Bosphorus bounty: A fisherman sorts his catch of mackerel.
LEON TROTSKY WAS PERHAPS the most reluctant visitor ever to arrive in Istanbul. Even before he had stepped ashore, he handed a note to the customs official who boarded his ship. “Dear Sir,” he wrote, addressing Mustafa Kemal. “At the gate of Constantinople, I have the honor to inform you that I have arrived at the Turkish frontier not of my own choice, and that I will cross this frontier only by submitting to force. I request you, Mr. President, to accept my appropriate sentiments.”
The note was dated February 12, 1929. It was one of the coldest winters ever. Trams had to be dug out from snowdrifts, wolves were spotted in outlying neighborhoods, and for the first time in more than a century, ferries stayed moored to their piers to avoid the chunks of ice that floated down the Bosphorus. The train from Paris spent several days buried in a snowdrift, the incident that would inspire Agatha Christie’s Murder on the Orient Express. Trotsky and his wife, Natalya Sedova, had spent the previous twenty-two days on trains as well, slowly covering some three thousand miles westward from Kazakhstan to the port of Odessa. For two years, the family had been in internal exile in Central Asia, relegated to the far reaches of the Soviet Union by Joseph Stalin.
Although Trotsky had been one of the makers of the Bolshevik Revolution—a close associate of Vladimir Lenin and leader of the Red Army during the civil war—Lenin’s death in 1924 had opened the door to Stalin’s ambition. Stalin had chipped away at the edges of the old Bolshevik elite for years, but by the late 1920s he was powerful enough to take on Trotsky, the figure with the widest following outside Stalin’s own circle and the clearest claim to succeed Lenin as leader of the Soviet Union. On Stalin’s orders, the Soviet secret police, the OGPU, first escorted Trotsky and Natalya to the windy plains of Kazakhstan. Then the police were on hand in Odessa to supervise the family’s transfer to the steamer Ilyich, with no cargo and no civilian passengers besides the Trotskys and their son Lyova, and the voyage to Istanbul. Turkey had agreed to allow the family to enter the country, but this was not a gesture of sympathy for Trotsky’s politics. It was the opposite: evidence of the fact that, by the late 1920s, the Turkish state believed it had adopted the most useful bits of the Soviet model while successfully scotching direct Soviet influence.
In any case, the Soviets intended to keep an eye on their most famous exile. Trotsky was accorded the full courtesy of the Soviet Embassy as he made arrangements for housing. For the next several weeks, a wing of the embassy was reserved for his use. Yakov Minsky, the Istanbul representative of the OGPU, was put in charge of keeping tabs on him as well as helping the family to find longer-term living quarters. It was odd for Trotsky to be treated like a guest by a government that had officially condemned him, in absentia, for counterrevolutionary activity and plotting the overthrow of the state. It was even stranger for the government to allow him to write letters of protest to the New York Times and other Western newspapers. But no one, least of all Trotsky himself, believed his predicament would last for long. He had arrived in the city under duress, and he had no intention of staying.
Trotsky had been exiled twice before, to Siberia and the Russian North, during his period as an underground revolutionary in the tsarist era, and he was used to the concept of starting a new life as an émigré. The two earlier periods of exile had given way to triumph: the 1905 Russian revolution that forced the tsar to create a Russian parliament and the October 1917 revolution that elevated the Bolsheviks to power. He had no desire to stay in a country where he could not speak the local language, he told Turkish journalists, and he hoped that soon a visa would come through for Germany, Britain, or France. There, he would be able to continue his political work on behalf of international socialism while also railing against the usurper Stalin.
The Soviets likewise believed his Turkish exile would be a temporary affair. Istanbul had the triple virtue of being an easy sail from the Soviet coast, located in a country willing to take in Trotsky, and full of people who might relish the chance to kill him. After all, with plenty of Whites still hanging around the back alleys of Pera, someone would surely find irresistible the prospect of assassinating an old Bolshevik enemy. Minsky, the Soviet secret police agent, even seems to have kept Trotsky informed about all the White and foreign spies working in Istanbul. That may have been a way of helping Trotsky avoid them. It may equally have been a clever trap: a way of arousing Trotsky’s curiosity and laying the groundwork for branding him a foreign spy himself, if he ever happened to have contact with capitalist operatives.
Natalya and Lyova were allowed to leave the embassy to look for housing, and Trotsky himself could occasionally be seen walking along the trolley tracks in Pera, bundled up against the winter cold and flanked by guards. Minsky was nervous about keeping the Trotskys in the embassy for too long, for fear that he would become the de facto landlord of Stalin’s nemesis. In the end, Minsky became a reluctant real estate agent. He came forward with multiple options for accommodation, all of which failed to suit Trotsky’s specifications, especially in terms of security. Exasperated, Minsky finally booted the family out of the embassy and down the street to the Tokatlian Hotel, from which Natalya could continue the housing search on her own. After another move to an apartment, in late April 1929 she managed to find a place an hour and a half by ferry from the city center. It was a house where Trotsky could continue his writing and political work in relative safety while making plans for his next move.
Büyükada, or Prinkipo, was the largest of the Princes Islands, a group of nine arid islands popping up like a dinosaur’s back from the Sea of Marmara. A convent on Büyükada had once served as the preferred locus of exile for Byzantine nobles who had run afoul of the emperor, and smaller islands in the chain had continued to be dumping grounds as late as the Young Turk era. Stray dogs, for example, had been one of Istanbul’s public health hazards for centuries, and beginning around 1910, in a rolling campaign for order and cleanliness, the city government ordered tens of thousands of them rounded up and shipped to the rocky Hayırsızada—Good-for-Nothing Island. Rival packs formed to guard rainwater pools and fight over stray birds. For years afterward, it was said that on quiet evenings, with just the right southerly wind, Istanbullus could still hear their yelps and howls.
In the 1840s, the Ottomans had begun regular ferry service to the habitable islands, and Büyükada in particular became the major summer residence for the city’s wealthy merchants, especially Greeks. Wood-frame houses with whitewashed verandas and louvered doors provided relief from the stifling summer heat. Private automobiles were (and still are) prohibited, so horse-drawn phaetons carted locals and visitors around the island’s few roads, cushioned by a deep layer of pine needles. At the height of the summer season, white and purple oleander and bougainvillea framed the roadsides and spilled over garden walls. Along the leafy Çankaya Avenue, which wound down to the ferry landing, massive villas and their dependent guesthouses looked out on the turquoise sea and the low hills of the Anatolian coast.
Like Karl Marx in the previous century, Trotsky relied for his well-being on the kindness of capitalists he one day hoped to crush. One after another prominent Turkish businessman came forward to help him begin a new life in exile, perhaps attracted by the thrill of being close to a political celebrity or eager to court an enemy of Stalin. A former Ottoman official offered to rent the guesthouse of his villa. The expansive grounds lay on the downhill side of Çankaya Avenue and ended in a small cliff facing the sea. “The waves of the Sea of Marmara lapped the shore a few steps from our new home,” Natalya recalled. “It was a beautiful place, spacious, peaceful, set in the blue sea and bathed in golden sunlight most of the time.”
A fire, probably caused by a faulty water heater, raced through the house in March 1931. Trotsky reportedly sued both his landlord and his housekeeper for negligence, but that did not solve the immediate problem of finding new accommodation. The family was once again on the move—first to a hotel on the island, then to a walled house in the Moda neighborhood on the Asian mainland, then back to a red-brick house on Büyükada owned by a Turkish shipping magnate and located a short walk from the original residence. There they settled into life amid plum and fig trees inside what islanders called a rakı kö
kü—a small house built for sipping anise-flavored liqueur and enjoying the view north toward Istanbul proper. It was now the unlikely home of the prophet of world revolution.
Throughout his stay on the island, Trotsky grew increasingly fearful for his own safety. With both White Russians and Bolshevik agents present in the city, he had reason to be afraid. He routinely carried a small pistol and never appeared outside without a guard. Like a crotchety old man yelling at children to get off his property, he might yank at the beard of a Greek Orthodox priest to make sure he was not an assassin in disguise or pull a gun on a local fisherman who had suspiciously trawled the same spot for too many days in a row.
Islanders were less than enthusiastic about their most famous resident. Trotsky hired local guards, gardeners, and servants, but stories circulated about his peculiar requirements: for deaf cooks, so they would not be able to report on his conversations, or for illiterate cleaning people who would not be able to read his correspondence. His conversation was normally laced with sarcasm. When he happened to find someone in the household taking a rest or reading a book, he would exclaim, “Here is the Russian emigration!” He also had the habit common to people too comfortable with their own power: He would christen those around him with odd nicknames that then became, in his mind, their new identity.
The only friendship he seems to have struck up was with a local Greek fisherman, Haralambos. The two could be seen in a small boat, usually with guards or houseguests, bobbing in the water and drag-netting or line-fishing for red mullet and bonito in season. The fishing party would load up the boat with stones and cast them into the sea to drive the great schools of fish toward the nets. Trotsky and Haralambos would call out to each other in their own private language braided from Turkish, Greek, Russian, and French. In these moments, Trotsky seemed most playful and at ease. “Ah, Comrade Gérard!” he once teased his lawyer, Gérard Rosenthal, “if you strike the bourgeoisie like you attack the fish, they’ll have a pretty long life!”
Even then, Trotsky rarely felt truly safe. Once, a small girl—later the distinguished Turkish writer Mîna Urgan—swam toward the boat and grabbed onto the gunwales. An agitated Trotsky yelled at his guard to shoo her away and whack her fingers with his rifle butt. When the fishing was good, though, he would return to the house in excellent spirits and spin off new writings, dictated to a secretary with feverish speed.
Unfettered by the restrictions imposed on his work in the Soviet Union, he could fully speak his mind and communicate with the international socialist community. He began editing—and almost singlehandedly writing—a new bulletin that reported on the work of the anti-Stalinist opposition. He started writing his autobiography, My Life, based on notes he had already made while in Kazakhstan; he finished a draft within a few months of his arrival in Istanbul. He also made initial notes for a history of the Russian revolution. Book contracts and publishing deals came from Germany and the United States. Editorials and political essays streamed in the opposite direction to major Western newspapers eager to publish Trotsky’s thoughts on the world situation—his “ululations from the Bosphorus,” as Winston Churchill, one of Trotsky’s targets, called them. The revolution was surely over, Churchill said, when “the Communist instead of bombs produces effusions for the capitalist Press, when the refugee War Lord fights his battles over again, and the discharged executioner becomes chatty and garrulous at his fireside.”
Lyova was marshaled in to serve as his father’s secretary, managing the tide of correspondence and assisting Trotsky with the growing numbers of guests making the pilgrimage from the mainland to see someone who had become Istanbul’s—and perhaps the world’s—most sought-after has-been. Letters arrived from graphologists requesting handwriting samples. Methodists wrote to explain the advantages of Christianity. Astrologists offered readings of his star chart. Autograph collectors kindly asked to add his signature “to those of two American presidents, three heavyweight champions, Albert Einstein, Colonel Lindbergh, and of course Charlie Chaplin,” Trotsky recalled. He later employed a small staff—or chancellery, as he termed it—to deal with the workload of manuscript preparation, letter writing, and monitoring of international affairs.
Trotsky’s break with Stalin had been a spectacular development, but it was one part of the larger differentiation among the world's socialists: those who still looked to the Soviet Union as the leader of global revolution, those who were forging their own paths to communism, and those who believed that the Russian experiment was destined to burn itself out, soon to be succeeded by new movements arising in Europe’s overseas colonies. Trotsky now came to assume a role he had never held: a pole around which disaffected radicals around the world—especially those most committed to permanent revolution and the spread of revolutionary ideas—could coalesce. Like many famous exiles, he was becoming chiefly a totem, essentially powerless except for the force of his personality and words. “Here on this island of quiet and oblivion echoes from the great world reached us delayed and muffled,” he jotted in his diary.
It was one thing to imagine Trotsky as the sage of Büyükada. It was another actually to meet him. Visitors to the island almost always found themselves on a kind of anti-pilgrimage. “He seems too small for the struggle,” wrote Max Eastman, the American poet and political radical, who visited in 1932. Eastman expected to engage in deep discussions about the inevitable triumph of the socialist cause, but he found Trotsky obsessing about more mundane concerns, especially his finances.
His writing generated substantial sums of money. A string of newspaper articles brought in fees of ten thousand dollars. The American edition of My Life garnered an advance of seven thousand. The Saturday Evening Post paid forty-five thousand to serialize his History of the Russian Revolution. But Trotsky was spending more than a thousand dollars a month on bodyguards, housing, food, and especially books, since his library and extensive collection of photographs from the revolution had been destroyed in the fire at the first house. To economize, he kept little in the way of furniture, wandering about worriedly in mainly empty rooms. He let the garden go to seed. His dog, Tosca, chased birds through the tall grass and saplings. “We seemed to camp rather than live there,” recalled one of his secretaries.
Eastman had signed on as Trotsky’s literary agent and was largely responsible for the income flowing into his bank account. But in their conversations, Trotsky tended to talk down to Eastman, complaining about the stinginess of Western capitalists and the tightfistedness of American publishers, even though Eastman was an old friend and one of the leading voices of the American Left. Trotsky squirmed out of contracts and groveled for extensions. He promised to deliver commissioned manuscripts but then insisted he had never done so. During Eastman’s visit, Trotsky spent most of their time together trying to convince Eastman to collaborate on a stage play about the American Civil War. Trotsky believed it would be a hit on Broadway, a work that would combine Eastman’s knowledge of American history with his own expertise on troop movements and tactics. Eastman considered the idea ridiculous.
Trotsky had “followers and subalterns,” Eastman concluded, but he was incapable of having real friends. Trotsky would not have disagreed. “I do not measure the historical process by the yardstick of one’s personal fate,” he wrote. “On the contrary, I appraise my fate objectively and live it subjectively, only as it is inextricably bound up with the course of social development.” Enemies, he would say routinely, should be shot. He saw this philosophy as a virtue, but most of the people who knew him during his exile seemed to see it as his signature flaw, both as a person and as a politician. He preferred the safety of the podium and the blinding anonymity of the limelight to intimate conversation and real engagement. He was unsuited to exile not because he lost power—his political influence had been waning throughout the period when Stalin’s was rising—but because it robbed him of the two things that made it possible for him to live in the world of reality: a platform to inhabit and a program to implement.
Like the Whites, Trotsky believed that both of these things might one day return if he could only move out of Istanbul and find his feet again. When he was not writing essays or corresponding with adherents, he was filling out visa applications. Germany declined to admit him, as did the Netherlands, Italy, Austria, and Spain. Denmark allowed only a short trip to Copenhagen. The British socialists Sidney and Beatrice Webb, founders of the London School of Economics and Political Science, visited Büyükada two months after Trotsky’s arrival, but even they could not convince the British government, then under sympathetic Labour Party control, to grant him admission. Trotsky ended My Life with a wry chapter he called “The Planet Without a Visa.”
Finally, through the intercession of French socialists, he managed to secure asylum in southern France, with the proviso that he never visit Paris and remain under continuous police surveillance. The years in Istanbul had been among the calmest, most creative, and “least unhappy” of his entire exile, according to his preeminent biographer, Isaac Deutscher. Trotsky recorded the final Büyükada days in his diary: “Our house is already almost empty; wooden boxes stand below, and young hands are busy hammering nails. In our old and neglected villa, the floors this spring were decorated with paint of a composition so mysterious that tables, chairs, and even feet stick lightly to the floor even now, four months later.” He couldn’t pass up the obvious metaphor. He felt that his feet somehow had become stuck to the island. He had aged there. His hair had gone white, and his brow had furrowed. Heart trouble and gout had set in. In July 1933, he and Natalya—Lyova had already managed to move to Berlin—made their way down Çankaya Avenue for the last time and boarded a small ship bound for Marseille.
Trotsky had been delivered from his Turkish exile and was on his way to a new life, first in France, then in Norway, then finally in Coyoacán, a borough of Mexico City. He and Natalya carried newly issued Turkish passports that made their status clear. “The bearer of this passport,” declared the first page, “is not under the protection of the Turkish state.” But as he sailed along the coast of the island, past the charred upper floor of his first Turkish house and into the open sea, he was now in more danger than ever before. Istanbul, in a way, was going to follow him.
At the beginning of the 1920s, John Dos Passos had come downstairs to find the lobby of the Pera Palace in chaos. In the lounge, Hellenic, Italian, and French gendarmes were trying to converse, each in his own language. A British member of parliament was downing a cocktail while attempting to explain something to a soldier. Bellhops and doormen were carrying out a man in an astrakhan hat and frock coat, leaving behind a pool of blood on the mosaic floor and a stained, plush-red armchair. The hotel manager was walking back and forth with sweat beading up on his brow, trying to learn what had happened. The envoy from Azerbaijan had been assassinated, someone said, and the gunman was a bearded Armenian. Or perhaps it was a clean-shaven Bolshevik, someone else said, who came right up to the doorway and shot him dead. Meanwhile, a waiter implored guests to settle their bills.
It was not an unusual scene, both during and after the Allied occupation. Intrigue of some sort seemed to be the city’s common currency. With so many Russians living in Istanbul and its outskirts, the city became both a battleground for intra-Russian disputes and a potential target for Bolshevik agents. In October 1921, the Wrangels’ residential yacht, the Lucullus, was rammed and sunk by a steamer while at anchor in the Bosphorus, a probable assassination plot that the general and his wife escaped only because they happened not to be on board at the time. A certain Kuznetsov, lodged at the Pera Palace, was known to be the centerpiece of Bolshevik propaganda efforts, with a particular interest in turning Cossacks and other White Russians to the communist cause.
“The Bosphorus was a dumping ground of all Europe’s war crooks and spies,” recalled Robert Dunn, an American naval official. The Pera Palace and Graveyard Street were natural points of attraction for foreigners and locals caught up in the game of intelligence gathering. The British Embassy stood at one end of the street, with a Turkish policeman permanently stationed outside to direct traffic to and from the Grande Rue. Farther along was the old Petits-Champs Park, with its theater and clubs. Next to the park was the Pera Palace itself and, next to that, the small grounds of the American Embassy. Then came the YMCA, followed by a British police station. During the Allied occupation, the headquarters of British naval intelligence and the officers’ mess of the British contingent were located in buildings just across the street. Bertha Proctor’s bar and sometime brothel anchored the southern end.
Even by the late 1920s, when the foreign presence in the city was much diminished, it was still advisable to be careful with conversation and to check around corners in that section of Pera. Settling in Istanbul had involved “little deceptions and coercions,” Trotsky’s wife, Natalya, recalled. Trotsky may have seemed a conspiratorial eccentric to the islanders on Büyükada, but paranoia is a reasonable response if someone really is out to get you. The Soviet Embassy, today the consulate of the Russian Federation, was Trotsky’s first home in the city, but it was also the headquarters of the surveillance system that kept constant tabs on him. It lay at the center of a large and growing web of secret agents who hoped to make Istanbul the base for intelligence operations throughout southern Europe and the Near East.
“The network of spies was well-organized at Constantinople,” recalled Georgy Agabekov, a senior official in the foreign intelligence branch of the OGPU. Agabekov claimed that virtually all the correspondence of major anti-Soviet émigré groups in Istanbul, such as Ukrainian nationalists and Caucasus highlanders, found its way into Soviet hands. The Soviets were careful to balance the desire to infiltrate enemy organizations with the need for keeping operations low-key enough to avoid offending the Turks. Agabekov claimed that the Soviets had managed to finagle informers inside the Japanese, Austrian, and other foreign embassies; to intercept mail destined for White associations and for Trotsky himself; to sign up an Armenian bishop as a paid agent; and even to place an informant inside Trotsky’s house on Büyükada. Much of this was little more than enthusiastic bumbling, however. Agents were proud of their roles as zealous defenders of Bolshevism—too proud, in many instances—and stood out like sore thumbs to counterintelligence operatives in Istanbul, Paris, London, and other cities—“prancing along in [a] blue serge suit made to order by some Russian émigré tailor,” noted one disillusioned Soviet official.
Agabekov himself had the dubious honor of being the first defector from Stalin’s secret police, and it was his time in Istanbul that caused him to flip sides. In 1929 and 1930, he had been working in the city to set up a string of intelligence operations in Greece, Syria, and Palestine, while leaving Turkish affairs to his OGPU colleagues working out of the embassy. Agabekov always claimed that he had become disenchanted with the Soviet system, but the proximate cause was probably more prosaic. He seems to have fallen in love with a young English woman, Isabel Streater, whom he had hired as a language tutor. He at first offered himself to British diplomats as a defector, but they suspected a trap and treated him coolly. Finally, in January 1930, Agabekov and Streater fled separately to Paris, she via the Orient Express and he by sea, and eventually began a new life together as husband and wife.
Agabekov’s defection was a blow to the Soviet effort, but the Istanbul operation was accustomed to the regular turnover of personnel. Less than a year before Agabekov’s departure, sometime near the middle of 1929, Yakov Minsky, the OGPU station chief who had originally helped Trotsky settle in the city, fell ill and returned to Moscow. His successor was a dark-haired, round-faced operative with a reputation as a personable comrade. His gray-green eyes and witty demeanor seemed to make him irresistible to a string of female coworkers. Even today it is difficult to establish with clarity to whom he was married and when; he may have been married to several women at the same time. His official cover was that of a diplomat at the Soviet Embassy. His travel documents identified him as someone named Naumov. His superiors gave him the code names “Tom” and “Pierre.” His real name was Leonid Eitingon.
In many ways Eitingon had the ideal background for a Soviet agent, especially for someone working in an era long before the clear battle lines of the Cold War had been imagined. For more than a generation his family had cultivated the ability to live in many places at once. Eitingon was part of the extended family of Chaim Eitingon, a prominent Russian-Jewish furrier. The elder Eitingon had built up a fur-trading empire that stretched across the Russian Empire and abroad. When the empire ended, his family remained the principal conduit for the Soviet fur business, a major source of wealth for the new regime.
From Moscow to Leipzig to New York, the family oversaw an import–export firm that weathered the Russian civil war and remained lucrative well into the 1930s, when the Depression and the Stalinist nationalization of key industries shut off the spigot. Chaim’s son, Max, had grown up in the midst of a wealthy central European and Jewish world. He was the emblem of a family that had reinvented itself within a single generation, moving from the edges of a Russian shtetl to the European beau monde. Trained as a doctor, Max went on to become one of Sigmund Freud’s earliest acolytes and the chief codifier of Freudian training in psychoanalysis.
Max’s cousin, Leonid, was from the less-wealthy branch of the Eitingon clan. Born in 1899 in the Mogilev district in what is today Belarus, he was the son of a minor bourgeois factory owner and followed the path of many upwardly mobile Jewish young men in the waning days of the Russian Empire: he joined the communists, at first signing on with the Socialist Revolutionary Party and then, after the Bolshevik coup, enlisting in Trotsky’s Red Army. In the civil war, he fought to root out counterrevolutionaries in his native district as a member of the Cheka, Lenin’s secret police, a job that he seems to have carried out ruthlessly. He was the first generation of good soldiers fighting for the new socialist motherland and, in those days, for world revolution as well—an outcome that Lenin, Trotsky, and other Bolshevik leaders believed was all but inevitable.
Shortly after the end of the civil war, Leonid Eitingon was assigned to foreign intelligence work in Harbin, a Chinese city that was in many ways the East Asian equivalent of Istanbul at the time. It harbored a large community of former White Russians who had chosen to escape east, rather than south, as Bolshevik armies swept through the old empire. Like Istanbul, it was both cosmopolitan and a hotbed of espionage and intrigue, a small island of old Russian culture in a foreign sea. Eitingon’s activities—gathering information, turning Whites to the Bolshevik side, and quite possibly arranging the assassination of key leaders in the White community—eventually raised the ire of the Chinese authorities, who, like the Turks, were reluctant to see their country become a battleground for someone else’s disputes. When Chinese police broke into the Soviet Consulate in Harbin and searched its files, Eitingon’s true identity as a secret police agent was discovered. He was sent packing to Moscow.
In 1929, when he was transferred to Istanbul, Eitingon was immediately placed in charge of the real prize in Soviet foreign espionage: keeping an eye on the aging exile who had recently taken up residence on Büyükada. It was a sign of Eitingon’s fine-tuned political sense that he managed to weather his time in Turkey without acquiring even a hint of Trotskyite leanings. One of the professional hazards of being stationed in Istanbul and monitoring the Soviet regime’s archenemy was that the assignment placed an agent in the dangerous position of possibly being turned himself—brought over to the Trotskyite camp and made an informant for the man sitting in isolation on the island. In the 1930s, when Stalin began his purge of the Soviet bureaucracy, at least one former Istanbul agent, Yakov Bliumkin, was dismissed and executed for having gone over to the Trotskyites. There is no evidence that Trotsky’s supporters ever managed to engage in such counterespionage on a large scale, but authorities in Moscow clearly feared the magnetic power of Trotsky’s personality and ideas.
Eitingon, however, survived the Stalinist purges untainted. After leaving his Istanbul assignment, he was placed in charge of espionage operations in western Europe, serving as one of the most experienced and highest-ranking secret operatives working abroad. He briefly served as case officer for Guy Burgess, the famous British traitor and member of the so-called Cambridge Five spy ring. During the Spanish Civil War, Eitingon served as the Stalinist secret police’s deputy head of mission in Spain, training legions of commandos to fight the rightist forces of Francisco Franco and developing a friendship—perhaps even more—with a young Spanish communist named Caridad Mercader. Like Eitingon, Mercader was the product of a bourgeois family and someone whose own political convictions had pushed her into the anticapitalist camp. She had signed up with the anarchists and, after the defeat of the Left by Franco, fled with Eitingon to Moscow. Eitingon’s experience in Spain, his reputation for efficient work throughout Europe, and his personal relationship with Caridad all recommended him to head up a new operation that would soon unfold half a world away.
On a late August afternoon in 1940, Eitingon found himself in one of two cars idling on a dusty street on the fringes of Mexico City. He was monitoring an asset, much as he had done many years earlier in Istanbul. The asset was Ramón Mercader, Caridad’s handsome son, but things were not going well. Eitingon knew that relying on Ramón was a shaky way to run a mission.
Three years earlier, Eitingon had personally trained him as a commando and dispatched him to the front lines against Franco’s army, only to have him return wounded and gun shy. He was indecisive and given to nervous sweats. His only real advantage in the current operation was the fact that he had managed to ingratiate himself with the person who lived in the walled compound down the block, an old man whom Eitingon had personally given the Russian code name of “Utka,” the Duck. That personal connection was important, since Ramón’s mission was to kill him.
A house alarm was sounding. Dogs were barking. There was a commotion behind the front gate. The backup plan had been for Ramón to use his revolver if the mission went awry, but the absence of gunfire meant that even the fallback plan had gone badly. Eitingon ordered the cars to depart, leaving the assassin to find his own way out of the mess he seemed to have made. It was not until sometime later, once Eitingon was safely back in the Soviet Union, that he learned the details of what had happened.
That day, August 20, Ramón had arrived much as he had done each afternoon, parking his car outside the compound and waving at the armed guards to let him in. He made his way to the study where the old man sat working on a text. Minutes later, he pulled out a short-handled ice ax he had concealed in his raincoat and brought it down on the back of Leon Trotsky’s head.
Trotsky let out a piercing cry, so loud that Eitingon might well have heard it down the street. Natalya rushed into the study to find the two men separated, Trotsky leaning against a doorway and Ramón looking on dazed, seemingly surprised that the initial blow had not killed him.
Blood was everywhere. Trotsky’s guards burst in and grabbed Ramón, nearly pummeling the young man to death before Trotsky could order them to stop. Ramón’s testimony, after all, might be used to uncover who had planned the attack. Trotsky was still able to speak when an ambulance delivered him to a nearby hospital. “I don’t want them to undress me. I want you to do it,” he told Natalya before slipping into a coma. He died the following evening.
As Eitingon sped away, he could not have known that his career had just reached the high point from which he would begin a very long fall. Eitingon had the distinction of being the only Soviet agent whose own career had bookended Trotsky’s exile. He had arrived in Istanbul around the same time as Trotsky and then personally planned the attack that would liquidate him eleven years later. For his service, he and Caridad were awarded the Order of Lenin in a private ceremony in the Kremlin—he as the chief conspirator and she as the mother of the literal hatchet man. Ramón, ever the sap, spent the next twenty years serving a murder sentence in a Mexican prison.
By the early 1950s, however, Eitingon had fallen from grace. He was accused of playing a central role in the Doctors’ Plot, an alleged conspiracy by Soviet physicians, many of whom happened to be Jewish, to assassinate key Soviet leaders. In reality, the plot was a fabrication spurred on by Stalin’s paranoia over internal enemies, but the effort to unmask the supposed conspirators produced a frenzied antisemitic campaign that targeted senior Jewish communists. Eitingon was arrested, stripped of his medals, and jailed. He was eventually released but spent the rest of his life, until his death in 1981, as an outcast from the intelligence services, working as an interpreter. “There is one small guaranteed way not to end up in jail under our system,” Eitingon once joked to his boss. “Don’t be a Jew or a general in the state security service.” The old Bolshevik mastermind, who had quietly hounded Trotsky from Istanbul to Mexico City, of course was both, and he died in his own kind of internal exile.