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Oleg Vladimirovich Penkovsky (Russian: Олег Владимирович Пеньковский; born 23 April 1919, Vladikavkaz, North Ossetia, Soviet Russia; died 16 May 1963, USSR), codenamed HERO, was a colonel with Soviet military intelligence (GRU) during the late 1950s and early 1960s who informed the United Kingdom and the United States about the Soviet emplacement of missiles in Cuba.
Penkovsky's father died fighting as an officer in the White Army in the Russian Civil War. Penkovsky graduated from the Kiev Artillery Academy in the rank of lieutenant in 1939. After taking part in the Winter War against Finland and in World War II, he had reached the rank of lieutenant-colonel. A GRU officer, Penkovsky was appointed military attaché in Ankara, Turkey in 1955. He later worked at the Soviet Committee for Scientific Research. Penkovsky was a personal friend of GRU head Ivan Serov and Soviet marshal Sergei Varentsov.
There are two very different opinions about Oleg Penkovsky. While the majority of observers seem to feel that he was a genuine defector as described in The Penkovskiy Papers, Peter Wright, a scientist with MI5 in Britain, was convinced that Penkovsky was a Soviet plant designed to lead the United States to the conclusion that the USSR's intercontinental missile capabilities were much less developed than they actually were.
The defector account says Penkovsky approached American students on the Moskvoretsky Bridge in Moscow in July 1960 and gave them a package, which was delivered to the Central Intelligence Agency. CIA officers delayed in contacting him because they believed they were under constant surveillance. Penkovsky eventually persuaded the British spy Greville Wynne to arrange a meeting with two American and two British intelligence officers during a visit to London in 1961. Wynne became one of his couriers. In his autobiography, Wynne says that he was carefully developed by British intelligence over many years with the specific task of making contact with Penkovsky.
The CIA regretted their earlier mistake, but were included by the British and they shared future information. For the following eighteen months, Penkovsky supplied a tremendous amount of information to his British Secret Intelligence Service handlers in Moscow, Ruari and Janet Chisholm, and to CIA and SIS contacts during his permitted trips abroad. Most significantly, he was responsible for arming President John F. Kennedy with the information that the Soviet nuclear arsenal was much smaller than previously thought, that the Soviet fueling systems were not fully operational, and that the Soviet guidance systems were not yet functional.
The view of Peter Wright is quite different. Wright was struck by the fact that, unlike Igor Gouzenko and other earlier defectors, Penkovsky did not reveal the names of any illegal Soviet agents in the West but confined himself to organizational detail, much of which was known already. Wright noted that some of the documents were originals which in his opinion would not have been so easily taken from their sources. Wright scathingly condemned the leadership of British intelligence throughout nearly the whole Cold War period. He reportedly believed that the Soviet agents (Philby, Maclean, Burgess and Blunt) could all have been identified more quickly using the scientific methods that he proposed. In Wright's view, British intelligence leaders became even more paralyzed when Philby and the others defected to the Soviet Union. British intelligence became so fearful of another fiasco that they avoided taking risks. Aware of this sensitivity, Wright says, the Soviets planted Penkovsky to buoy up the sagging fortunes of their ineffective—and therefore highly useful—counterparts in British intelligence. Wright wrote: "When I first wrote my Penkovsky analysis Maurice Oldfield (later Chief of MI6 in the 1970s), who played a key role in the Penkovsky case as Chief of Station in Washington, told me: 'You've got a long row to hoe with this one, Peter, there's a lot of K's [knighthoods] and Gongs [medals] riding high on the back of Penkovsky,' he said, referring to the honors heaped on those involved in the Penkovsky operation." Wright was more complimentary of the CIA and even of the FBI, who were initially suspicious (and remained suspicious) of Penkovsky. Greville Wynne seems convinced that Penkovsky was genuine and that Wynne's own sacrifices, including 18 months in the Lubyanka Prison, were worthwhile.
Former KGB major-general Oleg Kalugin does not once mention Penkovsky in his comprehensive book. KGB defector Vladimir Sakharov, suggests Penkovsky was genuine, saying, "I knew about the ongoing KGB reorganization precipitated by Oleg Penkovsky's case and Yuri Nosenko's defection. The party was not satisfied with KGB performance ... I knew many heads in the KGB had rolled again, as they had after Stalin." While the weight of opinion seems to be Penkovsky was genuine, the debate underscores the difficulty faced by all intelligence agencies of separating fact from fiction.
Soviet leadership started the deployment of nuclear missiles in the belief that Washington would not detect the Cuban missile sites until it was too late to do anything about them. Penkovsky provided plans and descriptions of the nuclear rocket launch sites on Cuba. Only this information allowed the West to identify the missile sites from the low-resolution pictures provided by U.S. U-2 spy planes. Former GRU Colonel and defector Viktor Suvorov writes, "And historians will remember with gratitude the name of the GRU Colonel Oleg Penkovsky. Thanks to his priceless information the Cuban crisis was not transformed into a last World War."
Penkovsky's activities were revealed by Jack Dunlap, a double-agent working for the KGB. The KGB swiftly drew the conclusion that there was a mole in their ranks and set about uncovering him. Penkovsky was arrested on 22 October 1962—before Kennedy's address to the nation revealing that U-2 spyplane photographs had confirmed intelligence reports and that the Soviets were installing medium-range nuclear missiles on the Caribbean island—code named Operation Anadyr. Thus President Kennedy was deprived of a potentially important intelligence agent that might have lessened the tension during the ensuing 13-day stand-off; intelligence such as the fact that Nikita Khrushchev was already looking for ways to defuse the situation. Such information, arguably, would have reduced the pressure on Kennedy to launch an invasion of the island—an action which, it is now known, might have led to the use of Luna class tactical nuclear weapons against U.S. troops. The Soviet commander, General Issa A. Pliyev, commander in charge, had been given permission to use these weapons without consulting Moscow first.
Penkovsky is said to have been convicted of treason and espionage in a trial in 1963. Some sources[who?] allege Penkovsky was executed by the traditional Soviet method of a bullet to the back of the neck, cremated and his ashes buried in the New Donskoy Cemetery in Moscow. Former MI5 officer Peter Wright believed Penkovsky was actually a double agent who, having completed his task of taking in the western intelligence services, was, after a show trial, awarded a suitable post out of sight in the Soviet Union. This, claims Wright, explains why Penkovsky never defected to the West when he had the chance.
GRU agent Vladimir Rezun, known for his controversial books under the pseudonym Viktor Suvorov following his defection from the Soviet Union to the United Kingdom, alleged in Aquarium to have been shown a black and white film in which a GRU colonel was bound to a stretcher and cremated alive in a furnace as a warning to potential traitors and since Penkovsky is the only known executed GRU colonel, this description was attributed by many to his fate. A similar description of the process was later included in Ernest Volkman's popular book and Tom Clancy's novel Red Rabbit. Suvorov in interview later denied  that the man in the film was Penkovsky.
Penkovsky was portrayed by Christopher Rozycki in the 1985 BBC television serial Wynne and Penkovsky. His spying career was the subject of Episode 1 of the 2007 BBC Television docudrama Nuclear Secrets, entitled The Spy from Moscow in which he was portrayed by Mark Bonnar. The programme featured original covert KGB footage showing Penkovsky photographing classified information and meeting with Janet Chisholm. It was broadcast on 15 January 2007.
Penkovsky was referenced in three of Tom Clancy's Jack Ryan books: The Hunt for Red October, The Cardinal of the Kremlin, and Red Rabbit. In the Jack Ryan universe, he is described as the agent who recruited Colonel Mikhail Filitov as a CIA agent (code-name CARDINAL), and in fact had urged Filitov to betray him in order to solidify his position as the West's top spy in the Soviet hierarchy. The "cremated alive" hypothesis appears in several Clancy novels. Furthermore, Penkovsky's fate is also mentioned in the Nelson DeMille spy novel The Charm School.