The first major slave revolt in the Americas occurred in Santo Domingo on December 25, 1521, when enslaved Muslims of the Wolof nation led an uprising in the sugar plantation of admiral Don Diego Colon, son of Christopher Columbus.

In another move, which would destroy Hispaniola's sugar industry, in 1561 Havana, more strategically located in relation to the Gulf Stream, was selected as the designated stopping point for the merchant flotas, which had a royal monopoly on commerce with the Americas.

Except for the city of Santo Domingo, which managed to maintain some legal exports, Dominican ports were forced to rely on contraband trade, which, along with livestock, became the sole source of livelihood for the island dwellers.

By the middle of the century, the population was bolstered by emigration from the Canary Islands, resettling the northern part of the colony and planting tobacco in the Cibao Valley, and importation of slaves was renewed.

With the outbreak of the Haitian Revolution in 1791, the rich urban families linked to the colonial bureaucracy fled the island, while most of the rural hateros (cattle ranchers) remained, even though they lost their principal market.

It led to large-scale land expropriations and failed efforts to force production of export crops, impose military services, restrict the use of the Spanish language, and eliminate traditional customs such as cockfighting.

After repulsing the last Haitian invasion, Santana negotiated a treaty leasing a portion of Samaná Peninsula to a U.S. company; popular opposition forced him to abdicate, enabling Báez to return and seize power.

The Cibanian tobacco planters, who were ruined when inflation ensued, revolted and formed a new government headed by José Desiderio Valverde and headquartered in Santiago de los Caballeros.

[36] Pedro Santana inherited a bankrupt government on the brink of collapse and initiated negotiations with Queen Isabella II of Spain to have the eastern two-thirds of the island reconverted into a Spanish overseas territory.

[44] The Captain-General of Santo Domingo, José de la Gándara, adopted a strategy of occupying the northern ports to isolate the dissident Dominican government in Santiago from outside support.

Unable to extract concessions from the disorganized rebels, when the American Civil War ended, in March 1865, Queen Isabella annulled the annexation and independence was restored, with the last Spanish troops departing by July.

The Partido Rojo (Literally "Red Party") represented the southern cattle ranching latifundia and mahogany-exporting interests, as well as the artisans and laborers of Santo Domingo, and was dominated by Báez, who continued to seek annexation by a foreign power.

Ruling the country from his hometown of Puerto Plata, enjoying an economic boom due to increased tobacco exports to Germany, Luperón enacted a new constitution setting a two-year presidential term limit and providing for direct elections, suspended the semi-formal system of bribes and initiated construction on the nation's first railroad, linking the town of La Vega with the port of Sánchez on Samaná Bay.

Over the following two decades, sugar surpassed tobacco as the leading export, with the former fishing hamlets of San Pedro de Macorís and La Romana transformed into thriving ports.

[51] An 1884 slump in prices led to a wage freeze, and a subsequent labor shortage was filled by migrant workers from the Leeward Islands—the Virgin Islands, St. Kitts and Nevis, Anguilla, and Antigua (referred to by Dominicans as cocolos).

Allying with the emerging sugar interests, the dictatorship of General Ulises Heureaux, who was popularly known as Lilís, brought unprecedented stability to the island through an iron-fisted rule that lasted almost two decades.

His government undertook a number of major infrastructure projects, including the electrification of Santo Domingo, the beginning of telephone and telegraph service, the construction of a bridge over the Ozama River, and the completion of a single-track railroad linking Santiago and Puerto Plata, financed by the Amsterdam-based Westendorp Co.[53] Lilís's dictatorship was dependent upon heavy borrowing from European and American banks to enrich himself, stabilize the existing debt, strengthen the bribe system, pay for the army, finance infrastructural development and help set up sugar mills.

[56] The Cibao politicians who had conspired against Heureaux—Juan Isidro Jimenes, the nation's wealthiest tobacco planter, and General Horacio Vásquez—after being named president and vice-president, quickly fell out over the division of spoils among their supporters, the Jimenistas and Horacistas.

[58] In 1907, this agreement was converted into a treaty, transferring control over customs receivership to the U.S. Bureau of Insular Affairs and providing a loan of $20 million from a New York bank as payment for outstanding claims, making the United States the Dominican Republic's only foreign creditor.

After suppressing a rebellion in the northwest by Jimenista General Desiderio Arias, his government brought political stability and renewed economic growth, aided by new American investment in the sugar industry.

After the provisional presidency of Ramón Báez, Jimenes was elected in October, and soon faced new demands, including the appointment of an American director of public works and financial advisor and the creation of a new military force commanded by U.S. officers.

In what was referred to as la danza de los millones, with the destruction of European sugar-beet farms during World War I, sugar prices rose to their highest level in history, from $5.50 in 1914 to $22.50 per pound in 1920.

This was facilitated by the military government's introduction of regulated contract labor, the growth of sugar production in the southwest, near the Haitian border, and a series of strikes by cocolo cane cutters organized by the Universal Negro Improvement Association.

By the time of his death, he had accumulated a fortune of around $800 million ($8.2 billion in today's money); he and his family owned 50–60% of the arable land, some 700,000 acres (2,800 km2), and Trujillo-owned businesses accounted for 80% of the commercial activity in the capital.

[77] He exploited nationalist sentiment to purchase most of the nation's sugar plantations and refineries from U.S. corporations; operated monopolies on salt, rice, milk, cement, tobacco, coffee, and insurance; owned two large banks, several hotels, port facilities, an airline and shipping line; deducted 10% of all public employees' salaries (ostensibly for his party); and received a portion of prostitution revenues.

(Military Intelligence Service), a secret police and death squad, headed by Johnny Abbes García, who briefly operated in Cuba, Mexico, Guatemala, New York, Costa Rica, and Venezuela.

The United States broke diplomatic relations with the Dominican Republic on August 26, 1960, and in January 1961 suspended the export of trucks, parts, crude oil, gasoline and other petroleum products.

These elections, in December 1962, were won by Juan Bosch, a scholar and poet who had founded the opposition Partido Revolucionario Dominicano (Dominican Revolutionary Party, or PRD) in exile, during the Trujillo years.

Immediately, conservative military forces, led by Wessin and calling themselves Loyalists, struck back, strafing the rebel-held national palace with four World War II–vintage P-51 Mustangs, losing one to ground machine-gun fire.

Rising inflation and unemployment diminished support for the government and helped trigger a wave of mass emigration from the Dominican Republic to New York, coming on the heels of the similar migration of Puerto Ricans in the preceding decades.