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A Picture from History: Oleg Penkovsky

We look into Oleg Penkovsky, a Soviet double agent who funneled thousands of intelligence documents to the West during the Cold War.

    The Cold War was growing hotter by the hour. The threat of nuclear war — always hanging overhead — was now at a fever pitch as American intelligence reports proved that Soviet nuclear warheads had been stationed on the island of Cuba.

    And those nukes? 

    They were pointed directly at Florida. 

    Cuban launch sites
    Cuban launch sites

    As the world sat just two minutes to midnight on The Doomsday Clock, John F. Kennedy and American intelligence officials scrambled for information.

    If they could figure out weaknesses and where they resided, they could exploit them…

    Enter Oleg Penkovsky 

    Oleg Penkovsky
    Oleg Penkovsky

    Born deep in the heart of Russia, Penkovsky soon found himself fighting against Germany as an artillery officer during World War II.

    Wars don’t last forever, though, and after the shots quit ringing out, Penkovsky would go on to enter the Soviet version of the CIA — the GRU. 

    GRU emblem
    GRU emblem

    While the KGB concerned itself with internal “threats,” the GRU focused on international concerns.

    Penkovsky soon found himself placed as a senior official in the State Committee for the Coordination of Scientific Research. 

    His job? 

    To find out as much as he could about Western scientific advancements so that the Soviets could use that information to benefit Russia.  

    Oleg Penkovsky's passport
    Oleg Penkovsky’s passport

    There was just one problem. 

    Penkovsky was growing tired of the Soviets. 

    A Coincidental Acquaintance

    In April 1961, Penkovsy made an acquaintance that would change his life forever.

    He met British MI6 spy Greville Wynne, a businessman with an export business that gave him excellent cover for his frequent travels between England and Russia. 

    Greville Wynne
    Greville Wynne (center)

    An alliance was formed, and from that point on, Penkovsky would serve as a double agent.

    As he passed over a massive package filled with classified Soviet intelligence to Greville, he finally burned his bridges. There was no going back. 

    Western intelligence organizations were floored by the amount of information that was contained in that initial packet of documents.

    It was astounding, and Penkovsky would be given the codename “Hero” as a result. 

    Oleg Penkovsky (left, with pipe) and Greville Wynne (center)
    Oleg Penkovsky (left, with pipe) and Greville Wynne (center)

    Spy Craft

    Over the next year, Penkovsky would utilize dead drops with messages contained in cigarette cartons and other pieces of rubbish to smuggle over 5,000 photos, 111 rolls of exposed film, and countless pages of other vital information to the West.

    Penkovsky even stepped in for interviews with MI6, producing over 140 hours of dialogue. 

    The telephone pole that Penkovsky used to send messages
    The telephone pole that Penkovsky used to send messages

    He told the West about how the guidance systems for Soviet nukes weren’t functional yet. He discussed how their missile fueling systems weren’t ready.

    The range of the Cuban missiles, their age, their strength — all of this information was gleaned from Penkovsky, allowing JFK to make the decisions necessary to help to bring the Cuban Missile Crisis to an end.

    An SA-2 missile site in Cuba
    An SA-2 missile site in Cuba

    But unfortunately, all of this spying brought Penkovsky to his end as well. 

    The End of the Mission

    Though nobody knows how the leak was traced back to Penkovsky, he was arrested by the Soviets on October 22, 1962

    His trial began a few months later, and he was promptly sentenced to death for treason.  

    Penkovsky (right) during his trial
    Penkovsky (right) during his trial

    What happened next is unclear. Wynne — who was also arrested for espionage — would claim that Penkovsky committed suicide in prison. Wynne had a notorious track record for fabrications, however.

    KGB interrogator Alexander Zagvozdin said Penkovsky was “questioned” roughly 100 times and then shot. GRU agent and writer Viktor Suvorov claimed to have witnessed Penkovsky strapped to a stretcher and burned alive in a crematorium.  

    Viktor Suvorov
    Viktor Suvorov

    Whatever the case, what is certain is that on May 16, 1963, Oleg Penkovsky ceased to live on this earth. But the contributions he made to the United States? They lived on. 

    Want to learn more about Oleg Penkovsky? Check out his journal, published after his death, titled The Penkovsky Papers.

    This is a new style of article for Pew Pew Tactical, if you liked it — let us know in the comments! If you didn’t enjoy it…well phooey. To catch up on previous Pictures from History, click on over to our History Category.

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    5 Leave a Reply

    • Commenter Avatar

      Loved the article, please keep them coming!

      November 21, 2022 2:55 pm
    • Commenter Avatar

      Great article and very enjoyable. Do more.

      I was in 6th grade when the Cuban Missile Crisis occurred. We were having the "hide under your desk to survive the atomic bomb drills" at school. Talk about naïve.

      November 20, 2022 6:47 pm
    • Commenter Avatar
      Chuck Cochran

      I'd memory holed that until you mentioned it. Philby, the lead member of the Cambridge Five, and the damage they caused. You're right though, as highly placed as Philby was, anything JFK told MacMillan would have landed right in Kruschev' lap.
      I was a child at the time, but remember reading about Philby in the 70's as a teen. It was not a good time or look for MI6, as there was a lot of internal house cleaning after the jig was up.
      Rereading it now, it's almost like a very bad James Bond plot. It seems so obvious in hindsight.

      November 20, 2022 4:13 pm
    • Commenter Avatar
      Zoe Rainham

      Reading today's press, It looks like fact, fiction and history are all meeting to end the world as we know it! In 1983 the USSR reckoned that NATO’s Able Archer exercise was a smokescreen and that NATO was planning to deliver a genuine nuclear first strike.

      The extent to which John F Kennedy took his NATO partners into his confidence during the Cuban crisis remains debatable. In 1962, the British Prime Minister Harold Macmillan, colloquially known as SuperMac, was supposedly JFK’s chief confidant and adviser throughout the crisis. What were the consequences of that?

      For starters it meant that anything JFK (via the CIA) and/or SuperMac shared with MI6 about how best to manage the crisis was also shared with Nikita Khrushchev and Fidel Castro via Kim Philby who was then in his heyday. In addition, Dr Richard Alan Fairclough (ex MI1 and a leading British scientist) was a close confidant of SuperMac.

      Since then Richard Fairclough (aka Roger Burlington) featured in The Burlington Files series of fact based spy novels which were centred on the life and times of his son Bill Fairclough (aka Edward Burlington, real life MI6 codename JJ).

      One could ask were the Fairclough family involved in the seventies in the Haitian equivalent to the Cuban Bay of Pigs? Before it's too late we had all best read Beyond Enkription, the only novel published to date in The Burlington Files series, to find out what has been disclosed to date on all these issues. As for today's concerns, hopefully in 50 years from now we can read about today's Kim Philby and Oleg Penkovsky.

      November 19, 2022 4:05 am
    • Commenter Avatar

      This was a pleasant surprise - thanks!
      Not long ago, we watched tge movie, "The courier", with Cumberbatch.

      November 18, 2022 9:22 pm
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