1963: Oleg Penkovsky, Cuban Missile Crisis spy

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It is 50 years today since Soviet military intelligence officer Oleg Penkovsky was executed for spying for the Americans.

Penkovsky, whose father died fighting for the anti-communist Whites during the Russian Civil War, lived up to his western handlers’ HERO codename by tipping the Soviets’ operational plans for missile deployment in Cuba — helping precipitate the Cuban Missile Crisis.

This speech inaugurated some of the darkest days of the Cold War … but they were probably even worse for Oleg Penkovsky, who was arrested just hours before Kennedy delivered it. He might have been shopped by a U.S. intelligence mole working for Moscow.

Penkovsky and his British contact, businessman Greville Wynne, faced a public show trial in May 1963 — resulting in the spy’s prompt execution. (Wynne got a prison sentence, and was later exchanged back to the West for Portland Spy Ring principal Gordon Lonsdale.)

The late spy’s journal was published in 1965 as The Penkovsky Papers. A variety of documents from Penkovsky’s CIA case file are available on the spy agency’s own site.

As befits the shadow world of espionage, Penkovsky’s activities and motivations are still disputed to this day. While some consider him among the most valuable/damaging spies in the Cold War, former MI5 officer Peter Wright claimed that Penkovsky was a loyal Moscow agent all along actually trafficking disinformation — and that he was not executed at all but cashiered to a comfortable secret retirement after his show trial “condemnation.”

But here’s the conventional take:

On this day..

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