Tag Archives: Dominican Republic

Francis Drake’s Sack of Santo Domingo: A Case of Terrorism?

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Santo Domingo, sacked by Francis Drake in 1586. Note the small harbor protecting only a handful of ships.

We believe that we live in an age of terrorism. But terror is as old as humankind. Just ask the unsuspecting population of Santo Domingo on the island of Hispaniola which on January 1, 1586, woke up to Francis Drake (c. 1540 – 1596) and his marauding mercenaries ransacking their city. Santo Domingo, founded in 1496, is the oldest colonial city in the New World and at that time as the seat of a real audiencia still was a Spanish administrative center for the Caribbean. But it long had lost the political and strategic centrality it enjoyed during the years of the Conquest, and its pivotal role in the Transatlantic trade had been passed on to nearby San Juan, Puerto Rico, as I have discussed in a different post. When Francis Drake arrived, Santo Domingo was well past its prime.

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The Fortaleza Ozama, built 1502-1505, with its modest size was no match for Drake’s forces.

Drake’s men took the city by surprise, both by shelling the Fortaleza Ozama and by entering the city through the poorly defended gates on the land side. The pirates plundered and vandalized the city, burned down parts of it, and started to destroy stone buildings and monasteries to extort a ransom. He set up his headquarters in the cathedral where he looted the altars, destroyed all religious art, plundered the tombs, taking anything that was of value, and quite literally defecating on all things Catholic. Finally, a ransom of  25,000 ducats was negotiated–an extraordinary sum that only could be amassed by forcing citizens to surrender gold and jewels. At the nearby Casa del Cordón Drake installed a scale to weigh the exact amount of gold and jewels that were turned in by citizens.  Drake and his men left again a month later, turning their attention to Cartagena which was sacked and plundered in a similar fashion.

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Catedral de Santa María la Menor: Drake housed in a chapel to the right of the main altar.

Drake left behind not just a city that was a smoldering ruin, he also left behind a humiliated and traumatized city. To be sure, most of the churches and houses were restored, but the Spanish did not update the defense installations as they did in San Juan, Cartagena and other strategic points in the Caribbean. Simply put, the Spanish stopped investing into Santo Domingo. Very little of importance happened here after 1586, and the Spanish colonial Baroque architecture and culture of the 17th and 18th centuries which flourished in Mexico and South America completely bypassed Santo Domingo.

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The Puerta de la Misericordia, built in 1543 and expanded in 1568, could not stop Drake’s attack on land.

In a modern definition, terrorism involves non-state actors fighting enemy states, their representatives, institutions, and populations in asymmetrical warfare. In that sense, Robespierre‘s Reign of Terror in post-revolutionary France in 1793-94 does not qualify: this is just a case of a despot savagely abusing his own people. We have seen many since: from Stalin and Hitler to native sons “El Jefe” Trujillo and “Papa Doc” Duvalier who more recently traumatized the two nations that now share the island of Hispaniola.

Obviously, we have to see Francis Drake’s savage pillaging in the geopolitical context of the time: England challenging the Habsburg hegemony (the Habsburgs ruled Spain, Austria, and the Low Lands and controlled the Empire), supporting the Dutch in their wars of liberation against the Spanish, taking an active role in fighting Catholicism, and striving to become a maritime and colonial power in its own right.

In fact, Francis Drake, Sir Francis Drake if you are British, was sailing to the West Indies in something of an official mission. His acts of piracy in the Caribbean clearly were part of an English strategy to weaken the Spanish control over the Caribbean and the Transatlantic trade. But his fleet of 30 ships was financed by merchants who clearly had an interest in developing a trade network in the Caribbean, and his mission was not to take land and plant the English flag. His mission was to plunder and destroy, to take ransom, in short to inflict terror. Drake may have been the original of the “Pirates of the Caribbean.” He ushered in a century of piracy that left the Caribbean an unsafe, violence-filled space.

Like most explorers and navigators of the time, Drake also was a privateer, entrepreneur and free agent who worked for himself first and foremost. This agency is also an attribute of modern terrorists. Like many terrorists today, Drake had the implicit support by a state actor, the English crown, and had the financial backing of his own commercial network. Most importantly, the trauma of this humiliation he inflicted on Santo Domingo more than four centuries ago lives on today.* That is the very definition of terror.

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Iglesia de San Francisco, constructed 1544-1556. The Franciscan convent in Santo Domingo was mostly destroyed by Drake, then partly restored, damaged again in earthquakes in 1673 and 1751, abandoned in 1795.

* Note added 5/22/14: Gabriel García Márquez in his novel Chronicle of a Death Foretold (NY: Vintage Books, 1983, p. 98) describes the Palace of Justice in Riohacha on Colombia’s Caribbean coast with this apparently random phrase: “decrepit colonial building that had been Sir Francis Drake’s headquarters for two days.” This is the only overt historical reference in the book and indicates how Drake’s terror lives on in the collective memory in the areas he affected.

Santo Domingo, San Juan, and the First Age of Globalization

Santo Domingo, Dominican Republic, and San Juan, Puerto Rico, were the two first cities the Spanish built in the Americas, in that order. But the histories of the two cities located on two neighboring islands in the Caribbean and only 254 miles apart could not be more different. A close look at the architecture in these two cities makes this evident.

Santo Domingo became the early hub of all Spanish activities in the Americas and was booming in the first half of the 16th century. The first stone houses were built there in 1502, just ten years after Columbus first had arrived, a real audiencia was established in 1511, and a magnificent cathedral followed. All early conquistadors, like Cortés and Pizarro, came through this city, owned or rented houses, and spent months or years preparing for their respective conquests. The earliest fortifications were built starting in 1502, and in the 1540s a city wall was built to protect the entire city. Yet, building activity dropped off in the second half of the 16th century, and the fortifications remained modest in size and scope.

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The modest Fuerte de San Gil, erected 1503-1510, overlooks the entrance to Santo Domingo harbor.

The Spanish established the Real Audiencia (1528) and the Viceroyalty of New Spain (1532) in Mexico City, and political power gradually began to shift there. The Pedro de Mendoza expedition to the Río de la Plata region in 1534 was the first allowed to bypass Santo Domingo altogether, thus diminishing the role of the city as the hub of the Conquest. The sack of Santo Domingo by the pirate Sir Francis Drake in 1586 dealt a final blow to the aspirations of this city, as I have discussed in a different post, and little of significance seems to have been built in the 17th and 18th centuries.

San Juan, by contrast, features two of the most massive forts the Spanish ever built in the Americas to protect city and harbor, and the entire city was surrounded by a massive wall 40 feet tall and 18 feet thick. The military installations were a work in progress: starting with the first small fort in 1534, the Spanish continued to expand walls and bastions until 1790.

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Castillo San Felipe del Morro, built 1539-1786 to protect the entrance to San Juan Bay and San Juan harbor.

And all this in spite of the fact that San Juan never played a major role in the Spanish colonial administration. Ironically, it remained under the jurisdiction of the Real Audiencia of Santo Domingo. But Santo Domingo failed to thrive because it could offer only a modest seaport consisting of the mouth of the Río Ozama, a minor river, which was protected by a small barrier island. The harbor was difficult to defend, in spite of the Fortaleza Ozama next to it, built 1502-1505. As trade picked up substantially within a few decades, this port could neither provide the needed capacity nor offer sufficient protection.

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Entrance to the Santo Domingo harbor, protected by a small barrier island, seen from the Fortaleza Ozama (1502-05).

The Spanish needed a large and safe seaport as the Western anchor of the Atlantic crossing. This was critical as ships sometimes needed to wait for weeks or months for favorable trade winds to guarantee safe and expedient passage to Spain. Inversely, Puerto Rico was the first large island with food, a reliable fresh water supply, shelter and a secure deep-water port the weary sailors en route from Spain encountered in the Americas. It also was important to have a safe place to repair ships and to tend to sick crew members. San Juan Bay offered all of that.

These factors, plus the favorable location on the course of the eastern trade winds, gave San Juan and Puerto Rico great military, economic, and strategic importance: its harbor could protect merchant fleets and offered a safe point from which warships could be dispatched to maintain control over the Caribbean. While the Spaniards ceded the Western portion of Hispaniola (now Haiti) to France in 1697 and lost control of Santo Domingo in 1801, they vigorously defended San Juan and its strategic harbor entrance for almost 400 years–until Puerto Rico was ceded to the United States in 1898.

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Castillo San Felipe del Morro controlling the entrance to San Juan Bay–the most important half mile in the Americas.

Puerto Rico is only a footnote in the history of the Conquest as it never played a major political role–in contrast to Santo Domingo which was the political center of the first phase of the Conquest. So the fact that the Spanish invested heavily in the massive defense infrastructure in San Juan is surprising to the uninitiated visitor. But we tend to overlook the centrality of trade and commerce in the Conquest of the New World. San Juan became a major hub in the Spanish trade in silver and gold, and that is the true significance of the city: the San Juan seaport was used by merchant and military ships traveling from Spain as the first stopover in the Americas, but it also was the port where ships heading to Spain prepared for the transatlantic voyage. So the fortifications served to protect the lucrative trade in silver and gold and thus one of the major hubs in the early modern trade network and of the first age of globalization.

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The large, protected San Juan Bay could give shelter to large merchant fleets and to Spanish war ships. Today, it is lined with harbor installations. As these two large cruise ships indicate, San Juan now is part of a different kind of global network.