MLAS 270-23, Contemporary Caribbean
Professor William Frank Robinson
“A Brief History of Piracy in the Caribbean: 1500 – 1730”
By Stephen Doster
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In 1502, on his final voyage, Columbus came upon a Maya trading canoe near the
Honduras coast, which the Admiral’s men quickly plundered. This act of piracy presaged
a legacy that would continue in various iterations over the course of the next two
centuries.1
Piracy in the Caribbean can be segmented into five distinct overlapping cycles, which
this paper will examine:
the French Corsairs, 1500 – 1559
the Elizabethans, 1558-1603
the Dutch Sea Rovers, 1570-1648
the Buccaneers “Golden Age,” 1630-1697
the Freebooters, 1700-1730
Several factors played a part in attracting individuals and governments to acts of
piracy. For one thing, the items being seized – gold, silver, gems, sugar – were compact,
easily transportable compared to lumber or slaves, and highly desired in European
markets.
For many individuals, both those who pirated and those who defended towns against
pirates, it was a fast route to fame, fortune, and political and military promotion
regardless of social status. Shipwrecks and stragglers, vessels that were separated by
storm from guarded fleets or those that couldn’t keep up with armed escorts, became easy
prey.
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The crowns of Europe turned a blind eye toward privateers as they could perform the
tasks of a standing navy without the government having to expend currency or raise
additional revenues for defense through taxes.
Political and religious conflicts between major economic European powers (Spain,
England, France, the Netherlands) reached out like tentacles across the Atlantic and
manifested themselves in the form of acts of piracy and retaliation in the Caribbean. The
communications time delay between Europe and the Caribbean ensured that atrocities,
such as Henry Morgan’s 1668 raid on Panama City and Portobello, would continue
months after hostilities between home countries had ceased.
In 1494, by papal decree and the subsequent Treaty of Tordesillas,2 Spain and
Portugal divided the known world into halves, one for each realm, giving Spain rights to
explore lands west of “the line,” established 2,000 kilometers west of the Cape Verde
Islands. It was a line that would be quickly crossed by Spain’s enemies.
The simplest way to understand the pirates’ methodologies for hijacking Spain’s
wealth is to examine the routes treasure fleets took to transport precious metals.
After the discovery of gold and silver in the New World, sea routes were quickly
established. Bi-annual convoys (flotillas) left the port of Cadiz in January and August so
as to avoid the hurricane season. The typical route included provisioning in the Canary
Islands before sailing southwest driven by the northeasterly trade winds for the monthlong sea passage. Upon nearing the Caribbean, some merchant vessels split off for stops
at ports along the Lesser and Greater Antilles to trade manufactured goods, such as wine,
cheese, cloth, tools, and paper in exchange for raw goods like cocoa, indigo, and tobacco.
The rest of the fleet continued on into the Caribbean Ocean where it divided again with
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some treasure ships and their escorts bearding northeast for Veracruz and the rest sailing
to Cartegena and Portobello.3
Gold and emeralds of New Granada, pearls from Margarita, and indigo, tobacco, and
cocoa from Tierra Firma – present day Columbia and Venezuela – traveled by river and
overland to the port of Cartegena.4 Gold and silver from the mines of Peru were sent by
ship northward along the west coast of South America to Panama City, located on the
Pacific shore of the Isthmus of Panama. From there, mule trains carried the treasure
across the isthmus to Portobello, located on the Atlantic shore. Meanwhile, gold mined
in Mexico made its way to Veracruz, located on the western shore of the Gulf of Mexico.
In addition, gold, sugar and tobacco on Hispaniola as well as pearls from the islands of
Cubagua and Margarita off the northeast coast of Venezuela were transported to the
treasure ships.
Once the vessels’ hulls were filled at Cartegena, Portobello, and Veracruz, they sailed
to Havana for final provisioning and repairs before sailing back to Spain, a two to three
month voyage crossing via the westerly trades with stops at the Azores or Madeira. To
return, they had to pass through the relatively narrow, reef-laden Florida Straits, which,
combined with adverse weather conditions, claimed numerous ships.
Pirates and privateers alike soon discerned Spain’s weak points and exploited them.
So-called “choke points” included narrow passageways between the islands, which pirate
ships would prowl in search of stray merchant vessels and slave ships arriving from
Africa. The Florida Straits was a major choke point from which pirate captains could
bide their time. Gold-laden vessels that ran aground represented easy prey, and the
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treasure fleet could be followed back to Spain where one or two ships might fall behind
or be separated in a storm.
Another source of wealth included the provisioning towns of San Juan (Puerto Rico),
Santiago and Havana (Cuba), Veracruz (Mexico) Portobello and Panama City (Panama),
and Cartegena (Tierra Firma). These towns, where wealth could be accumulated by
merchants and landowners, were repeatedly raided beginning with the French corsairs
through the Golden Age of the buccaneers.
So great was the risk of piracy or storm-damage to ships that Spain considered the
idea of transporting its treasures by land that would circumscribe a route across the east
coast of Mexico and the southern coast of present day Texas, Louisiana, Mississippi,
Alabama, and Florida to St. Augustine, then north to South Carolina where treasure boats
could complete the final leg across the Atlantic.5
Even so, the last stage of the journey was fraught with danger as the fleet entered
what would become known as the Atlantic Triangle, an area from the Canaries to the
Azores to Spain, back to the Canaries. Here, as early as 1498, Columbus feared attacks
by French sea marauders waiting for Spanish ships near Madeira.6
The French Corsairs, 1500-1559
It wasn’t until Cortez’s conquest of Mexico (1519-21) that significant amounts of
treasure began flowing back to Spain.7 As noted above, French corsairs were already
plying the waters of the Atlantic Triangle. The first instance of a ship raid by the French
occurred in 1536 near the Chagres River on the north coast of Panama.
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A year later (1537) French corsairs attacked the ports of Cartagena, Nombre de Dios
(Panama), Havana, and Santo Domingo (Hispaniola). The town of La Yaguana on
Hispaniola was repeatedly attacked to the extent that it was eventually abandoned.
Emperor Charles V of Spain was urged to fortify these and other settlements.
However, the king, busy with numerous Old World conflicts that included war with
France during the 1540s and 1550s, chose not to fund the New. At the time, even the
larger Caribbean ports were little more than hamlets with populations of under five
hundred. These ports were, after all, merely staging areas from which to load precious
metals and raw materials for transport to Spain. The large gold and silver producing
interior areas of Peru and Mexico were relatively highly populated and well-protected
from invasion as were the routes used to transport precious metals to the ports.
Some settlements, especially the smaller outposts, took defensive measures into their
own hands. In one instance, Spaniards on the pearl producing island of Cubagua
informed the local natives that raiding Frenchmen were sodomites who would make the
Indians “serve as women.”8 The Indians, using poison-tipped arrows, drove off a corsair
vessel which never returned. After repeated pirate attacks, the town of San German,
Puerto Rico moved inland to the hills of Santa Marta, bringing further raids to an end.9
Even though Spain and France officially ended hostilities in 1559, French Huguenots,
lead by Jean Ribault, began to settle along the east coast of Florida. In 1565 King Philip
II (Charles V’s son), fearing French attacks on galleons traversing the treacherous Florida
Straits, ordered captain-general Pedro Menendez de Aviles to rid La Florida of the French
menace. Ribault and his men were slaughtered in what would prove to be one of
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numerous examples in which European conflicts continued to be played out in the
Caribbean after official peace had been declared.
During this period corsairs, such as and François Le Clerc who destroyed Santiago de
Cuba and Jacques de Sores who nearly did the same to Havana, “set the standard for
pirate cruelties in the Americas; from the 1550s onward, Spanish subjects could be
expected to be tortured, murdered, and extorted at random by foreign raiders from the
sea.”10
The Elizabethans, 1558-1603
During the reign of the fiercely protestant Elizabeth I, England would be engaged in
an on-again, off-again war with Spain. Several well-known seamen, John Hawkins and
Francis Drake, who started out in the slave trade, would turn their efforts to privateering,
a form of piracy that was sanctioned by the crown during periods of war. From 1558 to
1603, seventy-six crown-sanctioned expeditions sailed to the Caribbean.
In 1572 Drake raided Panama, crossing the isthmus to attack Panama City, and
returned with a fortune in gold. His “Famous Voyage” of 1577 included the capture of
two Spanish ships laden with gold from Peru before he circumnavigated the globe. On
this trip he took landscape artists who rendered accurate paintings of coastlines and
islands for cartographers and English mariners’ use.
Drake left England in 1585 for the Caribbean with a massive fleet of twenty-two
vessels and 2,300 men. Among them were several companies of soldiers. This voyage
included attacks on Santiago (Cape Verde), Santo Domingo, Cartegena, and St.
Augustine.11 Though the expedition didn’t yield enough in loot to break even, it
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succeeded in spreading fear and panic throughout the Spanish realm. A subsequent
preemptive attack on Cadiz caused enough destruction to delay Spain’s attempted armada
invasion of England, which Drake helped to defeat in 1588.
It is little wonder that Drake earned the epithet “Draco” (the dragon) in the eyes of the
Spanish. Though his exploits in the larger view did little more than “singe the king’s
beard,” and though Spain’s alliance with Portugal solidified its preeminent position as a
world power, Spain was forced to acknowledge the growing English threat to its interests
and responded in order protect its colonial waters from the English who “hovered around
every Caribbean port like flocks of vultures.”12
Spain’s Response
After decades of repeated attacks on their key Caribbean provisioning ports, Spain
embarked on a costly campaign of fortification that would take a hundred years to
complete. The project included constructing the massive strongholds of El Morro in San
Juan; Castillo del Morro, Havana; El Morro, Santiago, Cuba; San Felipe, Cartegena; San
Juan de Ulua, Veracruz; and a citadel at Portobello. Juan de Tejeda and Juan Bautista
Antoneli, two prominent military architects, were sent to oversee the construction
projects. Materials and labor – stones, tools, slaves – were costly as were ongoing
expenses to maintain the structures. In addition, the outlay for garrisoned soldiers who
required wages, arms, and food incurred additional expenses for the Spanish crown,
especially given that they faced no enemy most of the time.
Spain attempted to improve the safety of its treasure fleets by building faster and
better-armed ships including expensive war frigates (galibrazas). The averia (tax) already
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imposed on merchants for protection of their vessels (one round trip per fleet could cost
1.4 million pesos) was increased from “under 2 percent in 1585 to 4 percent in 1587, and
to 8 percent in 1591.”13 Predictably, the increase in the averia along with customs and
sales taxes increased the cost of goods sold not only in the colonies but in Spain as well.
New galleys designed to protect the ports of Santo Domingo, Cartagena, and Havana
were built to replace the ones destroyed by Drake. Spanish patrols (Guardia de la Costa),
similar to the present day Coast Guard, were established but had little success in finding
and capturing privateers.14
Drake’s final foray into the Caribbean ended with his death by fever in 1596 (a
common malady that affected many privateer crews) off the coast of Panama. In 1598,
the Earl of Cumberland sacked and pillaged San Juan, marking the last major raid during
the age of the Elizabethans. However, as was the case with France and England, Spain
had another enemy, the Netherlands, which would extend the conflict into the Caribbean.
The Dutch Sea Rovers, 1570-1648
In 1580 Portugal was added to the united kingdoms of Spain, causing a number of
Low Country provinces (the Netherlands, a region Philip II inherited from Charles V) to
declare themselves free of Hapsburg rule, which added fuel to what would later be known
as the Eighty Years War. Like Elizabeth’s war with Spain, it would be an on-again, offagain conflict.
Dutch privateers, under the auspices of Dutch trading companies, were already
present in the Caribbean during the Elizabethan period, purchasing contraband dyewoods
from Brazil and sugar, ginger, and hides from the Caribbean. The two prominent Dutch
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trading firms, the East India Company and the West India Company, backed much of the
piracy and privateering efforts of Dutch sea rovers during this period, bringing to bear the
first real threat to Spanish and Portuguese sovereignty in the Caribbean. Stockholders in
the companies received up to 75% returns on profits realized through the activities of
these privateers. In 1630, northeastern Brazil was captured, and in 1642 the Dutch
attempted to establish colonies in Chile after having planted a colony on Curacao and
other locations in 1634.
One major impetus for the Dutch establishing a base in the Caribbean was the need
for salt which was used to preserve herring for sale to Baltic nations, a huge industry then
and now. With their sources cut off from the major salt producers – Spain and Portugal –
the Dutch began to raid the naturally occurring salt pans of the Araya Peninsula of Tierra
Firma in present day northern Venezuela. Between 1599 and 1605, one hundred 200-400
ton hulks visited the peninsula annually until the practice was squelched rather severely
by Spain.15 Though Portugal’s salt soon became available to the Dutch (at a
considerably higher price), sea rovers continued to engage in contraband trade, including
the bartering of tobacco in Trinidad.
In 1628 Piet Heyn, under sail of the Dutch West India Company, entered the
Caribbean with 22 ships, 700 cannon, and 3,500 men. On September 8, in the middle of
hurricane season, he encountered a small, fifteen-ship Spanish treasure convoy on the
way to Havana. Outnumbered, the Spanish flota commanded by Juan de Benavides tried
to seek safe harbor in Matanza Bay, just east of Havana. Several treasure ships, with
their guns pointing the wrong way, ran aground on offshore shoals. Heyn and his men
seized all fifteen ships, taking half with them and burning the rest. He sailed back to
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Holland with 4.8 million “in gold, silver, silk, dyestuffs, and other valuables.”16 In 1634
Juan de Benavides would be executed in Seville for “negligence and abandonment of
duty.”17
Heyn’s good fortune would prove to be perhaps the largest single haul of booty by a
single pirate or privateer. While West India shareholders earned dividends of 75%,
underpaid soldiers and sailors who participated in the raid rioted in the streets of
Amsterdam. The next wave of Caribbean pirates would be comprised of such
discontented soldiers and sailors who would establish a more democratic form of piracy.
The Buccaneers, 1630-1697 – “Golden Age” of Piracy
The so-called Golden Age of piracy coincided with the decline of Spain’s fortunes
and the rise of the British, French, and Dutch as economic powers. While Spain
continued to protect its interests in South America and Mexico, it conceded parts of the
Caribbean during an era that saw the development of non-Spanish colonial bases in
Hispaniola (French), Jamaica (English) and St. Thomas (Dutch). In these places harbors
would serve as havens where pirates could “put in at friendly ports to sell stolen
merchandise, find drink or other pleasure, rest and recover strength, and seek letters of
marque for further privateering ventures against the Spanish.”18
Embittered sailors, abandoned colonists, and abused indentured servants were
attracted to a way of life that could afford opportunities for advancement otherwise
unavailable to them.19
On the northeast coast of Hispaniola, renegades and marooned sailors hunted feral
cattle and swine and sold hides and the meat – a jerky cooked on a boucan, a Taino-style
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wooden frame – to passing English, French, and Dutch vessels. The jerky-makers came
to be called boucaniers or buccaneers, a term that would be applied to pirates and
privateers of the period, regardless of nationality. The buccaneers of Hispaniola were
soon raiding Spanish merchant vessels in dugout canoes. After such raids, they came to
the rocky island of Tortuga to divide the booty among raiders and spend their earnings
before returning to Hispaniola for more cattle hunts.
Pirate bases were established at Tortuga and on Jamaica during this period where
island governors not only sanctioned raids but received a share of the spoils brought back
to port. It was also a period when England entered into hostilities with the Dutch and
their allies, the French.
By the 1660s, Port Royal, Jamaica had become the Las Vegas of the Caribbean,
sporting 19 taverns, 11 buccaneer captains, and 4,500 residents who benefited from the
riches seized at sea and spent at port. Privateers like Henry Morgan and Christopher
Myngs, who looted 200,000 to 300,000 British pounds worth of treasure from the coast
of Venezuela, epitomized the buccaneers of this period.
In 1668, Morgan and 400 men attacked Puerto Principe, Cuba where he killed the
governor and tortured and robbed its citizens. Next, like Drake before him, he seized the
town of Portobello, using captured Jesuit priests as human shields to take the fort before
embarking on an arduous journey across the isthmus. There, he sacked Panama City and
tortured its residents to no avail as no treasure could be found. Morgan and his men left
with approximately 250,000 pesos worth of booty including 100,000 ransomed from the
governor of Panama in exchange for vacating Portobello. The economic loss to Spain
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was estimated to be in the millions of pesos in terms of buildings, fortifications, ships,
and merchandise destroyed and slaves killed.
Because Morgan’s raid was conducted during a period of peace between England and
Spain, he was sent to London for trial in 1672. Morgan proved he had no knowledge of
the peace treaty, was eventually knighted and sent back to Jamaica in the capacity as
Lieutenant Governor where he continued to encourage privateering even as the acting
governor, Lord Vaughan and the British admiralty, attempted to crack down on piracy.
In 1677 Vaughan was granted the legal concept of “oyer and terminer” which allowed
the Jamaica Admiralty to issue death sentences without appeal.20 By 1680, under
pressure from the home government and the rising class of planters who demanded a
stable environment in which to conduct commerce, the political winds had shifted enough
that Morgan, in a complete turnabout, adopted a prosecutorial attitude toward his former
colleagues.21 Anti-pirate legislation, including the Jamaica Act of 1683, represented the
beginning of the end of piracy in the Caribbean, forcing many buccaneers to ply their
trades in the Pacific and Indian oceans. However, one final wave of piracy would soon
play out on the Caribbean stage.
The Freebooters, 1700-1730
Curiously, it is the last cycle of piracy, the Freebooters, that comes to most people’s
minds when the topic of pirates is brought up, even though it represents the swan song of
piracy in the Caribbean. Perhaps the freebooter period conjures images of the old west
before it was “civilized,” where gangs of robbers roamed freely, and each man took the
law into his own hands.
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With the end of the Queen Anne’s War thousands of naval seamen were put out of
service. Some became coasting captains along the Atlantic shores of North America.
Others remained in the Caribbean, where pirate operations shifted to the Bahamas in part
due to the wreck of an entire Spanish treasure fleet off Cape Canaveral, Florida in 1715,
which attracted salvagers and those who attacked the salvaging crews, including former
buccaneers.
Between 1716 and 1726, an estimated 5,000 pirates roamed the waters of the
Bahamas. New Providence (modern day Nassau) replaced Tortuga and Port Royal as the
base of pirate operations. One distinguishing feature of the freebooters is that they
concentrated attacks on trading vessels and wrecks and engaged in little if any land raids.
A typical freebooter was a 27-year-old male of Anglo-Saxon heritage. He was
unmarried, from the lower-class, with some experience as a mariner and little regard for
religious or national authority. Prominent freebooters included William Kidd and
Edward Teach, also known as Blackbeard. Two female pirates, Anne Bonny and Mary
Read, also found acclaim. Mary Read, like most pirates, was recruited into the trade as a
captive who agreed to join a pirate ship.22
Seamen who joined a pirate crew were required to sign a contract and agree to a code
of conduct that included strict rules and punishments for violations [Appendix 1]. In
general, the codes were democratic in that booty was distributed according to rank and
seniority, and crewmen could be compensated for injuries. Typical daily rations included
whatever fish could be caught, salt meat (pork, beef), cheese, butter, peas, hard biscuit,
and boiled dumplings.
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Edward Teach learned his trade in the Bahamas and North America where he raided
vessels along the Atlantic coast. In 1718, he returned to the Caribbean where he captured
a French vessel that he renamed Queen Anne’s Revenge and used it to attack French and
English ships in the West Indies, the Gulf of Honduras, and St. Kitts. But he soon
returned to the North Carolina coast to take advantage of amnesty being granted to
pirates. The governor, Charles Eden, allowed Teach to continue pirating ships in return
for a portion of the spoils. However, Virginia’s governor, Spotswood, commissioned a
British naval force that corralled and killed Teach at Ocracoke Inlet, North Carolina on
November 22, 1718.23
Meanwhile, the British admiralty continued to aggressively pursue, prosecute, and
hang pirates in the Bahamas and Caribbean, and by 1730 piracy had been effectively
brought to an end.
Legacy and Significance of Piracy to Home Countries
The legacy of piracy in the Caribbean continues to this day in the form of films, like
Captain Blood, The Black Swann, Blackbeard’s Ghost, and Pirates of the Caribbean, and
through classic literature such as Robinson Crusoe and Treasure Island, which has never
gone out of print.
Contraband trading and acts of piracy never really left the region for good. Slaves
were smuggled from the Caribbean into the United States long after the slave trade was
abolished. Alcohol was brought to U.S. soil by boat and by plane during Prohibition.
Contraband cigars, rum, and marijuana continue to be exported as does the trafficking of
humans from Cuba, Haiti, and other Caribbean nations.
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The legacy of Caribbean piracy varies by each nation involved in its history. For
Spain, it was the price one could expect to pay for generating and transporting highly
valued, compact materials over a wide, unsecured area. The Spanish crown paid for it
with millions spent on fortifications, naval vessels, troop garrisons, and towns destroyed
by land raids. In the final analysis, the wealth they generated and preserved far
outweighed that which was lost to piracy. However, the sheer volume of land and ports
they conceded in the Caribbean to other countries was significant.
For England, France, and the Netherlands, piracy allowed them to establish footholds
in the Caribbean from which they extended their realms by expanding into the New
World. With the acquisition of Jamaica and Trinidad, England (including Ireland and
Wales) increased its land area by more than one fifth. The new colonies gave these
nations access to natural resources and raw materials that could be traded and sold on the
world market. In time, the Caribbean islands they occupied would house military bases
and naval ports from which their home fleets could find provisions and safe harbor an
ocean away.
The language, laws, religion, cultural and economic impact each nation brought to the
region can still be seen today on the islands they once occupied [Appendix 2].
The net effect was that their Caribbean presence, which began with piracy, helped to
establish England, France, and the Netherlands as budding economic powers which they
ultimately became. Indeed, the argument could be made that challenging Spain – a world
power – through piracy and privateering helped lead to their emergence as world powers
with wide geographical reaches.
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Notes
1. Blood & Silver: A History of Piracy In The Caribbean And Central America, Kris E.
Lane, Signal Books, Ltd., Oxford, United Kingdom,1999 (formerly Pillaging the
Empire: Piracy in the Americas, 1500-1750), xvii.
2. Ibid., 9.
3. The Buccaneers In The West Indies In The XVII Century, C. H. Haring, Methuen &
Co. Ltd., London, 1910, 14.
4. The Buccaneers, 16.
5. Laboring in the Fields of the Lord: Spanish Missions and Southeastern Indians,
Jerald T. Milanich, Smithsonian Institution Press, Washington, DC, 1999, 76.
6. Blood & Silver, 10.
7. Ibid., 16.
8. Ibid., 20.
9. History of Puerto Rico: A Panorama of Its People, Fernando Pico, Markus Wiener
Publishers, Princeton, NJ, 2006, 78.
10. Blood & Silver, 24.
11. The Buccaneers, 39.
12. Blood & Silver, 48.
13. Ibid., 50.
14. Pirates and Privateers Of The Caribbean, Jenifer Marx, Krieger Publishing
Company, Malabar, Florida, 1992, 256.
15. Ibid., 103.
16. Blood & Silver, 68.
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17. Pirates and Privateers Of The Caribbean, 123.
18. Blood & Silver, 97.
19. Pirates and Privateers Of The Caribbean, 10.
20. Blood & Silver, 125.
21. Pirates and Privateers Of The Caribbean, 246.
22. Lives Of The Most Notorious Pirates, Charles Johnson, The Folio Society, London,
1962, 82.
23. Ibid., 48.
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Appendix 1
Sample Pirate Code of Conduct
1. Everyone shall obey orders.
2. Booty will be shared out as follows: 1 share to every ordinary seaman; 1 1/2
shares to the captain; 1 1/4 shares to the master carpenter, boatswain and gunner.
3. Anyone keeping secret of attempting to desert will be marooned. He may take
only a flask of gunpowder, a bottle of water, a gun and some shot.
4. The punishment for hitting a man is 40 lashes on the bare back.
5. Anyone being lazy or failing to clean his weapons will lose his share of booty.
6. Everyone may vote on all important decisions.
7. Everyone may have a share of captured drink and fresh food.
8. Anyone found stealing form another member of crew will have his ears and nose
slit open and be set ashore.
9. Gambling with cards and money is forbidden.
10. The penalty for bringing a woman aboard in disguise is death.
11. No one may leave the crew until each man has made 1,100 pounds.
12. The compensation of losing a limb is 800 silver dollars.
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Appendix 2
British Caribbean Possessions: Anguilla, Bahamas, British Virgin Islands, Jamaica,
Trinidad
French Caribbean Possessions: Western Hispaniola (Haiti), Martinique, Guadeloupe,
French Guiana, French St. Martin, Marie-Galante, La Desierade, Les Saintes, SaintBarthelemy, portions of Dominica, St. Lucia, Grenada, St. Thomas
Dutch Caribbean Possessions: Curacao, Aruba, Bonaire, Saint Eustatius, Saba, St.
Maarten
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