Charming Facts About Stede Bonnet, The Gentleman Pirate

August 6, 2023 | Edward Sakowsky

Charming Facts About Stede Bonnet, The Gentleman Pirate

The story of Stede Bonnet is an odd one. Born into luxury, it seemed as if his life would have taken the course of an ordinary gentleman—but it became nothing of the sort. He shocked everyone with his strange decision to give up his privileged life and seek adventure on the high seas. Read on to discover the singular tale of Stede Bonnet, the Gentleman Pirate.

1. He Was Born Into Luxury

Stede Bonnet came into the world in 1688. He was born into an immensely wealthy family of colonists in Barbados, who owned at least 400 acres of land. If that wasn't enough, his father, Edward Bonnet, also presided over a large sugar plantation. Life should have been relatively easy for a member of the Barbados elite—but misfortune arrived at the doorstep of the Bonnet family somewhat unexpectedly.

stede bonnet

2. He Experienced Tragedy At A Young Age

In 1694, when Stede should have been experiencing the simple joys of childhood, tragedy tore his world apart. Both of his parents passed on at a young age, abruptly turning him into an orphan. On top of it all, he had two sisters who were now also orphans—but what about his family fortune?

Stede Bonnet facts Wikipedia

3. He Inherited A Massive Fortune

Fortune may have deprived young Stede of his family—but it did hand him riches beyond many of our wildest dreams. As soon as he was old enough, he inherited the sugar plantation that his parents had left behind. With his money, he chose to attend university, and acquired all the trappings of a young gentleman…but something was missing.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

4. A Rich Girl Intrigued Him

They often say that opposites attract, although some likeness usually helps. Sometime around 1709, Stede, now in his early 20s, met Mary Allamby, who was around two years his junior. She stemmed from the same ilk as Stede. Her father, just like Stede's, owned a plantation. The two must have clicked, because that same year, they decided to take their relationship even further.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

5. They Married Young

The young lovers soon tied the knot and Mary Allamby soon became Marry Bonnet. They made their home in Stede's hometown of Bridgetown, where their household quickly grew. They had four children to keep them company: three boys and a single girl. Finally, Stede had the family that he’d missed as a young boy—but his domestic bliss didn’t last for long.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

6. His Family Suffered A Cruel Loss

Stede had finally found happiness—only for it to be horrifically shattered before his eyes. His young son Allamby Bonnet perished suddenly. The Bonnet family was devastated—and as time would tell, Stede would never again be the same.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

7. He Had A Tremendous Midlife Crisis

On the surface, it seemed like Stede Bonnet had it all. He’d considerably advanced his foothold in social circles when he was granted the position of Major in the militia, as well as a justice of the peace in 1716. His affairs seemed to be going extraordinarily well, but something bubbled underneath.

Some say that married life bored Stede, while others suggest that the emotional turmoil of his so far short life, like having been orphaned and enduring the loss of his son, threw him into a midlife crisis. Either way, the next thing he did was a shock to everyone.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

8. He Vanished Overnight

On one quiet night in 1717, Stede Bonnet suddenly vanished. He left his wife and three surviving children behind. Where did he go? It might sound absurd, but Stede decided to become a pirate. At night, under cover of darkness, Stede Bonnet sailed away in a rather unusual ship he had just purchased.

Stede Bonnet facts Wikimedia Commons

9. He Gave His Ship An Enigmatic Name

Pirates usually give their ships simple names. A name like The Royal Fortune explains itself pretty well. Stede’s choice of name was particularly sinister. He called his flagship The Revenge. Whose revenge and for what? Who exactly wronged the rich gentleman from Barbados?

The cryptic name wasn’t the only aspect of his “career shift” that drew attention.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

10. He Had Unusual Habits

The spoils of plunder may have replaced stable wages for the early modern buccaneer, but on The Revenge, things were different. Bonnet paid his pirates a steady rate. All 70 of them. They had more job security than many people can claim today—and that wasn’t the only odd thing about Stede’s ship.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

11. They Gave Him A Nickname

When a pirate captain runs their ship like a legally bound corporation, or a rich estate, it’s no surprise that he receives the nickname of The Gentleman Pirate. Apparently, Stede even outfitted his own quarters with a library, so that he could read his favorite books whenever he pleased. Of course, not everyone was thrilled with the way Stede lived his life.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

12. His Crew Despised Him

Mark Twain once said that the main difference between a man and a dog is that the latter will not bite you if you take care of him. Stede learned that lesson the hard way. Despite paying his crew steady wages, they did not respect him. Perhaps his crew were wary of his background, and how different he was from them.

Despite their lack of reverence for their captain, he wouldn’t allow anyone to prevent him from pursuing his dreams, so he continued, regardless of how dismissive his crew may have been.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

13. He Set Sail For North America

Any place with seafaring vessels is a perfect spot for a pirate, but Stede had his eyes set on North America. Why? The further from Barbados, the better. He sailed to the coast of Virginia and plundered his first four vessels. His crew probably wanted to take everything valuable they could get their hands on. However, Stede captured these ships for only one peculiar reason.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

14. He Plundered Vessels For A Strange Reason

Tales of pirates waging violent battles at sea for spoils are not a far cry from the truth—except in Stede's case. The gentleman pirate didn't care about valuable trinkets or gold, and instead took only provisions or other necessities to maintain his seafaring life as a pirate. In other words, clothes, food, ammo, and so on. No wonder why his crew disliked him.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

15. He Had A Mysterious Habit

Although appropriately nicknamed the gentleman pirate, Stede Bonnet had a brutal dark side. After capturing and plundering vessels, he often set them free. Unless, of course, they hailed from Barbados. When Stede and his crew overtook a sloop from Barbados in 1717, he tore it apart. He used some of its parts to repair The Revenge, and then set it on fire.

Unfortunately for Stede, not every mission was as successful—and one nearly put his days of being a pirate to an end.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

16. An Unfortunate Occurrence Met Him At Sea

It's easy to rule the seas when you only encounter merchant vessels. Up until September 1717, Stede only plundered smaller ships, mostly ones that transported provisions. But that month, The Revenge had a rude awakening. Stede and his men encountered a gigantic Spanish frigate, and he made a grave mistake. For the first time in his swashbuckling career, he went up against a Man-of-war. Could the amateur pirate take on a vessel built solely for battle?

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

17. He Faced A Crushing Defeat

Everything came crashing down in the autumn of 1717. The Spanish warship all but demolished The Revenge, whose crew nearly perished in the onslaught. Even Stede was wounded during the battle, but he luckily managed to escape with his life, as well as with the remains of his crew and boat. He quickly scurried to his destination at Nassau.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

18. He Escaped To A Pirate Haven

The Caribbean of the 18th century has been endlessly mythologized in film and books, but it really did provide a sanctuary to pirates. After his humiliating defeat, Stede hid away in the sequestered pirate den, slowly recovering. In his spot, many would pack up their bags and return home to a comfortable life of luxury—but not Stede. He must have had no regrets—because he soon showed determination to get vengeance for his defeat.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

19. He Recovered From His Failure And Returned Stronger

Success normally only comes after hard work and often failure. Stede must have known that as well, because, instead of wallowing in his mistakes, he began repairing his ship, enlisting new crewmates, and increasing The Revenge's cannons. The gentleman pirate who at first avoided naval combat for as long as he could, now prepared for it. A pleasant surprise also awaited him.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

20. He Met A Legendary Pirate

A lawless haven should be a great place to find other pirates, but little did Stede know that he would encounter such a legendary one. Stede ran into none other than Edward Teach, also known as Blackbeard. The two struck up an unusual deal. Stede gave up his position of captain to Blackbeard, who took command of The Revenge.

The still-wounded Stede probably wanted someone to shoulder his burden his ship while he recovered, and he couldn't have found a more capable captain.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

21. He Became His Disciple

The ancient Greek philosophers thought that the best way to learn something was to watch a professional. Stede had exactly that opportunity now. In fact, he could now witness the most notorious pirate of his time at his work. For Stede, such an experience must have been of inestimable worth, even if it meant temporarily relinquishing his command. However, it began to appear as if his subsidiary role may not have been temporary.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

22. He Had His Command Usurped

What started as a friendly business arrangement soon took a nasty turn. In early October 1717, a captain whose ship was captured by Blackbeard recalled that Stede seemed to be walking around his ship as if in a stupor. He walked around deck in a sickened state, in his bedclothes. It was if only an observer on his own ship, without any power. Hopefully Stede at least enjoyed the sights.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

23. Together They Successfully Plundered Eleven Ships

Stede Bonnet may have been temporarily without power, but if one positive thing can be said about his experience, it's that he was certainly witnessing a master at work. Throughout the season, Stede observed Blackbeard capture and plunder at least 11 ships around Delaware bay. They even captured a ship full of booze. One vessel that they encountered, however, tops them all.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

24. They Captured A Titanic Vessel

Blackbeard must have grown tired of North America, because he soon steered Stede’s ship into the warm waters of the Caribbean. Warm weather wasn't the only thing that greeted his crew on their return. A titanic, 200-tonne ship named Concorde stood within their path. Familiar with harrowing exploits, Blackbeard ordered The Revenge to bombard the vessel with a few volleys, to which it then surrendered. The massive Concorde now belonged to Blackbeard.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

25. They Celebrated Their Conquest By Partying

A grand feat must always be followed by an equally grand celebration, and pirates are no strangers to carousing. Once Blackbeard and Stede Bonnet captured the Concorde, they discovered a golden treasure on board. This called for a celebration: the crew of The Revenge dined luxuriously. French food was served on silver plates, and they drank and even listened to music—but the victory ran so much deeper than that.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

26. He Resumed Command Again

Having taken a passenger seat for so long, Stede had nearly forgotten what it felt like to be a captain. Now that Blackbeard commandeered a far superior ship, he no longer needed The Revenge, so he generously returned it to his friend. But their story wasn’t over yet. Together, they wreaked havoc across the Caribbean, and plundered a vessel full of sugar.

They were a force to be reckoned with.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

27. They Separated

The easy victories of Blackbeard and Stede Bonnet must have instilled the latter with false confidence. Sometime in the winter of 1717 or early 1718, the friends temporarily separated. In the early spring of 1718, Stede encountered a massive merchant vessel called Protestant Caesar, which weighed around 400 tonnes. Possibly eager to test the skills he had learned from Blackbeard, and maybe even best his friend, Stede readied to attack the vessel.

Protestant Caesar was to be his Concorde, and now he only had to prove it.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

28. He Suffered A Humiliating Defeat

Stede had suffered a humiliating defeat before, but he would not let that faze his current goal. He took on the Protestant Caesar off the coast of Honduras—but things didn't go as planned. Some accounts insist that the merchant vessel quickly escaped from The Revenge, while others describe The Revenge as having been defeated by it.

One thing is for certain, the crew of The Revenge was disgusted by such a poor command. Something had to be done.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

29. His Crew Conspired Against Him

In April 1718, the mutinous atmosphere of The Revenge reached a fever pitch. Stede anchored in the bay off Honduras, possibly in the hopes of quelling his rebellious crewmates. By some coincidence, Blackbeard had also anchored in the bay, not far from The Revenge. When Stede and his crew went onboard to greet his friend, it all began to fall into place.

His crew pleaded with Blackbeard to do something for them.

Stede Bonnet facts Our Flag Means Death (2022-), HBO Max

30. His Friends Betrayed Him

The romantic illusion of piracy would soon vanish for Stede—and he faced a truly devastating betrayal. Blackbeard sided with Stede’s crewmates, and he removed from command. He did it with subtlety, convincing Stede to come aboard Queen Anne's Revenge, which housed much more comfortable quarters.

Blackbeard then appointed one of Stede's underlings to command The Revenge. After such a short stint as a captain, Stede returned to being merely a spectator of piracy.

Blackbeard factsPirates of the Caribbean: On Stranger Tides (2011), Walt Disney Pictures

31. He Regretted Piracy

The illusion continued unraveling. Stede Bonnet began to see things how they really were. He only had a few friends left, but to them he poured out his heart. He revealed to them how he regretted his life as a pirate, and said he considered changing his ways. If he could make his way to Spain or Portugal, he might give up criminality altogether.

For now, though, those thoughts would have to be put on hold, for an old enemy stood in his way.

Stede Bonnet factsOur Flag Means Death (2022-), HBO Max

32. He Encountered An Old Foe

People don't always get a second chance on some things, but one now presented itself to Stede. In the bay of Honduras, not far from Stede and Blackbeard, lay the Protestant Caesar. Not even a week had gone by since Stede's defeat. Spotting their foe, Blackbeard reportedly claimed that he wanted to ensure that no one would brag about 'beat[ing] a pirate', especially one of their own.

Blackbeard factsBlack Sails (2014–2017), Starz!

33. He Had His Revenge

Stede's friend Blackbeard hadn't lost any time in strengthening his fleet, which now numbered five vessels. The fleet approached the Protestant Caesar while hoisting blood red and black flags. But they were in for a big surprise. Fearing for their life, the merchant ship immediately surrendered. The pirates ejected the crew and set the Protestant Caesar aflame. The Revenge finally had its revenge.

Blackbeard factsBlack Sails (2014–2017), Starz!

34. He Was Stranded

Just like any other vehicle, boats require proper maintenance, especially large vessels like the Queen Anne's Revenge. Heading north towards North Carolina, Stede and Blackbeard wanted to repair their ship, so they looked for an appropriate spot to dock it. They had their eyes on Topsail Island, a barrier island next to North Carolina's coast.

Unfortunately, they lost control of their ship and went a little too close to the shore. Queen Anne's Revenge went aground. The pirates were in trouble, and it seemed as if they had nowhere to go.

Blackbeard factsWikipedia

35. He Asked For A Pardon From The King

Asking the authorities for help is the last thing a pirate wants to do. In this case, unfortunately, it was the only remaining option. Stede, following Blackbeard, went to the capital of North Carolina, and capitalized on a recent law King George I had created. The law, colloquially known as the Acts of Grace, allowed pirates to be pardoned if they turned themselves in.

Stede and Blackbeard did so, and so the governor of Bath pardoned them. That is, so long as he renounced being a pirate forever.

George II factsWikipedia

36. He Received Clearance To Become A Privateer

What the governor didn’t know was that Stede had come up with a plan. He may have sworn that he would never return to swashbuckling, but he instead found a loophole to continue doing what he loved. He planned on becoming a privateer, which is a fancy word for a pirate who follows the law. A privateer, in this case, meant a person and or vessel that only plundered ships that were in conflict with the British Crown. That is, Spanish ships. The governor greenlighted Stede—and his profession as a privateer began.

Stede Bonnet factsOur Flag Means Death (2022-), HBO Max

37. His Friend Left Him An Awful Surprise

If Stede's story had a title, it might be called “A Series of Unfortunate Betrayals”. Upon returning to Topsail Island, Stede could not find Blackheard anywhere. Instead, he found his former crew, now marooned, and his former vessel robbed. Most of his provisions had also disappeared. Not only that, but Stede had to rescue his crew, who Blackbeard left to die, from different parts of the island—and that was just the start of his ordeal.

Stede Bonnet factsOur Flag Means Death (2022-), HBO Max

38. He Wanted Revenge

Stede may have been nicknamed the gentleman pirate, but being double-crossed for the second time was the final nail in the coffin. He quickly set sail to chase after his old friend, and even discovered promising information about his whereabouts. Blackbeard was hiding away in Ocracoke Inlet, an estuary in Northern Carolina.

Unfortunately for Stede, his crafty friend easily eluded him. Stede never found his treacherous friend again.

Blackbeard factsBlack Sails (2014–2017), Starz!

39. He Returned To Piracy

Desperate times sometimes call for desperate measures. Stede had sworn that he would never again return to piracy, but one major issue troubled him. He lacked basic necessities. Blackbeard, after all, had taken most of his supplies. Stede, however, thought of a plan. He changed the name of his ship from The Revenge to the Royal James, which referred to the royal James Stuart, and he also referred to himself from now on as Captain James.

Perhaps he thought that might give others the idea that he was no longer a pirate—but he went even further in concealing his return to piracy.

Stede Bonnet factsOur Flag Means Death (2022-), HBO Max

40. He Tried To Conceal His Offenses

If you blatantly rob ships, then it's difficult to argue that you're not a pirate—but Stede came up with a clever way to elude attention. And on the next two ships he robbed, he tested his idea. When he boarded them, instead of obviously plundering them, he acted as if he were trading instead of robbing his victims.

Stede must not have been as charming as he thought he was, because it didn’t really work well—and he decided to go back to his old ways.

Stede Bonnet factsOur Flag Means Death (2022-), HBO Max

41. He Broke His Pact

The whole charade eventually vanished. In the summer of 1718, Stede returned to piracy with a vengeance. In July alone, he took on and plundered at least eleven ships. Two of these vessels became a part of his fleet, which now totaled three. Stede also did something that he had never done before—he took spoils and gave them to his crew.

He no longer paid his crew simple wages. Stede Bonnet finally became a true pirate in every respect.

Stede Bonnet factsOur Flag Means Death (2022-), HBO Max

42. He Hid In Cape Fear For Months

A crooked life on the high seas isn't easy. Not only do you have to hide away from the authorities, but you also have to take refuge from hurricanes. Stede found a comfy estuary in the Cape Fear River and decided to hide there for the season. His badly damaged ship also needed repairs, so he took the opportunity to fix his vessel.

Little did he know, news of his presence circulated among the authorities.

Stede Bonnet factsOur Flag Means Death (2022-), HBO Max

43. He Made The Biggest Mistake Of His Life

Stede Bonnet was in for a seriously unpleasant surprise. In early September of 1718, two merchant sloops entered the Cape Fear River, and Stede sent his men to capture them. The vessels, however, actually belonged to the British Navy, commanded by William Rhett, a colonel tasked with capturing Stede by any means necessary.

The colonel had at least 130 troopers on board, and two vessels with eight cannons, but they did not realize that Stede spotted them. He decided that he would fight them in the morning.

Stede Bonnet factsWikipedia

44. He Fought Valiantly

The most important day of Stede's life took place on September 27, 1718. Stede literally began the fight with a blast. His fleet of three vessels fired at Colonel Rhett's ships. Even after having the jump on the British forces, they were easily outmaneuvered. The British ships pincered the Royal James, which crashed onto the shore. Continuing their pursuit, the British ships also crashed onto shore. They all sat and waited in their positions for the next few hours, stuck in a brutal stalemate.

Stede Bonnet factsBlack Sails (2014-2017), Starz

45. And Eventually Lost

The nerves of Stede's forces must have been palpable, because so much depended on the outcome of the next few hours. Unfortunately for Stede, it seems as if nature itself conspired against him. The stalemate ended when the tide rose high enough to free Colonel Rhett's ship, to which he then surrounded Stede's vessel. Determined to not surrender, Stede’s next move was as disturbing as it was desperate.

He ordered his crew to detonate their remaining ammo, which would have blown his ship to bits, along with every soul in it. Unsurprisingly, they refused, and the fight ended with his capture.

Stede Bonnet factsOur Flag Means Death (2022-), HBO Max

46. His Escape From Prison Was Legendary

It all sounds like a Hollywood blockbuster. Only three weeks after his capture, on October 24th, Stede Bonnet somehow managed to escape from prison by disguising himself in a woman's dress. His sailing master, David Harriet, also escaped with him, as well as an Indigenous man and a slave. Some speculate that a merchant by the name of Richard Tookerman assisted them in their getaway.

Stede Bonnet factsOur Flag Means Death (2022-), HBO Max

47. He Nearly Escaped From His Pursuers

The escape almost went perfectly. Key word: almost. After eluding the authorities, Stede and his companions managed to secure a boat. Unfortunately, and yet again, he had the worst of luck when it came to the weather. Awful winds prevented Stede from considerably distancing himself from his pursuers.

His pursuers finally caught up to him, firing upon his companions, ending David Harriet, and forcing him to reluctantly surrender. Once again, he found himself in prison.

Stede Bonnet factsOur Flag Means Death (2022-), HBO Max

48. He Lost His Mind

The ending of Stede’s story is unfortunately a brutal one. He fell into a pitiful state, prompting many Charlestonians to beg for his release, but to no avail. Stede begged the authorities to release him, writing them letters. He pleaded to his enemy, Colonel William Rhett, to help get him out, but nothing came of that either. In perhaps the most telling—and also twisted—letter, Stede clearly showed that he’d lost his mind.

What did he write? He agreed to having all of his limbs dismembered from his body, as long as he might live.

Stede Bonnet factsOur Flag Means Death (2022-), HBO Max

49. He Was Executed At A Young Age

Stede’s requests went unheeded. Despite the population of Charleston pitying the former pirate, and calling for his release, the governor remained unmoved. He apparently delayed the execution a few times due to Stede’s mental state, but eventually carried it through. On December 10, 1718, in a lush, green public park, Stede Bonnet took his final breath after an executioner hung him. He was only 30.

Stede Bonnet factsOur Flag Means Death (2022-), HBO Max

50. His Legacy Lives On

During his life, Stede Bonnet may have been mostly known as the companion of Blackbeard– a subsidiary set piece and or observer to the actions of a legendary pirate, but he also made his own legacy. His battle with Colonel Rhett immortalized his name for posterity. After his passing, the estuary he fought in received a new name to commemorate his monumental last stand. They called it Bonnet's Creek.

Stede Bonnet factsOur Flag Means Death (2022-), HBO Max

Sources:  1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12

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