.

NARRATOR: Understandable, given recent events. But this means that a guard controls access to the villa - somebody is listening. A gun, then, is out of the question.

HENRY SCHLESINGER: So they needed a way to kill Trotsky silently, so he could leave the house and then just walk out and be buzzed out by a trusted guard or a trusting guard.

NARRATOR: Ramon Mercader would need to take a subtler approach to Trotsky’s killing. If he could murder him without drawing undue attention, then he would be on his way out of the country before anyone on the estate discovered the body and raised the alarm. So then, the question is: How best to dispense with the troublesome revolutionary?

HENRY SCHLESINGER: So they had originally planned on using an iron bar. He was strong enough and he was battle-hardened. He wouldn't have hesitated. 

NARRATOR: But by chance, Eitingon and Caridad come across a more suitable weapon, one more likely to deliver the intended result.

HENRY SCHLESINGER: At the last minute, they find this climbing ax. Most people believe it's an ice pick, the kind they use in a cocktail lounge. In fact, it's an ice ax used for mountain climbing, a very nasty-looking tool. 

NARRATOR: The head of an ice-ax is made up of two parts; the pointed pick, and the adze, a hammer-like implement for breaking apart tougher sections of ice. The adze can deliver the kind of focused blunt force trauma that should induce unconsciousness with a minimum of fuss. Then, it’s just a case of finishing the job.

HENRY SCHLESINGER: And they find it in the storage shed or at the motel where they're staying. It belongs to the son of the owner. And they cut it down from 32 inches to 12 inches, the handle, so he could hide it effectively. 

NARRATOR: On the 20th of August, 1940, the plan was put into action. Ramon Mercader enters Trotsky’s estate. Nothing unusual about that. He claims that he wishes to get the great man’s feedback on an article he has written for a communist paper.

MICHAEL SMITH: It was odd because Mercader is wearing a raincoat when he arrives, and it's hot weather in Mexico. 

NARRATOR: But the raincoat does serve a purpose - to conceal the ice ax. Before long, Ramon has an audience with Trotsky. He lays his raincoat on the table. The moment that the target bows his head to read the article that the Spaniard has brought to him, Ramon strikes.

MICHAEL SMITH: He hits him over the head with it, with the blunt end.

NARRATOR: The ice ax drives more than two inches into Trotsky's skull, piercing his brain. This should be a clean kill. But the old Bolshevik puts up a fight. 

HENRY SCHLESINGER: It hurts. Trotsky is still conscious. He lets out a large, loud scream.

NARRATOR: This has not gone to plan. 

MICHAEL SMITH: Trotsky isn't killed. He tries to wrestle with Mercader, and there's noise, it's far from quiet. Trotsky's bodyguards come in and they pretty much try to kill Mercader. 

NARRATOR: Before they can, Trotsky - ever the loyal friend - steps in.

MICHAEL SMITH: Trotsky says: “No, we need to know why he's done this.”

NARRATOR: The guards hold Mercader until he can be arrested by the Mexican police. Luckily, the NKVD has prepared a contingency for this outcome.

HENRY SCHLESINGER: In Mercader's pocket there's a letter, a long rant against Trotsky about how Trotsky prohibited him from marrying Ageloff, which was to throw off the scent of the police in case he was captured. 

NARRATOR: On the surface, this seems like a crime of passion, rather than a targeted assassination by a state apparatus. Outside the estate, two cars await Ramon’s reappearance. When he fails to return, they tear away.

HENRY SCHLESINGER: Mercader's taken into custody, Caridad and Eitingon, they were waiting outside the compound for him. They take off and there's a plane waiting for them. They fly out.

NARRATOR: If you’re thinking about your own mother, and hoping against hope that she’d stick around if you were caught in a similar jam, then remember this - both Caridad and Ramon were true-believing communists in the Stalinist mold. Ideology always came first. Meanwhile, Leon Trotsky is admitted to the hospital. A day later, on the 21st of August, he succumbs to blood loss and shock. For him, the revolution is over. Mercader is found guilty of his murder.

HENRY SCHLESINGER: He's given 19 and a half years. He serves all of it.

NARRATOR: On his release, just like Anna Chapman 70 years later, he is given a warm welcome in the Motherland. Along with his mother, he is designated a Hero of the Soviet Union. And Leonid Eitingon? Does he get a happy ending too?

HENRY SCHLESINGER: He returned to Moscow and got caught up in the Purges. 

NARRATOR: Stripped of his titles and accolades in a purge that targeted Russian Jews within the Kremlin, Eitingon died in relative obscurity in 1981, at the age of 82. Which just leaves Sylvia Ageloff. Naturally, as the lover of Ramon Mercerder, she falls under immediate suspicion in August of 1940.

HENRY SCHLESINGER: The Mexican authorities couldn't believe that Ageloff wasn't involved. 

NARRATOR: In fact, a subsequent investigation by the FBI and Mexican authorities is convinced that Ageloff knew exactly what she was doing. They’re about to throw the book at her when she’s cleared by higher-ups. To this day, we don’t know exactly why.

HENRY SCHLESINGER: She was cleared and she returned to Brooklyn and became a kindergarten teacher, changing her name. At first, she was portrayed as a femme fatale, a tall, willowy blond in the local press, and then that faded away. 

NARRATOR: No accolades, no fame, no fortune. Whatever her true involvement, Sylvia Ageloff was glad to wash her hands of this insalubrious period in her life. A quiet note on which to end one of the most famous, but little-understood honeypot operations of the 20th century. It’s a case that brims with the essence of spycraft - its ability to empower individuals, or small groups, to cause powerful ripples in history. Who needs an Army when you have an ice ax? Before we go, we’d like to thank Henry Schlesinger and Michael Smith for lending their expertise to this anthology. Henry’s latest book, Honeytrapped: Sex, Betrayal and Weaponized Love, is available now. 

HENRY SCHLESINGER: And it's a history of sexpionage.

NARRATOR: And in August, you can pick up Michael Smith’s latest work, The Real Special Relationship.

MICHAEL SMITH: And it's an astonishing truth of the relationship between British intelligence and American intelligence, that is the real special relationship, 

NARRATOR: I’m Vanessa Kirby. Join us next time, as we follow the CIA’s first mission in Afghanistan in the aftermath of 9/11. Or, if you’re a subscriber to *Spyscape Plus* on Apple Podcasts, there’s no need to wait: you can listen to the first episode right now.

Guest Bio

Henry Schlesinger (pictured) is a New York author and journalist who has covered intelligence technologies, counterterrorism, and law enforcement. His work has appeared in many publications including Popular Science, Technology Review, and Smithsonian magazine. He is also the author of Spycraft.

Michael Smith served in the British Army Intelligence Corps and has worked as a journalist for the BBC, Daily Telegraph, and The Sunday Times. He is also the author of several books including The Secrets of Station X, The Spying Game, and Foley. He lives in England with his wife and family.

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