A History of Sir Francis Drake’s Attack on Cartagena de Indias

In 1586, infamous English pirate Sir Francis Drake occupied Cartagena for over a month, burning and looting much of the city before being paid a hefty ransom.  Read on to learn about the history of Drake’s sack of Cartagena.

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Background to Drake’s Raid on Cartagena:  Growing Tensions

The 16th century saw growing tension between England and Spain.  These tensions fit into the larger context of religious tension and political tensions across Europe in this period.

Martin Luther’s publication of his 95 theses in 1517 had set off a wave of challenges to the power of the Catholic Church.  In 1534, King Henry VIII of England, after failing to get approval for an annulment of his marriage, took England out of the Catholic fold.

Queen Elizabeth I, upon her succession to the throne in 1558, worked to institutionalize this change.  Shortly after becoming queen, she adopted laws that upheld the Church of England as separate from the Roman Catholic Church but remained fairly moderate.  With her excommunication by the Pope in 1570 and the Catholic Counter-Reformation underway, King Phillip II of Spain saw her as an enemy.

In the context of these religious tensions, economic and political tensions also emerged.  By this time, Spain had established a budding empire in the Americas based largely on the looting of gold from indigenous peoples and, increasingly, from the silver mines at Potosí in modern day Bolivia.

England meanwhile was yet to emerge as a true international power.  Its first ill-fated colony in the Americas at Roanoke was not established until 1585.  However, it had become a growing naval power, and commercial power.

Increasingly, Elizabeth hoped to thrust herself and her England into the upper echelon of European powers. This would have included ambitions to establish colonies in the Americas. It’s easy to forget based on later history, but the “New” World was originally the domain of only Spain and Portugal.

If you’re looking for an interesting look at Elizabethan England’s naval adventurers and early colonial expansion, check out the book New World, Inc. The book argues that, contrary to popular belief, commerce, not religious freedom was the main motivation in English settlement of North America. It’s a unique look and gives good context to the international situation at the time.

Privateers

England’s growing international naval power was based heavily on the use of privateers. Privateers were privately outfitted ships and expeditions that were given licenses to attack the naval trade of another country. 

Put another way, they were akin to pirates who worked for a particular country.  Raids carried out by English privateers against Spanish shipping and colonies had only increased the tensions.

*Did you know Cartagena later employed privateers to raid Spanish trade themselves a couple hundred years later during the independence era? Learn more about them in the excellent book No Limits to their Sway. It’s one of my favorite books on Cartagena’s history. See my review or check it out on Amazon.

Enter the “Sea Dog” Sir Francis Drake

One of such privateers employed by the English was Francis Drake, who would go down as the most famous of Elizabethan England’s privateers or “Sea Dogs.”

Drake had become a crewman on a trading ship in his early teens, and eventually went to work for John Hawkins, who led several slave trading expeditions to the Americas in the 1560s, including one where he sold slaves in Riohacha in modern day Colombia.

Drake first sailed to the Caribbean in 1567 on another slave trading expedition led by John Lovell.  He then joined Hawkins’s third Caribbean voyage which set out in October of 1567.

After arriving off the Venezuelan coast and failing to find anyone willing to trade with them at Margarita (trade with the English was illegal), they proceeded to Santa Marta where they sold over 100 slaves.

They sailed by Cartagena, but the city’s guns opened fire upon their arrival, and they sailed away.

When arriving at Veracruz, Mexico, Hawkins and Drake were duped by a false offer of a truce. It was broken in a surprise attack by the Spanish garrison.

The attack destroyed much of their fleet.  Both men were able to escape and eventually return to England.

However, this experience undoubtedly instilled in Drake a deep desire for revenge.  Along with a Protestant zeal, Drake now saw himself practically as on a crusade against the Spanish (granted one that also allowed him to make lots of money).

Drake led another expedition to the Spanish Main (the commonly used name of Spain’s Caribbean trading ports) in 1572 and 1573.

This expedition included a venture to Cartagena where he found a fleet waiting for him.  Not willing to risk a full scale confrontation, he opted to land farther north and raid a Spanish silver shipment traveling across Panama. Then he sailed back to England.

He next organized an expedition to the Pacific, sailing through the perilous Magellan Strait and raiding Spanish colonies and trading vessels up the Pacific coast of South America.  There he succeeded in capturing a Spanish treasure ship carrying gold and silver worth as much as $75 million dollars today.

He then sailed as far north as the coast of Canada before sailing across the Pacific, through the Indian Ocean, around Africa, and finally arrived back in England in mid-1580.  His voyage had lasted 33 months and it made him the second person to have successfully circumnavigated the globe.  He was hailed as a hero, was knighted, and was now fabulously wealthy to boot.

*If you’d like to learn more about Drake, check out some of the following books:

• Sir Francis Drake by John Sugden
• The Queen’s Pirate:  Sir Francis Drake by Kevin Jackson
• The Life, Voyages, and Exploits of Admiral Sir Francis Drake: With Numerous Original Letters from Him and the Lord High Admiral to the Queen and Great Officers of State by John Barrow

Drake’s Great Expedition

Drake’s exploits may have made him a celebrated figure in England, but in Spain he was loathed.  His raids had only added to the tensions in the growing Cold War-esque conflict between England and Spain.

Those tensions had come to a head by the mid-1580s with Elizabeth’s support for Protestant rebels in the Spanish held Netherlands.

Drake’s Pacific expedition, and Elizabeth’s embrace of him (not to mention the fact that she had been a secret investor in the expedition) brought them to the breaking point. 

Sensing war was on the horizon, Elizabeth hoped that a daring raid on Spanish colonial possessions in the Caribbean would serve three purposes.

First, it would put England on the initiative.  Second, the plunder would help provide funds to fund a future war.  Finally, and perhaps most importantly, that plunder would come at the expense of Phillip, making it more difficult for Spain to carry out a war.

Naturally, it would fall to the now infamous Drake to lead the expedition.  In fact, he himself had long been a proponent of just such an expedition.  He began planning and readying what he would call his Great Expedition.

The expedition was funded as a joint-stock venture (lest we ever forget the origin of investing), and different people contributed money, ships, men, and/or resources in exchange for a promise of a share in the expected loot.  Many of England’s most prominent officials as well as Queen Elizabeth herself were secret shareholders in the venture.

Drake’s fleet numbered 29 ships with around 800 crewmen and 1,600 soldiers.  It was the largest fleet England had ever sent to the Americas up to this point in history.

Officially, Drake was to demand redress and compensation from the Spanish authorities for his earlier losses on the voyage with Hawkins.

However, in reality, this was nothing but a pretext. The expectation was the Spanish would refuse, giving Drake supposed justification in using force. The real goal was an attack on the Spanish Main meant to disrupt Spanish trade, raid its colonies, and possibly even capture the annual treasure fleet.

Drake’s fleet set sail from Plymouth on September 14, 1585.  After setting sail, he narrowly missed intercepting the returning treasure fleet off the coast of Portugal.

He then raided the Cape Verde Islands, off the western coast of Africa. There he burned two towns.  Likely he was using them as an example to help ensure the Spanish would be willing to pay ransoms rather than let their colonies in the Caribbean suffer a similar fate.

In November, he set out across the Atlantic to the Caribbean.  His crew suffered badly from a virus and more than 300 died on the voyage across the ocean.

After reaching the West Indies and taking some time for his remaining men to recuperate, he set his sights on Santo Domingo, capital of Hispaniola (in present day Dominican Republic).

Santo Domingo was a major religious, commercial, and administrative center of the Spanish colonies, and Drake undoubtedly chose it as much for its symbolic value as its potential for loot.  Attacking it would send the message he could attack any city in the Americas.

During the assault, Drake practiced the same tactic he would later use at Cartagena, using his ships as a diversion by bringing them up as if he planned to conduct a frontal naval assault, while a land force marched from outside the city.

The assault took place on New Years Day 1586.  Drake’s forces easily took the city and his men set to work to plunder it.

Under threat of its complete destruction, the governor was forced to pay a ransom of 25,000 gold ducats.  This was less than Drake had hoped to get, but he was eager to continue his expedition rather than try to hold out for more.

With rumors reaching Spain and the rest of the colonies of his actions, Drake’s fame continued to grow.  The only question was where he would strike next.

*If you’re interested in more about Drake’s Great Expedition, check out The Great Expedition:  Sir Francis Drake on the Spanish Main in 1585-86, one in a series of books on great raids in history, and which I used extensively for research on this post.

Drake’s Attack on Cartagena

That next target would be none other than Cartagena de Indias.  He chose it due to its importance as a major treasure port where much of the gold and silver extracted from the mainland colonies was stored before being shipped back to Spain.

Drake’s Arrival to Cartagena

Luckily, the people of Cartagena had received warnings from Spain and Santo Domingo, and knew Drake was likely to hit them next.

Governor Don Pedro Fernandez de Busto made preparations for Drake’s impending attack, mustering militia and shoring up the city’s defenses.

Drake first arrived to Riohacha before sailing along the coast towards Cartagena, giving them more time to prepare.

Cartagena’s geography made it difficult to attack.

While the city sat on the coast facing the Caribbean, strong winds and currents made it difficult to anchor there and nearly impossible to successfully land a ground force.

That meant that Drake would have to enter the harbor through one of the two narrow channels known as Bocagrande and Bocachica that lie on either side of the island known today as Tierrabomba.

Later, in large part due to Drake’s successful attack, a series of forts was built on Tierrabomba to protect the entrance to the bay. However, at this point there were no defenses at the entrances or the outer bay.

After sailing into the outer harbor and anchoring his ships out of range of the city’s and inner bay defenses’ cannons, Drake began to plan his assault.

Drake’s Assault on Cartagena

When looking at Cartagena today, it’s important to keep in mind that at this point the only part of the city that had been developed was the Centro commonly called the Walled City today. However, the the city’s iconic stone walls were yet to bet built (they were in fact built largely as a response to Drake’s raid).

The city did have some wooden walls and earthworks as well as a fort named El Boquerón that protected the entrance to the inner harbor near where the marina in Manga stands today.  However, many of the city’s guns were old and in disrepair, leaving it vulnerable to a fleet as large as Drake’s.

Therefore, Drake chose to land foot soldiers on the strip of land off the Bocagrande Channel. Commonly referred to as Bocagrande today, it was little more than an uninhabited sand bar with some vegetation at the time.

His men landed on the beach overnight on February 9 near where the Bocagrande Hospital is located today in Castillogrande. They then marched towards the city.

It’s hard to picture today, but the geography was similar but different at the time. Only a very narrow stretch of land connected Bocagrande and the city. Today, it is much wider and arrives to the corner of the wall near the San Pedro Claver Church.

At the time, this area was still covered by the water of the inner bay. The sand bar connected to the are where the city was built at the corner where Café del Mar stands today, near the Santo Domingo Church. The photo just above this section would have been more or less where Drake’s men marched on the city.

Knowing this was a potential weak spot, the Spanish had built an earthen wall with a trench in front of it and four cannons to fire on the approach.  Two ships in the inner harbor also were in position to fire on the advancing English.

However, there was still one glaring weakness.  The English had arrived at low tide, leaving a gap on the Spanish right where the earthen wall ended and only a handful of wine barrels filled with sand blocked passage up the exposed beach.

The English force made for this gap and after a brief struggle succeeded in throwing aside the barrels and opening up a breach in the defenses.  The Spanish defense quickly routed and within minutes the English were inside the city

By dawn of February 10, the Drake’s forces were in firm control of the city.

The two Spanish ships in the harbor were damaged and scuttled in the fighting, however the fort of El Boquerón held out.  Its defenders abandoned it the next night, leaving Drake in complete control of the city on February 11.

Casualties on both sides were remarkably low.  The Spanish reported only 9 men dead, while the English lost 28.  Drake had ordered his men not to pillage the city but when they entered many looted and ransacked many of the city’s homes before they were brought under control.

*See also:  Visitor’s Guide to Cartagena’s Naval Museum where there are some excellent dioramas recounting Drake’s attack on Cartagena. You can also get a printed version of Drake’s map of the city (depicted at the top of this post) and even get it on a magnet.

Drake’s Men Loot Cartagena and He Negotiates a Ransom

However, many of Cartagena’s citizens had taken their valuables with them when fleeing before Drake’s arrival, not leaving that much to loot.  Drake took up residence in the home of Alonso Bravo, a Spanish captain who had been wounded in the fighting, and set to work to negotiate a ransom for the city.

Interesting fact:  the home where Drake stayed is now the hotel Casa de Alba, one of the best boutique hotels in Cartagena.

Drake demanded both smaller ransoms from wealthy individual citizens like Bravo as well as a larger one from the city at large.  He first demanded an outrageous 400,000 pesos (if Drake had been born today, he would be natural street vendor in Cartagena) but the Spanish offered only 25,000.

At that, Drake began burning houses in the city.  In total, almost 250 houses were burned before the Spanish relented and offered more. Drake had even threatened to knock down the incomplete Cathedral of Santa Catalina Alejandría, firing on a column and doing damage that delayed its completion.

Drake agreed to accept 107,000 pesos in addition to the smaller individual payments.  For several days mule trains carried gold and silver to Drake’s ships.

When factoring in all of the loot and ransoms as well as all the cannons of the city, Drake’s total haul from Cartagena is estimated at around 500,000 pesos, even more than what he had gained from his treasure ship in the Pacific.

However, overall, this was a disappointing number. The loot and its profits would have to be shared between the massive crew, not to mention the large numbers of investors. This sum simply did not live up to the enormous expectations for the expedition.

Drake and his advisors now decided what to do next.  Some argued that Cartagena should be turned into an English colony, but that would have required massive expenditures from the crown to supply and protect it.

So, they decided it best to abandon the city and set about making preparations to do so.

Drake Sails Away

During their stay in the city, many of Drake’s men came down with another tropical fever.  More than 100 of them died in the weeks following the battle.  That left Drake eager to leave.

Before leaving, the English took all the goods they could scrounge up for supplies or to sell elsewhere.  The fleet sailed away from Cartagena on April 12, 1586.

It was a good date to leave. Drake had narrowly escaped capture. Just two days later, a Spanish fleet arrived to trap him in the city.

With his crew too weakened to continue his original plan to raid the rest of Spain’s other major ports in the Caribbean, Drake set his sights on home with the hope of raiding one last colony on his way, perhaps Havana.

He also wanted to visit Sir Walter Raleigh’s new colony Roanoke in North America.

*You can get a poster sized copy of the map above on Amazon.

He did in fact make landfall on the southern Cuban mainland, where according to legend his sickened soldiers mixed limes and cane liquor from the local indigenous people to help remedy their fevers, supposedly inventing an early version of the Mojito.

However, strong winds blew him off course when he attempted to round the eastern tip of the island.

He therefore settled to sail north towards the fledging English colony.  On the way, he raided St. Augustine in Florida, burning much of it to the ground.

He then headed up the North American coast until he encountered Raleigh’s colony on an island just inside the Outer Banks of North Carolina. He found the colony struggling, and the colonists decided to set sail back for England with Drake

Just two weeks later, a boat with a years worth of supplies and more settlers from England arrived. By 1590, the site had been abandoned.  What happened to them and the ill-fated colony of Roanoke remains one of history’s unsolved mysteries.

Drake finally arrived back to Plymouth in England by the end of July 1586 after a 10 month expedition that had led to the deaths of hundreds of his crew but did return a fair amount of plunder, even if it was less than originally expected.

Perhaps most importantly, Drake’s raid also pointed out the vulnerability of the Spanish and would go on to have consequences for English-Spanish relations as well as for the city of Cartagena.

Consequences of Drake’s Attack on Cartagena

Financially speaking, Drake’s expedition was not so successful.

Officially, the investors actually took losses, only receiving 75% of their original investment, however the goods that were returned to be sold would have covered them and produced some profit.  Still, overall the so called Great Expedition was a financial failure and didn’t bring the riches many had hoped it would.

Drake’s Great Expedition did have important diplomatic consequences, however.

Diplomatic Consequences

Although Drake’s original plan to raid all of the major ports on the Spanish Main did not come to fruition due to the toll of disease, in many ways, his expedition had accomplished its major goal.

It had made Spain look vulnerable.  The successful attack and razing of two of its most important early colonial cities was a major humiliation for Spain and destroyed any illusions of invincibility.

Drake’s raid on Cartagena also likely made war inevitable.  Although one of the motivations was to cause such a loss to Spanish coffers as to make them think twice about going to war, there was little chance the Spanish would ever have accepted such an affront with out wanting to take revenge.

After the Spanish succeeded in putting down the English supported rebellion in the Netherlands, King Phillip decided to deal with the English threat directly.  The Spanish began making plans for a full scale invasion of England.

This invasion force was of course the Spanish Armada, which was defeated by English sailors, with Drake amongst them, in 1588.  This upset victory helped establish England as a major power to be reckoned with and competitor to the Spanish and French in the Americas.

As for Drake, he and his mentor Hawkins both died at sea from disease during another raid on the Spanish Main in 1595-96.

Consequences of Drake’s Attack for Cartagena

Drake’s raid was disastrous for Cartagena. The ransom had to be paid with royal funds and it would take years for the city to repay the royal treasury.

Many of the city’s homes had also been destroyed.  The governor, Don Pedro wrote to King Phillip about the raid declaring, “I do not know how to begin to tell your Highness of my misfortune.”  He and the city’s residents now had to set about rebuilding their homes and the city’s defenses.

Drake’s raid had pointed out severe flaws and perhaps what had been overconfidence in the Spanish defense of its colonies.  It was this attack that led to the start of the construction of a series of stoneworks that eventually were linked to form Cartagena’s City Wall beginning in 1602.

*See also: 10 Things You Probably Didn’t Know About Cartagena’s Walls

In 1657, a small fort was constructed on the San Lázaro hill just outside the city.

The city did suffer one more successful privateer attack from the Frenchman Barón de Pointis in 1697 and was forced yet again to pay a ransom. However, the city would redouble its defenses afterwards.  Several forts were constructed around the approaches to the harbor.

The fort at San Lázaro was rebuilt and renamed to the Castillo San Felipe, which played the crucial role in the successful defense of the city from Edward Vernon’s fleet in the 1741 Battle of Cartagena de Indias.  It was later even further expanded to the massive fortress it is today.

*See also:  History of the Castillo San Felipe, Visitor’s Guide to the Castillo San Felipe, and History of the Battle of Cartagena de Indias.

Fortunately, after Vernon’s failed attack, no others dared try to attack Cartagena.  However, Drake, celebrated as a hero in England, would forever be remembered and reviled in Cartagena for his attack and looting of the city.

Want to know more about Drake’s sacking of Cartagena?

Check out the following books from Amazon:
The Great Expedition:  Sir Francis Drake on the Spanish Main in 1585-86
Sir Francis Drake by John Sugden
The Queen’s Pirate:  Sir Francis Drake by Kevin Jackson
The Life, Voyages, and Exploits of Admiral Sir Francis Drake: With Numerous Original Letters from Him and the Lord High Admiral to the Queen and Great Officers of State by John Barrow

*Keep in mind you can get a free 30 day trial of Amazon Prime, which not only gives you free 2 day shipping, but also free kindle rentals and access to lots of movies and tv shows. You can also check out Kindle Unlimited or if you prefer listening to audio books, Amazon Audible.

Did you like this post?

Check out these others you might like:
Comprehensive History of Cartagena (long read)
A Primer on the History of Cartagena (short read)
Cartagena’s Declaration of Independence
The Siege of Cartagena
Visitor’s Guide to the Cartagena Historical Museum