The new president wasn’t so keen. Kennedy did not want his term of office to begin with an American-sponsored invasion, and he insisted that the exiles land at the Bay of Pigs, a hundred miles from their original target. He also scaled back the air support that the CIA intended to provide, removing the initial air strike, and postponing the second until after it was clear the invasion had succeeded. CIA Deputy Director Richard Bissell felt this would seriously jeopardize the outcome, but his hands were tied.
Launched on 17 April 1961, the invasion was a catastrophic failure, with hundreds of the Cuban exiles killed or captured, and thousands on both sides injured. Kennedy took full responsibility publically: ‘There’s an old saying that victory has a hundred fathers and defeat is an orphan… What matters is only one fact, I am the responsible officer of the government.’ Behind the scenes, he accepted Allen Dulles’ resignation as DCI of the CIA, and Richard Bissell resigned after he was demoted. An internal CIA report castigated the Agency for ‘exceed[ing] its capabilities in developing the project from guerrilla support to overt armed action without any plausible deniability’ and its ‘failure to realistically assess risks and to adequately communicate information and decisions internally and with other government principals.’
This didn’t mean that the US government’s desire to see Castro removed from power disappeared, and in November 1961, Kennedy approved Operation Mongoose, whose aim was to ‘help Cuba overthrow the Communist regime’, through ‘a revolt which can take place in Cuba by October 1962’. This was masterminded by the administration’s Attorney-General, Kennedy’s brother Robert.
Over the next few years, assorted plans to assassinate Fidel Castro were drawn up by the CIA, many of these focusing on the dictator’s trademark cigars. At different times, they considered lacing them with hallucinogenic drugs, poisons, depilatory chemicals and even explosives! To cover their tracks, the agency contemplated an alliance with the Mafia: documents declassified in 2007 recount meetings between a CIA go-between, Robert Maheu, and mob bosses Momo Salvatore Giancana and Santos Trafficante, with Giancana suggesting that ‘some type of potent pill that could be placed in Castro’s food or drink would be much more effective’.
The NSA increased its surveillance of Cuba greatly, generating nearly six thousand reports during the six months from April 1962. However, as the NSA’s own history points out, the events of that autumn ‘marked the most significant failure of SIGINT to warn national leaders since World War II’. Equally, they would prove that one man in the right place can dramatically alter the course of world history.
That man was Colonel Oleg Vladimirovich Penkovsky, a GRU officer who actively spied jointly for the CIA and MI6 from spring 1961 until his arrest at the height of the Cuban Missile Crisis in October 1962. Penkovsky had approached American authorities in Moscow after the Powers trial, but his overtures were rebuffed. Penkovsky was eventually brought on board by a British businessman with links to MI6, Greville Wynne. The material Penkovsky was able to provide gave both British and American intelligence an insight into the workings of the KGB and the GRU, and the sometimes tetchy relationship between the two. He also passed over technical information on the Soviet war machine, especially with regard to their missile and rocket-launching capabilities, and suggested that Premier Khruschev may not be as willing to push the world to nuclear war as his rhetoric might suggest.
Penkovsky visited London with a trade delegation in summer 1961 and returned to the Soviet Union that autumn. The KGB began to suspect there was a leak in spring 1962 after observing Janet Chisholm, the wife of the British station head, receiving a package from an unidentified man. Surveillance on Western embassies showed Penkovsky making an unauthorized, and un-cleared visit to a British embassy reception — which one of Penkovsky’s drinking friends, head of the GRU and former KGB chief General Serov would later try to excuse — and then in July he was seen visiting Wynne in his hotel room, and taking standard precautions to avoid being overheard (turning on the taps and the radio). Penkovsky’s apartment was searched and bugged.
By this time, the situation in Cuba had escalated. Khruschev had taken Kennedy’s inaction during the Bay of Pigs crisis — in particular, not sending troops in to back up the Cuban exiles when it was clear that things were going wrong — to indicate that he lacked a strong backbone. He therefore decided that the Soviet Union would install missiles in Cuba, and Kennedy would have to accept it as a fait accompli. Soviet scientists travelled to Cuba under cover of an agricultural delegation, and began constructing the sites.
New CIA Director John A. McCone was suspicious of the Soviet activity that was revealed by the NSA signal tapping as well as by agents on the ground. This included a report from the French intelligence’s Washington chief of station, Thyraud de Vosjoli, who had visited the Cuban capital, Havana, and noted that four to six thousand Soviet military personnel had arrived there since the start of July. This prompted a U-2 mission that confirmed that the Soviets had brought Surface to Air Missiles (SAMs) to the island. Unfortunately, a release of information to the Washington Post by the State Department resulted in the Russians adopting radio silence, severely denting the NSA’s ability to gain further information about their activity — which meant that the imminent arrival of nuclear ballistic missiles aboard merchant ships steaming towards Cuba was not picked up by the NSA. Based on the information they did have, they believed that Khruschev was telling the truth: ‘The Soviet Union is supplying to Cuba exclusively defensive weapons intended for protecting the interests of the Cuban revolution.’
That was all to change on 14 October when the first overflight of the island in six weeks revealed the presence of Soviet ballistic missiles, which had actually arrived over a month earlier. President Kennedy was briefed early the next morning, and for the next few days, the ultimate game of brinkmanship took place between him and Nikita Khruschev. The information that Penkovsky provided had assisted in the identification of the missile sites, and in reading Khrushchev’s character.
Other spies would also play their part in the crisis. A KGB agent in Washington, journalist Georgi Bolshakov, had built a relationship with Attorney-General Robert Kennedy, and this was used by Khruschev as part of the attempt to blindside the Americans. President Kennedy regarded the communications as a private hotline to Khrushchev, and felt that he had been personally betrayed when the truth about the missiles was revealed.
As the crisis reached its climax, with Kennedy preparing for an invasion of Cuba, which was pretty certain to lead to nuclear war if the Soviets reacted militarily, the KGB Resident in Washington, Aleksandr Feklisov, rang an ABC reporter, John Scali, whom he knew had access to the White House. He passed on a message: if the Soviets removed their missiles, would the US pledge not to invade Cuba? It was the first move in the negotiations that would bring the crisis to a resolution, with Khrushchev sending a personal letter shortly after that in similar terms which officially started the endgame (albeit one that still came perilously close to going wrong, when a Soviet SAM downed a US plane, and the US Navy depth-charged a Soviet submarine that was carrying a tactical nuclear warhead).
Penkovsky and Greville Wynne did not see the resolution of the crisis as free men. Seen handling a forged passport at his flat, Penkovsky was arrested; Wynne was apprehended in Budapest a few days later. Both were tried; Penkovsky was shot and Wynne was eventually exchanged for Gordon Lonsdale in 1964. Penkovsky’s friend, General Serov was dismissed from the GRU and committed suicide shortly afterwards.