"The Flower of the West: Sir Francis Drake's Raid of Santo Domingo"

January 1st, 1586. The clanging of metal and trudging of boots are muffled by the dense jungle that surrounds Captain Walter Bigges and his armed band of 900 English corsairs. They march under the cover of darkness in the direction of the flower of the west, the great city of Santo Domingo, under orders from Sir Francis Drake to capture the city and obliterate Spanish prestige in the region.

Starting in 1585, the English increased their efforts to disrupt Spanish naval dominance and commercial activity within their recently established colonial empire. The Anglo-Spanish War (1585–1604) saw the ample participation of privateers, private individuals that engaged in maritime robbery on behalf of the crown.

Drake’s previous raids at Vigo and Santiago had left his crew weakened and undermanned. After resupplying on the nearby island of Dominica on December 15th, Drake sent scouting vessels ahead and began his preparations for an attack on the most important administrative center of the new world.

His scouts returned with reports explaining the sturdy construction of the walls overlooking the harbor and the protection provided by the cannon-armed, stone-built fortress complementing these walls, "Fortaleza Ozama."

Due to the state of his men, a frontal assault attempting to take the city walls was out of the question for Drake. Henceforth, an alternative route was proposed by a captured Spanish scout that involved landing in the vicinity of the Haina River, approximately 10 kilometers west from the city and deep within the wilderness of La Hispaniola at the time.

Despite the inherent risk of attempting to land in what chroniclers claimed to be "A coral-filled waterway", this seemed like a plan with a decent success rate, in stark contrast to the easily predictable outcome a frontal naval assault would bring.

900 men under the command of captain Walter Bigges, take their pikes, swords, and arquebuses and climb down their ships into smaller boats with the objective of slowly rowing their way to the interior of the river on the night of December 31st, 1585, at approximately 9:00 PM.

Dawn came upon the inhabitants of Santo Domingo, accompanied by the sight of the massive wooden hulks comprising Drake's Fleet, visible from the harbor. A militia was hastily assembled by Governor Cristobal de Ovalle. This militia numbered approximately 500 to 600 men, as well as 50 horsemen armed with "old swords and pikes that they had inherited from their grandfathers," as well as a minimal amount of arquebuses.

Under the impression that the main English assault would come from the river Cristobal began the preparation of earthworks, trenches, and walls made out of earth and mud, in order to increase his chances of success against the assault.

Cristobal was, however, horribly unprepared for the seemingly massive wave of screaming Englishmen running out of the jungle and towards his right flank at noon. Completely taken by surprise, a detachment of Spanish arquebusiers makes a brave attempt to halt the English advance by firing on them from a nearby dirt road. Drake’s experienced men and constant naval bombardment prove to be an overwhelming force, and they retreat into the walled city.

As for Cristobal himself, he mounted his horse and began such a hasty retreat towards the wilderness that he even left his own wife behind in Santo Domingo. Later to be captured by Drake himself.

?After dividing their forces and organizing a joint assault on both city gates that was met by minimal resistance from the local militia, the English have control of the city of Santo Domingo and at 4:00 PM find themselves on "a place of very fair, spacious square ground before the great Church". What today is called "Parque Colon"

There is, however, one last bastion of Spanish resistance within the city. The last 200 militiamen barricaded themselves within Ozama fortress and are waiting for an English assault. The moment they gaze upon the Englishmen bringing in artillery to take down the fortress walls, some of the defenders jump into the river and escape, others surrender and are taken prisoner.

Drake and his men establish headquarters at the biggest church in Santo Domingo, currently named "Cathedral of Santa Maria la Menor", and the usual looting and pillaging of warfare descends upon the city. Windows are shattered, tapestries are torn apart, and private homes are ransacked and burned. Woven into the fabric of Dominican folklore is the tale that even the cathedral’s ceremonial bell was taken down and stolen by Drake.

After the looting ceases, negotiations between both parties are set to begin when, suddenly, a young, escaped slave belonging to the English delegation is killed by a Spanish lancer while delivering a message. Upon receiving the news, Drake orders the construction of a set of wooden gallows and hangs three Dominican clergymen. A harrowing warning message is announced to the inhabitants of the city: two prisoners will be hanged every day that the murderer is not brought forward for punishment. The Spanish lancer is handed over the very next day and hanged in plain view of the entire city.

Later, the negotiations take another deadly toll on Santo Domingo. Drake demands a ransom of 1 million Ducats. In today’s terms, 1 ducat would be the equivalent of 3.545 grams of solid gold, or $150 USD. Drake’s total ransom today amounts to approximately $150,000,000 USD. The Spanish negotiator, Garcia de Torquemada, tries to reason with Drake and explain that the colony simply does not have that amount of gold in its treasury. Sensing treachery coming from the negotiator, Drake commands his mariners to begin the destruction of additional buildings within the city. As recorded by Captain Bigges in his diary:

“We ordained each morning by daybreak, until the heat began at nine of the clock, that two hundred mariners did naught else but labor to fire and burn the said houses without our trenches, whilst the soldiers in a like proportion stood forth for their guard: yet did we not or could not in this time consume so much as one third part of the town. And so in the end, what wearied with firing, and what hastened by other respects, we were content to accept of five and twenty thousand Ducats for the ransom of the rest of the town”

One third of the greatest city in the new world had been destroyed during the 1-month-long occupation by the English. On his departure on February 1st, 1586, Sir Francis Drake took home 25,000 Ducats, or approximately $3,750,000 USD, all 200 cannons found within Ozama Fortress, and the three biggest ships available in the harbor. All 27 remaining ships were put to the torch.

The damage inflicted on the colony of Santo Domingo was so immense that Torquemada would write back to the Spanish crown after the raid, simply noting:

“This thing must have had divine sanction, as punishment for the people's sins.”