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On November 2nd, 1962, the Cuban Missile Crisis was winding down. It had been the absolute height of the Cold War; the event that brought the US and USSR closest to nuclear war. The crisis had in large part been mitigated due to the placement of an incredible CIA source within the Soviet GRU; Colonel Oleg Penkovsky. He provided accurate intelligence on missile placement in Cuba. The CIA went to great lengths to protect his identity, including giving the impression that the information was coming from multiple sources, not just one.
Penkovsky was ultimately undone by a mole within the British government. The mole reported that Janet Chisholm, the wife of a British intelligence officer working in Moscow, was also active in collection activities herself. The KGB surveilled Janet and witnessed her meeting with Penkovsky. He was arrested on October 22nd. Eleven days later he sent an emergency signal to his CIA handlers that an imminent Soviet surprise attack was about to commence. The CIA couldn’t afford to ignore this possibility and sent case officer Richard Jacobs to check the pre-arranged dead drop; a matchbox hidden behind a radiator in an apartment building on Pushkinskaya Street. The KGB was waiting. Immediately after taking this photograph they seized Jacobs. He was able to drop the matchbox through a slit in his overcoat pocket and kick it away from himself, for what little good it did.
Jacobs was quickly kicked out of country, and Penkovsky was soon executed for crimes against the state. One of the best moles the West ever had in Moscow lasted just eighteen months. Rumors persisted for years that Penkovsky was cremated alive, and footage of his death was shown to GRU trainees afterwards as a warning of what happened to spies.
Originally posted to r/spycraft101.
Very interesting story. Thank you for posting 👍
Can I ask what was in the match box or the purpose of it ?
Can someone explain what a dead drop location is?
Smiley or Karla?
Just so I understand the entire story.
Once the undercover Russian (Oleg Penkovsky) was captured it says he sent a signal to the CIA 11 days after his capture? So this means in those 11 days he was interrogated, and once they knew the whole organization of things he was forced to send out the signal (which was fake and a trap) by his captors in order to capture this guy at the dead-drop location?
If anyone wants to read a great book on the spy who I think this is, read the Spy and the Traitor.
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Hey guys here’s where we did super secret stuff.
Nah it’s just Ivan getting his western drugs from the dead drop location. Little does his dealer know he is distributing it to the people, not sell it like capitalist pig!
What is a dead drop location?
Man, that is a long time to sit for a picture.