Battle during the golden age of piracy in the Caribbean

Piracy in the Caribbean: Putting the Arrr in History

When we think of pirates, we often think of the scalawags who roamed the Caribbean Sea in the giant, three-masted ships with a jolly roger flying in the wind. And while some of the romantic notions we have about piracy in the Caribbean are true, the actual history of pirates is so much more fascinating.

What Led to Piracy in the Caribbean?

From the mid-sixteenth to the early eighteenth century, piracy in the Caribbean flourished. There were times where it must have seemed like pirates were as much a part of the ecosystem as the native flora and fauna. 

Related: 13 Best Pirate Books for Swashbuckling History Lovers

But, pirates were an invasive species. And they didn’t end up in the Caribbean by accident. While the rise of piracy in this area of the world was a complicated mixture of social, political, and financial realities, there are three main factors I want to address here: the opportunity to steal from Spain’s immense New World empire, how this led to the rise of buccaneers, and the Caribbean’s geography.

Hijacking Spanish Wealth

Painting of a Spanish galleon
Painting of a Spanish galleon

The first, and perhaps most important, factor that led to piracy in the Caribbean was that there was wealth for the taking. In the century following Christopher Columbus’s “discovery” of the New World, the Spanish established themselves as the main imperial power in Central and South America, and the Caribbean.

In this time, Spanish conquistadors conquered the largest empires in the Americas (and, indeed, the world), the Inca and the Aztec empires. From these conquests and the exploitation of indigenous peoples and natural resources, the Spanish crown made a fortune. Overnight, the kingdom of Ferdinand and Isabella had become one of the most powerful political entities in the world.

But, having all that wealth sitting around Mexico, Peru, and other conquered territories wasn’t going to do them much good. Using ships called galleons, the Spanish began shipping vast quantities of New World resources back to Europe. The riches they exported included gold, silver, gems, and sugar.1 Items that Europeans, especially the wealthy ones, quickly became addicted to.

On the way across the Atlantic, Spanish sailors often stopped at one of the Caribbean islands Spain controlled (which was most of them) for one final restocking before the arduous six- to eight-week journey home.

Though necessary, this journey through the Caribbean made these Spanish ships easy prey.  

The Rise of Buccaneers

Buccaneers lounging on a beach
Henry Morgan and fellow buccaneers

The worst consequence of Spanish colonization of the Caribbean was the total depopulation of the islands. The Taíno, Arrowak, and other peoples who had inhabited the Caribbean and Bahaman islands before the arrival of Spanish conquistadors died of disease, were killed in war, or were sold off as slaves. 

Larger islands, like Hispaniola and Cuba, became centers of Spanish power. The Spanish may have been the first European kingdom to establish a massive New World empire, but they were not the only ones who sent ships across the Atlantic. Portuguese, French, English, and Dutch ships routinely crossed to the ocean on trading and colonizing missions.

Jealous of the Spanish empire, these other powers began sponsoring raids on Spanish shipping. Lucky for them, there were already Europeans living on the fringe of Spanish Caribbean settlements.

Living in the Spanish territory of Hispanola and its tiny neighboring island, Tortuga, these groups started as hunters.2 As they made their living hunting wild boar with long-barreled muskets, these groups came to be known for the grill they used to smoke meat: viande boucanée. Eventually, boucanée became buccaneers.3

By the mid-sixteenth-century, the French had taken possession of Tortuga. Using their proximity to the buccaneers to their advantage, they began paying them to raid Spanish shipping leaving Hispanolia. Eventually the practice spread across the entire Caribbean, and the English and Dutch joined the French in sponsoring the proto-pirates.

Buccaneers quickly gained fame and infamy. Men like Henry Morgan (more on him below) undertook daring raids, but not just on Spanish ships. As the buccaneers gained confidence, they even began sacking major port cities. 

Eventually, buccaneers struck out on their own and became true pirates. No longer answering to government officials, they worked outside the law of every government – they had morphed into the outlaws we all know and love.

The Geography of the Caribbean Sea

Map of the Caribbean from the 1600s
17th-century map of the Caribbean

One of the reasons that piracy in the Caribbean flourished had nothing to do with people at all. 

For pirates to succeed, they need somewhere to hide. And Caribbean islands offered that in droves. The islands that dot the sea offered thousands of bays and natural harbors where pirates could avoid detection by imperial authorities.4

With the ships and manpower that the European empires had at their disposal, there was no way they could even know about every nook-and-cranny that existed in the Caribbean, let alone patrol it.

Pirates quickly realized this and took full advantage.

The Golden Age of Piracy

Battle during the Golden Age of Piracy in the Caribbean

Piracy in the Caribbean was now off and running and there was nothing anyone could do. But, pirates were no longer just hunting Spanish galleons. Once buccaneers morphed into true pirates, they attacked ships belonging to any European power. Now the English, French, and Dutch had their Caribbean-bound ships assaulted by the very men they had armed.

The Golden Age of Piracy lasted from roughly 1680 to 1720.5 Though these dates are contested by historians, this seems to be the best estimation possible. The rise of the Golden Age of Piracy was an evolutionary process, with no fixed beginning. So it seems appropriate to use one of the longer time periods suggested by historians.

But, what exactly was the Golden Age of Piracy? It was the age you think of when you think of pirates. This was the period of the outlaw pirate who was, in one historian’s words, the enemy of all nations. It was also the time when the most pirates roamed the Caribbean. During these four decades, it’s estimated that some 5,000 men lived as pirates.6

Toward the end of the Golden Age, we also see a shift away from piracy as just a criminal act, to one of social and political revolution. The last 15-20 years of the Golden of Piracy was marked by men who sought the life of a pirate to escape the authoritarian regimes of European empires, the social mores of their societies, or both. During this period, pirate recruits came from all walks of life: escaped slaves, men looking to leave behind a life of toil aboard fishing and trade ships, well-to-do lads looking for adventure, and even a few women seeking self-autonomy. For about 12 years, a group of pirates even founded their own republic in Nassau!

Famous Pirates That Roamed the Caribbean

What did it take to be a successful pirate? At any one time, thousands of pirates roamed the Caribbean Sea and Atlantic Ocean aboard dozens of ships. But only a few pirates made such a name for themselves that we remember them today. Let’s briefly examine the lives and careers of some of the most famous pirates to learn just what it took to become a scourge of the high seas (maties!).

Sir Henry Morgan

Portrait of Captain Henry Morgan
Portrait of Sir Henry Morgan

Henry Morgan has been called buccaneer, pirate, and even “king of the privateers.” A daring and bold leader, he was truly one of the larger-than-life figures of piracy in the Caribbean. 

Born to well-off farmers in Wales (near present day Cardiff – go Bluebirds!), it’s unclear how exactly Morgan ended up in the Caribbean. Some say he was kidnapped from Wales, while others assert he left home voluntarily as a lowly ship hand. Either way, once he made it there, history would never be the same. 

It’s believed that Morgan took part in the English capture of Jamaica from the Spanish in 1655. And, seven years later in 1662, took part in the English invasion of Cuba.7 His story gets more clear from here. By 1688, Morgan was the captain of an English privateering vessel. Now Captain Henry Morgan, he undertook some of the daring pirate attacks the Caribbean would ever see.

In 1671, Morgan led an attack on Spain’s American capital – Panama City. Panama’s Caribbean port, and one of the wealthiest cities in the world, it was the crown jewel of pirates and privateers. Having earned a reputation as an effective (and possibly ruthless) captain, the citizens of Panama feared Morgan’s approach and vacated the city before he arrived, taking their wealth with them.8 Nevertheless, Morgan’s crew razed the city.

Unfortunately for Morgan, England had just signed a peace treaty before his attack on Panama. So, to not make matters worse, the English recalled him to London where he was imprisoned. But privateers like Henry Morgan didn’t come around often and England was quickly at war again, this time with the Dutch. 

So Morgan was released, knighted, and sent back to the Caribbean to bedevil the Dutch colonies there.9

By the end of his life, Sir Henry Morgan was a wealthy man with extensive land holdings in Jamaica. Not bad for the “king of the privateers.”

Anne Bonny

Anne Bonny and Mary Read, during the Golden Age of Piracy in the Caribbean
Anne Bonny (left) and Mary Read (right)

One of the few women to become a successful pirate, Anne Bonny had a short but successful career in piracy. 

Born in Ireland as Anne Cormac, she moved to Charles Towne, South Carolina (now Charleston) with her father at age 13. When, at 20 years old, her father attempted to marry her to a man she didn’t care for, Anne ran away with, and married, a sailor named John Bonny.10 Though their marriage didn’t last long, Anne continued to use his surname for the rest of her life. 

While in the Caribbean with John Bonny, Anne met the notorious pirate John “Calico Jack” Rackham. Anne Bonny became enamored with Calico Jack and joined his crew in August 1720. Captains usually didn’t allow female pirates aboard their ships, but Anne was undeterred. One account even says that she stabbed a shipmate in the heart for making disparaging comments at her. A natural pirate!11

Soon after Anne Bonny had joined Calico Jack’s crew, another of the most infamous female pirates, Mary Read, came aboard. Though how exactly Read joined the crew is uncertain, she and Bonny became fast friends, and some even suspected them of being lovers. In battle, Read and Bonny found side by side, wearing an outfit now closely associated with the golden age of piracy: trousers, large and billow jackets, and handkerchiefs around their head. 

By October 1720, Bonny’s career as a pirate was over. When Rackam’s ship was defeated by a ship in the English Royal Navy, every crew member except for Read and Bonny were executed. Sent to prison, they were spared because they were pregnant.

Edward Teach

Picture of Edward Teach, aka Blackbeard, during the Golden Age of Piracy in the Caribbean
Edward Teach, aka Blackbeard

One of the most famous pirates of all time, is better known as Blackbeard. Born around 1680, Teach began his career as a privateer in the English Royal Navy during the War of Spanish Succession. When the war ended, Teach turned to piracy. To make this career transition he became an apprentice of sorts to Benjamin Hornigold.12

Teach Becomes Blackbeard

In 1716, Hornigold’s crew found themselves in the Caribbean island of Martinique, then controlled by the French government. It was here that Edward Teach’s transition into Blackbeard gained steam. Off of Martinque’s coast, Teach helped to capture a French slave ship named La Concorde. Hornigold put Teach in charge of the new ship, and he quickly renamed it Queen Anne’s Revenge.13

Now in possession of the pirate ship that would help make him famous, Blackbeard began his reign of terror over the American seaways. When attacked another ship, Teach placed twisted, lit coils in his long hair and beard, to make it appear as if the devil himself was their ship. It was also rumored at the time that Blackbeard tortured his victims and was cruel to his own pirate crew. Though recent research has cast doubt on that, Blackbeard used this to his advantage: it made keeping his crew in line and capturing other vessels. 

Blackbeard’s Career as Pirate Captain

After taking and rechristening the Queen Anne’s Revenge, Blackbeard toured the Caribbean. He sailed to the Grenadines and the Lesser Antilles where he took shops at St. Vincent, St. Lucia, Nevis, and Antigua. Then, he moved north and went hunting off the coast of Puerto Rico, the Dominican Republic, and Honduras. Along the way, Blackbeard would take on ships and men so that his flotilla grew to 300 men!14

Blackbeard’s most daring attack came in May 1718, when he took the Queen Anne’s Revenge and three other ships to blockade the Charleston harbor. Floating outside the city for a week, Blackbeard’s crew seized multiple ships attempting to enter the port. Eventually he received his ransom (which included medicine for his pirate crew) and left. Heading from his successful attack on Charleston, Blackbeard grounded the Queen Anne’s Revenge in a sandbar off the coast of North Carolina. 

Though he was forced to abandon his flagship, this did not deter Blackbeard. From here, he moved his practical activities to Ocracoke Inlet in North Carolina. Out of this new base, Blackbeard was able to bribe the governor, Charles Eden, to ignore this piracy. For eighteen months, Blackbeard and his crew became the scourge of the Atlantic waterways.15

The End of Blackbeard

By 1718, the English colonies had had enough. Still smarting from his humiliation at the hands of Blackbeard, North Carolina’s governor personally appealed to Virginia for help. More than happy to be rid of the feared pirate, Virginia governor Alexander Spotswood enlisted Robert Maynard to chase down Blackbeard. Spotswood even went so far as to offer a bonus for killing Teach.

A lieutenant in the Royal Navy, Maynard took to the role of pirate hunter naturally. By November of 1718, he had found the notorious pirate off the cost of Ocracoke, North Carolina. 

When Blackbeard saw the two ships under Maynard’s command he quickly fired on them, doing damage to both of them. Thinking quickly, Maynard used this to his advantage. He ordered the crew of his ship below decks to make it seem like they had abandoned it. Blackbeard, cunning though he was, fell for it. 

As Blackbeard’s men attempted to board  Maynard’s damaged ship, they were surprised by the hidden crew. Though they fought hard, the pirates were defeated by Maynard’s men. Blackbeard himself died after suffering five gunshots and 25 stab wounds.

After the battle, Blackbeard was decapitated, his head hung from the front of Maynard’s ships, and his body was thrown into the Atlantic ocean.16

A Note on Blackbeard’s Flag

Blackbeard's flag

For a long time, Blacbeard has been credited with a rather interesting jolly roger, or flag. Lure has it that he flew a black flag on which a skeleton stabbed a heart with one hand while drinking out of a chalice with the other. 

While this certainly would have been an incredible flag, it most likely is not true. In fact, this flag design did not appear in the historical record until 1912 when it was printed by Mariner’s Mirror magazine!17

So, what did Blackbeard’s flag look like? According to a newspaper from 1718: 18

“…a large Ship and Sloop with Black Flags and Deaths Heads in them and three more Sloops with Bloody Flags all bore down upon the said ship Protestant Caesar…the Ship had 40 Guns and 300 Men called the Queen Anne’s Revenge, commanded by Edward Teach…”

This means that Blackbeard’s ships most likely flew three types of flags: 

  • Black flags: This is exactly what it sounds like, a plain black flag. Though not quite as fun as the fictional flag of Blackbeard, it would have scared any sailor who saw. Black was (and is) and color associated with death and was often used by pirates.
  • Death heads: Death heads doubled down on visual allusions to death by putting white skulls or a skull and crossbones over the dreaded black flag. 
  • Bloody flags: Bloody flags were simply red flags. The insinuation was the blood would soon be spilled.

Sources on Piracy in the Caribbean

  1. Stephen Doster, “A Brief History of Piracy in the Caribbean: 1500-1730,”
  2. “Who Were the Real Pirates of the Caribbean?”
  3. “Buccaneer,”
  4. “Who Were the Real Pirates of the Caribbean?”
  5. Tim Travers, Pirates: A History, (Stroud, Glouchestershire, UK: The History Press, 2007).
  6. Ibid
  7. “Sir Henry Morgan,”
  8. Ben Johnson, “Sir Henry Morgan,”
  9. Ibid
  10. “Anne Bonny,”
  11. Karen Abbott, “If There’s a Man Among Ye: The Tale of Pirate Queens Anne Bonny and Mary Read,”
  12. “Who Were the Real Pirates of the Caribbean?”
  13. “Blackbeard: History of the Dreaded Pirate,”
  14. Ibid
  15. “Blackbeard (aka Edward Teach),”
  16. Ibid
  17. Jordan Baker, “The Terrifying Flag of Blackbeard,”
  18. “Did You Know Blackbeard’s Flag Is a Modern Design,”

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