Stede Bonnet, Gentleman Pirate: how a mid-life crisis created the 'worst pirate of all time'

From childhood, Bonnet lived a life of privileged luxury. He was provided a liberal education and enjoyed generational wealth as the heir to a bustling sugar plantation on the Caribbean island of Barbados. He married well and fathered four children.

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Bonnet was also well respected in the community. He was a part of the Barbadian elite, a justice of the peace [a local magistrate] and member of the Barbadian militia (which was responsible for tracking down and returning escaped slaves), in which he was given the title of major.

In short, Bonnet had everything necessary for a life of respect, pomp and luxury. But even in the midst of such bounty, he did not adjust well to family life – and in 1717 he left it all behind. In what might easily be described as one of the worst mid-life crises of all time, Stede Bonnet decided to become a pirate.

Why did Stede Bonnet become a pirate?

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.

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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.

Stede Bonnet in Our Flag Means Death

Stede Bonnet is the star of period comedy Our Flag Means Death, which follows the ‘Gentleman Pirate’ through his mid-life crisis, abandoning his life of plenty to become a pirate. It does not go well.

Our Flag Means Death arrives in the UK on BBC Two and BBCiPlayer from 4 January 2023.

Bonnet’s idiosyncrasies are apparent even before he set sail. Rather than steal a ship, he bought one with own money – a sloop, which he named the Revenge – and modified it to carry a dozen cannon. He didn’t stop with the mere necessities, instead equipping the vessel with all the comforts a man of his status would expect ­– including a full library of books in his private quarters.

Likewise, when it came to crew, Bonnet did something unusual: he paid the men he hired out of the Barbadian port a wage out of his own fortune. Most pirates of the time would have taken a cut of plunder, not regular pay.

Was Stede Bonnet really a bumbling ‘gentleman’ pirate?

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.

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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.

Stede Bonnet and Blackbeard

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.

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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.

How was Stede Bonnet caught?

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.

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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.

Was Stede Bonnet a bad pirate?

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.

Jeremy Moss is a historian of early modern piracy and author of The Life and Tryals of the Gentleman Pirate, Major Stede Bonnet (Koehler Books, 2020) and Colonial Virginia’s War on Piracy: The Governor and the Buccaneer (publication forthcoming, June 2022). Follow him on Twitter: @StedesRevenge