In July, 1947 Bissell was recruited by Averell Harriman to run a committee to lobby for an economic recovery plan for Europe. The following year he was appointed as an administrator of the Marshall Plan in Germany and eventually became head of the Economic Cooperation Administration. Bissell also worked closely with the Office of Strategic Services (OSS) which had helped to organize guerrilla fighting, sabotage and espionage during the war.
Bissell moved to Washington where he associated with a group of journalists, politicians and government officials that became known as the Georgetown Set. This included Frank Wisner, George Kennan, Dean Acheson, Desmond FitzGerald, Joseph Alsop, Stewart Alsop, Tracy Barnes, Thomas Braden, Philip Graham, David Bruce, Clark Clifford, Walt Rostow, Eugene Rostow, Chip Bohlen, Cord Meyer, James Angleton, William Averill Harriman, John McCloy, Felix Frankfurter, John Sherman Cooper, James Reston, Allen W. Dulles and Paul Nitze.
Most men brought their wives to these gatherings. Members of what was later called the Georgetown Ladies' Social Club included Katharine Graham, Mary Pinchot Meyer, Sally Reston, Polly Wisner, Joan Braden, Lorraine Cooper, Evangeline Bruce, Avis Bohlen, Janet Barnes, Tish Alsop, Cynthia Helms, Marietta FitzGerald, Phyllis Nitze and Annie Bissell.
Bissell worked for the Ford Foundation for a while but Frank Wisner, persuaded him to join the Central Intelligence Agency (CIA). Its role was to evaluate intelligence reports and coordinate the intelligence activities of the various government departments in the interest of national security. In 1954 he was placed in charge of developing and operating the U-2 spy plane. The U-2 was designed by Kelly Johnson, who had previously been responsible for the P-38 and the F-104 fighter planes. It was essentially a glider with a jet engine. It was so light it could fly at an altitude of 70,000 feet and travel over 4,000 miles. It took two years and $19m to develop. President Dwight Eisenhower gave permission for the U-2 to fly over Moscow and Leningrad for the first time on 4th July, 1956.
The U-2 spy plane was a great success and within two years Bissell was able to say that 90% of all hard intelligence about the Soviet Union coming into the CIA was "funneled through the lens of the U-2's aerial cameras". This information convinced Eisenhower that Nikita Khrushchev was lying about the number of bombers and missiles being built by the Soviet Union. Eisenhower now knew that United States enjoyed a major advantage over the Soviet Union and allowed him to control defence spending.
In December, 1956, Frank Wisner, head of the Directorate for Plans, an organization instructed to conduct covert anti-Communist operations around the world, suffered a mental breakdown and was diagnosed as suffering from manic depression. During his absence Wisner's job was covered by Richard Helms. The CIA sent Wisner to the Sheppard-Pratt Institute, a psychiatric hospital near Baltimore. He was prescribed psychoanalysis and shock therapy (electroconvulsive treatment). It was not successful and still suffering from depression, he was released from hospital in 1958.
Wisner was too ill to return to his post as head of the Directorate for Plans (DPP). Allen W. Dulles therefore sent him to London to be CIA chief of station in England. Dulles decided that Bissell rather than Richard Helms should become the new head of the DPP. Helms became Bissell's deputy.
The Directorate for Plans was responsible for what became known as the CIA's Black Operations. This involved a policy that was later to become known as Executive Action (a plan to remove unfriendly foreign leaders from power). This including a coup d'état that overthrew the Guatemalan government of Jacobo Arbenz in 1954 after he introduced land reforms and nationalized the United Fruit Company.
Other political leaders deposed by Executive Action included Patrice Lumumba of the Congo, the Dominican Republic dictator Rafael Trujillo, General Abd al-Karim Kassem of Iraq and Ngo Dinh Diem, the leader of South Vietnam. However, his main target was Fidel Castro who had established a socialist government in Cuba.
In March I960, President Dwight Eisenhower of the United States approved a CIA plan to overthrow Castro. The strategy was organised by Bissell. Sidney Gottlieb of the CIA Technical Services Division was asked to come up with proposals that would undermine Castro's popularity with the Cuban people. Plans included a scheme to spray a television studio in which he was about to appear with an hallucinogenic drug and contaminating his shoes with thallium which they believed would cause the hair in his beard to fall out.
These schemes were rejected and instead Bissell decided to arrange the assassination of Fidel Castro. In September 1960, Bissell and Allen W. Dulles, the director of the Central Intelligence Agency (CIA), initiated talks with two leading figures of the Mafia, Johnny Roselli and Sam Giancana. Later, other crime bosses such as Carlos Marcello, Santos Trafficante and Meyer Lansky became involved in this plot against Castro.
The strategy was managed by Sheffield Edwards and Robert Maheu, a veteran of CIA counter-espionage activities, was instructed to offer the Mafia $150,000 to kill Fidel Castro. The advantage of employing the Mafia for this work is that it provided CIA with a credible cover story. The Mafia were known to be angry with Castro for closing down their profitable brothels and casinos in Cuba. If the assassins were killed or captured the media would accept that the Mafia were working on their own.
The Federal Bureau of Investigation had to be brought into this plan as part of the deal involved protection against investigations against the Mafia in the United States. Castro was later to complain that there were twenty ClA-sponsered attempts on his life. Eventually Johnny Roselli and his friends became convinced that the Cuban revolution could not be reversed by simply removing its leader. However, they continued to play along with this CIA plot in order to prevent them being prosecuted for criminal offences committed in the United States.
As the end of his presidency approached, Dwight Eisenhower, decided to take a decisive step towards ending the Cold War by arranging a summit meeting with Nikita Khrushchev. The two sides agreed to meet in Paris on 16th May, 1960.
On 1st May, 1960, a high-altitude American photographic reconnaissance aircraft, a Lockheed U-2, was shot down over the Soviet Union and the pilot, Gary Powers, was taken prisoner. Six days later Khrushchev announced to the world what had happened and demanded a full apology from the United States government. President Eisenhower replied by admitting that the Central Intelligence Agency had carried out these spying missions without his authority. However, he argued that the United States government had the right to protect its security by collecting the maximum of information about Soviet military strength.
On 15th May Nikita Khrushchev made another appeal to Dwight Eisenhower to apologize for carrying out aerial spying on the Soviet Union. When he refused, the Soviet delegation left Paris and the summit meeting never took place. Some suspected that some hardliners had purposely undermined Eisenhower's attempts to bring an end to the Cold War.
In March 1960 Bissell had drafted a top-secret policy paper entitled: A Program of Covert Action Against the Castro Regime (code-named JMARC). This paper was based on PBSUCCESS, the policy that had worked so well in Guatemala in 1954. In fact, Bissell assembled the same team as the one used in Guatemala (Tracy Barnes, David Atlee Phillips, David Morales, Jake Esterline, Rip Robertson, E. Howard Hunt and Gerry Droller Frank Bender). The only one missing was Frank Wisner, who had suffered a mental breakdown in 1956. Added to the team was Desmond FitzGerald, William Harvey and Ted Shackley.
The policy involved the creation of an exile government, a powerful propaganda offensive, developing a resistance group within Cuba and the establishment of a paramilitary force outside Cuba. In Guatemala this strategy involved persuading Jacobo Arbenz to resign. Bissell knew of course that Fidel Castro would never agree to that. Therefore, Castro had to be removed just before the invasion took place. If this did not happen, the plan would not work.
John F. Kennedy was given a copy of the JMARC proposal by Bissell and Allen W. Dulles in Palm Beach on 18th November, 1960. According to Bissell, Kennedy remained impassive throughout the meeting. He expressed surprise only at the scale of the operation. The plan involved a 750 man landing on a beach near the port of Trinidad, on the south coast of Cuba. The CIA claimed that Trinidad was a hotbed of opposition to Castro. It was predicted that within four days the invasion force would be able to recruit enough local volunteers to double in size. Airborne troops would secure the roads leading to the town and the rebels would join up with the guerrillas in the nearby Escambray Mountains.
In March 1961 John F. Kennedy asked the Joint Chiefs of Staff to vet the JMARC project. As a result of plausible deniability they were not given details of the plot to kill Castro. The JCS reported that if the invaders were given four days of air cover, if the people of Trinidad joined the rebellion and if they were able to join up with the guerrillas in the Escambray Mountains, the overall rating of success was 30%. Therefore, they could not recommend that Kennedy went along with the JMARC project.
At a meeting on 11th March, 1961, Kennedy rejected Bissells proposed scheme. He told him to go away and draft a new plan. He asked for it to be less spectacular and with a more remote landing site than Trinidad. It appears that Kennedy had completely misunderstood the report from the JCS. They had only rated it as high as a 30% chance of success because it was going to involve such a large landing force and was going to take place in Trinidad, near to the Escambray Mountains. After all, Fidel Castro had an army and militia of 200,000 men.
Bissell now resubmitted his plan. As requested, the landing was no longer at Trinidad. Instead he selected Bahia de Cochinos (Bay of Pigs). This was 80 miles from the Escambray Mountains. What is more, this journey to the mountains was across an impenetrable swamp. As Bissell explained to Kennedy, this means that the guerrilla fallback option had been removed from the operation.
As Allen W. Dulles recorded at the time: We felt that when the chips were down, when the crisis arose in reality, any action required for success would be authorized rather than permit the enterprise to fail. In other words, he knew that the initial invasion would be a disaster, but believed that Kennedy would order a full-scale invasion when he realized that this was the case. According to Evan Thomas (The Very Best Men): Some old CIA hands believe that Bissell was setting a trap to force U.S. intervention. Edgar Applewhite, a former deputy inspector general, believed that Bissell and Dulles were building a tar baby. Jake Esterline was very unhappy with these developments and on 8th April attempted to resign from the CIA. Bissell convinced him to stay.
On 10th April, 1961, Bissell had a meeting with Robert Kennedy. He told Kennedy that the new plan had a two out of three chance of success. Bissell added that even if the project failed the invasion force could join the guerrillas in the Escambray Mountains. Kennedy was convinced by this scheme and applied pressure on those like Chester Bowles, Theodore Sorenson and Arthur Schlesinger who were urging John F. Kennedy to abandon the project.
On 14th April, Kennedy asked Bissell how many B-26s were going to be used. He replied sixteen. Kennedy told him to use only eight. Bissell knew that the invasion could not succeed without adequate air cover. Yet he accepted this decision based on the idea that he would later change his mind when the chips were down.
Allen W. Dulles was in Puerto Rico during the invasion. He left Charles Cabell in charge. Instead of ordering the second air raid he checked with Dean Rusk. He contacted Kennedy who said he did not remember being told about the second raid. After discussing it with Rusk he decided to cancel it.
Instead the operation tried to rely on Radio Swan, broadcasts being made on a small island in the Caribbean by David Atlee Phillips, calling for the Cuban Army to revolt. They failed to do this. Instead they called out the militia to defend the fatherland from American mercenaries.
At 7 a.m. on 18th April, Bissell told Kennedy that the invasion force was trapped on the beaches and encircled by Castros forces. Then Bissell asked Kennedy to send in American forces to save the men. Bissell expected him to say yes. Instead he replied that he still wanted minimum visibility.
After the air raids Cuba was left with only eight planes and seven pilots. Two days later five merchant ships carrying 1,400 Cuban exiles arrived at the Bay of Pigs. Two of the ships were sunk, including the ship that was carrying most of the supplies. Two of the planes that were attempting to give air-cover were also shot down.
That night Bissell had another meeting with John F. Kennedy. This time it took place in the White House and included General Lyman Lemnitzer, the chairman of the Joint Chiefs of Staff and Admiral Arleigh Burke, Chief of Naval Operations. Bissell told Kennedy that the operation could still be saved if American warplanes were allowed to fly cover. Admiral Burke supported him on this. General Lemnitzer called for the Brigade to join the guerrillas in the Escambray Mountains. Bissell explained this was not an option as their route was being blocked by 20,000 Cuban troops.
Within seventy-two hours all the invading troops had been killed, wounded or had surrendered. Bissell had a meeting with John F. Kennedy about the Bay of Pigs operation. Kennedy admitted it was his fault that the operation had been a disaster. Kennedy added: "In a parliamentary government, I'd have to resign. But in this government I can't, so you and Allen (Dulles) have to go."
As Evan Thomas points out in The Very Best Men: "Bissell had been caught in his own web. "Plausible deniability" was intended to protect the president, but as he had used it, it was a tool to gain and maintain control over an operation... Without plausible deniability, the Cuba project would have turned over to the Pentagon, and Bissell would have have become a supporting actor."
John F. Kennedy asked Maxwell Taylor to investigate what went wrong during the Bay of Pigs operation. Taylor asked Lyman Kirkpatrick, the CIA's inspector general, to write a report on the failed project. Kirkpatrick was highly critical of both Bissell and Tracy Barnes. He claimed that they had misled the president and that "plausible deniability was a pathetic illusion".
Kennedy was still determined to overthrow Fidel Castro. He created a committee (SGA) charged with overthrowing Castro's government. The SGA, chaired by Robert F. Kennedy (Attorney General), included Allen W. Dulles (CIA Director), later replaced by John McCone, Alexis Johnson (State Department), McGeorge Bundy (National Security Adviser), Roswell Gilpatric (Defence Department), General Lyman Lemnitzer (Joint Chiefs of Staff) and General Maxwell Taylor. Although not officially members, Dean Rusk (Secretary of State) and Robert S. McNamara (Secretary of Defence) also attending meetings.
At a meeting of this committee at the White House on 4th November, 1961, it was decided to call this covert action program for sabotage and subversion against Cuba, Operation Mongoose. Attorney General Robert F. Kennedy also decided that General Edward Lansdale (Staff Member of the President's Committee on Military Assistance) should be placed in charge of the operation.
Robert F. Kennedy now took the leading role in trying to overthrow Castro. At a meeting in November, 1961, Kennedy accused Bissell of "not doing anything about getting rid of Castro and the Castro regime." CIA agent Sam Halpern complained that "Bobby (Kennedy) wanted boom and bang all over the island... it was stupid... the pressure from the White House was very great." Bissell did what he could to arrange the assassination of Castro. This included asking William Harvey to take over the Mafia contracts from Sheffield Edwards.
John F. Kennedy did not actually sack Bissell. Instead he offered him the post as director of a new science and technology department. This would place him in charge of the development of the SR-71, the new spy plane that would make the U-2 obsolete. Bissell turned down the offer and in February 1962 he left the Central Intelligence Agency and was replaced as head of the Directorate for Plans, by Richard Helms.
Bissell became head of the Institute for Defense Analyses (IDA) in 1962. IDA was a Pentagon think tank set up to evaluate weapons systems. Later he worked for United Technologies in Hartford (1964-74). He also worked as a consultant for the Ford Foundation.
Richard Bissell died in 1994. His autobiography, Reflections of a Cold Warrior: From Yalta to the Bay of Pigs, was published two years later.