The first major slave revolt in the Americas occurred in Santo Domingo during 1522, when enslaved Muslims of the Wolof nation led an uprising in the sugar plantation of admiral Don Diego Colon, son of Christopher Columbus.
Many of these insurgents managed to escape to the mountains where they formed independent maroon communities. By the 1530s, maroon bands had become so numerous that in rural areas the Spaniards could only safely travel outside their plantations in large armed groups. By 1545, there were an estimated 7,000 maroons beyond Spanish control on Hispaniola. The Bahoruco Mountains were their main area of concentration, although Africans had escaped to other areas of the island as well. From their refuges, they descended to attack the Spanish.
One preeminent leader of slave revolts was Sebastián Lemba. By directing a strategy of mobile, hit-and-run warfare, Lemba succeeded in resisting and evading the colonial forces for all of 15 years. Burning and sacking their way from Higüey to Yaguana, Lemba's group of guerrilleros negros evaded the Spanish authorities until 1547, the year in which the troops captured and executed the rebel leader, hanging his severed head from a gateway as an example to others who would dare disobey their white masters. Slave insurrections continued through the mid-century. As accounts indicate, slave revolts in the colony of Santo Domingo anticipated Saint-Domingue's uprisings by some 267 years.
Enriquillo was a Taíno cacique who rebelled against the Spaniards from 1519 to 1533. Known as "Enrique" by the Spaniards, his rebellion is the best known rebellion during the early Caribbean period. He is considered a hero of indigenous resistance for those in the modern Dominican Republic and Haiti. Dominican friar Bartolome de Las Casas, who documented and railed against Spanish abuse of the indigenous, wrote sympathetically of Enriquillo.
His father, along with eighty other regional chieftains and his aunt Anacaona, was killed by Nicolás de Ovando while attending supposed “peace talks” with the Spanish in Jaragua. During the talks, Spanish soldiers ambushed the chieftains, also known as caciques, set the meeting house on fire, and proceeded to kill anyone who fled the flames (causing his father's death). Enriquillo was then raised in a monastery in Santo Domingo. One of his mentors was Bartolomé de Las Casas.
Most historians agree that Enriquillo was the same person as the cacique Guarocuya which would mean that Enriquillo belonged to the highest house of the Jaragua cacicazgo. Guarocuya was the nephew of Anacaona, sister to the cacique of Jaragua Bohechío and his eventual successor once Bohechío was killed. Anacaona was married to Caonabo who was the cacique of the neighboring Maguana kingdom. A minority of historians, however, claim that Guarocuya was captured and hanged, while Enriquillo succeeded in his revolt. Most historians believe both rebels were the same person, arguing that the tales of Guarocuya's demise are identical to the more verifiable accounts of the capture and execution of his aunt Anacaona and the stories have been conflated. It is also well documented that the character of Enriquillo was married to Mencía, the mestizo granddaughter of Anacaona.
His name Enriquillo would come after his baptism as a Catholic and his new given name, Enrique, in which the name Enriquillo "little Enrique," which was probably due to his age at the time of the baptism.
Enriquillo also had a wife, called Mencía, later with the noble title Doña due to Enriquillo's high standing and relations with the Spaniards. She was raped by a Spaniard named Valenzuela. When Enriquillo tried to take the issue to the Spanish courts, nothing could be done, since it was Doña Mencia's word against the Spaniard's word. This, according to some writers, was the tipping point for Enriquillo which led to his revolt in the Bahoruco mountains.
