Spain In the late 1930s, Grigulevich was sent to
Spain to monitor the activities of the Workers' Party of Marxist Unification (
POUM, the militia with which
George Orwell served), in the midst of the
civil war in that country. Grigulevich worked under
NKVD general
Alexander Orlov, using the code names MAKS and FELIPE, and organized so-called "mobile groups" that killed, among other actual and suspected
Trotskyists, POUM leader
Andreu Nin. In this mission Grigulevich apparently collaborated with the assassin
Vittorio Vidali, known in Spain as "Comandante Carlos Contreras." To help justify the murder of Nin and the Stalinist campaign against the Trotskyites in Spain, Orlov instructed Grigulevich and a Spanish journalist to manufacture a dossier of "documentary evidence" of the collaboration of Nin and his associates with the
nationalist forces of General
Francisco Franco (which the Soviets identified as "fascists"). The Soviet defector
Walter Krivitsky had learned of the plot and sent a warning to Trotsky through the US activist and "
fellow traveller"
J. B. Matthews. Trotsky acknowledged the warning, writing in a letter that "Krivitsky is right. We are the two men the
OGPU is sworn to kill."
Argentina After the failed attempt to assassinate Trotsky, Grigulevich and two of his accomplices (Laura Araujo Aguilar and
Antonio Pujol Jimenez) were helped by
Pablo Neruda to escape from the Mexican police. After
Ramón Mercader killed Trotsky, Grigulevich was awarded with the
Order of the Red Star.
United States During the late 1940s, Grigulevich's background as a Lithuanian-born Karaite and a polyglot who had lived outside of the USSR for most of his life marked him out as a target of the Stalinist campaign against "
rootless cosmopolitans". In 1948, Grigulevich's Mexican-born wife was taken hostage by his Soviet bosses. While his wife was imprisoned, Soviet intelligence officials demanded several loyalty tests from Grigulevich, who was sent to operate a
dead drop for another Soviet spy,
Rudolf Abel, in
New York City. Grigulevich later declared that, during this time, he was in constant fear for his life. Grigulevich pretended to be the illegitimate son of a wealthy Costa Rican coffee producer, already deceased, and styled himself
Teodoro B. Castro (using a middle initial in the "American manner"). He successfully established an import-export business in
Rome and made extensive personal contacts with business figures and prelates of the
Catholic church. Castro also became a friend and business partner of former Costa Rican president
José Figueres, who promoted his appointments in the Costa Rican diplomatic corps. In 1951, Castro became ''chargé d'affaires'' of the Costa Rican embassy in Rome, serving also as advisor to the Costa Rican delegation to the sixth session of the General Assembly of the
United Nations, in Paris. In 1952, he officially became the Costa Rican
ambassador to both Italy and Yugoslavia. In Rome, he befriended Prince Giulio Pacelli, a nephew of
Pope Pius XII who served as Costa Rica's representative to the
Holy See. In 1953, Castro was inducted as a knight of the Catholic
Order of Malta. At the same time, he was secretly granted membership in the
Communist Party of the Soviet Union.), Grigulevich met with Tito on several occasions. However, the death of Stalin in March 1953 prevented the assassination plans from going forward. At this time,
Alexander Orlov, who had once managed Grigulevich in the Soviet spy network and who had later defected to the US, began to publish ''The Secret History of Stalin's Crimes''. For fear that his identity would be exposed by Orlov, Grigulevich was summoned back to Moscow. In Rome, the sudden disappearance of the Costa Rican ambassador, along with his wife and daughter, created a stir, with rumors of
Mafia involvement circulating in diplomatic circles. ==Historian==