Excerpt from HistoryExtra article, “Stede Bonnet, Gentleman Pirate: how a mid-life crisis created the ‘worst pirate of all time’” available here.
History has not been particularly kind to Bonnet. Many know him as ‘the worst pirate of all time’ and portions of Bonnet’s story are, admittedly, so absurd they are best suited for comedy.
Nonetheless, Bonnet sailed with some of the most fearsome men of the times, fearlessly (or more appropriately, ignorantly) taking on larger vessels with significant courage. Whether Bonnet fulfilled the yearnings that caused his midlife crisis, we’ll never know.
For the full Stede Bonnet story, The Life and Tryals of the Gentleman Pirate, Major Stede Bonnet is available on Amazon and through all major booksellers.
Excerpt from HistoryExtra article, “Stede Bonnet, Gentleman Pirate: how a mid-life crisis created the ‘worst pirate of all time’” available here.
After receiving his certificate of pardon, Bonnet was absolved of his piratical crimes and looked, at least temporarily, for legal means of continuing his adventure. England, allied with France and the Netherlands, was now at war with Spain, and Bonnet saw the opportunity to secure a letter of marque permitting him and the crew of the Revenge to go privateering against the Spaniards – if only he could reach the Danish-controlled island of St Thomas to acquire it.
It was not to be: Bonnet lapsed into a piratical career, adopting the alias Captain Thomas and renaming the Revenge the Royal James in a bid to keep his pardon intact. By July 1718, he was reaving with as much impunity as before.
In August, Bonnet entered the Cape Fear River of North Carolina, where he had decided to ride out the hurricane season. His presence did not go unmarked, however, and the reports of pirates in the river prompted the governor of neighbouring South Carolina to send two ships to capture them.
In late September 1718, two ships under the command of Colonel William Rhett had arrived at the river mouth, prompting Bonnet to challenge him head-on in a running fight. Comically, all three ships involved in the battle ran aground, and those aboard instead shot at each other for hours with small arms. It was only with the coming of high tide that the battle ended; it freed Rhett’s ship first, allowing them to close on Bonnet and threaten him with boarding. Outnumbered, all he could do was surrender.
Rhett returned Bonnet and his crew to Charleston for trial, though Bonnet would not remain incarcerated for long: three weeks later, he effected a brazen escape by dressing as a woman. He was able to obtain a small boat, but strong winds forced him back onto a nearby island, where he was recaptured by Rhett once more. 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. There were additional pleas for mercy by the citizens of Charleston, many of whom saw Bonnet more as gentleman and peer than a criminal. It was all to no avail, and Bonnet was executed on 10 December 1718. Approaching the gallows, Bonnet clutched a wilted bouquet of flowers, in many ways symbolic of his own life, in his shackled hands.
For the full Stede Bonnet story, The Life and Tryals of the Gentleman Pirate, Major Stede Bonnet is available on Amazon and through all major booksellers.
Excerpt from HistoryExtra article, “Stede Bonnet, Gentleman Pirate: how a mid-life crisis created the ‘worst pirate of all time’” available here.
Bonnet himself could not have known the impact his arrival in Nassau would have on the course of pirate history and lore, or on colonial commerce and trade. It was here that Bonnet met Edward Thatch (or Teach), known to the world as Blackbeard, with whom his legacy would be forever connected.
Blackbeard and Bonnet struck up either a friendship or a business arrangement, with Blackbeard taking over as captain of the Revenge (an upgrade for his current, smaller vessel) and Bonnet staying aboard as an observer and apprentice to one of the most feared pirates of all time.
Their working relationship grew more complicated as the two sailed throughout the Caribbean, the Gulf of Mexico and the east coast of the American colonies. Working together on-and-off between September 1717 and late summer 1718, they took dozens of prizes and pulled off one of the era’s most significant naval blockades, holding the walled-city of Charleston hostage for six days and effectively stopping all commerce to the city.
Blackbeard soon amassed a large flotilla under his command, including a new flagship, the Queen Anne’s Revenge.
It was in the summer of 1718 that Blackbeard and Bonnet arrived in North Carolina to take advantage of King George I of Great Britain’s pledge to pardon pirates who turned themselves in.
Sending Bonnet first to meet with Governor Eden of North Carolina, Blackbeard stayed with the flotilla near Topsail Inlet. But while Bonnet was ashore, Blackbeard double-crossed the Gentleman Pirate, looting his ship and marooning most of the Revenge’s crew onto an island with no food or water.
Upon his return, Bonnet was furious. He quickly resumed his captaincy of the Revenge, picked up the marooned men and chased Blackbeard up the Carolina coast. Perhaps luckily for Bonnet, he never again saw any signs of Blackbeard.
For the full Stede Bonnet story, The Life and Tryals of the Gentleman Pirate, Major Stede Bonnet is available on Amazon and through all major booksellers.
Excerpt from HistoryExtra article, “Stede Bonnet, Gentleman Pirate: how a mid-life crisis created the ‘worst pirate of all time’” available here.
In spring 1717, Bonnet set sail in search of fame, fortune, and adventure. Eager to leave his life behind, he travelled north of Barbados for his fresh start. He was sighted off Jamaica, then made his way to Virginia, where the Revenge enjoyed early success pillaging several English ships for plunder. Bonnet would spend the next few months off the coasts of North Carolina, New York, South Carolina and Florida.
Like other pirates, most of what Bonnet plundered was not treasure, gold, silver or jewels, but was actually more mundane, day-to-day necessities (provisions, clothes, ammunition and rigging) to stay afloat and to trade for money.
Bonnet and his crew rarely engaged in full-fledged sea battles (when they did, it did not go well). Instead, Bonnet – like other pirates – would fire a warning shot across the bow of a ship and fly its Jolly Roger to garner a quick surrender.
Records of his interactions with other ships showed ‘the Gentleman Pirate’ treated most of his captives with respect, with one exception: Bonnet routinely burned all ships based out of Barbados, presumably to either mask his identity or exact revenge on his former homeland.
Despite his initial successes, Bonnet’s inexperience and ignorance soon became obvious.
Off the coast of Florida around August 1717, Bonnet attacked a large Spanish man-of-war, likely sent to patrol and secure the remaining treasure of a sunken Spanish treasure fleet.
Bonnet was among those injured in the initial broadside, and half his crew was killed. The few able-bodied men remaining aboard the Revenge were able to flee, making their way to the pirate haven of Nassau.
For the full Stede Bonnet story, The Life and Tryals of the Gentleman Pirate, Major Stede Bonnet is available on Amazon and through all major booksellers.
Excerpt from HistoryExtra article, “Stede Bonnet, Gentleman Pirate: how a mid-life crisis created the ‘worst pirate of all time'” available here.
The reason Bonnet left his comfortable island life is likely more complicated than the prevailing view that he suffered “discomforts he found in a married state” caused by a nagging wife.
In fact, there are many other plausible explanations – that Bonnet’s early life as an orphan caused him to carry emotional baggage that was too much to sustain an already fragile marriage; that the emotional stresses of losing a young son created irreconcilable fissures for both Bonnet and his wife, Mary Allamby; that he possessed straightforward wanderlust, owing to a big imagination and access to all the voyage narratives of the time.
But, like much of pirate history, Bonnet’s real motivations are forever lost, hidden from the historical record.
What we do know is that Bonnet is among the most unique figures in pirate history – which is saying something considering some of the other famous pirates that we know of.
For the full Stede Bonnet story, The Life and Tryals of the Gentleman Pirate, Major Stede Bonnet is available on Amazon and through all major booksellers.
For those interested in the history of the real Stede Bonnet (and loosely the #OFMD Stede Bonnet), the Bonnet sugar plantation is still shown on Barbadian maps in 1747-1775, years after Stede’s death.
If you zoom out, you can also find the Allamby plantation where Stede’s wife grew up and her family remained.
FWIW, Bonnet’s wife moved from the Bonnet estate into Bridgetown after he left the island and family and the land was sold in 1764. The plantation likely continued to be operated in the same manner as when Stede was present (mostly through the use of enslaved labor).
Map Sources: Library of Congress (https://www.loc.gov/resource/g5140.ar208501/)
Even after studying the life and death of Stede Bonnet, it is this question of “WHY?” that remains a mystery.
In writing my book, The Life and Tryals of the Gentleman Pirate, Major Stede Bonnet, THAT is really THE question. WHY and, possibly, HOW, at least mentally, did Bonnet do what he did – leaving his family and wealth behind for the dangerous, dirty and grueling life of a pirate.
The short answer is WE DONT KNOW WHY Bonnet did what he did. And, although we have clues that lead to theories, the likely reality is that we will never know the exact WHY.
What we doknow that even in the midst of such bounty, Bonnet did not adjust well to family life.
Stede suffered, as the author of A General History of the Pyrates: From their First Rise and Settlement in the Island of Providence, to the Present Time (A General History)described in, “some Discomforts he found in a married State” that eventually caused Bonnet “a Disorder in his Mind.”
The reasons for the “Discomforts” of the Bonnet marriage are not well-preserved, however, but I have some theories:
Perhaps Stede’s early life as an orphan (both of his parents did when he was six years old) caused him to carry emotional baggage that was too much to sustain an already fragile married.
Or, as noted by several historians, perhaps the emotional stresses (for Stede and for Mary) of losing their child Allamby at an early age creating irreconcilable fissures in the Bonnet marriage.
Almost entirely absent from the historical discussion about Stede Bonnet and Mary Allamby, however, is the contextual background of the Jacobite Rebellion of 1715. If Allamby supported George I, Stede and Mary would have a significant political divide between them.
Maybe Bonnet was trapped in a love life that did not suit his needs?
Much has also been made of Johnson’s description of the “discomforts” Bonnet found in his married life, and it is amusing for many to jest that a nagging wife forced Bonnet into piracy.
Or, it is possible the latter diagnoses from Captain Johnson, that Bonnet suffered “a Disorder in his Mind,” that is more accurate. It is quite possible that Bonnet suffered from a true disorder, with possibilities ranging from simple wanderlust to bipolar disorder or, more likely, dementia, that evidenced itself in Bonnet’s behavior.
Stede Bonnet arrived in Nassau (in the Bahamas) in late-Spring 1717 (May), where he first met Blackbeard.
By mid-September 1717, Bonnet and the Revenge (with Blackbeard now onboard and as captain) was ready to sail, and approximately 150 pirates headed north toward the Delaware Bay.
The working relationship between Blackbeard and Bonnet grew more complicated as the two sailed throughout the Caribbean, Gulf of Mexico and east coast of the American colonies. Blackbeard and Bonnet would sail together off-and-on for the next nine month, taking dozens of prizes and pulling off one of the most significant naval blockades (the blockade of Charleston) of the era.
Eventually, the large pirate flotilla that included Blackbeard’s flagship, the Queen Anne’s Revenge, Bonnet’s Revenge and several other ships, sailed to North Carolina to take advantage of the King’s pardon of pirates who turned themselves in.
Sending Bonnet first, Blackbeard double-crossed the Gentleman Pirate in June 1718, looting his ship, marooning most of the Revenge’s crew onto an island with no food or water, and separating from Bonnet forever…
With the popularity of the HBO Max series, “Our Flag Means Death,” Stede Bonnet has joined Blackbeard as one of the most famous and popular pirates.
But, a question is often raised…”did they really know each other?”
The answer is a resounding, “yes.” Stede Bonnet and Blackbeard really did know each and sailed together off and on between 1717 and 1718.
Bonnet was amongst the most unique figures in pirate history (a history riddled with colorful characters). With his own money, Bonnet bought a sloop from the Barbadian harbor, the Revenge, and modified it to carry a dozen cannons and more than one hundred men.
Bonnet didn’t stop with the mere necessities of a maritime vessel, equipping the Revenge with comforts a man of his status would expect, including a full library of books in his private quarters.
Stede hired 126 men out of the Barbadian port, paid them a wage out of his own fortune (uncommon at the time, for pirates always took a piece of the plunder, not a wage), and in spring 1717 set sail in search of fame, fortune, and adventure.
Bonnet would spend the next several months off the coasts of Jamaica, Virginia, North Carolina, New York, South Carolina, and Florida before making his way to Nassau in the Bahamas (learn exactly why Bonnet and his crew travel to Nassau in my book “The Life and Tryals of the Gentleman Pirate, Major Stede Bonnet“).
It was in Nassau that Stede Bonnet met Blackbeard.
Blackbeard and Bonnet struck up either a friendship or a business arrangement and Blackbeard took over as captain of the Revenge (an upgrade for his current, smaller vessel) while Bonnet stayed aboard as an observer and apprentice to one of the most feared pirates of all time.
I suppose it wasn’t a hostile takeover, more like a trade of assets. Blackbeard had more experience and Bonnet had a better ship.
The working relationship between Blackbeard and Bonnet grew more complicated as the two sailed throughout the Caribbean, Gulf of Mexico and east coast of the American colonies over the next year and a half, resulting in one of the most interesting tales of friendship, treachery and piracy that history provides…
Stede Bonnet was living the life by the age of 28 – at a young age he had inherited generational wealth, he was well-educated, well-married with four children and his family lived on a 400-acre estate on Barbados, a lush Caribbean island.
An heir to an established landowning aristocratic family in Barbados, Bonnet enjoyed luxuries equal to that of the finest houses in London.
And, his liberal education ultimately was held against him as an aggravating factor at his trial. The passage below, from attorney general Richard Allein, sums up the government’s position,
I am sorry to hear some expressions drop from private persons, (I hope there is none of them upon the jury) in favor of the pirates, and particularly of Bonnet: that he is a gentleman, a man of honor, a man of fortune, and one that has had a liberal education. Alas, gentlemen, all these qualifications are but several aggravations of his crimes.
How can a man be said to be a man of honor, that has lost all sense of honor and humanity, that is become an enemy of mankind, and given himself up to plunder and destroy his fellow creatures; a common robber, and a pirate?
Nay, he was the archipirata, as it is now taken in the worst sense, or the chief pirate, and one of the first of those that began to commit those depredations upon the seas since the last peace.
I have an account in my hand of above twenty-eight vessels taken by him, in company with Thatch, in the West Indies, since the 5th Day of April last, and how many before, nobody can tell.
His estate is still a greater aggravation of his offence, because he was under no temptation of taking up that wicked course of life.
His learning and education is still a far greater aggravation; because that generally softens men’s manners, and keeps them from becoming savage and brutish.
But when these qualifications are perverted to wicked purposes, and contrary to those ends for which God bestows them upon mankind, they become the worst of men, as we see the present instance, and more dangerous to the Commonwealth….
The Hanging of Major Stede Bonnet: this engraving was published in the Dutch version of Charles Johnson’s A General History of the Pyrates—Historie der engelsche zee-roovers … door Capiteyn Charles Johnson (1725), Amsterdam: Hermanus Uytwerf
