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Fidel and other combatants celebrate the triumph of the revolution.

Progressive and revolutionary thinkers and revolutionary movements have had a strong impact on the political history of the Caribbean, and the Americas in general. The first revolutionary movement in the Americas was the U.S. revolution of 1776, followed by the Haitian Revolution of 1791 and later by the struggles for independence from the Spanish empire that were led by Simon Bolivar in Venezuela in the early 19th century. Later came the Mexican Revolution of 1910, with figures such as álvaro Obregón, Francisco "Pancho" Villa, Venustiano Carranza and Emiliano Zapata. Added to this list are the struggles led by José Martí in Cuba in the late 19th century or those led by Augusto César Sandino in Nicaragua in the early 20th century and the Cuban Revolution in the middle of the century. In the second half of the 20th century, revolutionary activity continued and the region saw revolutionary movements in Nicaragua with the Sandinista Revolutionary Front (FRS, for its Spanish acronym), in El Salvador with the Farabundo Martí National Liberation Front (FMLN, for its Spanish acronym), in Chiapas, Mexico with the Zapatista National Liberation Army (EZLN, for its Spanish acronym) led by legendary Subcommander Marcos, in Colombia with the Revolutionary Armed Forces of Colombia (FARC, for its Spanish acronym), and even more recently, in Venezuela with the Bolivarian Revolution led by Hugo Chávez. The region has been, without doubt, a hotbed of revolutionary political ideas.

The region has also been known for the presence of totalitarian governments (in many cases, in the form of dynasties) in the period following independence, and many of those dictatorships arose in the region during the course of the 20th century: Fulgencio Batista en Cuba (1952-1959), the Duvalier dynasty in Haiti (François "Papa Doc" Duvalier from 1964 to 1971 and Jean-Claude "Baby Doc" Duvalier from 1971 to 1986), Manuel A. Noriega in Panama (1983-1989), and Rafael Leonidas Trujillo in the Dominican Republic (1930-1961). In Guatemala, a chain of fascist military dictators governed the country form 1970 to 1986, from Colonel Carlos Manuel Arana Osorio (1970-1974) to José Efraín Ríos Montt (1982-1983) and óscar Humberto Mejía Victores (1983-1986). The Somoza dynasty ruled in Nicaragua (Anastasio Somoza García from 1950 to 1956 and Luis Somoza Debayle from 1956 to 1963). In addition to these examples, there are many single-party systems in the region, or systems in which more than one party exists in theory, but only one has held power nearly indefinitely. In Trinidad and Tobago, for example, the People's National Movement remained in power from 1956 to 1986. In Antigua, the Antigua Labour Party has maintained almost exclusive control of power since 1951. In St. Kitts and Nevis, the Saint Kitts and Nevis Labour Party has not lost an election since 1962. And in Grenada, the Grenada United Labour Party was in power from 1951 to 1979, the year that Maurice Bishop led a Marxist coup de etat. In Cuba, the dynasty of brothers Fidel and Raúl Castro has governed since 1959 without interruption.

The political environment in the region has also been strongly affected by the numerous interventions by the United States government. Since 1823, the U.S. foreign policy toward the Caribbean region has been motivated by zealous opposition to interventions by European governments in the Americas and the idea that "America is for Americans" was recognized in the Monroe doctrine, stated in 1823 by James Monroe. The Monroe doctrine was used to defend the struggles for independence in South America. Also, in accordance with the Monroe doctrine, President Theodore Roosevelt introduced a corollary called big stick diplomacy, which came to be part of U.S. foreign policy in the 20th century. The phrase came from a West African proverb that says "Speak softly and carry a big stick and you will go far." In practice, the Monroe doctrine and the big stick diplomacy led to numerous interventions by the U.S. government in the Caribbean region, both in the form of military involvement and operations by the Central Intelligence Agency (CIA). The change of policy implemented by President Franklin Delano Roosevelt in 1933, called the Good Neighbor Policy, implied even greater involvement in the region through financing for national and local security forces. The list of interventions by the United States in the political affairs of Caribbean countries in the 20th century is extensive: Honduras (1903, 1907, 1911, 1919, 1924-1925, 1982-1990, 2009), The Dominican Republic (1903-1904, 1914, 1916-1924, 1965-1966), Cuba (1898-1902, 1906-1909, 1912, 1917-1933, 1961, 1962), Nicaragua (1907, 1910, 1912-1933, 1981-1990), Panama (1908, 1912, 1918-1920, 1921, 1925, 1958, 1964, 1989), Mexico (1912, 1913, 1914-1918), Haiti (1914-1934, 1994-1995, 2004-to today), Guatemala (1920, 1954, 1966-1967), Costa Rica (1921), El Salvador (1932, 1981-1992), Puerto Rico (1950), Grenada (1983-1984), and Venezuela (2002). Most notable among these was the military occupation of Nicaragua for 20 years (1912-1933), of Haiti for 19 years (1914-1934), of the Dominican Republic for 8 years (1916-1924) and of Cuba for 16 years (1917-1933). Apart from military interventions and intelligence operations, the U.S. government has also maintained a strong military presence in the region through numerous naval and air bases strategically located in relation to the Panama Canal: the Soto Cano base in Palmerola, Honduras, the Guantánamo base in Cuba, the Coolidge Airfield on the island of Antigua, the Atlantic Undersea Test and Evaluation Center (AUTEC) in the Andros islands of the Bahamas, and the Waller Air Force Base in Trinidad and Tobago (1940-1949). Added to this list are approximately 25 military bases that the United States maintained on the island of Puerto Rico at various times during the 20th century, including the Ramey Air Force Base in Aguadilla, Roosevelt Roads Naval Station in Ceiba and the Atlantic Fleet Weapons Training Facility in Vieques (until 2003), and Fort Buchanan in San Juan. More recently, as part of the fight against drug trafficking, the U.S. military has maintained permanent personnel at the Queen Beatrice base in Aruba and the Hatos base in Curaçao. The obvious militarization of the region has greatly contributed to an environment of tension and creates the setting in which Caribbean political thinking has developed. In addition to the militarization of the region, many social scientists have pointed to the existence of a highly authoritarian, selfish, intransigent pan-Caribbean political culture with little democratic experience as one of the many causes of the tense environment and constant political unrest in the region.