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 the royal government of 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

Who won the Battle of Santo Domingo and why?

Drake's English expedition won. Carleill's soldiers landed unseen far from the city while the fleet drew the defenders' eyes to the harbor, and a militia short of guns, powder and leadership broke at the gates. The governor fled, the castle was abandoned in the night, and the English held the city for a month.³

Background: Drake's West Indies voyage

By 1585 England and Spain were close to open war, over English help for the Dutch rebels, 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 helped to pay for herself, to do as much damage as he could to Spain's overseas empire. EBSCO counts twenty-three or twenty-five ships with 1,600 to 1,900 men, the sources differing.⁴

Drake was the most famous seaman in England. He carried an old grudge against Spain: in the late 1560s a slaving and trading voyage he sailed on with John Hawkins had been attacked by the Spanish at San Juan de Ulúa off Mexico, and many of its men were killed. Since then he had raided the Spanish Main in the 1570s and sailed round the world between 1577 and 1580. For this voyage Martin Frobisher was his vice admiral, and Christopher Carleill commanded the soldiers as lieutenant general.⁵ › Francis Drake

The fleet left Plymouth on 14 September 1585 and sacked Santiago in the Cape Verde Islands. On the Atlantic crossing a fever broke out and killed two or three hundred men within days. After reaching Dominica in the Caribbean on 18 December and resting the sick, Drake resolved to strike at once at the greatest prize in reach, Santo Domingo, on the south coast of Hispaniola.⁶

Armies and commanders

Santo Domingo was believed to be strongly fortified. Its harbor was guarded by a bar and by the castle at the mouth of the Ozama River, and the coast near the city offered no safe place to land. The Spaniards had sunk ships in the harbor to bar the way in.⁷

On the way the English captured a vessel whose Greek pilot gave them a full description of the defenses and showed them a landing place some ten miles to the west of the city.⁸

The defenders were weak. Reyes Sánchez counts a militia of about 800 men on foot and 100 on horseback, armed mostly with pikes and lances and with few arquebuses and little powder. The Spanish naval historian Cesáreo Fernández Duro, cited by Julian Corbett, put the force that could actually be mustered far lower, at thirty mounted lancers and fifty arquebusiers. Both agree that the city was caught unprepared and that its governor, Cristóbal de Ovalle, fled.⁹

The commanders' decisions

Drake chose a method that had already worked at Santiago in the Cape Verde Islands: land the soldiers by night well away from the town, march them on it from the landward side and let the fleet threaten the harbor at the same time, so that the defenders faced two attacks at once. Reyes Sánchez notes that Drake made most of his attacks from the land side, against the least defended points.¹⁰

The Spanish governor, Cristóbal de Ovalle, made the opposite choices. When English sails were reported on 10 January by the Spanish calendar, he at first made little of it, although the crown attorney Francisco de Aliaga urged precautions; the Dominican historian Carlos Esteban Deive, quoted by Reyes Sánchez, thinks Ovalle believed a landing at Haina was impossible. In his own account, which Irene Wright summarizes from a copy of his letter, Ovalle says that he readied the fortress, called out foot and horse and had three hulks laid across the bar, and that he had 1,500 men that night but only 110 by the next morning.¹¹

No one held the landing place in strength. The English came ashore at the mouth of the Haina River, where reefs and heavy surf were thought to rule out a landing, guided by the Greek pilot taken on the way. As the columns approached, Ovalle left the city by boat up the river.¹²

The battle in phases

The landing. At nightfall Drake put his soldiers into the boats and pinnaces, and at the break of day on New Year's Day, by the English reckoning, they landed nine or ten miles west of the city. Bigges writes that Drake, having seen them all landed in safety, returned to his fleet and left them to God and the good conduct of Carleill.¹³

The feint. Drake then brought the fleet up before the city and opened fire on the castle, as if he meant to land under its guns. Meanwhile Carleill's force, about a thousand men, marched on the city from the west in two columns.¹⁴

Cattle and cannon. The Spaniards drove a herd of cattle at the English to break their ranks, and their horsemen tried to charge, but the columns held together and kept marching. At the gates a few Spanish guns fired into them at close range; Reyes Sánchez writes that only three pieces could be set up at the Lemba gate, and only one used.¹⁵

Into the city. The English charged the guns. Carleill entered at one gate and Captain Powell, his second, at another, and they swept into the streets pell-mell with the fleeing defenders. The castle, still in Spanish hands, held out for some hours and was abandoned in the night, its garrison escaping across the river in boats.¹⁶

Turning point: a city held for ransom

The two calendars give this day different dates. English narratives, written in the Julian calendar still used in England, date the capture to 1 January 1586, which was 11 January in the Gregorian calendar Spain had already adopted. Reyes Sánchez, following Spanish sources, has the English columns appear before the city on 12 January and take the Ozama fortress that day. The English, Bigges writes, said the Spaniards had given them the town as a New Year's gift.¹⁷

Drake's aim was money, not conquest. His men fortified the center of the city and searched it, and the governor said he could not pay the ransom demanded. To press him Drake sent parties of sailors out every day to burn the city piece by piece, and Reyes Sánchez describes another district, church or convent going up in flames after each failed meeting.¹⁸

Then came a killing that hardened the occupation. Drake sent a Black boy who served him to meet a Spanish officer under a flag of truce, and the officer ran him through with his lance. In reprisal two Dominican friars held prisoner were hanged, and Drake did not stop until the Spaniards had executed the officer themselves.¹⁹

Counting the losses

No source gives a full count of the dead. On the English side, Bigges and Corbett say that several men fell to the Spanish guns at the gate, one of them close beside Carleill, before the charge carried the guns. On the Spanish side, the two Dominicans hanged in reprisal are named in Spanish records as the priest Juan de Caravia, or Sarabia, and the lay brother Juan de Illanes, or Llanes.²⁰

For the English the voyage was costly as well. EBSCO puts the investment at £40,000, of which the queen paid half; Corbett gives the cost up to the day of sailing as more than £60,000, which Drake agreed to reduce to £57,000. The audit allowed the investors 15 shillings in the pound, so they lost a quarter of their money, as Reyes Sánchez also reports.²¹

Aftermath

In the end the Spaniards offered 25,000 ducats, and Drake, convinced that no more could be found, took it. Before leaving he exchanged worn ships for better Spanish ones, renamed one of them the New Year's Gift, burned the rest of the shipping and carried off guns and bells. Galley slaves and enslaved servants used the chance to go over to the English. About a month after the landing the fleet put to sea.²²

The damage is told differently. Corbett writes that the houses were so solidly built that a month of burning destroyed only about a third of the city; Reyes Sánchez, following Dominican historians, writes that more than three quarters of the buildings went up in flames, among them the churches and convents of Santa Bárbara, La Merced, Regina, San Francisco and Santa Clara. Irene Wright, from the Spanish claims for damages, lists what was left standing: about 300 houses, the cathedral, the fortress, the government house, the wharves and the city hall.²³

From the government palace the English also took the royal arms of Spain, with a horse leaping from a globe under the motto Non sufficit orbis, the world is not enough, a boast that Santo Domingo had just made look hollow.²⁴

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 send to the Americas money meant for Europe. Drake went on to Cartagena, the capital of the Spanish Main, which he took in February with the same method of a night landing backed by the fleet's guns, and then to St. Augustine in Florida. The naval war that followed led to the Armada of 1588.²⁵

Legacy and memory

The raid was told to Europe in Walter Bigges's account, published in Latin in 1588 and in English in London in 1589, with Baptista Boazio's hand-colored plans of the four captured towns. The plan of Santo Domingo shows the fleet in the bay, the columns marching on the gates and, in the sea, a crocodile drawn from life.²⁶

In England the raid was a triumph. Julian Corbett, the naval historian, judged that although it paid less than hoped, the blow to Spanish prestige was enormous and English confidence rose with it, and EBSCO notes that the voyage raised England's reputation at sea and its interest in colonies of its own. Spain, for its part, learned that its oldest colony in the Americas could fall in a morning.²⁷

In the Dominican Republic the sack is remembered as a disaster. Reyes Sánchez, writing for the Dominican Academy of History, counts it the most devastating attack by a pirate in the city's history, the work of a corsair backed by the Queen of England.²⁸

Visiting today

The streets the English columns stormed are now the Colonial City of Santo Domingo, a UNESCO World Heritage Site. Its cathedral survived the burning of 1586, and the fortress at the mouth of the Ozama, which the Spaniards abandoned in the night, still guards the river.²⁹