The Fascinating Tale of Stede Bonnet: The Gentleman Pirate

Can a gentleman be a pirate? There was one man who went against these seemingly opposite stereotypes and became both: Stede Bonnet. 

Born a gentleman, he turned to piracy in his later years. Bonnet was born to moderately wealthy English landowners in Barbados in 1688. He was educated like most English scions and was even described as bookish. 

So, what drove him to piracy?

Stede Bonnet, Surrender of Bonnet, from the Pirates of the Spanish Main series, 1888

Bonnet the Gentleman

Bonnet had a comfortable life. He was born on July 29, 1688, to Edward and Sarah Bonnet.

His family had a 400-acre sugar plantation in Barbados. His father died when he was just 12. He lost his mother at a young age too, although there were no accounts of the year when she passed. Although Bonnet and his siblings were orphans, they were well taken care of. 

The Bonnet guardians ensured the children were well educated. Some people who knew Bonnet even described him as bookish. 

He was a gentleman in the sense that he came from a landed gentry. 

As an adult, he joined the militia and earned the rank of Major. He then got married to Mary Allamby on November 21, 1709. They had four children — three sons, named Allamby (who died in 1715), Edward, Stede Jr., and daughter Mary. 

But the surviving children were not even five years old when Bonnet left and turned to a life of piracy.

Bonnet the Pirate

Bonnet became a pirate during the Golden Age of Piracy which was from 1650 to 1720. During this time, over 5,000 pirates were reportedly at sea. They would rob merchants on the water who were transporting goods or target ships that had wealthy passengers. 

Some of the most notorious pirates advertised their “brand” through their flags. The most common sign is the Jolly Roger. This is the iconic image of a skull and crossbones on a black flag. It became the most popular flag of the worst pirates. To this day, the Jolly Roger’s flag is used in pop culture to denote piracy. 

The most terrifying pirates would take over ships and make passengers “walk the plank.” People would be blindfolded and ordered to walk on the edge of the ship to their deaths. Some pirates simply threw people overboard. 

But why did people become pirates? It all boiled down to money. 

In England, many people were driven out of their homes because of greedy landowners. They had to flee to London where overpopulation was a problem and there weren’t enough jobs for all the internal migrants. Piracy was a “safe” option for young strapping lads. 

Escaped slaves had similar experiences. Slavery was still legal at the time. To escape a life of servitude, many Africans escaped and became pirates. 

Historian Colin Woodard’s words described the growth of piracy in the Smithsonian Magazine, “Ordinary people were upset about the growing gap between rich and poor, and the growing authoritarian power of the British empire.”

Most people who chose a life of piracy did so out of poverty or slavery but Bonnet was neither poor nor enslaved.

The Exception to the Rule

Did Bonnet just want a life of adventure? According to some accounts, Bonnet simply wanted to escape his wife’s nagging. 

Blackbeard, Captain Kidd, and Calico Jack were all fearsome pirates. But Bonnet was pitied according to Charles Johnson’s book, A General History of the Pyrates. Some people thought Bonnet lost his mind. 

Part of Johnson’s book reads:

It was very surprizing to everyone, to hear of the Major’s Enterprize, in the island where he liv’d; and as he was generally esteem’d and honoured, before he broke out into open Acts of Pyracy, fo he was afterwards rather pitty’d than condemned, by those that were acquainted with him, believing that this Humour of going a pyrating, proceeded from a Disorder in his Mind.

Johnson, A General History of the Pyrates

Johnson also noted that it appeared as though Bonnet experienced some discomfort in his marital life but there were no specific explanations given. 

In the same Smithsonian Magazine article about Bonnet, another historian, David Moore, echoed Johnson’s observation of mental illness. He said, “There have been a number of theories that it was something mental.”

“Bonnet may have been unbalanced,” Woodard agreed. “From the genealogical record, we know there had been disruptions in his life. One of his children had died.”

Another theory speculated that it was politically motivated. Though unsure about the hypothesis, Woodard offered that Bonnet may have been a Jacobite, a political movement in support of James Stuart as King of England rather than the monarch at the time, King George I who was born in England. 

Since he had the money, Bonnet easily commissioned a sloop or a ship with one mast. The move was quite unusual since most pirates commandeered vessels that they decided to plunder. But Bonnet was an exception to the rule and had the money for it. 

He named his ship Revenge. He hired 70 men, bought 10 guns, and sailed to the Capes of Virginia in 1717. The Revenge successfully plundered many ships during its maiden voyage.

Early Pirate Life

Because of his inexperience, Bonnet had to acquiesce many decisions to some of his crew members. But even more bizarre was the fact that crew members were paid wages rather than just shares of the loot. Clearly, money was not an issue for Bonnet. 

The Revenge sailed to New York and the Carolinas where they plundered more ships, kidnapped passengers, and burned whatever was left of the looted boats. Captives were usually released on another island. 

Among Bonnet’s first troubles at sea was en route to Nassau, the capital of Bahamas and a famous pirate den. The Revenge encountered a Spanish warship. Ill-equipped for the battle against a fully armed man-of-war, the Revenge was badly damaged, Bonnet heavily wounded, and half the crew was either dead or injured. 

When the Revenge reached Nassau, Bonnet, with his unlimited funds and looted treasures, simply retrofitted his ship and hired more crew members. The Revenge now had 12 guns.

Meeting Blackbeard

Blackbeard is probably the most famous pirate in history. Born Edward Teach or Thatch, Blackbeard was an English pirate who settled on New Providence Island in the Bahamas. Little is known about his early life. But he was a notorious pirate who terrorized most of the West Indies and the eastern coast of Britain’s colonies in the Americas. 

Blackbeard was in cahoots with another notable English pirate, Captain Benjamin Hornigold. But in the middle of 1717, Hornigold retired from piracy and took some vessels with him. 

It was a timely abandonment as it was when Blackbeard met a wounded Bonnet. Blackbeard needed a sloop to captain and Bonnet needed help. Aside from being wounded, Bonnet was still inexperienced. The gentleman pirate allowed Blackbeard to take command of the Revenge but stayed onboard. It was Bonnet’s chance to learn from an experienced pirate. 

Since history books don’t have first-hand accounts of the relationship between Blackbeard and Bonnet, there is some debate on whether it had been a friendship or a kidnapping. The comedy series, Our Flag Means Death, also puts a romantic spin on the relationship. 

While it’s hard to confirm their real connection, it’s worth noting that the notorious Blackbeard could have easily tossed Bonnet into the sea if it had been an antagonistic relationship. 

The Revenge, through the captaincy of Blackbeard and with Bonnet as a guest, plundered as many as 11 ships in the span of a few months. In one of their exploits, they seized a 200-ton ship named Concorde. Blackbeard took control of the seized ship and renamed it Queen Anne’s Revenge which was supposedly meant as an insult to King George I. 

Toward the end of 1717, Bonnet and Blackbeard parted ways and Bonnet regained command of the Revenge

On his own, Bonnet finally earned a fearsome reputation. He started killing prisoners and threatening civilians while abusing his crew. In other words, Bonnet had finally become a real pirate, thanks in part to Blackbeard’s tutelage.

Blackbeard the Pirate, circa 1724

The End of Piracy for Bonnet?

As Bonnet gained a notorious reputation, he became a target of the authorities. 

Despite his growing reputation, his inexperience was still apparent to the more veteran crew members. Case in point: In March 1718, the Revenge encountered a 400-ton merchant vessel off Honduras known as Protestant Caesar. It was ripe for the picking but the ship escaped which frustrated Bonnet’s crew. 

The lack of prospects made the crew restless. So, when the Revenge met Blackbeard’s Queen Anne’s Revenge again, the crew jumped ship — literally and figuratively. 

Bonnet was surprised by the betrayal and was left with no choice but to give up control of his ship to Blackbeard. The skilled pirate sent his associate, Richard, to captain the Revenge. Bonnet stayed on Queen Anne’s Revenge, but whether as a captive or guest, nobody can confirm. 

Discouraged, Bonnet told some of his loyal crew mates that he was ready to give up a life of piracy. He wanted to instead live in exile on the Iberian Peninsula. 

The Revenge and Queen Anne’s Revenge had a successful few months at sea. But in the spring of 1718, Queen Anne’s Revenge ran aground and got lost en route to Topsail Island. Without a boat, Blackbeard and Bonnet traveled to Bath, North Carolina where they were arrested. 

In the name of King George, Governor Charles Eden pardoned the two but on the condition that they abandon the pirate’s life. Bonnet thus requested that he be allowed to become a privateer against Spain on St. Thomas Island and got his wish.

But Bonnet wasn’t done with piracy.

Back on the Revenge

When Bonnet returned to Topsail Island, he learned that Blackbeard robbed the Revenge and left the crew on land. 

Bonnet went back to a life of piracy by refitting his ship, taking on his original crew, and rescuing some of the crew members that Blackbeard abandoned. Bonnet also sought news about Blackbeard as he planned to make him pay for looting the Revenge. But the two never met again. 

Privateering was still at the back of Bonnet’s mind. So, as a pirate, he used the alias, Captain Thomas. His boat also took on the alias Royal James. Bonnet aka Captain James had a successful run on the Royal James. They looted several ships and captained a few of them. 

When the ship started to leak, Bonnet anchored it in a small waterway that’s now known as Bonnet’s Creek near Cape Fear River. Royal James and its crew stayed there for more than a month. 

Authorities heard of the mooring of Royal James. In August 1718, South Carolina Governor Robert Johnson ordered Colonel Willaim Rhett to arrest the pirates at Cape Fear River which was technically under North Carolina’s jurisdiction. 

Rhett and his crew confronted Bonnet and his men in what is now known as the Battle of Cape Fear River. Bonnet’s crew was outnumbered but they fought valiantly. After hours of fighting, Bonnet and his crew surrendered. Bonnet wanted to blow up the Royal James and die fighting but he was overruled by his men. 

That was the end of Bonnet’s life as a pirate.

The Death of the Gentleman Pirate

There was still a bit of fight left in Bonnet in jail. He took advantage of his gentlemanly background and blamed everything on Blackbeard. 

Bonnet’s men were hanged one by one as Bonnet’s trial dragged on. The historian Moore described the trial’s transcript as “one of the most valuable historical records we have about Bonnet and Blackbeard.”

Months after his arrest, Bonnet was finally convicted of piracy. He was hanged on December 10, 1718. This was less than two years after he gave up his gentlemanly life to become a pirate.


Most men dream of having a gentleman’s life. Many pirates, during the Golden Age of Piracy, probably wanted to become wealthy landowners too. Stede Bonnet seemed to have it all — acres of land and a family. But he gave it all up for the dangerous life of a pirate. 

There are only a few historical accounts of Stede Bonnet or any pirate for that matter. But the recorded stories about Bonnet’s short stint have more adventures than an average person’s life. He was certainly extraordinary in the sense that he lived two very different lives — that of a gentleman and a pirate.

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