Drake takes Santo Domingo, 1586: a New Year's raid on Spain's Caribbean capital

Santo Domingo was the oldest Spanish city in the Americas and the seat of royal government in the Caribbean. Its fall to a few hundred English soldiers in a single day was, as Miguel Reyes Sánchez writes in the journal of the Dominican Academy of History, the most devastating pirate attack in its history.²

Drake's West Indies voyage

By 1585 England and Spain were close to open war over the Netherlands, religion and trade. When Spain seized English grain ships in its ports that June, Queen Elizabeth I sent Sir Francis Drake to sea with a fleet that she half financed herself. EBSCO puts it at twenty-three or twenty-five ships with 1,600 to 1,900 men, the sources differing; Reyes Sánchez gives 23 ships and 2,300 men. Martin Frobisher was vice admiral, and Christopher Carleill commanded the soldiers.³ › Francis Drake

The fleet left Plymouth on 14 September 1585, raided the Cape Verde Islands, lost several hundred men to disease on the Atlantic crossing, and reached the Caribbean island of Dominica on 18 December. Its next target was Santo Domingo, on the south coast of Hispaniola.⁴

Landing at Haina

The city's harbor was well protected. A sandbar guarded the channel, the Spaniards had sunk two or three ships on it to block the way, and an armed galley lay behind the barrier. Drake did not attack from the sea. His habit, as EBSCO notes, was to land soldiers at night some distance from a town and to bring his ships up to fire in support. A Greek pilot taken from a captured Spanish vessel showed the English a way through the reefs at the mouth of the Haina River, west of the city.⁵

The governor, Cristóbal de Ovalle, believed an attack from Haina impossible and took little notice of the warnings. When messengers rode in from the coast, they reported that six or seven hundred men had landed and were marching on the city; EBSCO puts the force at about a thousand.⁶

Two columns at the gates

The English came on in two columns, one under Carleill and one under his second, Powell, pikemen behind a screen of arquebusiers. A Spanish counterattack by some thirty horsemen was beaten off. Within half an hour the English were at the walls, Carleill at the main gate and Powell at the gate nearer the sea, and by midafternoon they held most of the city; the Ozama fortress held out until night. The militia, about 800 foot and 100 horse armed mostly with pikes and lances, could do little, and the governor and many citizens fled inland with what valuables they could carry.⁷

The two accounts date this differently. English narratives, written in the Julian calendar still used in England, give the attack as 1 January 1586. Spanish records, dated in the Gregorian calendar that Spain had already adopted, place the landing on 11 January and the attack on the 12th. The sailors of the Primrose boasted that the Spaniards had given them the town as a New Year's present.⁸

A month of ransom

Drake's aim was money, not conquest. He demanded a ransom, and when it was refused his men stripped the town of cash, brass guns and church bells. Reyes Sánchez writes that he first asked 200,000 ducats, and that after each failed meeting with the Spanish negotiators he ordered another district, church or convent burned. By his count more than three quarters of the buildings went up in flames; the cathedral survived because the English used it as their headquarters, storehouse and prison.⁹

Two Dominican friars were hanged. English accounts say Drake ordered it in reprisal for the killing of an African boy he had sent to parley under a flag of truce; the Spanish chronicler Pedro Simón says the friars died for protesting the burning of the churches.¹⁰

In the end the Spaniards offered 25,000 ducats, all that the governor and the citizens had carried away, and Drake accepted it, taking also the royal coat of arms that hung over the Audiencia, with its motto Non sufficit orbis, the world is not enough. He exchanged worn ships for better Spanish ones, renaming one the New Year's Gift, and sailed away after about a month.¹¹

What the raid meant

Financially the voyage disappointed its investors, since the loot did not cover the cost. Its effect on Spain was larger. EBSCO calls the attack a substantial psychological and financial blow to Philip II, which exposed how weakly Spain's colonies were defended and forced him to divert to the Americas money meant for Europe. Drake went on to take Cartagena in February and burn St. Augustine in May, and three years later Baptista Boazio's maps of the voyage, with the fleet in the bay and a crocodile in the sea, were printed with Walter Bigges's account. The war at sea that followed led to the Armada of 1588.¹²