Meet the rich gentlemen who gave up good life to become pirates

In 1679, William Dampier had a bright future ahead of him. The 28-year-old from a small village in Somerset, England, had a young wife—Judith, a relative of the Duchess of Grafton—and a small estate of his own in Dorsetshire. He seemed destined to become a wealthy and respected British gentleman, and that might have been his path . . . until he discovered pirates. 

It happened during a plantation management apprenticeship in Jamaica. He abhorred the experience, writing in his journal that he was “clearly out of my element.” He found distractions at the nearby Port Royal, where he noticed that visiting buccaneers — a k a pirates — were different from the typical scruffy seafarers.

They “wore elegant silk waistcoats, colorful sashes, and gold and jewels to excess,” writes Keith Thomson in his new book, “Born to Be Hanged: The Epic Story of the Gentlemen Pirates Who Raided the South Seas, Rescued a Princess, and Stole a Fortune” (Little, Brown), out now.

Joining them was not the smart move for a man with his opportunities. His parents, both farmers, had died while he was still a child, but had secured for Dampier a scholarship at King’s Bruton, a posh Somerset boarding school where he received a classical education and “an open door to the prestigious career of his choice,” Thomson writes. His commercial success and life as a gentleman had been all but guaranteed for him.

But Dampier had other ideas. Before settling down to the life his late parents wanted for him, he decided to indulge his “inclination for the sea,” as he described it in his journal. This apparently meant joining the crew of Captain Bartholomew Sharp and leaving his wife to explore (and plunder) the world.

More than 5,000 buccaneers chose a life at sea during the 17th and early 18th centuries, sometimes called the Golden Age of Piracy. But not all of them were stereotypical pirates, rum-soaked degenerates with no education and few other career options. Some, like Dampier, were well-off or well-connected young men looking to pirate ships either as a way to sow their oats or find something they couldn’t get in their otherwise genteel existence.

They include men like Stede Bonnet, a wealthy plantation owner in Barbados who abandoned his wife and kids to become a full-time pirate, befriending actual criminals like Edward “Blackbeard” Thatch and earning the nickname “the Gentleman Pirate,” a not entirely complimentary nod to his embarrassing lack of experience. (His life has been fictionalized in the HBO Max series “Our Flag Means Death.”)

Other less famous but equally unqualified buccaneers included Lionel Wafer, a 20-year-old surgeon whose “life was laid out before him like a golden path,” writes Thomson. And Basil Ringrose, a gifted 26-year-old mathematician and navigator from London, fluent in Latin and French, who “had his pick of employment opportunities in the West Indies” but opted for a pirate’s life instead, writes Thomson.

Call them trust fund pirates — slumming it with the outlaws and scoundrels when their pedigrees could’ve gotten them vocations where the retirement plan didn’t involve walking the plank or a hangman’s noose.

Why did they do it? The 1724 book “A General History of the Pyrates” speculated that Bonnet was driven to piracy by “some discomforts he found in the married state.” His nagging wife, in other words. When Dampier returned to London to be with his family in 1691, after a twelve-year absence — he only came home to escape justice in Indonesia —domestic life didn’t agree with him. “It wasn’t long before he was off to the Caribbean for more pirating,” writes Thomson.

For the men too young to have wives to escape, the lure of piracy often came from literature. Ringrose, like many of his peers, was enamored by “The History of the Bucaniers (sic) of America,” a book first published in Dutch in 1674 and soon translated into several languages. It was a huge bestseller, written by former pirate Alexandre Exquemelin about his adventures on the sea, including the 1671 sack of Panama. It single-handedly ignited Europe’s fascination with pirates, and “blazed a path to adventure for educated young men such as Ringrose and Wafer,” writes Thomson.

In April of 1680, Ringrose, Wafer, and 364 other fledgling pirates were given their first big shot at adventure when an indigenous tribe on Golden Island (today known as Isla Seletupa in Panama) hired them to rescue the chief’s daughter, who had been kidnapped by Spanish soldiers and was being held captive in Santa Maria. Rescue his daughter, the chief promised, and they could keep all of the Spaniard’s abundant riches.

The spoils were not exactly as promised. Instead of mansions filled with silver and gold, they found only “a small quantity of gold dust stored in jars made of hollowed-out pumpkins,” Thomson writes. The entire haul was barely enough to buy every man his own cow, “hardly what they’d braved caiman-infested rivers for,” Thomson writes.

Financial disappointment was not uncommon for pirates. The tales they read about in books were mostly hyperbole, and more often than not, they were lucky to break even. In his journal, Dampier recalled a 1677 raid of Veracruz, on the Mexican coast, where they’d been anticipating Spanish treasure. Instead, when they finally captured the fort, losing almost a dozen of their comrades in the fight, they discovered “only caged parrots—hundreds of them,” writes Thomson.

Another surprise to many new young buccaneers were the dangers involved in the job, who apparently were unclear “just how easily and arbitrarily pirating could cost them their lives,” writes Thomson. The unofficial pirate motto, “A merry life and a short one,” was seemingly not a joke.

Wafer observed this firsthand when he learned that his job description involved not just treating the entire crew for STDs like syphilis — the treatment involved a urethral syringe filled with mercury, which cured patients by way of mercury poisoning that usually led to death — but amputating his colleagues and sometimes his captain after particularly bloody battles. Wafer was not “the first surgeon to inadvertently slice off the fingers of either the flailing patient or the assistants attempting to restrain him,” notes Thomson.

‘It wasn’t long before he was off to the Caribbean for more pirating.’

Author Keith Thomson, on one young privateer forsaking a stable home life for the call of the open sea

But many young pirates found a purpose beyond the stolen loot and not losing an appendage. For Dampier, piracy became “the day job that facilitated his true avocation, naturalism,” Thomson writes. Besides plundering, his other passion was exploring the natural world, which he documented in his 1697 book, “A New Voyage Round the World,” a pirating memoir that conveniently neglected to mention the many crimes he’d committed. 

It was not only “a judicious sidestepping of self-incrimination but also a prudent literary choice,” writes Thomson. “To seventeenth-century readers, his ‘richly detailed account of people, places, things, plants, fishes, reptiles, birds, and mammals’ was as fresh and engaging as Apollo 11 transmissions from the moon would be to viewers almost three centuries later.”

For others, however, the real spoils of pirating were the tall tales. Even when they left empty-handed, they had stories to tell.

Ringrose had one such tale when he took part in a 1681 attack on a rich Spanish settlement of Arica, a port city in northern Chile. Despite being badly outnumbered, the band of pirates — a little more than a hundred men — found their “rage increasing with our wounds,” wrote Ringrose. So they pushed ahead and “filled every street in the city with dead bodies.”

They were not victorious. The band of pirates was eventually chased into a church, where they were hit by cannon fire and surrounded by “a thousand armed Ariqueños and soldiers who added to a rain of projectiles that blew out the church’s windowpanes,” writes Thomson. Their injured couldn’t be treated, as the pirate’s battlefield surgeons had all gotten drunk on the church’s communion wine. And the survivors just got sicker when they tried to stave off dehydration by drinking their own urine. 

Eventually, they shot their way out of the church. The 47 remaining pirates “formed a circle around their wounded, turned to face the sea of soldiers, and, one last time, raised their muskets and fired with hellish precision,” writes Thomson. Despite being fired upon by thousands of soldiers, from every possible direction, “they emerged from the city without sustaining a single gunshot wound.”

Even their enemies were impressed. One anonymous native wrote that the pirates fought “with superhuman vigour, with the ferocity and fury of lions, fighting with feigned contempt for all risks and mocking death.”

That kind of excitement just couldn’t be found with a respectable job. Which may explain why Dampier, who finally accepted a legitimate ship’s captain post in 1699, didn’t last long. When he was given command of the English Admiralty’s expedition to explore New Holland — today better known as Australia — he found it “lacked the exhilaration of ducking incoming musket balls.” In 1702, he returned to “privateering,” as he preferred to call the pirating life.

He was still at it in 1709, at the ripe old age (by pirate standards) of 58 years old, when he helped plunder the Spanish ship Nuestra Señora de la Encarnación y Desengaño, liberating it of about £150,000 worth of gold, gems, and other cargo. 

Dampier was a pirate until the end. Writes Thomson: “Only his death, in 1715, would keep him from returning to sea.”