Meet Stede Bonnet, The Rich Plantation Owner Who One Day Decided To Become A Pirate (2024)

While Stede Bonnet is featured in the comedy series "Our Flag Means Death," the 18th-century Barbadian pirate lived a much wilder life than the show portrays.

Meet Stede Bonnet, The Rich Plantation Owner Who One Day Decided To Become A Pirate (1)

Charles Johnson/Wikimedia CommonsA depiction of Stede Bonnet made less than a decade after Bonnet’s death.

The life of a gentleman was not always easy in the 18th century. Luxuries like a verdant plantation, voluminous libraries, and silk jackets lined with lace were not enough for Stede Bonnet. And in 1717, the landowning gentleman gave up everything for the life of a pirate.

But Stede Bonnet quickly learned that piracy required very different skills from those cultivated by a gentleman. Bloody battles, a failed pirate apprenticeship, and double-crossings all cut Bonnet’s career as a pirate short.

A Gentleman Becomes A Pirate

In the Golden Age of Piracy, the promise of freedom was a siren song for Stede Bonnet.

Born in 1689 in Barbados, Bonnet grew up surrounded by advantages. He became a major in the army and owned a sugar plantation. He married and had four children. Then, Bonnet walked away from his respectable life to become a pirate.

Meet Stede Bonnet, The Rich Plantation Owner Who One Day Decided To Become A Pirate (2)

Allen & Ginter/Metropolitan Museum of ArtAn 1888 depiction of the surrender of Stede Bonnet.

What caused Bonnet’s turn to piracy? At the time, contemporaries blamed “some discomforts he found in the married state,” according to Smithsonian. Others have speculated that a mid-life crisis sent Bonnet to sea.

Whatever drove him, in 1717 Bonnet borrowed a sum equivalent to $400,000 in today’s dollars. Instead of investing the money in his plantation, Bonnet purchased a ship and 10 cannons. He then hired 70 men – without telling the crew his intentions – and set off.

Once at sea, Bonnet revealed his plan. He declared the ship’s name – the Revenge – and told the crew they were pirates. Anyone who disagreed would be left behind on a deserted island.

The Struggles Of “Gentleman Pirate” Stede Bonnet

There was one problem with Stede Bonnet’s plan. He’d only ever been a passenger on a ship. With no training in navigation and no idea how to be a pirate, Bonnet quickly found himself in over his head.

Fortunately, piracy was relatively straightforward in the 1710s. A pirate ship could simply raise its flag in the vicinity of a merchant vessel, blast a warning cannon shot, and seize the ship’s cargo.

Meet Stede Bonnet, The Rich Plantation Owner Who One Day Decided To Become A Pirate (3)

Wikimedia CommonsStede Bonnet’s flag showed a skull over a single bone, flanked by a dagger and a heart.

In spite of early successes, Bonnet and his crew did not find much treasure at sea. Instead, they mainly seized cloth, raw material, and ammunition that they traded for money.

The Revenge sailed up and down the Atlantic coast – until Bonnet made a costly mistake. A few months into his pirate journey, Bonnet aimed his sights on a Spanish man-of-war. Outmanned and outgunned, Bonnet lost half his crew and sustained an injury.

Bonnet and his remaining crew limped to Nassau, a pirate haven. There, he met none other than Blackbeard, the most fearsome pirate of the Golden Age of Piracy.

Stede Bonnet And Blackbeard

Meet Stede Bonnet, The Rich Plantation Owner Who One Day Decided To Become A Pirate (4)

Unknown/Wikimedia CommonsBlackbeard in around the 1720s-1730s.

The Gentleman Pirate and Blackbeard had a complicated relationship. When Stede Bonnet arrived in Nassau in the fall of 1717, he had recently lost half his crew in an ill-fated sea battle.

It was clear to Blackbeard, the more experienced pirate, that Bonnet had no idea what he was doing. The two came to an arrangement – Blackbeard would become captain of the Revenge and Bonnet would become his apprentice.

As Blackbeard’s apprentice, Bonnet watched the pirate seize dozens of ships and blockade the city of Charleston. According to one sighting, Bonnet walked the deck of Blackbeard’s ship “in his morning gown” and devoted his days “to his books, of which he had a good library aboard.”

But the mentor soon double-crossed his loyal apprentice.

In the summer of 1718, King George promised a pardon for pirates who surrendered. Blackbeard was curious – but he wasn’t going to risk his new flotilla. So he sent Bonnet to negotiate with North Carolina’s governor.

As soon as Bonnet left, Blackbeard looted the Revenge and stranded Bonnet’s crew on a deserted island.

When Bonnet learned of Blackbeard’s treachery, he once again became captain of the Revenge and vowed to track down Blackbeard. But the clever pirate stayed one step ahead of Bonnet.

The Capture Of Stede Bonnet

Meet Stede Bonnet, The Rich Plantation Owner Who One Day Decided To Become A Pirate (5)

Howard Pyle/Wikimedia CommonsStede Bonnet aboard the Revenge during a sea battle.

Piracy was a capital crime in the 18th century. And colonial powers wanted to stamp out pirates like Stede Bonnet.

Off the coast of South Carolina, Colonel William Rhett hunted pirates with orders from the governor. And in 1718, Rhett spotted Bonnet’s ship and gave chase.

The hunt became a comedy of errors. Bonnet had hidden his ship in Cape Fear River to make hull repairs. When Rhett’s two ships approached, they both ran aground. Bonnet’s men sighted the ships, leading to a scrambled escape plan. But then Bonnet’s ship ran aground — and when Rhett’s just-freed ships approached, they once again found themselves grounded.

Trapped in the shallow waters, Bonnet’s ship blasted its cannons at Rhett’s ships, which returned fire. For an hour, both crews watched the tides, waiting to see which ship would float first. Luck was not on the Gentleman Pirate’s side – Rhett had the advantage and captured Bonnet.

Bonnet knew the penalty for piracy. But he tried to escape the noose with bribes and social currency. Surely South Carolina would not execute a gentleman by hanging. Yet a court found Bonnet and his crew guilty of piracy and murder. On Dec. 10, 1718, Bonnet and 28 crewmembers died by hanging.

Meet Stede Bonnet, The Rich Plantation Owner Who One Day Decided To Become A Pirate (6)

Unknown/Wikimedia CommonsThe hanging of Stede Bonnet, as depicted in a 1725 image.

“All his resolution failed him,” wrote Charles Johnson, of Bonnet’s final moments, “and his fears and agonies so wrought upon him, that he was scarce sensible when he came to the place of execution.”

According to reports, Bonnet carried a handful of flowers to the gallows. After his death, many mocked the Gentleman Pirate as the worst pirate in history.

But Bonnet, like many other pirates, simply had bad timing. By 1720, the golden age had ended for pirates, as states cracked down on piracy. Yet Stede Bonnet’s name would live on as the Gentleman Pirate.

Now that you’ve learned about Stede Bonnet, dive into the true story of the pirate Blackbeard. Then, learn about history’s most famous female pirates.

Meet Stede Bonnet, The Rich Plantation Owner Who One Day Decided To Become A Pirate (2024)

FAQs

Why did Stede Bonnet become a pirate? ›

Stede Bonnet had abandoned his family, status, and wealth for a life of piracy. Although Stede Bonnet came from wealth, his desire to become a pirate may have also been financially motivated. In the early 18th century, piracy could be extremely profitable to anyone willing to risk the perils of the trade.

Who was the wealthy landowner who became a pirate? ›

Stede Bonnet (1688 – 10 December 1718) was a Barbadian-born pirate and military officer, known as the Gentleman Pirate because he was a moderately wealthy landowner before turning to a life of crime.

What did Stede Bonnet change his name to? ›

Returning to Topsail Inlet, Bonnet discovered that Teach had abandoned the Revenge and marooned twenty-five of the crew on a sand bar. After a futile pursuit of Teach, Bonnet returned to pirating, changing his name to "Captain Thomas" and that of his ship to the Royal James.

Why did Blackbeard betray Stede Bonnet? ›

Blackbeard saw how inexperienced Bonnet was and kept this in mind when he and Bonnet later met a second time. He decided to send his first mate over to the Revenge to captain the ship, while he kept Bonnet on the Queen Anne's Revenge effectively as his prisoner.

What makes a pirate a pirate? ›

A pirate is a robber who travels by water. Though most pirates targeted ships, some also launched attacks on coastal towns. We often think of pirates as swashbuckling and daring or evil and brutish, but in actual fact most of them were ordinary people who had been forced to turn to criminal activity to make ends meet.

Who was the first pirate in One Piece? ›

Pirates have been present in the world for at least 900 years; with the first known pirate being a figure known as Joy Boy.

Who is the richest pirate ever? ›

23 February 1689 – 26 April 1717), later known as "Black Sam" Bellamy, was an English sailor turned pirate during the early 18th century. He is best known as the wealthiest pirate in recorded history, and one of the faces of the Golden Age of Piracy.

Did pirates ever get rich? ›

Samuel “Black Sam” Bellamy (1689-1717)

Forbes magazine rated him as the highest-earning pirate of all-time, having helped himself to bounty worth an astonishing $120 million in today's money. What's even more remarkable is that he did this in a career as a pirate captain that lasted less than one year.

Who was the most feared pirate? ›

Blackbeard or Edward Teach (c. 1680-1718) is one of the most infamous pirates to have ever lived. Known for his fearsome image and daring acts on land and sea throughout the West Indies and along the North American East coast, his legacy has been the inspiration for many depictions of pirates throughout history.

How long was Stede gone? ›

Finally convicted of piracy, Stede Bonnet was hanged on December 10, 1718, after less than two years of adventure on the high seas. Bonnet's execution came a month after Blackbeard had met his own bloody end in battle with the British Royal Navy. By the 1720s, the golden age of piracy was over.

How much money did Stede Bonnet make? ›

Samuel Bellamy's treasure sank with him off Cape Cod, most of Bartholomew Roberts' fortune ($32 million) was taken after he died in battle in 1722 and Stede Bonnet's wealth ($4.4 million) was absorbed into the South Carolina treasury after his 1718 execution.

What was Blackbeard's real flag? ›

The design of the flag consisted of a horned skeleton raising an hourglass "toasting the Devil" in its right hand. In the skeleton's left hand, it held a spear pointing towards a red heart which had three drops of red blood below it, supposedly to signal that no quarter would be given. The historian E. T.

Why did Stede Bonnet get hanged? ›

Brought to trial on 10 November 1718, he was found guilty of piracy and sentenced to death by hanging. While in custody, Bonnet did all he could to avoid execution. He feverishly wrote letters to the judge, the governor and to Rhett himself asking for mercy.

What did Blackbeard keep under his hat? ›

He was reported to have tied lit fuses (slow matches) under his hat to frighten his enemies. He formed an alliance of pirates and blockaded the port of Charles Town, South Carolina, ransoming the port's inhabitants.

Who was the first pirate? ›

The earliest documented instances of piracy are the exploits of the Sea Peoples who threatened the ships sailing in the Aegean and Mediterranean waters in the 14th century BC. In classical antiquity, the Phoenicians, Illyrians and Tyrrhenians were known as pirates.

Did Brianna have feelings for Bonnet? ›

Well, at least until Bonnet wants to seal their agreement with a kiss, at which point he realizes Brianna has no real feelings for him. Unfortunately, he reacts in the worst way possible: by forcing Brianna to watch him have sex with a prostitute, and then selling Bree to a business associate for six pounds.

What happened to Stede Bonnet's black flag? ›

Captain Bonnet was known as the 'Gentleman Pirate' since he was a former plantation owner before he turned to piracy. He was hanged in South Carolina in 1718. Image from the computer game Assassin's Creed IV: Black Flag by Ubisoft.

What caused the golden age of piracy? ›

Factors contributing to piracy during the Golden Age included the rise in quantities of valuable cargoes being shipped to Europe over vast ocean areas, reduced European navies in certain regions, the training and experience that many sailors had gained in European navies (particularly the British Royal Navy), and ...

Why did Stede Bonnet leave ED? ›

Stede was very disappointed when Anne revealed this at the dinner table in front of Edward, who was greatly hurt to learn that the reason Stede had left him was to return to his wife.

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