The CIA’s Spectacular Blunder: A Gallery of Absurd Plots to Assassinate Castro
What is vaporwave? Much of today’s vaporwave art draws on Japanese anime and retro aesthetics from the 1980s and 1990s, yet the movement originated in the United States in the early 2000s. It began as a satire of runaway consumerism and capitalism. Bubble-era Japan embodied those excesses perfectly, which is why it became such a recurring source of vaporwave imagery.
Still, using Japanese pop culture to skewer capitalism was mostly a playful pastime. If you want real pushback against the system, look to the Cuban people.
As the archetypal capitalist superpower, what single word could the U.S. use to insult itself? And what single word could Cuba use to taunt the CIA? That word is Castro.
Cuba is an island nation in the Caribbean, home to around eleven million people and spanning roughly 110,000 square kilometers. At its closest point, it sits only 90 nautical miles from the U.S. mainland.
For decades, the United States projected force everywhere, from Arctic seabeds to Afghan mountain caves. Yet this small nation, right on its doorstep, stood firm in its anti‑American stance for more than fifty years and endured. Its very existence felt like a deliberate, unignorable rebuke to Washington.
No American from the pre‑revolution era could have imagined this outcome. Since 1962, the U.S. launched three direct landing operations against Cuba. Before the revolution, American capital controlled Cuba’s economic lifelines; no one in Washington expected serious unrest to erupt on the island.
In 1933, a sergeant named Fulgencio Batista led a revolt of fellow non‑commissioned officers to overthrow Cuba’s government. After seizing power, Batista promptly promoted himself from sergeant all the way to general and took charge of the army. For U.S. officials, Batista quickly proved himself a compliant ally, much to American satisfaction.
By 1952, the United States signaled to Batista: “You are a seasoned general now; it is time to become president.” Batista assumed the presidency, handed broad control of Cuba’s economy to U.S. corporations, and approved construction of the U.S. naval base at Guantánamo Bay. Under his rule, Cubans faced grinding poverty and rampant corruption — problems Washington chose to ignore.
In 1959, the Cuban Revolution triumphed, and Batista fled the country with his family. At first, U.S. leaders stayed calm, writing it off as just another routine regime change. They soon realized something was different. The man who had toppled Batista was Fidel Castro.
Fidel Castro was never one to submit to authority. Born into a wealthy Cuban landowning family with thousands of hectares of land, he sympathized deeply with the farmworkers on his family’s estate. At thirteen, he organized strikes among those laborers; his first target of rebellion was his own father. After university, Castro dedicated himself to anti‑imperialist work. He defended poor Cubans as a lawyer, joined anti‑colonial movements across Latin America, and set his sights on overthrowing Batista’s military dictatorship.
In 1953, Fidel Castro and his brother Raúl Castro led a band of young revolutionaries in an assault on the Moncada Barracks, firing the first shot against Batista. Castro’s fighters were vastly outmatched by government troops, but Batista’s regime was wildly unpopular, and Castro won broad support from ordinary Cubans.
In January 1959, rebel forces captured Santiago de Cuba, and Batista fled into exile. This episode even appears in The Godfather Part II.
Castro had not originally sought conflict with the United States, but his reforms proved unacceptable to Washington. Immediately after taking power, he pushed through land reform, starting with his own family’s holdings, to redistribute farmland to poor Cubans. The largest landowners on the island were American corporations. Castro seized those U.S. holdings without hesitation.
To American policymakers, Castro’s agenda seemed delusional. The U.S. imposed sanctions and cut off oil exports to Cuba. Cuba turned instead to the Soviet Union for petroleum. Washington ordered U.S.-owned refineries on Cuban soil to refuse Soviet crude; Castro nationalized those refineries. When the U.S. banned Cuban sugar imports, Cuba sold its sugar to the USSR. Backed by Soviet support, American sanctions largely failed to achieve their goals.
Seeing that neither pressure nor persuasion worked, the U.S. fell back on its familiar playbook: let the CIA launch an operation to remove Castro.
Castro’s reforms drove Cuba’s middle class, wealthy landowners, and former regime loyalists into exile in the U.S. The CIA recruited these exiles to plot the overthrow of Castro’s government. Small cross‑border infiltration attempts began almost as soon as Castro took power, yet every single one collapsed.
In 1960, the CIA presented newly elected President Kennedy with an ambitious plan: Operation Pluto.
Nearly all of the CIA’s intelligence on Cuba came from exiled Cubans. These exiles claimed a massive underground opposition waited inside Cuba, ready to rise up the moment they received a signal. The CIA embellished these reports for Kennedy, concluding that Cuba was like a rickety house — one firm kick, and it would collapse.
Here was the plan, laid out by CIA Director Allen Dulles: “We have recruited around 1,400 Cuban fighters, seasoned and formidable. If we arm them and send them ashore, they will link up with domestic opponents, install a new government, and request U.S. intervention. That will give us a clear legal pretext to step in.”
Fresh off the successful 1954 coup against Guatemala’s Jacobo Árbenz, the CIA won Kennedy’s reluctant approval. “Go ahead,” Kennedy told them.
Some advisors raised obvious objections: Cuba’s army numbered 30,000 men, while the exile force was barely one or two thousand. What if they were overwhelmed?
The CIA brushed the concern aside. They had selected a remote landing site where resistance would be light. Secure the beachhead, they insisted, and the rest would follow.
With presidential and Pentagon approval, the CIA began secretly assembling Brigade 2506. The secrecy, however, was comically thin. Within days of training starting, The New York Times ran a front‑page story warning Castro: the CIA was training Cuban exiles in Guatemala for an invasion.
And what of this brigade the CIA hyped as elite warriors? It resembled a bag of potato chips: large‑looking on the outside, with very little substance inside. Out of those 1,400 men, only about a hundred had prior military experience. Most were intellectuals, merchants and landowners. They were excellent at grand speeches, but not combat.
Before deployment, the brigade rested in Miami. Drunk on bravado in local bars, they bragged openly about marching into Cuba and killing Castro. A supposedly top‑secret mission became common gossip across Miami.
Before the landing, the CIA supplied the exiles with several B‑26 bombers to strike Cuba’s air force. The raiders destroyed only a handful of Cuban planes, yet returned and lied that they had wiped out Cuba’s entire air fleet. Believing the false report, Washington canceled air support for the landing day.
On the night of April 17, 1961, the invasion fleet set out, scheduled to hit two beaches on Cuba’s southern Bay of Pigs: Playa Larga and Playa Girón.
The CIA expected this to be its finest hour and even hired an advertising agency to broadcast news of the landing worldwide over radio. The frequency was misconfigured, so the whole world picked up the announcement — except the invading brigade itself, who still believed their movement stayed hidden.
That hardly mattered by then. When the boats reached Girón Beach, the invaders were stunned. The desolate, empty shore the CIA had promised was a popular public beach resort, packed with weekend visitors. Castro himself often fished there, and that landing day happened to be a Sunday.
Castro had been ready. He rushed to the front to lead the response, backed by Cuban troops armed with artillery and tanks. The exile brigade’s gear was shoddy: one machine gun, poorly mounted, tore loose from its boat under recoil and killed several of its own crew.
Cuban forces fought the brigade through the night. At dawn, the Cuban air force — supposedly eliminated days earlier — struck, sinking a supply ship carrying nearly all the invaders’ provisions. By the next afternoon, the brigade was breaking. Their commander Pepe urgently begged Washington for air cover to evacuate: “For God’s sake, get us out of here.”
Under CIA direction, four U.S. B‑26 bombers took off from Nicaragua to cover the retreat. The pilots arrived over the beach to find no ground team ready to guide them in, and all four planes were shot down. The reason for the disaster? Nicaragua and Cuba were one hour apart. The CIA had scheduled the mission without adjusting the pilots’ watches. They arrived an hour early and flew straight into Cuban anti‑aircraft fire.
The fight was over. On April 19, 1961, the surrounded brigade surrendered to Castro. The CIA operation was a total rout, remembered forever as the Bay of Pigs Invasion.
The fiasco sparked global outrage and turned the United States into an international laughingstock. CIA Director Allen Dulles resigned. Every U.S. agency scrambled to avoid blame. Kennedy later uttered his famous line: “Success has a thousand fathers, but failure is an orphan.”
Kennedy addressed the nation, accepted full responsibility for the defeat, and pledged not to repeat the mistake.
The fallout continued long after the speech. More than a thousand captured brigade members had families and ties in the U.S., and Washington needed to negotiate their release. With diplomatic ties broken, the U.S. sent attorney James Donovan to Havana to bargain for the prisoners.
Shockingly, the CIA, humiliated by the Bay of Pigs defeat, was already plotting new ways to kill Castro. Knowing Castro loved diving, agents prepared a wetsuit coated in poison, planning to have Donovan present it as a gift.
Before Donovan left, he inspected the package and thought the scuffed, worn‑looking suit was a terrible present. He discarded the poisoned suit and bought an expensive new one at his own expense to give to Castro.
Eventually, Donovan brokered a deal: the U.S. delivered millions of dollars worth of medicine and baby food to Cuba in exchange for the prisoners. It remains the only war reparations the United States has ever paid.
That trip also marked the first recorded failure in the CIA’s long running assassination campaign against Castro.
Assassinating Castro became a bizarre, decades‑long institutional project for the CIA. No one expected attempts on a single leader to drag on for so long. Cuban sources claim Castro survived 638 assassination plots. The true number of serious, operational attempts is lower, though it still runs into the hundreds. The CIA’s schemes were so outlandish they strain belief.
Because Castro loved diving, one agent proposed hiding explosives inside a brightly colored seashell, placed on the seabed to lure him close before detonation. Setting aside whether an adult would be drawn to a fancy shell, engineers calculated the shell would need to be nearly car‑sized to carry enough explosive to kill him underwater. Convincing Castro such a giant shell existed was arguably harder than the assassination itself.
Another plan relied on poison pills slipped into Castro’s milkshake at the Havana Hilton, with the help of a hotel employee recruited by the CIA. The agent stored the capsules in a freezer. When the time came, the pill froze fast to the freezer wall. He wrenched it free, the capsule split open, and the toxin leaked, nearly killing him instead.
The CIA also tested remote‑controlled bomb‑laden aircraft to strike Castro during public speeches. Radio technology of the era was unreliable, and on the day of the rally, the plane would not take off at all. Castro finished his address and left safely.
When direct CIA action risked exposure, the agency turned to the mafia. They struck a deal with mob boss John Roselli to arrange the hit. Roselli had a notorious backstory: in 1948, he burst into a Hollywood studio with a gun, holding up a woman’s photo and telling the executive to make her a star or die. The woman was Marilyn Monroe.
The CIA‑mafia partnership produced more darkly comic failures. In 1971, during Castro’s visit to Chile, two hitmen posed as journalists for a press conference, hiding firearms inside camera equipment. The plan seemed foolproof. Minutes before the event, one assassin suffered a sudden appendicitis and was rushed to hospital. The second, left without his partner, panicked, forgot the whole plan, and watched Castro speak from the crowd.
There were many more botched attempts. One gunman brought a rocket launcher, then backed out, fearing the blast would draw too much attention and trap him. Some handlers had second thoughts and abandoned the plot. Others surrendered to authorities after the CIA delayed payment.
Castro’s famous cigar habit inspired poisoned cigars and explosive cigars. But his cigars came from a tightly controlled, exclusive supply chain, inaccessible to outsiders. Just as agents neared a way to deliver the booby‑trapped cigars, Castro quit smoking.
By the early 2000s, the CIA abandoned its decades‑long quest. Castro once joked, “I am alive today entirely because of the CIA.”
After the Bay of Pigs, U.S.‑Cuban relations hit rock bottom. To survive, Castro drew closer to the Soviet Union. Khrushchev watched Kennedy’s embarrassment and quipped that Cuba was too tricky for Washington to manage.
Back in 1959, while the U.S. choked the new Cuban government with sanctions, the Soviet Union reached out. When the U.S. stopped buying Cuban sugar, Moscow contacted Che Guevara in Egypt and placed an order for half a million tons. At first, Castro hoped Cuba could stay neutral, but he quickly realized neutrality offered little safety for a small island nation.
That massive sugar order convinced him the Soviet Union was a reliable ally. In 1960, Anastas Mikoyan visited Cuba. On his return to Moscow, he warned Khrushchev that Soviet support could draw U.S. retaliation. Khrushchev disagreed: “With us behind them, the Americans will not destroy Cuba.”
Cuba and the Soviet Union needed each other. No other power on Earth could shield Cuba from U.S. pressure in that era. After the Bay of Pigs, Castro decided a loose alliance was not enough. The USSR was too far away; by the time Soviet reinforcements arrived after an American invasion, it would already be too late. Cuba needed to make it clear: an attack on Cuba would be treated as an attack on the Soviet Union.
The Soviet leadership also saw opportunity. The early Cold War heavily favored the United States. By 1961, the U.S. had three times as many intercontinental ballistic missiles and eight times as many strategic bombers as the USSR. Soviet nuclear weapons were still unreliable. Meanwhile, the U.S. had deployed missiles in Italy and Turkey, aimed straight at Soviet territory.
To rebalance the nuclear standoff, Khrushchev decided to ship medium‑range missiles and nuclear warheads to Cuba. As he put it, he was sticking a hedgehog down America’s trousers.
In August 1962, Castro’s personal pilot boasted in a bar that nuclear‑tipped missiles were already on Cuban soil. Word spread fast, and U.S. intelligence marveled at the Cubans’ poor operational security.
In October 1962, a trusted informant warned Washington that six medium‑range missile sites were under construction in Cuba. U.S. officials were skeptical. After Bay of Pigs, they dismissed Cuban intelligence as unreliable; the USSR had never stationed nuclear missiles outside its borders, and Cuba lacked heavy industry. Only the new CIA director John McCone pushed for verification. U‑2 spy planes flew over Cuba and took photographs. The imagery was unambiguous: missile launchers and transport vehicles were clearly visible. A nuclear threat, once thought far away, sat right off America’s coast.
Between October 18 and 19, Kennedy and his advisors debated two options: airstrikes or a naval quarantine. Fortunately, Kennedy chose quarantine. He judged that bombing Soviet troops in Cuba risked igniting a global nuclear war, and a surprise strike against a major power carried unknowable consequences.
Many in Congress and his own administration accused Kennedy of weakness. Kennedy assembled the largest U.S. military force since World War Two: eight aircraft carriers, ninety warships, more than a thousand warplanes, and imposed the naval quarantine of Cuba. Staff also drafted invasion plans calling for 340,000 troops.
The Soviet Union responded sharply, first denying the missile deployment, then refusing to dismantle the sites. One misstep could trigger World War Three, and the fate of the whole world hung over that Caribbean island. Several close military calls and misjudgments raised tensions to breaking point. Survivors recalled the suffocating atmosphere in those days.
After grueling negotiations, on the eve of a potential U.S. invasion, the two superpowers struck a deal. The USSR would remove its missiles. The U.S. would lift the quarantine and publicly pledge never to invade Cuba. In a secret side agreement, Washington promised to pull its missiles out of Turkey and Italy. The U.S. won the propaganda victory; the USSR secured real strategic concessions. Both sides claimed success.
One leader was furious: Fidel Castro. He opposed the withdrawal and Khrushchev had made the deal without consulting him at all. To calm Castro, Mikoyan returned to Havana in November 1962, explaining the Soviet Union’s difficult position, and brought a sweeping aid package for Cuba.
Soviet support was extraordinarily generous. The USSR bought Cuban sugar when the U.S. refused, supplied medicine Washington blocked, and shipped discounted oil. Starting in 1962, the Soviets purchased Cuban sugar at six to nine times the global market price. Between 1981 and 1985 alone, Soviet subsidies to Cuba reached $15.7 billion, effectively free aid.
Beyond direct subsidies, the USSR sold oil to Cuba at a forty percent discount, along with massive shipments of grain, fertilizer, raw materials and manufactured goods. Cuba received roughly $1.5 billion annually in low‑interest or zero‑interest loans, many of which were later forgiven. By the collapse of the Soviet Union, total Soviet economic aid topped $61.7 billion, plus $2.5 billion in military hardware. Cuba still owed $28 billion in outstanding debt when the USSR dissolved.
For decades, the Soviet Union effectively underwrote Cuba’s economy, supporting strong living standards through the Cold War. It is staggering to review Soviet aid figures and wonder how the USSR sustained itself until 1991.
Of course, the support came with expectations. Cuba acted as a Soviet proxy in global revolutionary campaigns. The 1970s saw the Soviet Union supply weapons while Cuba deployed troops across Latin America and Africa, the Ogaden War being the most famous example.
In 1979, the Soviet Union built radar stations and a submarine base in Cuba, triggering a second Cuban crisis. By that point the balance of power had shifted, and the U.S. chose to swallow its objections without major escalation.
The Cold War years were Cuba’s golden age. Its world‑renowned public health and education foundations were built in this era. Cuba became the only nation in Latin America to end widespread hunger, with stable public order and strong human development indicators, even while openly defying the United States.
That era seemed permanent, until 1991 shattered everything.
The collapse of the Soviet Union was catastrophic for countries dependent on Moscow. Even before the formal dissolution, Gorbachev slashed aid and demanded Cuba pay hard currency for Soviet imports. Soviet troops stationed on the island withdrew. Cuba lost its economic lifeline and its security guarantor overnight.
Under the Comecon trading bloc, Cuba’s economy revolved around sugar exports, relying on the USSR for nearly everything else. After 1991, Cuba had to compete alone against the capitalist world. Mechanized agriculture partially reverted to animal plowing. Cars sat idle for lack of fuel.
Fuel shortages crippled daily life. By 1992, Cuban cities faced an average of eighteen hours of blackouts each day, and eighty percent of 270 factories shut down. Food grew scarce; by 1993, the average Cuban lost nine kilograms of body weight. The U.S. tightened the screws further, imposing a rule that any ship docking in Cuba could not enter an American port for six months.
To survive, Cuba launched internal reforms starting in 1991. State farms gained more autonomy under a contract system. Military units joined agricultural production to ease food shortages. The country invested in wind power and domestic oil extraction. Tourism was designated a core economic sector in 1991, foreign investment rules relaxed in 1992, and remittances from overseas Cubans were legalized in 1993. In 1994, the economy bottomed out and posted a modest 0.7 percent positive growth rate.
Still, reforms were cautious. Private enterprise remained tightly limited. Castro believed market capitalism was ruthless and exploitative, fearing full liberalization would let U.S. capital seize control of Cuba’s economy.
Modern Cuba exists in a strange overlap of advanced social systems and material scarcity. Its healthcare and education systems remain models for the developing world, legacies of the Cold War. Cuban medical outcomes impressed even Barack Obama. Its healthcare budget is less than five percent of America’s, yet Cubans enjoy a life expectancy nearly matching that of the United States.
Education standards are equally strong. Roughly one in fourteen Cubans holds a university degree, and literacy sits near one hundred percent — exceptional for Latin America.
Yet the country faces persistent hardship. Domestic manufacturing remains weak, hard‑currency exports are limited, and consumer goods are chronically short. Its highly educated population struggles with insufficient formal jobs. Hospitals maintain a strong institutional framework but cope with constant shortages of drugs and equipment.
Cubans live inside this contradiction: world‑class public welfare paired with everyday material deprivation.
Fidel Castro died in 2016 at the age of ninety. Hundreds of CIA plots failed to kill him; the legendary Latin American revolutionary passed away naturally, handing leadership to his brother Raúl Castro.
Where Fidel was a charismatic orator, Raúl was a quiet, pragmatic administrator. His famous line sums up his priority: “Beans are more important than cannons.” Raúl pushed incremental economic reform and worked to thaw ties with the United States. His tenure saw the historic opening of U.S.‑Cuban relations.
On April 16, 2021, at the Eighth Congress of the Communist Party of Cuba, ninety‑year‑old Raúl Castro announced his retirement. The age of the Castro brothers came to an end.
Raúl’s story mirrors Cuba’s: a survivor of a vanished era. That old world is gone, and the future remains unpredictable. For Raúl, who lived through all of modern Cuba’s history, memories may feel warmer than forecasts. In those memories are his brother, Che Guevara, even Lenin and Khrushchev — voices from a passionate, idealistic age, still calling out: Comrade, let us break capitalism together.
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