Richard Bissell – The Connecticut Yankee Behind the Bay of Pigs

In 1959 Richard Bissell was named the CIA’s deputy director for plans. It was an unusual selection.

Bissell was replacing a man, Frank Wisner, who was his complete opposite. Wisner was direct from central casting as the shady OSS spy from World War II cleaning up to reflect the new CIA.

Wisner’s FBI file is full of scurrilous tales of his wild life during and after World War II. He lived in Romania with a beautiful Russian spy — a fact that was complicating relations with the industrialists in Romania who were rebuilding their country. He was accused of skimming relief supplies destined for the Red Cross and diverting them elsewhere. A rumor pursued by Sen. Joseph McCarthy suggested Wisner, a one-time Wall Street lawyer, profited off the sale of ships after the war — perhaps improperly.

By 1958 Wisner’s cowboy career as a spy was careening out of control. Diagnosed as bipolar, Wisner was hospitalized. When his return to the agency became impossible, he was exiled. Wisner would eventually commit suicide.

Searching for a replacement as deputy director of plans, CIA director Allen Dulles chose a man who could not be less like Wisner: Richard Bissell. Bissell was the very definition of a New England blueblood.

Richard Bissell was descended from Samuel Bissell, a member of George Washington’s spy corps during the American Revolution. Richard’s father was a successful insurance executive in Hartford who bought Mark Twain’s mansion, which became Richard Bissell’s childhood home. Summers were spent in exclusive Dark Harbor, Maine.

He was educated at Groton and Yale in economics and became a professor. A planned one-year term as an economist at the Commerce Department in Washington blossomed into an assignment that lasted throughout World War II. After the war, Bissell emerged as a rising star, overseeing elements of the Marshall Plan, which directed funds for the rebuilding of Europe following the war.

Bissell was also independent and self-confident. He refused membership in Yale’s Skull and Bones secret society. His circle of friends included intellectuals and spies alike. McGeorge Bundy, President Kennedy’s national security advisor, had been a student of Bissell’s at Yale.

The year 1951 found Bissell working at a Washington think tank and pondering his career options. Bissell was part of the Georgetown set of young professionals blossoming in Washington at the time, and the lure of spying was too strong a pull for Bissell.

At the urging of Wisner and Dulles, Bissell joined the CIA and moved the agency away from the old tools of the spy trade — informers, tipsters and tricksters — toward the electronic collection of data.

While rudimentary compared to today’s government electronic eavesdropping apparatus, Bissell championed the development of the U-2 spy plane program and satellite data gathering capabilities.

Older hands at the CIA raised eyebrows, but Dulles tapped Bissell to be his new deputy of plans in 1959 following Wisner’s flameout. Data gathering seemed a far cry from spy-vs-spy trickery that he now oversaw.

Communism was now enemy number one in Washington. President Eisenhower was intent on curbing communism in Central and South America. Fidel Castro had swept to power in a populist revolution in Cuba and initially bamboozled American diplomats about his intentions.

richard bissellWhen Castro eventually revealed himself to be a communist, the Eisenhower administration determined he needed to go. The CIA began developing schemes within the country to destabilize Castro. But fires, minor protest efforts and subversive radio broadcasts were getting nowhere.

A bolder plan was called for, and Bissell was the man for the job. Bissell’s CIA bio notes, ”He became a CIA legend because he dared to take risks during one of the nation’s darkest periods, the Cold War.” Calling the Bay of Pigs Invasion risky is an understatement.

Eisenhower, in one of his last meetings with the CIA managers, told them that they must act boldly to stop the spread of communism in the west. When Kennedy won the election, nothing was to change in the country’s approach to Cuba.

Bissell would write to a friend: “My guess is that Washington will be a more lively and interesting place in which to live and work. Even so . . . I am not sure how much longer I want to stay in this business.”

Kennedy Arrives in Washington

By the time Kennedy was inaugurated, the outlines of the Bay of Pigs invasion were well-sketched out. The CIA was actively training a 1,400-man fighting force of Cuban exiles in Guatemala to carry out the raid. They would launch from Nicaragua and topple Castro, or that was the plan.

The use of guerrilla fighters wasn’t so far-fetched. A CIA-backed group of guerillas had toppled Guatemala’s leader in 1954. Students of that coup say the CIA drew the wrong lessons from it. Far from being a masterful operation, the fighters in the Guatemala coup were incredibly lucky. Instead of inspiring a similar raid, it should have been a warning sign of what not to do.

One of Kennedy’s first questions about the Bay of Pigs plan was whether it had been vetted by the Joint Chiefs of Staff. When he learned it had not, Kennedy applied the brakes and asked for a review.

Within the CIA, the invasion plan was viewed with a mix of skepticism and awe. It was bold, no doubt. Sending a small army to invade Cuba was audacious. It was a far cry from smaller agency efforts such as acts of sabotage and disinformation campaigns. The plan struck some as flying in the face of some of the agency’s guiding principles. Small risk/big reward were the parameters of a typical CIA operation. The Bay of Pigs appeared to represent an enormous risk.

The plan as presented to Kennedy was relatively simple. A squadron of US bombers, painted and disguised as Cuban aircraft, would bomb Cuba’s airfields. A landing force of 1,400 men would arrive at the Cuban city of Trinidad, where Castro was unpopular.

With air cover for the landing troops, the men would create a stronghold and begin moving inland, soliciting support from anti-Castro locals to strengthen the invading force as it went. Supplies would arrive by ship and the force would, hopefully, oust Castro.

If things went badly, the fighting force would flee to the Escambray Mountains, where there was an existing anti-Castro resistance movement. There they would regroup and take part in a smaller resistance movement that might over time hobble Castro.

The Joint Chiefs’ review of the plan was quite critical. The logistical planning was inadequate. There was no bridge-building equipment called for, no lighting for night operations, inadequate men and equipment to handle heavy loads and very few men trained in amphibious assault.

Without a massive show of support from the residents of Trinidad, the invasion would sputter. Even moderate resistance would cripple the landing. And, the review noted, the attack, given its size, would not likely be a surprise.

Weeks before the assault, planned for April of 1961, a rework was called for. It was critical that the attack not be seen as an American enterprise. It should be lower profile, so that journalists would be slow to witness it. That meant Trinidad, as a target, was out.

The CIA scrambled to find a new target. The remote and lightly populated Bay of Pigs was chosen. The bay was unprotected and could be attacked, but the change undermined a number of elements of the original plan.

  1. It was unlikely to generate a mass uprising, as the area was remote and not anti-Castro.
  2. The beach was not easy to operate on, and it would be difficult for soldiers to move inland.
  3. It would be harder to operate at night in the remote setting, and.
  4. If the invasion failed, there was no chance to retreat into the Escambray Mountains to join up with fledgling anti-Castro resistance. There now was no plan B.

Finally, just hours before the attack, Kennedy gave one last instruction to Bissell. He wanted the invasion to be even quieter. The details he left to Bissell.

Bissell scaled back the air support for the attack. A fleet of 16 aging B-26 bombers had been acquired and doctored to look like Cuban aircraft. The older planes could plausibly have been stolen from Cuba’s aging air force fleet. Bissell ordered that eight planes should hold back. There would now be about 40 airstrikes to support the men on the ground.

Invasion Day Disaster

The disaster at the Bay of Pigs has been well cataloged. In brief, the first wave of bombing attacks damaged, but did not destroy, the Cuban air force.

Journalists got sight of the planes involved and immediately identified them as American planes, not Cuban. The press had already reported stories about the CIA training a Cuban invasion force. At the United Nations, Adlai Stevenson testified that the air strikes were nothing to do with the United States.

With soldiers readying to land on the beaches, the invasion plan was given one final haircut. President Kennedy cancelled additional air support for the invasion. With no air support, the invading troops were battered by the Cuban air force. Two supply ships that were to bring ammunition, weapons and food were sunk at sea, and others dared not approach the island.

One final use of air power was authorized to give ships cover to offload supplies. But the timing was miscommunicated and the resupply never occurred.

The end result was inevitable. On the American side, 122 men died; 176 Cubans were killed. With no weapons or supplies, the invading force surrendered.

The Aftermath

From Bissell’s perspective, the final nail in the coffin for the invasion plan came when President Kennedy rolled back the air support.

Bissell and his fellow deputy director Charles Cabell were at the White House as Kennedy weighed the decision to reduce the air support. Bissell was offered the chance to try to persuade the president personally, but he declined, leaving it to Secretary of State Dean Rusk to convey his opinions.

“Today I view this decision . . . as a major mistake,” he would later write. “For the record, we should have spoken to the president and made as strong a case a possible on behalf of the operation and the welfare of the brigade.”

Back at CIA headquarters, the decision to curtail the air war was greeted with outrage.

“This is the godamnest thing I have ever heard of..” one CIA planner would shout. Bissell wrote: “Probably out of cowardice I allowed Cabell to be the one to deliver the message, and so he bore the brunt of everyone’s anger.”

Bissell’s career with the CIA did not survive. He was offered the chance to return to work in an area in which he had excelled, improving the agency’s data collection and electronic spying capabilities. But he declined and resigned in 1962, eventually returning to Connecticut.

Kennedy would award Bissell the National Security Medal for his work with the CIA, and Bissell would end his career in private industry.

Bissell’s Thoughts

For the rest of his life, Bissell was linked to the Bay of Pigs, and he did not avoid the topic. He addressed it in detail in his memoir, Reflections of a Cold Warrior: From Yalta to the Bay of Pigs. Bissell never denied responsibility for the Bay of Pigs disaster, though he did feel unfairly treated in the reviews of the operation.

The CIA inspector general, Bissell felt, had gone out of his way to smear him — possibly to clear the way for Bissell’s rivals within the agency to ascend. Richard Helms reported to Bissell and had been passed over for Bissell’s position as deputy director.

Helms had given the Bay of Pigs operation a wide berth and would take over after Bissell’s resignation, and eventually rise to become CIA director.

Bissell bridled at charges in the inspector general’s report that no first-rate CIA staff was involved in the Bay of Pigs planning.

Some scholars maintain there was no chance for the Bay of Pigs insurgency to work because there was limited anti-Castro sentiment in Cuba. The larger Cuban military, they contend, would have put down the invasion regardless.

Others have suggested the anti-Castro Cubans hoped to draw the U.S. military into the fight. If they did, Bissell has said, they never got that impression from him or his men. The United States was never going to come to the rescue, he contended, and that was made clear from the start to all parties.

Bissell himself maintained that it was the cancellation of air support that doomed the mission. While the invasion might not have toppled Castro, Bissell argues it was the lack of air support that resulted in the invading force being thrashed.

So why didn’t he object more strenuously as the air support was whittled away from the plan? He wrote:

“We should have told (the president) clearly ahead of time that if he wanted to exclude that part of the plan the whole plan had to be reconsidered.”

“I think I retained too much confidence in the whole operation up to the end, more than was rational — but that’s the way it was.

“So emotionally involved was I that I may have let my desire to proceed override my good judgment on several matters.”

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