Enrriquillo's Rebllion

The few remaining natives that remained were still being used in the mines, the new trapiches and mills, as well as, cattle ranches. After the Hieronymites failed to ban the encomiendas, several rebellions began, one, in particular, stands out by a descendant of the cacique Aragua, named Enriquillo, who led an uprising in the Bahoruco mountains range which the Spanish where unable to dominate for 13 to 16 years, until the signing of a peace accord with the emperor Charles I in 1533.

Enriquillo had been educated in a Franciscan convent which provided him with a good understanding of Spanish culture and an admirable capacity to lead, managed to direct the first guerrilla war,using Spanish arms and military techniques and taking advantage of the steep territory of the Bahoruco mountains to impede enemy attacks and organize hideouts and farming to warrantee food supplies.

The clever cacique was kept up to date on the movements of the Spanish, through a network of spies within the encomiendas. His men multiplied daily , and like other escapees known as "Ciguayos" or "Tamayo", they attacked travelers and villas in the island's interior obtaining the arms and provisions they needed.

One of Enriquillo's best tactics was to constantly change the rendezvous spot with his men, so, “ni ellos sabían puntualmente donde habían de hallarlo; esto se hacia porque si los españoles los prendiesen, ninguno de ellos pudiese ir a avisar y a tormentos descubriesen donde quedaba”.5 (Not even his men knew before hand where it was going to be in case the Christians captured them, they wouldn't be able to denounce them under torture.)

Due to the large emigration of Spanish, the colonial government found itself short of human and monetary resources, finding it difficult to continue sponsoring the kind of armed incursions which had brought such great results in the Ovando era. The majority of Spaniards that were sent to fight Enriquillo were forced to do so by the Real Audiencia, institution which had already lost 80 to 100,000 Castellanos of the King's Treasure in these disadvantaged incursions.