The Penkovsky Era

Each man here is alone.

—Oleg Penkovsky quoted in the Penkovskiy Papers

Bad news, like every secret communication from Moscow, arrived at CIA Headquarters encrypted. The news that arrived mid-morning on November 2, 1962—as the Cuban Missile Crisis was winding down—was particularly bad. Colonel Oleg Vladimirovich Penkovsky, a career Soviet military intelligence officer and the Agency’s most spectacularly successful spy, was, in all likelihood, lost. Penkovsky had held a senior position in the Glavnoye Razedyvatelnoye Upravlenie (GRU), the Chief Intelligence Directorate of the Soviet General Staff while secretly reporting to U.S. and British intelligence. In the colorful parlance of espionage, he had almost certainly been “rolled up.”

At the new Agency compound at Langley, Virginia, the paint was barely dry on the walls when the Communications Center on the ground floor—Headquarters’ sole secure link to Moscow personnel—received the super-enciphered message. It arrived as an “IMMEDIATE” cable, a long, narrow strip of paper snaking out of a bulky machine, much like a price quote from an old-fashioned stock ticker. The encoded message was contained in an intricate pattern of perforations that ran along the paper’s length. When the transmission was complete, the paper was torn off by the communicator, and then run through a printer that produced a neat array of seemingly random numbers and letters on a sheet of standard letter-sized paper. A second level of decryption was needed to render the message into plain text. This phase of decryption guarded against the potential for security failures along the transmission path, whether over the air or via land lines. Like placing a strong, small safe inside a larger safe, this last layer of decryption could be performed only by one of a handful of authorized officers from the Soviet Russia Division (SR) of the CIA’s Directorate of Plans.

Although the DDP sounded like the dullest of bureaucracies, its name veiled the most secretive directorate in the Agency. Hidden beneath the vague acronym resided the responsibility for the CIA’s “cloak and dagger” work. Within the DDP, SR was particularly shrouded with “cloak.”

If asked about their job by neighbors or friends, SR personnel would repeat a carefully rehearsed cover story of working for one or another government department, but never the CIA. It was not unusual for DDP operations officers to remain undercover even after retirement, and maintain their cover stories until their deaths. Even the top-secret clearance, required for employment at the Agency, did not authorize someone to know rudimentary details regarding SR or its personnel. If an Agency colleague asked about an SR staffer’s job, they would receive only generalized replies and most knew better than to probe for details. Secrecy within the Agency was both enforced by official policy and expected as part of professional etiquette.

Virtually no one, with the exception of SR personnel, was allowed into SR spaces. A no-nonsense secretary immediately confronted any visitor who opened the unmarked, always closed, hallway doors that led into the division’s suite and friends of SR officers from other parts of the agency did not drop in to plan weekend activities or for office gossip. When SR officers left the area, even for a short time, security procedures mandated that desks be cleared and all work secured in one of the division’s high-security 500-pound black steel safes.

SR Division applied strict need-to-know compartmentation through BIGOT lists that restricted access to what many would consider routine information coming out of the Soviet Union. Within the division information was distributed like pieces of a jigsaw puzzle. Only a very few ever saw an entire operational picture. Those outside of SR could only assume that a puzzle existed. Within CIA’s instinctively tight-lipped security environment, SR’s added multilayered security cloak created a mystique that some viewed as arrogant and unnecessarily obsessive.

The term “BIGOT list” existed—and still exists—as a holdover from World War II when the most prized stamp on the orders of personnel traveling from England to Africa was “TOGIB,” meaning “to Gibraltar.” To reach Africa, the majority of personnel made the dangerous journey by ship through seas controlled by German U-boats. However, for a select few, there were the highly prized seats on a flight to Gibraltar. For these lucky individuals, the stamp on their orders was reversed to read BIGOT and the term thus acquired its special meaning in intelligence circles, carrying with it the inference of not only rarity, but also safe passage and a valued mission.

There were other levels of compartmentation as well. A top-secret clearance did not provide automatic access to specific operations or programs. TS, a security clearance level required for all CIA staff employees, only made one eligible for potential access to a compartmented program. The BIGOT access was granted based on responsibilities and an individual’s demonstrated need to know about the operation.

SR’s security policies extended to written communications within Headquarters. SR did not rely on the CIA’s usual interoffice mail couriers nor were its officers permitted to use the 1960-era state-of-the-art pneumatic tube system that carried classified documents to every corner of the 1.4 million-square-foot building. Everything regarding Soviet operations was hand-carried from office to office by either an SR operations officer or one of a dedicated cadre of women known as Intelligence Assistants.

It was standard operating procedure for the communicator to place the encrypted message in a heavy manila security envelope, securely seal it, and call SR to advise that a cable had been received from Moscow. On the morning of November 2, the young SR officer who walked to the communications vault, accepted the sealed envelope, and, without opening it, retraced his three-minute route to SR’s small warren of offices, could not have known that he now had a role in one of history’s most significant espionage events.

At his desk, the officer opened the envelope, removed the single sheet of paper, and, with painstaking care, began deciphering the message by hand. He used a one-time pad, or OTP, whose printed columns of numbers and letters exactly matched those used by the person who had composed the brief message. After the message was deciphered, the page of the one-time pad used was destroyed. The Soviet Union paid a heavy price during World War II when they reused one-time-pad pages for communicating with agents in different parts of the world. This seemingly innocuous error provided an advantage to U.S. code breakers who were able to unravel many Soviet ciphered communications that had been intercepted from Washington, D.C. and New York City. This secret would become known as VENONA and remains one of the notable achievements of the Army Security Agency and later the National Security Agency.

The cable did not mention Penkovsky by name. Rather, it reported that Richard Jacob, a CIA officer in Moscow, was apprehended while clearing a dead drop. After a nerve-shattering but relatively brief interrogation, the message continued, Jacob was released to the custody of the U.S. ambassador and returned to the safety of the U.S. embassy. Because he was a diplomat, Jacob could not be formally charged with a crime. Instead, he was “PNG’ed,” declared persona non grata by Soviet authorities and ordered out of the country.

Penkovsky’s arrest by the KGB was not confirmed during those first few hours, but it did not seem realistic to hold out much hope for the agent. As in the immediate aftermath of any roll-up, there were more questions than facts, but for those few who knew about the case, it required no imagination to conclude that Penkovsky either was dead or would be very soon.

The officer delivered the decrypted cable up the chain of command to the SR Division Chief. The Chief took the bad news to the Deputy Director for Plans who in turn briefed John McCone, the Director of Central Intelligence. Within twenty-four hours, McCone would personally inform President Kennedy. That so few understood the enormous impact Penkovsky’s arrest would have on America’s national security was partially due to the extraordinary secrecy surrounding the nearly eighteen-month operation and the care given to the handling of the remarkable intelligence he single-handedly supplied.

Intelligence reports based on Penkovsky’s information had been structured to suggest that the intelligence originated from multiple sources. To reinforce this illusion, the Penkovsky product circulated under two code names, IRONBARK for that material that was scientific or quantifiable and CHICKADEE for material that included his personal observations. For anyone outside the small group who knew the truth, the vast quantity of intelligence flowing from the Soviet Union looked like the work of an extensive spy network, coupled with mysterious and advanced technical collection, rather than the efforts of a single spy.

A small team of CIA and British intelligence officers ran Penkovsky. He was alternately known as HERO to his American handlers and YOGA to the British. Jacob had been chosen to service the dead drop because he had recently arrived in Moscow and had a strong cover in a traditionally non-alerting, low-level administrative position. As such, he was less likely to be identified as a CIA officer and draw KGB surveillance.

According to later accounts, Jacob entered the dingy hallway of an apartment house at 5/6 Pushkinskaya and removed an ordinary matchbox wrapped in a short length of wire that formed a hook to secure it behind a radiator. As Jacob was placing the matchbox in his pocket, the KGB team jumped him from their hiding places in the vestibule. During the ensuing scuffle, he managed to drop the matchbox to the floor through a slit in the lining of his raincoat pocket, ridding himself of incriminating evidence and avoiding the nasty legal and diplomatic problems arising from having Soviet state secrets on his person. The technicality did not matter to the KGB team, since it was obvious why the American was in the building. Once subdued, Jacob was hustled into a waiting car and whisked off to a nearby militia station.

The final act of the Penkovsky drama had begun that morning with two voiceless phone calls—silent calls—to a phone answered by a U.S. official. The silent call was a signal activating the communication plan issued to Penkovsky by his handlers when they had met outside the Soviet Union. Arguably the most critical piece of any operation, the commo plan provided agents, such as Penkovsky, with precise contact instructions and schedules to establish secure communication under both ordinary and extraordinary circumstances.

Because the CIA assumed that the KGB monitored all telephone calls to and from the U.S. officials, the silent call represented a clever piece of tradecraft that allowed a message to be sent, even if the call was monitored. Penkovsky had been instructed to go to a remote public telephone and call a specific number. When the phone was answered, he said nothing, but waited ten seconds before hanging up. The call to the specific number and the length of silence before hanging up were the message that directed intelligence officers to a telephone pole marked with a symbol written in chalk, an X. The simple chalk mark announced that the dead drop site at the Pushkinskaya apartment house had been loaded.

These standard pieces of tradecraft—the silent call, followed by a signal site marked with an X and dead drop—were part of a commo plan, code-named DISTANT, designed specifically for Penkovsky to provide an early warning of imminent Soviet attack on the West. The small matchbox that Jacob found tethered by wire behind the radiator might have contained information signaling the start of World War III.

With the silent call, Penkovsky, who had not been heard from or seen since early September, had apparently, reemerged. It was possible that nothing serious was wrong. If it was a trap—a provocation on the part of the KGB—then it was worth the chance. “We had been worried about him, it had been quiet for quite a while,” said the case officer who decrypted the message and whose memories are still vivid after more than four decades. “But in the past he had come up again. To my knowledge we had no warning, nothing to indicate they’d caught him.”

Now, with Jacob’s arrest, whatever glimmers of hope that might have existed with Penkovsky’s reemergence, seemed far-fetched. It was possible that a bystander had seen Penkovsky suspiciously fiddling behind the radiator as he loaded the dead drop and called authorities who then laid in wait. It was also possible that the KGB had not been fooled by Jacob’s cover and defeated his countersurveillance maneuvers en route to the dead drop site. Any number of other scenarios about Penkovsky’s fate was possible, but only a single distressing conclusion was probable.

Penkovsky’s handlers had grown increasingly troubled by recent events surrounding the operation. Penkovsky had vanished from operational sight for several weeks prior to the silent call and his GRU superiors abruptly canceled his scheduled trip to Seattle in the autumn of 1962. Additionally, the sheer volume of intelligence he was providing on his Minox film cassettes suggested a level of clandestine activity that could not continue undetected indefinitely. So voluminous was Penkovsky’s productivity during the first half of 1962 that his handlers decided to discontinue temporarily tasking him for new intelligence collection.

The operation would refocus on supporting his work for the GRU by providing comprehensively written technical articles to be published under his name and supplying harmless intelligence products he could take back to Moscow from trips to the West. The intent was to strengthen Penkovsky’s credibility among superiors, raising him above suspicion and moving him into circles of even greater access to Soviet secrets.

During a three-month period between October 1961 and January 1962, Penkovsky met with his contact in Moscow, Janet Chisholm, the young wife of British MI6 officer Roderick Chisholm, eleven times in public locations. During these brief encounters, she received thirty-five rolls of film containing hundreds of images of top-secret Soviet documents. In January, Penkovskyreported what he believed was surveillance on Mrs. Chisholm but showed no personal alarm. Rather, he suggested that dead drops replace their contacts “on the street.” Early successes, it seemed, emboldened Penkovsky but, in his handlers’ opinion, the agent’s level of productivity was alarming as well as gratifying.

Had Penkovsky dropped his guard or grown careless as the inherently dangerous work became routine? It was possible. Had he grown to feel invulnerable and above suspicion? That, too, was possible. It only became known much later that George Blake, an MI6 officer who spied for the Soviets, alerted the KGB that Janet Chisholm was actively supporting her MI6 husband in operations. Consequently, when the couple arrived in Moscow, KGB surveillance teams were waiting for them.

Confirmation of the disaster arrived a few hours after the first message with news of the arrest of Greville Wynne, a British businessman traveling in Hungary. A sometime contact between Penkovsky and his handlers, Wynne was arrested by a KGB team in Budapest, also on November 2, and flown back to Moscow.

The final curtain fell a month later. On December 12, a notice in the Soviet newspaper Pravda announced Penkovsky’s arrest in late October, more than a week before Jacob’s apprehension. Six months later, on May 7, 1963, Penkovsky stood in a courtroom before the same judge who had presided at the trial of Francis Gary Powers, the American pilot whose U-2 spy plane had been shot down in May 1960 over Sverdlovsk. 

The trial lasted four days. Penkovsky, in an attempt to save his life, admitted that he had passed secrets to the Americans and British. Prosecutors cited “moral degradation” among the reasons for his traitorous acts, while a witness bolstered this claim by testifying that he had seen the defendant sipping wine from a woman’s shoe during a night of heavy drinking.

On May 17, a public notice appeared that Penkovsky had been executed.

Rumors about his death eventually began to leak out. While the Soviet press announced an execution by firing squad, another, unconfirmed report, claimed that he had been burned alive in a crematorium and the grisly episode filmed as a warning to new GRU officers who might someday consider cooperating with the West.

Wynne was also tried, found guilty and sentenced to eight years in prison. He was released in 1964 as part of a spy swap for Gordon Lonsdale, a Soviet spy convicted in Britain.

Like a silent explosion, the capture, trial, and execution of Penkovsky sent shock waves of uncertainty, recrimination, and retribution through American, British, and Soviet intelligence circles. While the badly burned Soviets restructured the GRU, the British and Americans, uncertain about when and how Penkovsky was first identified, faced a flood of questions. If Penkovsky was under KGB suspicion as early as December of 1961, or January of 1962, did this mean the Soviets manipulated the information he provided? If so, when did he begin reporting controlled information designed to mislead American and British analysts? For that matter, could anything he reported be trusted?

Material long disseminated by analysts to policy officials was recalled and painstakingly reexamined. The eventual conclusion was that the Soviets had not played Penkovsky back against the Americans and British, but that left unanswered the mystery of why, if Penkovsky was suspected as early as December 1961, the Soviets continued to allow him access to secret files and materials.

Over the next several years, the Penkovsky case would become a cottage industry within the CIA as every aspect of the operation was analyzed to determine what was accomplished and what went wrong.

The Penkovsky operation had produced an astonishing amount of material. During his year and a half as an active agent, he supplied more than a hundred cassettes of exposed Minox film (each containing fifty exposures or frames). The more than 140 hours of debriefings in London and Paris produced some 1,200 pages of transcripts and reams of handwritten pages. He identified hundreds of GRU and KGB officers from photos, and provided Western intelligence officials with their first authoritative view of the highest levels of the post-Stalin Soviet Union. In fact, he supplied so much information that both the CIA and MI6 set up teams dedicated exclusively to processing the material, which resulted in an estimated 10,000 pages of intelligence reports. 

More than the quantity, the substance of the documents on the Minox film and his knowledgeable debriefings impressed both CIA and MI6. Penkovsky appeared at a crucial time during the Cold War when tensions and the potential for nuclear war between the Soviet Union and the West were at an apex. This volatility was heightened by a lack of certainty on each side about the intentions and capabilities of the other. 

The failed Soviet attempt to isolate the British-, French-, and U.S.-controlled sections of Berlin by blocking all ground and rail transportation and shipments into the city during 1948 and 1949 was still a fresh memory when the United States was caught off guard by unpredicted assertive Soviet technological, military, and political actions beginning in 1957. The USSR launched Sputnik in 1957; shot down Francis Gary Powers’s U-2 reconnaissance plane on May Day, 1960; and built the Berlin Wall in 1961. So anemic was U.S. intelligence access to the plans and intentions of the Kremlin that the text of Nikita Khrushchev’s famous speech denouncing Stalin at the Twentieth Party Congress in 1956 came to the CIA via a third party, an Israeli source operating behind the Iron Curtain.

Through the late 1950s, Khrushchev’s seeming obsession with the United States was rising to dangerous levels. His fixation with U.S. objectives was fueled first by an alarmist 1960 KGB report that falsely described the Pentagon’s intention to initiate war against the Soviet Union “as soon as possible” followed by a failed attempt to overthrow Castro in 1961. Then, in 1962, two erroneous GRU intelligence reports warned of an imminent nuclear first strike on the Soviet Union by the United States.

“Our production of rockets is like sausages coming from an automatic machine, rocket after rocket comes off the assembly line,” bragged Khrushchev.  

Penkovsky’s assignment to the State Committee for the Coordination of Scientific Research Work granted him access to the highest levels of military circles. He, in turn, provided the West with a contrasting view of both Soviet capability and Khrushchev’s belligerent stance. “His [Khrushchev’s] threats are like swinging a club to see the reaction. If the reaction is not in his favor, he stops swinging,” Penkovsky explained to the team in a Paris hotel room in 1961.

For the Kennedy administration, Penkovsky’s reporting put the lie to the Soviet leader’s braggadocio, while the intelligence he provided, combined with overhead intelligence, influenced downward revisions of Soviet missile production in National Intelligence Estimates.

Penkovsky also revealed the real dangers of diplomacy without independent and timely intelligence. As the Cuban missile crisis heated up, Soviet Ambassador Anatoly Dobrynin used back-channel communication through Attorney General Robert Kennedy, Adlai Stevenson, and other White House officials to assure President Kennedy that only short-range defensive, rather than offensive, missiles were going into Cuba. Similar false assurances also flowed through the back channels of diplomacy from GRU Colonel Georgi Bolshakov, working under cover of the TASS news agency, through Robert Kennedy.

However, the technical manuals provided by Penkovsky for the Soviet SS-4 medium-range ballistic missiles allowed CIA photo analysts to identify and match the deployment pattern or footprint with U-2 reconnaissance photos taken over San Cristobal, Cuba. Far from being defensive and of short range, the missiles were armed with 3,000-pound nuclear warheads and a range of some 1,000 nautical miles, and were more than capable of reaching Washington, D.C., and New York City.

Finally, Penkovsky’s information provided analysis of the Soviets’ overall lack of preparedness for war, allowing President Kennedy to face off against Khrushchev during the crisis. His insights, derived from personal access to Kremlin leaders, added independent weight to technical evidence that Soviet military threats were overstated, if not hollow. The American President was emboldened to act and denied the Soviets a nuclear missile foothold in the Western Hemisphere. For that brief and critical moment in time, history turned on the material provided by one man, Oleg Penkovsky.

In the wake of the Penkovsky case, the CIA undertook the unprecedented measure of bringing to press in 1965 The Penkovskiy Papers [sic]. The Agency, working with journalist Frank Gibney and the publisher Doubleday & Company, publicly exposed many of the operational aspects of the GRU revealed by Penkovsky. An immediate bestseller, the book presented most Americans with one of the first in-depth looks at Soviet intelligence operations in the West.

The Penkovskiy Papers offered remarkable details of Soviet tradecraft, from tips on American personal grooming and social customs (“Many Americans like to keep their hands in their pockets and chew gum”) to evading surveillance and selecting dead drop sites. One section warned of the dangers presented by squirrels running off with small packages left at dead drop sites in New York’s Central Park.

For American readers, the book confirmed their worst suspicions that Soviet spies were active and successful in the United States. It may have also implied an equally aggressive and thriving U.S. espionage capability in the Soviet Union. Unfortunately, this was not the case. The few who understood how dependent American intelligence had been on HERO’s production knew the time had come to change the game plan. The case had revealed grave deficiencies in the tradecraft needed to handle long-term agents inside the Soviet Union. America’s technology and the CIA’s Technical Services Division would become key players in a new operational strategy.

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