President Kennedy meets with Soviet Foreign Minister Andrei Gromyko in the Oval Office on 18 October 1962. The President knows but does not reveal that he is now aware of the missile build-up. Photo: Abbie Rowe. The John F. Kennedy Presidential Library and Museum, Boston.

Our goal is not the victory of might, but the vindication of right – not peace at the expense of freedom, but both peace and freedom, here in this hemisphere, and, we hope, around the world” — President John F. Kennedy

Oleg Penkovsky was a senior Soviet military intelligence officer who became a double agent for the United States and Britain during the Cold War. He was born in 1919 in Vladikavkaz, Russia, and never knew his father, who died fighting against the communists in the Russian Revolution.

Circa 1960. Graduating class of the Dzerzhinzkiy Artillery Engineering Academy in the USSR. Oleg Penkovskiy is the third from right in the front row. Photo:19 USSR Graduating Class. Central Intelligence Agency.

He joined the Red Army in 1937. He fought as an artillery officer in World War II and became a protégé of Chief Marshal of Soviet Artillery, Sergei Varentsov. He graduated from the Frunze Military Academy and the Dzerzhinsky Military Academy and worked as a staff officer and a military attaché. He joined the GRU, the Soviet military intelligence agency, in 1953.

The GRU, which stands for Glavnoye razvedyvatel’noye upravleniye (Main Intelligence Directorate), was responsible for collecting and analyzing military intelligence from foreign sources, as well as conducting covert operations and special forces missions. Penkovsky rose to the rank of colonel in the GRU, and served as a military attaché in Ankara, Turkey, before returning to Moscow in 1959.

Circa 1961. Colonel Oleg Penkovskiy’s military pass to the buildings of the General Staff and Ministry of Defense in Moscow, USSR (top). His military pass to the Intelligence Directorate of the Ministry of Defense (bottom). Penkovskiy provided the US and UK with valuable information about Soviet and Warsaw Pact military intentions. He was apprehended by the KGB in 1962, tried and found guilty of treason and espionage, and executed in 1963. Photo: Central Intelligence Agency.

In 1960, he contacted the CIA and offered his services as a spy, motivated by his disillusionment with the Soviet regime and his admiration for the West. He provided his Western handlers with secret information about Soviet missile installations, the weakness of the Soviet intercontinental ballistic missile program, and other aspects of Soviet military power. His data was crucial for the United States to detect and react to the deployment of Soviet missiles in Cuba in October 1962, which triggered the Cuban missile crisis. It also gave US President John Kennedy valuable information about Soviet weakness, which allowed him to confront Soviet leader Nikita Khrushchev and resolve the crisis without nuclear war.

CIA reference photograph of Soviet medium-range ballistic missile (SS-4 in US documents, R-12 in Soviet documents) in Red Square, Moscow. Photo: Central Intelligence Agency.

The Cuban Missile Crisis was a 13-day political and military standoff between the United States and the Soviet Union over the presence of nuclear-armed Soviet missiles in Cuba, just 90 miles from US shores. The crisis was a major confrontation at the height of the Cold War that brought both superpowers to the brink of a nuclear war.

The United States confirmed the existence of Soviet missiles in Cuba through aerial reconnaissance missions flown by U-2 spy planes operated by both the CIA and the Air Force. On October 14, 1962, two Air Force U-2s photographed portions of Cuba, revealing Soviet offensive nuclear missiles based only 90 miles from US shores. President Kennedy placed US forces on alert and ordered more U-2 and RF-101 reconnaissance flights over Cuba to monitor the situation. The latter aircraft sometimes flew at treetop level to avoid being detected by Soviet radar. The U-2 flights were risky, as they exposed the pilots to possible enemy fire from surface-to-air missiles or fighter jets. On October 27, 1962, Air Force Major Rudolf Anderson Jr. was shot down and killed by a Soviet missile while flying over Cuba, becoming the only US fatality by enemy fire during the crisis.

This U-2 reconnaissance photo showed concrete evidence of missile assembly in Cuba. Shown here are missile transporters and missile-ready tents where fueling and maintenance took place. Photo: Central Intelligence Agency.

Penkovsky was codenamed HERO by the CIA and YOGA by the British Secret Intelligence Service (SIS/MI6) and was considered one of the most valuable double agents in history. He was arrested by the Soviet authorities in October 1962, after being betrayed by George Blake, a British double agent working for the KGB.

Blake was a former MI6 officer who had been turned by the Soviets while he was a prisoner of war in Korea. He had access to many secrets of British intelligence, including Penkovsky’s identity and contacts. He passed this information to his KGB handlers, who eventually captured Penkovsky. Blake was sentenced to 42 years in prison in Britain, but escaped in 1966 and fled to the Soviet Union, where he lived until his death in 2020.

The KGB had also received information about Penkovsky from two other double agents working in Washington: William Whalen and Jack Dunlap. Whalen was a lieutenant colonel who served as an intelligence advisor to the Army Chief of Staff. Dunlap was a sergeant who worked at the National Security Agency as a courier of top secret messages. They both spied for the Soviets for money and gave them valuable information about American military capabilities and plans.

The KGB officers in Moscow monitored Penkovsky’s movements and communications, and raided his apartment where they found a camera that he had used to photograph secret documents.  He was arrested by the KGB in October 1962. They also arrested Greville Wynne, a British businessman who had acted as a courier for Penkovsky.

1963 Press photo of Colonel Oleg Penkovsky and guard in Russian military court. Photo: Associated Press / Public Domain.

Penkovsky was sentenced and executed in May 1963, after a show trial. His espionage activities are widely regarded as having changed the course of the Cold War and prevented a nuclear catastrophe. His legacy as one of the most important spies in history remains today.

*The views and opinions expressed on this website are solely those of the original authors and contributors. These views and opinions do not necessarily represent those of Spotter Up Magazine, the administrative staff, and/or any/all contributors to this site.

By Eugene Nielsen

Eugene Nielsen provides intelligence and security consulting services. He has a bachelor's degree in political science from the University of California. His byline has appeared in numerous national and international journals and magazines.

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