The spy who couldn't get arrested

The spy who couldn't get arrested

Oleg Penkovsky

Our Man In Moscow

The story of his defection is somewhat disappointing.

Wanting to become a double agent and eager to prove his credentials, he first approached two American students on a bridge in Moscow and persuaded them to deliver a package full of secrets to the CIA. The CIA officials eventually got the package but delayed meeting with him because they were under intense scrutiny by the Soviets. Furthermore, it's possible they thought that a defecting colonel of the GRU was too much of a godsend and perhaps to not be trusted.

But while the CIA dilly-dallied and dropped the ball, the British quickly assigned Penkovsky a handler, and so he became MI6's asset. Luckily, MI6 then shared Penkovsky's intel with the CIA.

Khrushchev's folly

This concerns a historical episode that became known as the Cuban Missile Crisis.

By becoming a Western asset, Oleg Penkovsky almost single-handedly stopped Russia from stocking nuclear missiles launchers right next to the US shore. Another hero of this episode was a Soviet submarine commander - Vasili Alexandrovich Arkhipov - who refused direct orders from Moscow to launch his own submarine's nuclear missiles at the US, but that's a story for another day.

Penkovsky gave his reason for becoming one of the most valuable assets in the CIA's history as revenge. His father fought for the monarchist White Army and was killed by the Soviets. He also was convinced that Khrushchev's blind ambition to create a global hegemony, with communist USSR the hegemon, would only lead to nuclear MAD.

He was a friend and protege of a Soviet general, and he had earned the rank of lieutenant colonel in combat in WWII. He fought in the Soviet Winter War against Finland.

As an allied asset, he also had a contact in Moscow, the wife of a British embassy spook, and traveled frequently out of the USSR as a representative of a scientific commission. On those occasions, he met with and passed a treasure trove of secrets to his British handlers. Especially in those moments, his life totally depended on the utmost secrecy. It must be said that a lot of the staff of any embassy are spooks, masquerading as 'attachés', who ply their trade under cover of diplomatic work. They simply walk or drive out of the embassy, pretending to go for coffee or a walk or a visit to the countryside and are immediately in the crosshairs of their opposite numbers, who follow them around employing sophisticated and well practiced surveillance techniques. Equally trained in evading such surveillance, the embassy spies covertly try and often succeed in evading their tails and meet their contacts, pick up dead drops or any other activity that defines embassy spies under diplomatic cover and immunity. All this is going on right now in every country, in every embassy, every day.

Even between friendly nations, one never knows. This is what LeCarré really meant by 'Our Game'.

Penkovsky smuggled an incredible amount of secret Soviet documents to his British and later CIA contacts, including plans of Soviet nuclear installations in Cuba. He is often touted as having been the most useful asset the West had in Soviet Russia.

On October 22, 1962, Soviet agents grabbed him off the street and put an end to that.

The unraveling

Everyone, it is said, has his or her fifteen minutes of fame. Oleg Penkovsky's came and went twice, in 1987 and then again in 2007, when first a serial docudrama and then a BBC one-hour teleplay retraced his career as a spy and subsequent execution in the infamous basement of the Lubyanka as a traitor of the Soviet Union. Since then, his memory has sunk back into obscurity, joining his cold remains in a mass grave at Donskoi Monastery cemetery in Moscow. Maybe. More on this later.

Greville Wynne, the spy who was his British contact, was picked up in Budapest by the Soviet secret services and spent eighteen months in the Lubyanka prison because of all this.

He deemed it was worth it.

When the intelligence services received a letter from Penkovsky asking them to go and get something at a dead drop, the agent who went to pick it up was arrested instead. That's how they knew that Penkovsky was done for.

Oleg Penkovsky's actions should not be forgotten. The defection of this colonel in the GRU, the Soviet military intelligence, was heavily instrumental in preventing the U.S.S.R. from setting up nuclear missiles in Cuba, just 90 miles from the coast of Florida, able to reach just about any target in continental US. They'd already started to deploy their nuclear warheads when his information gave JFK the impetus he needed to make sure this was not some paranoid fantasy.

Photo via Wikipedia. At right — a soccer field at Cazo Alcatraz. CIA release

Also decisive in that unfolding tragedy were secret U2 spy plane pictures of a stadium dedicated to soccer that Cuba had just constructed near a naval base. Those pictures made heads explode in the then-very-serious White House. Why?

Because baseball was Cuba's national sport.

Soccer was Russia's.

Cold bones?

This may be a tired cliché, but Oleg Penkovsky really was a 'Man of Mystery', as some today still hold the theory that he was planted by the Soviets as a double agent, sent to convince the West that the Soviet's nuclear capabilities were rudimentary. If so, he failed miserably given the results of his defection to the Western secret services.

One has to wonder if this suspicion perhaps has its roots in the natural Cold War mistrust of the Soviets by any opposing intel service, or maybe a lingering after effect of the debacle of the Cambridge Five barely ten years earlier. The Cambridge Five (the Soviets called them 'The Magnificent Five') were British moles who worked secretly for the soviets for many years, beginning in WWII, some attaining very high level positions in British Intelligence. One of them, Kim Philby, became an MI6 agent and British embassy liaison with American intelligence services in Washington. Between them, they had basically unraveled the British and American intelligence networks of the time.

Either way, Penkovsky was caught and reportedly interrogated over a hundred times. There are many theories concerning the manner of his death but Western intelligence's refusal to 'bring him in from the cold', even as he pleaded to be taken in, and his resulting execution at the hands of the Soviets is profoundly harrowing, and an unfortunate cautionary tale for future defectors. To this end, it is said that the Soviets circulated a film of Oleg Penkovsky, bound to a stretcher and being cremated.


This, to us, is the most believable theory, for this was an old technique known to have already been used by the Cheka since its inception.

A Spy's Dilemma

A Spy's Dilemma

A US intelligence disaster to rival the UK's Cambridge Five

A US intelligence disaster to rival the UK's Cambridge Five