Stalin’s Man in Belgrade

On the morning of 27 April 1953 Yugoslavia’s communist leader Josip Broz Tito received the Costa Rican diplomat Teodoro Castro in a simply furnished room at the White Palace in Belgrade.

Tito had split with Stalin and the Soviet Union in 1948, and the meeting with Castro was one more small step in a plan to forge new alliances across the globe and cement Yugoslavia’s status as a communist power independent from Moscow. The charming diplomat, in his late thirties, extolled Tito and hinted at rich trading opportunities: Costa Rica could sell Belgrade the best coffee and cocoa in the world, and in return it would buy cement and industrial machinery. The pair chatted in English, with a translator occasionally stepping in when Tito needed help with a word. Both men sucked at pipes with a cigarette tucked vertically into the end, Tito’s trademark smoking style, which his visitor aped out of respect.

When the good-humoured meeting ended, Tito remarked to his aides that the Costa Rican was likeable enough, but his silver-tongued flattery was undoubtedly aimed at concluding a favourable trade agreement for his country. Tito was right to suspect an ulterior motive behind Castro’s charm, but it had nothing to do with a trade deal. The man Tito met that morning was a genuine, accredited Costa Rican diplomat, but his real name was not Teodoro Castro and he had never even been to Costa Rica, despite his ability to spin lengthy anecdotes about his supposed homeland.

His real name was Iosif Grigulevich, and he was a Soviet ‘illegal’, a deep-cover spy hiding under a foreign identity. A few months before this meeting, Stalin had given Grigulevich an important mission: not to sign an economic deal with Tito, but to kill him.

The Soviet illegals programme began almost immediately after the October Revolution brought the Bolsheviks to power in 1917, and continues to this day, with Moscow’s spymasters training Russians for years in language and etiquette until they can convincingly pose as foreigners. Their missions can last decades. The history of the illegals programme is filled with extraordinary transformations, but even by those lofty standards Iosif Grigulevich’s rise to become a respected diplomat of a country he had never visited stands out as particularly impressive. Born in the Lithuanian city of Trakai in 1913, Grigulevich spent time in the revolutionary underground of Wilno (later Vilnius), before travelling to Argentina to join his father, who had emigrated there.

Within a couple of years he spoke almost flawless Spanish, and in 1936 he travelled back to Europe, convinced he could be of use to the communist cause in the Spanish Civil War. His KGB file, as recorded by KGB archivist Vasily Mitrokhin who secretly copied parts of it and later took it and other files to Britain when he defected, records that he was personally involved in long and likely violent interrogations and the ‘liquidation’ of enemies. Later, he was picked to lead an assassination attempt on Stalin’s archenemy Leon Trotsky in Mexico City in May 1940.

After some years moving around Latin America using various different identities, in 1945 Grigulevich settled into one that would stick. In Chile, he got to know the Costa Rican consul and cooked up a story to impress him. A recent press report mentioned a Costa Rican landowner and coffee grower who had died childless. Grigulevich posed as the old man’s son, claiming he had been disowned because he had been born out of wedlock.

Years earlier, the story went, he had emigrated to Chile to escape the sad fact that he was unwanted at home. Now that his father was dead, ‘Teodoro Castro’ wanted to rediscover his Costa Rican roots. Before long Grigulevich had a passport identifying him as Castro, as well as a letter of recommendation from the consul general.

In 1948 he was dispatched to Italy, one of the most hotly contested battlegrounds of the early Cold War, together with his wife Laura, a Mexican communist who was given a fake Uruguayan identity. On arrival in Rome, Grigulevich paid courtesy calls to the main players in the city’s Latin American diplomatic and business communities. Soon, aided by his natural charm and flattery, he had an impressive contacts book. When Costa Rica’s ambassador to Spain visited Rome in 1951 and Grigulevich managed to set him up a meeting with the pope, the visitor was so impressed that he cabled San Jose recommending the impressive young Costa Rican in Rome be given diplomatic status.

Grigulevich presented his credentials to the Italian president in 1952 and became a member of the diplomatic party circuit in Rome. He hosted lavish parties for Latin American holidays, and frequently called on the pope. When the new US ambassador Clare Boothe Luce arrived in Rome in April 1953 she said curtly that she would not interact with any communist ambassadors, and would not invite them to her residence, the 16th-century Villa Taverna. Yet her papers, in the archive of the Library of Congress, show that one of her very first meetings was with a certain Teodoro Castro. Grigulevich wrote short reports back to Costa Rica on his activities, and longer reports to his real bosses in Moscow.

When Grigulevich also got accredited as ambassador to Yugoslavia in 1952, Stalin saw an opportunity to finally rid himself of the most troublesome leader in the communist bloc. There were no diplomatic relations between the two countries and Tito had purged his inner circle of Stalinists. Now there was a chance to get a trained killer into the room with him. Moscow’s spymasters drew up a series of ambitious assassination plans. In one, Grigulevich would release a plague serum during an audience with Tito. It would kill everyone except the assassin, who would be pre-vaccinated. In another, he would present Tito with a poisoned jewellery box.

But just as the planning reached the final stage, Stalin died. The audacious hit was called off, and not long after Iosif was withdrawn to Moscow. Far too many people already knew him in his guise as the Costa Rican ambassador for him to take on a new identity abroad. Instead, he embarked on a new life as a Soviet academic specialising in Latin America. Over a three-decade career, now under his own name, he wrote dozens of books, including a biography of the Mexican painter David Siqueiros, which neglected to mention that its author had once led its subject in a failed attempt on Trotsky’s life. Grigulevich died in 1988, with only a few trusted colleagues aware of his remarkable past.

Shaun Walker is the author of The Illegals: Russia’s Most Audacious Spies and the Plot to Infiltrate the West (Profile, 2025).