US officials weighed assassination to remove Trujillo

By Desmond Okafor · August 10, 2026

Washington plotted a 'controlling junta' and an unofficial scheme to protect the dictator's loot from confiscation to prevent pro-Castro elements from taking power.

Henry Dearborn, the Deputy Chief of Mission in the Dominican Republic, was asked for a "very personal and confidential" appraisal of the man known as El Jefe. His conclusion was devoid of diplomatic nuance. Dearborn suggested that as long as Generalissimo Rafael Trujillo remained in the country—even if reduced to the role of "Governor of Santiago province or 'dogcatcher'"—he would continue to dominate the nation. To Dearborn, the only solution was the physical removal of Trujillo from the country, a move he asserted would likely only happen under a "threat of death."\ Dearborn went further, stating that if he were a Dominican, he would "favor killing Trujillo."

This assessment appears in an editorial note from the Foreign Relations of the United States (State Dept), which summarizes a wider body of documentation on U.S.-Dominican relations between 1958 and 1960. It captures a Washington administration attempting to balance its public rhetoric on democracy with the cold calculations of the Cold War.

"Governor of Santiago province or 'dogcatcher'"

By 1958, the Eisenhower administration viewed Trujillo not as a partner to be cultivated, but as a problem to be managed. While the Generalissimo promoted himself as "the Benefactor," the record notes his rule had become "increasingly harsh and dictatorial." Washington's primary anxiety was not the internal suffering of the Dominican people, but the risk of a vacuum. The "overwhelming problem" was how to ease Trujillo out of power without allowing "pro-Fidel Castro/anti-American elements to take over."

U.S. interests were explicitly mapped out by the Director of the Office of Middle American Affairs in January 1958: the strategic proximity of the Panama Canal, a U.S. guided missile tracking station on the northeast coast, and a general compliance with U.S. policies. When Ambassador Joseph S. Farland attempted to normalize relations in early February 1958, the effort stalled. Trujillo remained sensitive to congressional criticism and perceived slights against his family, ensuring that the relationship remained strained.

Trujillo's Family Fund

As the regime's grip weakened, the U.S. explored options that prioritized stability and the protection of assets over genuine liberation. In March 1960, retired General Edwin S. Clark made a secret visit to Ciudad Trujillo (Santo Domingo). His mission was to convince the Generalissimo to step down, but the incentive he offered was an "unofficial scheme" that reads more like a wealth-management strategy than a democratic transition.

Clark proposed the creation of a foundation funded by the money the Trujillo family had amassed during their three decades of rule. This fund would be administered by former U.S. and Latin American presidents. The stated purpose was to ensure the wealth was used for the "benefit of the Dominican Republic," but the record is candid about the primary goal: to "prevent confiscation of the Trujillo fortune by a successor government" and to ensure Trujillo did not take the money into exile. In the eyes of the State Department, the preservation of the dictator's loot was a necessary condition for his departure.

Fidel Castro and the Dictator's Mirror

By April 1960, the National Security Council feared that the U.S. effort to build a moderate opposition was "too little and too late." Vice President Richard Nixon warned that the "old story" was repeating: the pro-Castro elements were the only minority capable of "strong leadership." This fear drove a shift toward more aggressive contingency planning. On April 25, 1960, President Eisenhower discussed a plan to remove Trujillo and install a "controlling junta" that would eventually call for free elections.

However, the urgency was driven less by a desire for Dominican democracy and more by a branding problem in the Caribbean. By July 1960, Eisenhower concluded that Trujillo was "seriously deflecting attention" from the "real problem in Latin America, Fidel Castro." The record admits a glaring hypocrisy: it was "difficult to brand Castro a dictator and call for sanctions against him" as long as Trujillo remained in power. The Generalissimo had become a diplomatic liability, a mirror that reflected the U.S. government's own contradictions back at it.

"Increasing Possibility"

By the end of 1960, U.S. relations with the Dominican Republic were suspended following an OAS decision that the regime had attempted to assassinate President Betancourt of Venezuela. The window for a managed exit had closed. The State Department's Bureau on Intelligence and Research began to view the end of the regime not as a diplomatic goal, but as a statistical likelihood. They suggested that "assassination is an increasing possibility—perhaps even a probability, considering the desperate temper of the opposition."

The Eisenhower administration had tried to induce Trujillo to step down through secret visits and promises of financial shelters, yet the dictator held grimly to power. Six months after the close of 1960, he would be dead from an assassin’s bullet.