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Cuba

In 1947, Dominican exiles, including Juan Bosch, had concentrated in Cuba. With the approval and support of Cuba's government, led by Ramón Grau, an expeditionary force was trained with the intention of invading the Dominican Republic and overthrowing Trujillo. However, international pressure, including from the United States, made the exiles abort the expedition. In turn, when Fulgencio Batista was in power, Trujillo initially supported anti-Batista supporters of Carlos Prío Socarrás in Oriente Province in 1955; however, weapons Trujillo sent were soon inherited by Fidel Castro 's insurgents when Prío allied with Castro; Dominican-made Cristóbal carbines and hand grenades became the rebels' standard weapons.

After 1956, when Trujillo saw that Castro was gaining ground, he started to support Batista with money, planes, equipment, and men. Trujillo, convinced that Batista would prevail, was very surprised when Batista showed up as a fugitive after he had been ousted. Trujillo kept Batista until August 1959 as a "virtual prisoner". Only after paying US$3–4 million could Batista leave for Portugal, which had granted him a visa.

Castro made threats to overthrow Trujillo, and Trujillo responded by increasing the budget for national defense. A foreign legion was formed to defend Haiti, as it was expected that Castro might invade the Haitian part of the island first and remove François Duvalier as well. A Cuban plane with 56 fighting men landed near Constanza, Dominican Republic, on Sunday, 14 June 1959, and six days later more invaders brought by two yachts landed at the north coast. However, the Dominican Army prevailed.

In turn, in August 1959, Johnny Abbes attempted to support an anti-Castro group led by Escambray near Trinidad, Cuba. The attempt, however, was thwarted when Cuban troops surprised a plane he had sent when it was unloading its cargo.