How the CIA Helped Kill a Dictator—And Failed to Kill Another
- dthholland
- May 30
- 7 min read
In the early years of the Cold War, the CIA dreamed of a Caribbean sweep, one bullet for Trujillo, another for Castro. Only one found its mark.
Between 1959 and 1961, the United States, unnerved by rising tensions in Latin America, turned its clandestine sights on two of the most infamous strongmen in the Caribbean: Fidel Castro of Cuba and Rafael Leónidas Trujillo of the Dominican Republic. One ruled through Marxist revolution, the other through calculated terror. Both were seen by Washington as thorns in the side of American hemispheric dominance.
While the CIA’s obsession with removing Castro is the stuff of legend, exploding cigars, poisoned wetsuits, mafia hitmen—their far quieter, more direct involvement in the death of Trujillo is a case study in Cold War pragmatism. The Dominican dictator’s demise in 1961 came not from a flashy covert operation, but through a slow burn of back-channel support, rifles shipped in diplomatic pouches, and silent nods of approval.
The Caribbean as America’s Backyard
To understand the CIA’s interest, one must go back to 1823 and the Monroe Doctrine, which declared Latin America a sphere of U.S. influence. By the mid-20th century, this translated into a willingness to support dictators—so long as they weren’t communist.
Rafael Trujillo had been Washington’s man for decades. Rising to power in 1930 through a brutal campaign of intimidation and murder, Trujillo transformed the Dominican Republic into his personal fiefdom. He controlled its economy, ruled with unrelenting violence, and even renamed the capital after himself. The U.S. had long tolerated him, but by 1960, that patience had worn thin.
Castro, on the other hand, emerged from the Sierra Maestra as the face of a new threat: Soviet-aligned socialism in the Western Hemisphere. His overthrow of U.S.-backed Fulgencio Batista in 1959 sent shockwaves through Washington. For the CIA, this was no longer a game of chess, it was poker with nuclear stakes.
Assassination Attempts: From Absurd to Operational
Against Castro, the CIA was imaginative to the point of farce. They planned to dust his boots with LSD, poison his cigars, and enlist the American mafia to shoot him. Not one of the countless attempts succeeded. He survived more than 600 known plots, earning an almost mythical status as the man the CIA couldn’t kill.
With Trujillo, the strategy was more grounded. Though he once referred to Castro as “that shitty sergeant,” Trujillo feared Cuban-backed revolutionaries, especially after a failed 1959 invasion from Cuba by Dominican and Cuban exiles. His brutal retaliation—including tossing captured leaders out of planes mid-flight—cemented his status as a tyrant, but it also made him a liability.
When Trujillo attempted to assassinate Venezuelan President Rómulo Betancourt in 1960 with a car bomb, Washington’s mood turned from sour to lethal. President Dwight Eisenhower approved covert assistance to Dominican dissidents. The order was simple: get rid of Trujillo, quietly.
A Coup Without a Coup
The CIA began discreetly arming anti-Trujillo elements. In early 1961, the agency shipped M1 carbines, M3 submachine guns, pistols, and even sabotage equipment to the conspirators. It was all done under the guise of “plausible deniability.” No one in Washington wanted American fingerprints on the dictator’s corpse.
Following the failure of the Bay of Pigs invasion in April 1961, the Kennedy administration grew wary of any further entanglement in Caribbean assassination plots. Concerned about international perception and the volatility of the political climate, officials in Washington sought to distance the United States from the ongoing conspiracy to eliminate Rafael Trujillo. President John F. Kennedy issued a directive: the U.S. must not be seen to condone political assassination under any circumstances.
Nevertheless, events on the ground were already moving beyond recall. Despite the official policy shift, a cache of machine guns had already been delivered to the U.S. consulate in Ciudad Trujillo (now Santo Domingo), where they were held by the U.S. chargé d'affaires, Henry Dearborn. On 28 May, just two days before the planned attack—Kennedy sent a cable to Dearborn reiterating that the United States could not be linked to the attempt on Trujillo’s life.
Dearborn, acting as the last American official in contact with the dissidents, attempted to persuade them to abandon the plan. But it was already too late. On 30 April, he informed Washington that the conspirators were pressing ahead and had armed themselves with three M1 carbines, four to six 12-gauge shotguns, and an assortment of other small arms. With no further means of deterring them, the CIA authorised Dearborn to release the remaining rifles to the group.
One month later, on the evening of 30 May 1961, the plot reached its final act. A mechanic who worked in the garage where Trujillo’s 1957 Chevrolet was kept tipped off the conspirators—Antonio de la Maza, Salvador Estrella, General Antonio Imbert, and Lieutenant Amado García Guerrero, that the dictator planned to drive out that night to meet his mistress, Mona Sánchez. Armed with revolvers, pistols, a sawed-off shotgun, and at least two semiautomatic rifles—some of which had been supplied covertly by the CIA, the group laid in wait along a quiet stretch of highway near the Agua Luz Theater on the road to San Cristóbal.
By 8 p.m., the assassins were in position. At 10 p.m., Trujillo and his chauffeur set off, unaware that the end of his 31-year rule was imminent. As the Chevrolet passed the ambush site, Imbert gave chase in a second vehicle. In the chaotic seconds that followed, gunfire erupted. Trujillo’s car was hit by nearly 30 rounds. His driver returned fire with a machine gun, but the attack was overwhelming.
Badly wounded, Trujillo managed to crawl from the wreckage, reportedly still clutching a weapon, searching for his attackers. De la Maza and Imbert circled back, found the wounded dictator, and shot him dead at close range. His body was bundled into a car boot and left two blocks from the American consulate.
The assassins, aware that their actions would provoke swift retribution, scattered across the country. They hoped that the dictator’s death would trigger a broader uprising or political transition. But that hope was misplaced. Trujillo’s son, Ramfis, quickly took control, launching a brutal manhunt that would leave most of the conspirators dead within weeks.
The Aftermath of Trujillo’s Death: Retribution and Realignment
In the immediate wake of Rafael Trujillo’s assassination on 30 May 1961, the Dominican Republic did not erupt in revolution as the plotters had hoped. Instead, the regime responded with cold, methodical violence. Trujillo’s son, Ramfis Trujillo, who had recently returned from self-imposed exile in Paris, took the reins of power and initiated a brutal counteroffensive to avenge his father’s death.
Within hours, Ramfis mobilised loyalist elements of the military and police. A state of emergency was declared. Curfews were imposed. Roadblocks sprang up across the capital and countryside. Using information from informants and captured suspects, Ramfis’s forces began hunting down the assassins one by one.
The Fate of the Conspirators
The plotters, despite their careful planning, had no secure political apparatus in place to support them once Trujillo was dead. Their assumptions, that the military would rise in support, or that the United States would intervene to stabilise a transition, were misplaced.
Antonio de la Maza, one of the lead conspirators and a former friend of Trujillo who had turned against him after the dictator had his brother murdered, was killed in a shootout with government forces just days later.
Amado García Guerrero, a young army lieutenant who had pledged loyalty to the cause after being forced to witness state-sanctioned atrocities, was also tracked down and executed.
Salvador Estrella Sadhalá was captured, tortured, and executed along with others suspected of involvement.
Antonio Imbert Barrera, remarkably, survived. He went into hiding and later emerged after Ramfis fled the country. Imbert would eventually be declared a national hero and serve briefly as president during a transitional government in the 1960s.
Some of the conspirators met grotesque ends. CIA documents and later Dominican accounts allege that several were fed to sharks, others were publicly hanged or summarily shot. Wives, children, and extended family members of those suspected to be involved were imprisoned or persecuted. The regime’s vengeance was thorough, and the terror it unleashed served as a warning to anyone considering political dissent.
The U.S. Response: Ambiguity and Denial
In Washington, the Kennedy administration found itself in an uncomfortable position. Though the CIA had provided arms and tacit encouragement to the Dominican dissidents, the White House had tried (too late) to distance itself from the plot. After Trujillo’s death, the message from President Kennedy and the State Department was clear: the United States had not sponsored the assassination.
Henry Dearborn, the U.S. chargé d’affaires, cabled back to Washington immediately following the killing. His tone was coldly pragmatic:
“We don’t care if the Dominicans assassinated Trujillo… we just don’t want anything to pin this on us.”
The administration feared international backlash and potential exposure of covert involvement. In the days that followed, U.S. diplomats began quietly exiting the country. Dearborn was withdrawn soon after the assassination, and the embassy staff was reduced to a skeleton crew.
At the same time, the CIA continued to monitor the situation closely, concerned that chaos or a power vacuum might lead to a communist insurgency—particularly with Fidel Castro still in power in nearby Cuba. Yet that threat never materialised. Ramfis’s brutal reprisals were effective, but his leadership lacked both legitimacy and international support. By September 1961, after intense pressure from the Organisation of American States and growing unrest at home, Ramfis Trujillo fled the country with millions in looted funds. He would never return.
A Legacy of Intervention
In the years that followed, the Dominican Republic remained politically unstable. In April 1965, a civil war broke out in Santo Domingo. American embassy officials sent word to Washington that leftist forces were attempting a takeover. President Lyndon B. Johnson responded by dispatching 22,000 U.S. troops under the pretext of preventing a communist revolution.
In truth, the uprising was largely nationalist and constitutionalist in nature. The U.S. intervention was widely criticised across Latin America and beyond. It revealed the limits of American influence, and the long shadow cast by Trujillo’s three-decade rule.
In the end, the CIA succeeded in removing one dictator while failing spectacularly to remove another. Trujillo, once propped up by Washington, was eliminated with quiet U.S. complicity. Castro, the bête noire of American foreign policy, would outlast ten U.S. presidents.
Sources
Central Intelligence Agency, "Foreign Relations of the United States, 1961–1963, Volume XII, American Republics"
Gleijeses, Piero. The Dominican Crisis: The 1965 Constitutional Revolt and American Intervention. Johns Hopkins University Press, 1978.
Kornbluh, Peter. The Cuban Missile Crisis, 1962. The New Press, 1998.
U.S. Department of State, Office of the Historian archives (history.state.gov)
Hersh, Seymour. “The Castro Obsession.” The New Yorker, 1998.
Rabe, Stephen G. The Most Dangerous Area in the World: John F. Kennedy Confronts Communist Revolution in Latin America. UNC Press, 1999.
