Although Hispaniola never realized its economic potential under Spanish rule, it remained strategically important as the gateway to the Caribbean. The Caribbean region provided the opportunity for seafarers from Britain, France, and the Netherlands to impede Spanish shipping, to waylay galleons crammed with gold, and to establish a foothold in a hemisphere parceled by papal decree between the Roman Catholic kingdoms of Spain and Portugal. This competition was carried on throughout the Caribbean, but nowhere as intensely as on Hispaniola.

Sir Francis Drake of England led one of the most famous forays against the port of Santo Domingo in 1586, just two years before he played a key role in the English navy's defeat of the Spanish Armada. Drake failed to secure the island, but his raid, along with the arrival of corsairs and freebooters in scattered settlements, was part of a pattern of encroachment that gradually diluted Spanish dominance.

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Source: U.S. Library of Congress