John F. Kennedy is all too often given a pass in history in spite of his cascade of failures. It could be expected that if he were able to go on to a second term that if he had led the charge to the moon, the United States would have never arrived. Arguably his biggest blunder which nearly caused World War III was his half-and-half approach to the Bay of Pigs invasion. Irrationally fearful of public perception and of becoming too involved, Kennedy decided to enact less than half of the Cuban invasion plan while expecting full-scale results. This paper will focus on Kennedy’s and the CIA’s failure, along with the unit which had been forced to land on the Cuban shore without protection or aid which would’ve resulted in the fall of the Castro communist dictatorship.

The plan for the invasion of Cuban began under the Eisenhower administration. But the United States was caught in a tricky situation since Batista’s regime was hardly a bastion of democracy. And Castro’s communist followers would turn out to be just as, if not more, murderous and violent than Batista. Again, the very thing which would lead to the fall of the Bay of Pigs had essentially assured Castro’s victory; the United States backed neither side and waffled back and forth, opting for apathy.1 Even the Department of the Army would later call the US Policy between Batista and Castro, “…so inept and ineffectual that it was pro-Batista to Castro and pro-Castro to Batista.”2 This policy would lead to Castro’s victory a few years after the inept policy had been enacted and it would be one of the very few blights on the Eisenhower presidency.

In 1960 plans began for the overthrow of the Castro government which Eisenhower hadn’t cared to address just a few years earlier. The plan developed by the CIA was to establish a government in exile, create propaganda, begin covert action within Cuba and form a future paramilitary invasion force.3 Meanwhile, the US Government had hoped to create an air of plausible deniability. It was this part which would trip up Kennedy when he sought to straddle the line and deny an invasion which the entire world had already known was going to happen.

The United States had conducted successful coups in the past. Most recently one occurred within Iran and Guatemala after Guatemala’s new president showed, what the US had deemed, communist tendencies when the government instituted a land redistribution plan.4 It was after the successes in Guatemala that the United States would plot, “To keep Soviet influence out of the Americas, the United States would take any ‘economic or military action deemed appropriate.'”5 This new view, and one correctly taken if we look at the impoverished communist and socialist countries around the world, along with the very real threat that the Soviets had posed at the time, would be an appropriate path to take for the Americans if the Americans would act appropriately in their desire to carry a plan through to its proper end.

After Eisenhower, Kennedy, who’d been launched into the Presidency through Chicago, had to decide what he wanted to do with Cuba. Kennedy had much more information than Eisenhower and Kennedy had many more options which had been left behind by the previous administration. All there was to do was to begin the plans for invasion or to scrap the whole thing. Nixon wrote in his own memoirs that JFK tried to please everyone in the room by making compromises.6 These compromises would slaughter many Cubans and imprison many millions more for decades.

Kennedy proved how inept he was at handling the situation. Even on the eve of the invasion Kennedy was recorded as saying, “I’m still trying to make some sense out of it.”7 Instead of opting for a direct route and going for victory, many options would be taken at the same time and the dice would be rolled. In a world full of children, JFK was the one hitting all the buttons in the elevator and hoping for the best while a rational adult in the room would’ve directly pressed the button for the floor they were trying to reach.

While Kennedy is largely to blame for what would happen, the CIA does not escape unscathed. In a later report by Michael Warner who wrote about the CIA’s internal inspection, that the “agency’s principals” and Bissell had been derelict in their duty for not warning Kennedy enough about potential disasters.8 While this would hardly be the first time the US Government had been completely mismanaged and largely escaped without placing consequences directly on individuals, it should’ve been obvious to Kennedy and those in power, even without using the CIA, that the Bay of Pigs invasion hadn’t been a kept secret since the installment of the Kennedy administration. Even leading up to the invasion the CIA and the administration had neglected one of the key points that had been left out of Eisenhower’s four point plan: Not a single Cuban officer had been approached for possible defection.9 It was the hope of the CIA that the mere sight of a Cuban opposition force would turn the Communists against Fidel Castro, however, as Warner noted, this was “wishful thinking disguised as analysis.”10

There was also hope that in spite of not contacting the Cuban military, that the opposition force would be strong enough to overthrow the violent Communist government. Bissell had hoped to launch the invasion at the same time as the assassination of Castro11, a plan which had never come to fruition. To make matters worse, there were also conflicting reports that Castro’s assassination could stir more trouble and make an invasion more difficult; creating a martyr out of Castro could potentially rally even more Cubans behind his banner.12

As the planning stages of the invasion developed, Jacob Esterline (aka Jake Engler) was recruited to lead the training of the invading Cubans. He had fought a guerrilla campaign in Burma during World War II and had headed the overthrow of Guatemalan leadership in 1954. By 1960 he was tasked with leading the Cubans with instruction to overthrow the Communist government.13 At the same time, while the Kennedy administration walked back and forth indecisively, Antonio Varona who was a conspirator to assassinate Castro, had approached Kennedy stating that the Cubans had about three months before they were able to master their newly imported Soviet and Czechoslovak weapons.14 All delays, whether needed to train the Cubans who were in Guatemala, or political due to irrational indecisiveness, would make the invasion all the more difficult.

But before an invasion could be enacted, a Cuban invasion force needed to be trained. Early, as soon as the site for training had been selected, the entire mission should’ve been canceled. There was nothing secret about what the United States was doing in Guatemala with a bunch of Cubans with military equipment. As Persons described it, a U.S. Pilot sent to help train the Cubans, “This air base at Retalhuleu was located on a strip of land approximately one-and-a-half miles long by a half-mile wide. A six-foot-high fence made of corrugated metal siding blocked the field from the view of anyone traveling on the highway that paralleled the field on the west side. It blocked the view, that is, if everyone kept traveling. Anyone who stopped, and everyone did, to look through the wide spaces between the sheets of siding, could get a full view of the base. The east side of the field was bordered by a simple barbed wire fence that also closed in both ends on the field. The railroad from Tapachula to Guatemala City and San José ran along the edge of the field just outside the fence. Two trains a day went by pulling ten or 12 cars with people hanging out of all the windows, and standing between the cars. The base and all of the aircraft and associated activities were in full view of the passengers on these trains. We often stood on the roof outside the penthouse to wave to them. They always waved back.”15 As for the training itself, that was an entirely different matter.

Most of the men Persons had received had little to no training as pilots and bore the equivalent amount behind a weapon. To demonstrate their lack of ability, Persons noted a comment, “When we got down here most of the guys couldn’t hit the side of a barn. Some of them couldn’t even hit the pasture the barn was standing in.”16 And to provide a detailed example, a large target of a 50 gallon drum with bamboo poles was sent out into a small lake for target practice using 50-calibre machine guns which were installed in the nose of a B-26. Every day the Cubans had missed the target but after one attempt by the Birmingham pilots, the target had been destroyed.17 It was clear that the Cubans in the air were going to need help from the Americans if there were to be a successful invasion.

Further problems occurred which the CIA and the military should’ve recognized and ought to have resulted in the cancellation of the entire Bay of Pigs plot. Not only did the native Guatemalans know about the plan to invade, but so did Castro. One afternoon, Persons reports, a single, foreign B-25 was seen three or four thousand feet over the camp. When one of the Cubans on the ground recognized it as one of Castro’s planes, two B-26’s were launched into the air but by the time they had reached altitude the B-25 had safely fled.18 Soon thereafter, the American people and the world knew an invasion was imminent. Paul Kennedy, a correspondent for the New York Times, wrote, as Persons said, “accurately” on the description of the military base in Guatemala. Not only did he report accurately, but Kennedy was able to get two miles beyond checkpoints due to lazy security.19 In turn, the Guatemalan newspaper Diario de Centro Americo wrote, “Mr. Kennedy is an inaccurate reporter, a liar, and an imposter.” A week before the invasion Kennedy had attempted to return to Guatemala but was forced to leave the country.

The politics from the administration added to these problems. John Kennedy was fearful of having the United States implicated in the Cuban invasion, however as has been displayed, everyone knew not only that the United States was involved, but almost exactly how they were going to do it. Until the United States had decided to hamper the effort by limiting the amount of planes in the sky. Persons noted, “No one in camp explained why only eight B-26s had been launched to accomplish the vitally important purpose of this first raid. As many as 22 aircraft could have been launched, with the probable result that Castro would have been left powerless in the air for the rest of the campaign. If this had been accomplished the Bay of Pigs story would have had a different ending.” Furthermore, Persons added that groups of tanks, armor equipment, trucks, etc. were near the Cuban military academy, noted by U-2 reconnaissance photos.20 It took a great effort on behalf of the politicians in Washington to fail Cuba.

For such an invasion, as the Americans should’ve learned in the past, communication was also a very important part of any type of coordinated attack, especially one involving air working with an amphibious landing. Persons added that due to the type of radios in the Nicaraguan Mustang planes that they didn’t have the correct frequencies and even if they had, Persons admitted that he did not know Spanish and the Cubans didn’t know enough English.21 Apparently translators were not high on the CIA’s list either.

In spite of all of this, as has been noted earlier, the entire world knew of the oncoming attack. But as the days neared, not only did the world know the US was leading an invasion using a largely Cuban force out of Guatemala, but it was revealed the exact day the invasion would occur. Tad Szulc and Karl Meyer, both American journalists, were able to go through national publications to discover the day of the invasion however, they were convinced by the administration to not release their discovery. But, if two journalists, with minimal legwork, could uncover the day of the attack certainly the Soviets could as well. And in fact, they had. By early April the Soviets uncovered that the day the invasion would occur would be April 17.22 Obviously if the Soviets knew of the day of the attack, certainly Castro would as well.

The Kennedy administration, but more pointedly, Kennedy himself didn’t seem to care. In the naive mind of Kennedy, he still believed that if an invasion were to be launched, that the United States would have plausible deniability. On the idea of a large air campaign, Kennedy reportedly said, “Too spectacular. It sounds like D-Day. You have to reduce the noise level of this thing.”23 Dulles and Bissell were against this point of view, noting that without a strong air campaign, the mission was likely to fail.

Kennedy’s meddling in the military aspects, as though he were a seasoned strategist and not a naive boy from Boston, continued right up until the day of the initial aerial campaign. The CIA had wanted to use sixteen B-26 twin-engine light attack bombers, however with the distance from lift off to the invasion site, they’d only be able to provide air cover for less than 40 minutes. A few days earlier Kennedy and Bissell had a conversation where Kennedy said, “Well, I don’t want it on that scale [after Kennedy had learned 16 planes were going to be used]. I want it minimal.”24 The planes for the mission were cut in half to eight.

Castro’s own air force was admittedly small but it was not entirely ineffective. As Jones notes, Castro had feared defections or sabotage which had been why a number of his planes and material were collected in easily spotted areas. Jones adds that Castro had sixteen to eighteen aircraft and while few, they were more technologically advanced compared to the B 26’s coming out of Guatemala.25 If Kennedy had permitted the military to win the air battle, perhaps the war would’ve been won.

The day of the proper invasion had met with as many troubles as had the lead up to the event. The CIA had ignored reports about coral reefs which had slowed the thirty-six landing craft en route to the Blue Beach at Girón.26 The delays undoubtedly allowed Castro even more time, not that he needed it, to put up a strong resistance against the invading Cubans.

Not to be outdone, the Americans had bungled the invasion further by waiting until the last minute to find transport ships. There was only one crane to unload supplies once a beachhead was to have been established and floodlights had been left off the check list. Furthermore, not even the capacity to build bridges were brought along in spite of the knowledge that there would be swampland that needed to be crossed. In spite of all the other issues mentioned, a Joint Chiefs of Staff noted that the entire operation would crumble if only for these reasons alone.27 Trumbull went on to add that, “Castro was well aware of his urgent need to wipe out the beachhead before a provisional government could be established there. Not unusually, the parachutists had been fired upon by their own trigger-happy Brigade while dropping up to sixteen miles inland as highly essential blocking forces and, as is also customary in such operations, had lost much of their parachuted ammunition in the surrounding swamps.”28

But the Cubans who were landing on the beach had dedication and courage. They also knew the dangers not only the Castro regime wrought, but the horrors that communism naturally brings to every land it touches. But courage alone does not win a war. Grayston Lynch who was involved in these efforts wrote of the importance of air and the dangers the landings posed, “I was no novice in the field of warfare. I had landed on Omaha Beach in Normandy, fought in Korea, and only recently returned from Laos. Until now, I’d had only one small worry about this invasion. It was the huge JS-3 and JS-4 Stalin tanks that Fidel had received from the Soviets. I had studied these tanks for years, and I knew that the best weapon to stop these monsters was the aircraft rockets of the brigade’s B-26s. The 76mm high-velocity cannon of the brigade tanks could take them out only if they could strike them in the flanks. I also knew that if the Soviet tanks broke through the ‘shooting gallery’ exits, they would allow Castro’s forces to pour onto the beachhead.

“Whoever controlled the air over Cochinos Bay controlled Cuba.”29

Grayston would add that he was told through Bissell that “political considerations” were overtaking the military rational. Aside from this fact, fewer and fewer people were believing in the invasion due to Kennedy’s meddling from changing the air force numbers to even changing the location of the landing. By April 9, both Colonel Hawkins from the marines and Esterline from the CIA met with Bissell at his home in order to resign as they both believed the mission would fail.30

On the day of the invasion Castro’s air force won out. It had remained a dogged fight but the limited air force of the rebels and the Americans were no match for Castro’s planes which had remained close to home. While the rebels had sank one of Castro’s gunboats, two Sea Furies and two B-26’s and hit Red Beach hard, Castro’s T-33’s brought down four B-26s which caused the remainder to return to friendlier skies. The Americans had assumed that the T-33’s wouldn’t be much of a threat however its believed that they had been refitted by the Soviets with rockets under the T-33’s wings, attaching a pair of .50-caliber machine guns. And this while the rebel B-26’s didn’t even have tail guns.31 It is clear that a larger air force, perhaps even with the original number being as low as it was, it may have been adequate to not only knock out Castro’s air power before the invasion, or if it hadn’t, Castro would’ve been weak enough to have been shot out of the sky on invasion day. Additionally, the plot to have the locals press against Castro never arose. The landing zone Kennedy chose was less populated than the original plan and why would anyone change sides when the Americans weren’t even doing the bare minimum to win the initial, and most important, battle?

After landing, one of the leaders of the invasion who went by the name of Pepe had radioed late in the night asking if Washington was going to do anything. Jones reported Pepe as calling out, “Do you people realize how desperate the situation is? Do you back us up or quit? All we want is low jet cover and jet close support. Enemy has this support. I need it badly or cannot survive. Please don’t desert us. Am out of tank and bazooka ammo. Tanks will hit me at dawn. I will not be evacuated. Will fight to the end if we have to. Need medical supplies urgently.”32 Unnaturally, he and the invasion force was ignored and left on the island.

By the beginning of the third day, Pepe and his unit had made it to San Blas above Blue Beach where Castro rained artillery on him. Pepe led his group in a counterattack but swiftly had to retreat due to limited ammunition. At 3:30 AM Bissell had convinced Kennedy to provide air cover, of which Kennedy only permitted one hour beginning at 6:30 AM. Jones reported aptly, “Acting in less than ten minutes, the Joint Chiefs saddles the pilots of six unmarked jets from the Essex with the virtually impossible task of defending the transports and B-26s en route to the area without hitting ground targets or seeking combat. ‘We had permission to be there,’ declared an unidentified person at the Naval War college years afterward, ‘But not to engage. To conceal the American role if shot down, the pilots would carry no identification papers and, despite flying over shark-filled waters, ditch only at sea if necessary.”33

The limited allowance of air Kennedy had permitted resulted in only 6 more B-26’s, each leaving Puerto Cabezas two at a time and their departures spread out so they’d each arrive at the beachhead at different intervals. The CIA had even authorized Alabama Air National Guardsmen to occupy two of the planes.34 While the Cubans didn’t have a great air force, they still retained superiority. Before the promised jet support had arrived, the American planes with the National Guardsmen had been shot down. Two Americans parachuted and landed in the water but were quickly captured by Castro’s forces and executed. The other two Americans had crashlanded and were killed in a firefight.35 The promised American navy jets arrived roughly an hour after Castro’s T-33’s had begun their assault on the first American planes.

The 6 planes that Kennedy had offered was pathetic as was the timing of the jet support. Rightfully so, by that morning, Pepe again radioed in, “Have you quit? Aren’t you going to support me any more? Regardless of whether you help or not, I will fight on regardless.” While some resources were already on their way by the time of Pepe’s plea, most of those resources were poorly dropped, missing their target area entirely and fell into the sea.36 It ought to be mentioned by this time that Pepe, his unit and others were becoming entrapped and hadn’t been trained for guerrilla warfare. At this point, without full-out American support, the invasion would fail.

The rest of the morning showed the failure. Simply by displaying Pepe’s radio messages it can be observed how Kennedy had failed and ignored the Cubans, leaving them to die battling Castro. Jones lays out these messages in subsequent detail:

“At 11:18 A.M. of April 19: ‘We are out of ammo and fighting on the beach. Please send help. We cannot hold.’

“Thirteen minutes later, another message: ‘Out of ammunition. Men fighting in water. If no help given Blue Beach lost.’

“‘In water. Out of ammo. Enemy closing in. Help must arrive in next hour.’

“‘When your help will be here and with what?’

“‘Why your help has not come?’

“And, finally, ‘Am destroying all equipment and communications. Tanks are in sight. I have nothing to fight with. Am taking to woods. I cannot repeat cannot wait for you.'”37

The almost-attempted invasion had been wiped out by the end of the third day. There had remained some holdouts in the jungle but they would last no more than a week before their capture.

Castro had killed 114 men of the invading force and captured almost 1200, including Pepe. While Castro had suffered heavy losses at an assumed 3,650 casualties, including 1,250 deaths in battle and another 400 from wounds and insufficient medical care, Kennedy had emboldened Castro and made his status all the more secure.38 Furthermore, the failure of the invasion would lead to the Cuban Missile Crisis that, while many claim Kennedy had defused the issue, it would have never occurred had Kennedy not invited the environment to begin with.

Returning to Lynch, he wrote fondly of working with Pepe. In Lynch’s book, he wrote, “Pepe was not a field marshal, and he knew it. He never claimed to be, never claimed to be anything more than he was, but he was a damn fine officer and the best man for the job in the 2506 Brigade. He impressed me very much. I only regretted that I did not have time, on that short voyage, to get to know him better. After two days on the ship, I liked him. After three days and nights of the Cochinos battle, I also respected him.”39 If Kennedy had only followed the initial plan, or had remained out of the room altogether, either giving his approval to the initial idea or rejecting it outright, Castro likely wouldn’t have achieved his worldly, monumental status. And the thousand of Cubans who had invaded wouldn’t have suffered..

Interestingly, Ernest Halperin from the Massachusetts Institute of Technology met with Castro in Havana and asked Castro why he thought the invasion had failed. Castro replied simply, “Lack of aircover.”40 Castro went on to cite other failures as well such as landing zones, paratroopers but the lack of American aircover remained the primary reason for these failures.

Kennedy had failed in little time to live up to any of his promises. Grayston wrote succinctly, “The Kennedy administration had been inaugurated with the promise that it would ‘pay any price, bear any burden, meet any hardship, support any friend, oppose any foe, to ensure the survival and success of liberty.’ On this ‘Black Sunday’ in April 1961, it failed to keep a single one of its noble promises. It did not ‘support a friend,’ the 2506 Brigade. Instead, it considered the brigade a burden too heavy to bear. When it discovered the high cost of political embarrassment, it also found it could not pay any price. Nor did it face the foe represented by Castro, and it certainly did nothing to assure the survival and success of liberty in Cuba.”41 Kennedy’s mind was full of big dreams, great ambitions and self-delusions, but unfortunately, it omitted all critical thought, destroying the lives and generations of an entire nation and bringing the world to the brink of nuclear war.

Whether or not the invasion was a good plan or not doesn’t matter. Whatever the Eisenhower administration had put together, Kennedy had adopted it. From then, Kennedy had bastardized what the previous administration and intelligence agencies had come up with. While the CIA is hardly blameless and had plenty of faulty information, the one effect that had led to the failure of the invasion of Cuba lies squarely on Kennedy’s shoulders. He not only chose to go along with the invasion, but even when all the signs were pointing to abort, such as the discovery of not only the invasion force, Castro’s flights overhead and the journalists and Soviet discovery of the actual day of the invasion, Kennedy had stubbornly decided to go ahead with the plan. More than that, Kennedy had even altered the plan in a way to make it impossible to work as time went on. If Kennedy had simply approved the plan and stayed out of the way, even Castro admitted that he wouldn’t have been able to repel the invasion. Or if Kennedy had chosen to kill the plans for invasion, Castro wouldn’t have been lionized. Kennedy had built a monument for Castro on Kennedy’s own failures and the Cuban bodies Kennedy had left behind. JFK didn’t just make the United States vulnerable in the ensuing years and permit the imprisonment of millions of Cubans, JFK had also betrayed the spirit of the nation.

Works Cited

1. Murder, Inc. p 2

2 ibid. p 2

3 Gambling With Armageddon

4 Failures of the Presidents pp 180-1

5 ibid. pp 181

6 The Memoirs of Richard Nixon p 233

7 Anatomy of a Failure: The Decision to Land at the Bay of Pigs pp 484-5

8 The CIA’s Internal Probe of the Bay of Pigs Affair p 96

9 ibid. p 99

10 ibid. 100

11 The Bay of Pigs p 26

12 Murder, Inc. p 28

13 The Bay of Pigs p 26-7

14 ibid. p 37

15 Bay of Pigs: A Firsthand Account of the Mission by a U.S. Pilot in Support of the Cuban Invasion Force in Cuba 1961 p 46

16 ibid. p 53

17 ibid. pp 53-4

18 ibid. p 54

19 ibid. p 55

20 ibid. pp 80-1

21 ibid. p 97

22 The Bay of Pigs pp 65-6

23 Failures of the Presidents pp 183-5

24 ibid. p 186

25 The Bay of Pigs p 76

26 The Perfect Failure p 140

27 ibid. p 141

28 ibid. p 141

29 Decision For Disaster pp 70-1

30 The Bay of Pigs p 77

31 ibid. p 110

32 ibid. p 118

33 ibid. p 118

34 ibid. p 119

35 ibid. p 119

36 ibid. p 120

37 ibid. p 121

38 ibid. p 122

39 Decision For Disaster p 72

40 The Bay of Pigs p 125

41 Decision for Disaster pp 78-9


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Higgins, Trumbull. The Perfect Failure: Kennedy, Eisenhower, and the CIA at the Bay of Pigs. W.W. Norton, & Co., 1989.

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