Rafael Lenidas Trujillo Molina ( troo-HEE-yoh, Spanish: [rafael leonias tuxio molina]; 24 October 1891 30 May 1961), nicknamed El Jefe (Spanish: [el xefe], "The Chief" or "The Boss"), was a Dominican dictator who ruled the Dominican Republic from February 1930 until his assassination in May 1961. He served as president from 1930 to 1938 and again from 1942 to 1952, ruling for the rest of the time as an unelected military strongman under figurehead presidents. His rule of 31 years, known to Dominicans as the Trujillo Era (Spanish: El Trujillato), is considered one of the bloodiest political regimes ever in the Americas, and centered around a personality cult of its leader. Trujillo and his regime were responsible for many deaths, including between 12,000 and 30,000 Haitians in the infamous Parsley massacre in 1937.

During his long rule, the Trujillo government extended its policy of state terrorism beyond national borders. Notorious examples of Trujillo's reach abroad are the assassination attempt in Caracas against Venezuelan President Rmulo Betancourt in 1960, the abduction and subsequent disappearance in New York City of the Spaniard Jess Galndez in 1956, and the murder of writer Jos Almoina in Mexico, also a Spaniard.By 1960, Trujillo had amassed a net worth of $800 million ($5.3 billion today). On 30 May 1961, Trujillo was assassinated by conspirators sponsored by the Central Intelligence Agency (CIA). In the immediate aftermath, Trujillo's son Ramfis took temporary control of the country, and vowed revenge for his father. By 19 November 1961, Trujillo's relatives and allies were forced to leave the country. An example is Joaqun Balaguer, who fled to New York City. Before leaving, those allies killed the surviving members of the assassination plot.

The Trujillo era unfolded in a Hispanic Caribbean environment particularly susceptible to dictators. In the countries of the Caribbean Basin alone, his dictatorship overlapped with those in Cuba, Nicaragua, Guatemala, El Salvador, Honduras, Venezuela, and Haiti. In perspective, the Trujillo dictatorship has been judged more prominent and more brutal than those that surrounded it. Trujillo remains a polarizing figure in the Dominican Republic, as the sheer longevity of his rule makes a detached evaluation difficult. While his supporters credit him for bringing stability and prosperity to the country, others criticize his heavy-handed and violent rule scorning civil rights and freedoms.

Cuba ( (listen) KEW-bə, Spanish: [ˈkuβa] (listen)), officially the Republic of Cuba (Spanish: República de Cuba [reˈpuβlika ðe ˈkuβa] (listen)), is a country comprising the island of Cuba, as well as Isla de la Juventud and several minor archipelagos. Cuba is located where the northern Caribbean Sea, Gulf of Mexico, and Atlantic Ocean meet. Cuba is located at the east of the Yucatán Peninsula (Mexico), south of both the American state of Florida and the Bahamas, west of Hispaniola (Haiti/Dominican Republic), and north of both Jamaica and the Cayman Islands. Havana is the largest city and capital; other major cities include Santiago de Cuba and Camagüey. The official area of the Republic of Cuba is 109,884 km2 (42,426 sq mi) (without the territorial waters). The main island of Cuba is the largest island in Cuba and in the Caribbean, with an area of 104,556 km2 (40,369 sq mi). Cuba is the second-most populous country in the Caribbean after Haiti, with over 11 million inhabitants.The territory that is now Cuba was inhabited by the Ciboney Taíno people from the 4th millennium BC until Spanish colonization in the 15th century. From the 15th century, it was a colony of Spain until the Spanish–American War of 1898, when Cuba was occupied by the United States and gained nominal independence as a de facto United States protectorate in 1902. As a fragile republic, in 1940 Cuba attempted to strengthen its democratic system, but mounting political radicalization and social strife culminated in a coup and subsequent dictatorship under Fulgencio Batista in 1952. Open corruption and oppression under Batista's rule led to his ousting in January 1959 by the 26th of July Movement, which afterwards established communist rule under the leadership of Fidel Castro. Since 1965, the state has been governed by the Communist Party of Cuba. The country was a point of contention during the Cold War between the Soviet Union and the United States, and a nuclear war nearly broke out during the Cuban Missile Crisis of 1962. Cuba is one of a few extant Marxist–Leninist socialist states, where the role of the vanguard Communist Party is enshrined in the Constitution. Under Castro, Cuba was involved in a broad range of military and humanitarian activities throughout both Africa and Asia.Culturally, Cuba is considered part of Latin America. It is a multiethnic country whose people, culture and customs derive from diverse origins, including the Taíno Ciboney peoples, the long period of Spanish colonialism, the introduction of enslaved Africans and a close relationship with the Soviet Union in the Cold War.

Cuba is a founding member of the United Nations, the G77, the Non-Aligned Movement, the Organisation of African, Caribbean and Pacific States, ALBA and the Organization of American States. It has currently one of the world's only planned economies, and its economy is dominated by the tourism industry and the exports of skilled labor, sugar, tobacco, and coffee. Cuba has historically – both before and during Communist rule – performed better than other countries in the region on several socioeconomic indicators, such as literacy, infant mortality and life expectancy.Cuba has a single-party authoritarian regime where political opposition is not permitted. There are elections in Cuba, but they are not considered democratic. Censorship of information (including limits to internet access) is extensive, and independent journalism is repressed in Cuba; Reporters Without Borders has characterized Cuba as one of the worst countries in the world for press freedom.