True Spies: Espionage | Investigation | Crime | Murder | Detective | Politics The Great Illegals, Part 2: The Ambassador | NKVD
Aug 19, 2025
Shaun Walker, a journalist specializing in Russian espionage and author of 'The Illegals,' dives into the thrilling world of Iosif Grigulevich, a cunning spy embedded in Italy's diplomatic circles. He discusses Grigulevich's rise amid Stalin's purges and the botched assassination of Trotsky, showcasing espionage's dark and dangerous twists. The tension between Tito and Stalin is examined through a lens of political maneuvering and identity transformation. Shaun reveals how espionage mirrors complexity in human relationships, leaving listeners on the edge of their seats.
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Early Spycraft In Spain
- Yosef Grigulevich used a flawless Spanish accent and charm to operate as a deep-cover NKVD translator and operative.
- He combined charisma with ruthless loyalty and violence learned in the Spanish Civil War to rise in Soviet intelligence.
The Botched Trotsky Raid
- Grigulevich led an assassination squad that attacked Trotsky's compound in Mexico posing as a Frenchman called Philippe.
- The raid failed to kill Trotsky but showcased Yosef's operational role and daring methods for Stalin's service.
Creating Teodoro Castro
- Yosef invented the identity Teodoro Castro using a Costa Rican writer's vouch and obtained a real passport and diplomatic backing.
- He and his wife used the cover to marry, travel, and embed in Latin America for long-term spycraft.
