Oleg Penkovsky
Russian spyWikipedia
10
MENTIONS
5
EPISODES
4
PODCASTS
Search complete. 10 mentions across 5 episodes found for "Oleg Penkovsky".
Oct 16, 2026
Charlton HestonNARRATOR
October 1962, a CIA spy in Cuba reported something strange going on in the Cuban countryside.
Jay DyerHOST
By the way, the Oleg Penkovsky stuff is in the Benedict Cucumber Snatch movie, The Courier, which we covered in the live stream.
Jay DyerHOST
If you want a bigger breakdown of that, go watch my breakdown of The Courier.
Charlton HestonNARRATOR
His report prompted a U-2 flyover of the island.
Charlton HestonNARRATOR
Photographs from this and subsequent flights revealed what the CIA believed were missile sites under construction.
Charlton HestonNARRATOR
CIA analysts checked the photographs against the manual of the Russian SS-4 medium-range missiles Penkovsky had given them.
Charlton HestonNARRATOR
In the manual was a diagram which showed exactly what a completed missile firing position should look like.
Charlton HestonNARRATOR
By comparing the diagram with the U-2 photographs, the CIA was able to determine that it would be several days before the missiles could be ready for firing.
Jay DyerHOST
This is huge piece of the puzzle, and if you don't get this, you don't know anything, and you won't be able to understand anything that's going on, and no one should listen to you until you know these things.
Jay DyerHOST
So if you haven't watched those movies, I recommend watching them because, by the way, The Courier is about Oleg Penkovsky, the defector, uh, and that will be...
Jay DyerHOST
He will be mentioned in this documentary, actually.
Jay DyerHOST
So let's, let's get back to the documentary.
Ben MacintyreGUEST
But the truth is, Michael, I think MI6 was rather surprised and indeed, um, somewhat Taken aback to have not one, but two KGB officers running simultaneously inside that hitherto really impenetrable organization.
Ben MacintyreGUEST
No one had ever had one, uh, since Penkovsky, who was a GRU officer, inside the building, you know, looking outwards.
Ben MacintyreGUEST
So to have two, they, which was another reason why they were a little distrustful of their own spycraft, was a, a, an extraordinary windfall for the time.
Michael FeinbergHOST
So your statement about the British approaching asset recruitment much more from a relationship perspective rather than a transactional encounter is something that I think holds true even today.
5 MINS LATER
Ben MacintyreGUEST
If the Iranians had caught them They would have, you know, that would have been it.
Ben MacintyreGUEST
They, they would probably have ended up in prison and possibly have been executed.
Michael FeinbergHOST
Yeah, just so people understand the stakes, um, you mentioned a different spy for the West earlier, Penkovsky, and if I'm not confusing historical personages in my own mind, I believe he was caught by the Russians, executed in particularly brutal fashion, and the execution was actually filmed and shown to intelligence trainees early in their training as a cautionary tale for what would happen if you betrayed the Soviet Union.
Ben MacintyreGUEST
Yes.
Bill CostanzaGUEST
And so it's just basically, and I talk about this a little bit in the book about, you know, when we establish categories, they have survival value, but there's drawbacks as well.
YolandaHOST
In your book, Bill, Aldrich Ames betrayed agents for money, while figures such as Oleg Penkovsky risked everything to help the West.
YolandaHOST
How can the same psychological framework genuinely explain both men?
Bill CostanzaGUEST
Well, y- if you look at Aldrich James, and in fact I, I met him once.
AkashiHOST
Okay, here it comes.
Lynn BuchananSOUNDBITE_SPEAKER
Finally, Russian Colonel Penkovsky tried to defect.
Lynn BuchananSOUNDBITE_SPEAKER
And he brought with him papers showing that the Russians had developed that And they were getting our secrets using psychic spies.
Lynn BuchananSOUNDBITE_SPEAKER
And everybody had a good laugh about that.