English, French and Dutch pirates preyed on Spanish wealth in 1586

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The English soldiers stepped out of their pinnaces into the foaming surf on the island of Hispaniola. As they strode through the water toward the sandy beach, they made every effort not to get their firelock muskets and pistols wet.

The soldiers, under the command of Captain Christopher Carleille, had been dispatched from galleons in a fleet commanded by Francis Drake, whose mission was to wreak havoc throughout the Spanish Main. Drake’s instructions to Carleille were to march 20 miles through the jungle and attack the Spanish settlement of Santo Domingo. Drake’s thinking, which turned out to be true, was that the defenders of the town would expect an attack by sea, not land.

Early on the morning on January 1, 1586, the English foot soldiers assaulted the town from the west. They struck in two columns directed at separate gates leading into the town. Meanwhile, cannon balls fired from the English galleons whistled overhead and crashed into the town’s fragile buildings. Outnumbered five to one, the Spanish garrison had little chance of holding off Elizabeth I’s pirate force led by the wily Drake.

When Drake saw the flag with the cross of St. George raised over the city, he ordered his ships to sail into Santo Domingo’s inner harbor. Once Spanish resistance had been quashed, Drake’s men rampaged through the city, looting from the town’s residents whatever valuables they had and burning buildings at will.

A Spanish emissary asked Drake what tribute they must pay to stop the destruction. Drake’s reply was that it would take one million ducats to compel him and his men to depart. Knowing they could not come up with that amount, the Spanish nevertheless set about gathering whatever wealth they could gather as a counteroffer.

Drake’s attack on Santo Domingo was typical of the hit-and-run tactics of English privateers on the Spanish Main. The term “main” in its strictest sense referred to the northern coastline of the South American mainland, but by the mid-16th century the term also meant “sea” and was being used in reference to any part of the Caribbean basin. During the period from 1568 to 1713, English, French, and Dutch pirates attacked Spanish settlements and hunted Spanish treasure ships throughout the Spanish Main. The pirate activity was carried out during periods of open war as well as periods of undeclared war between Spain and her enemies.

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