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Mad, Bad & a Total Gent: the Demons of the Pirate Stede Bonnet


The Life and Tryals of the Gentleman Pirate, Major Stede

Köehlerbooks, 2020. 206 pages

Paperback £13.55/$12.90

By Sean Kingsley

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Of all the misfits who went on the account in the golden age of piracy, none made as little sense as Stede Bonnet. Men, and the odd woman, took to the high seas for the cash or to escape the chains of social injustice. Many pirates jumped ship from navies to get away from the shackles of harsh colonial life, beatings and being press ganged.

Bonnet was no such creature. He was born in Barbados in 1688 with a silver spoon in his mouth. The Bonnets made a fortune out of the triangular slave trade that saw West African slaves shipped to the Caribbean in horrendous numbers to fuel the sugar revolution. Major Stede’s family owned over 400 acres of sugarcane plantations, a townhouse and manor house, two windmills, a cattle-driven mill and 94 slaves.

Well educated, born rich and “a Gentleman of good Reputation” whose family lived like “little sovereigns”, the great mystery surrounding Bonnet is not his achievements as a pirate but why he walked out on the life of Riley in the first place. For a curious and complex character who sailed shoulder to shoulder with Edward Thatch or Teach – Blackbeard – and raked in $5.5 million in ill-gotten gains (in modern value), very little ink has been spilled on Major Stede Bonnet’s life and times and what persuaded him to walk out on his wife, Mary, four children and financial stability. He had it all and lost it all.

Jeremy Moss’s new book lifts the lid on one of piracy’s most fascinating characters. Its three sections robustly cover his movements from hearth to hangman’s noose, his trial and then various appendices, including a table of all the prizes Bonnet seized between June 1717 and October 1718. For a man who outwardly ticked all the pirate boxes (a portfolio of prizes, a bounty on his head, hanging), the morose major has somehow fallen through the cracks of popular history. The Life and Tryals of the Gentleman Pirate, Major Stede is one of only two modern books dedicated to him. Moss restores Bonnet to his rightful place in the pantheon of pirate lords, warts and all. It’s about time.

Stede Bonnet was a justice of the peace on Barbados when he gave the royal two-fingered salute to lawfulness. Moss rigorously traces all the major’s pirating moves and his many mistakes. Bonnet’s actions will fascinate many, but Moss compellingly exposes the devil in the gentleman pirate’s mind. Bonnet, you see, was a tad mentally unhinged. A General History of the Pyrates claimed the major suffered from “some Discomforts he found in a married State” that eventually brought about “a Disorder in his Mind.” Moss wonders rightly whether Stede’s early life as an orphan created too heavy a burden of “emotional baggage that was too much to sustain an already fragile marriage.” Perhaps he was tipped into the abyss by losing his son Allamby at an early age that “created irreconcilable fissures in the Bonnet marriage.”

Aged 28, the major bought a sloop called the Revenge in December 1716 and vanished from high society. On paper, Bonnet was a triumphant sea rogue. He seized 53 prize ships from New York to Charles Town (Charleston) and Honduras carrying money, ammunition, sugar, rum, slaves, silver, gold dust, cows, pigs and indigo. But deep down Bonnet never found what he was searching for at sea.

The swell with a tricorne hat, fashionable wig, silk stockings and pointed shoes with gold buckles was never taken seriously. He was a poor leader and “nothing but Confusion seemed to attend all their Schemes,” as Charles Johnson put it in 1724. Bonnet took some very bad turns, attacking a Spanish merchant vessel that proved to be a warship, so that half his crew was killed or wounded in battle.

It was in Edward Thatch, Blackbeard, that Bonnet found his greatest ally – or perhaps what psychologists would call the father figure he longed for? Bonnet’s ship was superior to Thatch’s but lacked a skilled captain to command. Blackbeard had all the charisma and experience to control a large sloop. It was a match made in hell. Only a year into his new life of piracy, Bonnet had been “critically injured, beaten in battle, and now had lost control of the Revenge,” Moss shows. The sea failed to rest his soul. Instead, the major felt helpless, melancholic and “reflected upon his past Course of Life, and was confounded with Shame,” even though his crew loved him for his human flaws.

By the spring of 1718, HMS Scarborough and HMS Seaford had set out to seek and destroy the pirates of the Caribbean, starting with Charles Vane. Bonnet was captured in late September 1718 and imprisoned in Charles Town. Despite escaping dressed in women’s clothes, and a staggering £700 bounty put on his head – one of the highest ever raised for a pirate – the vice-admiralty court of Charleston quickly found 29 of Bonnet’s crew guilty of piracy.

Curiously, Bonnet tried to play innocent, claiming he was a prisoner onboard Blackbeard’s ship for 11 months after his sloop was seized and he never had “any benefit or share by his actions, but on the contrary was a very great loser by him…” The court was unmoved. On 10 December 1718, Major Stede Bonnet was carted to the gallows at White Point in Charleston grasping a wilted bouquet of flowers and hung. He was all of 30 years old.

Today you can’t help but wonder whether a US court would have sentenced Bonnet to a lethal injection or the mental asylum. What was really up with the major? Moss argues that Bonnet quite possibly “suffered from a true disorder, with possibilities ranging from simple wanderlust to bipolar disorder or, more likely, dementia… The progression of symptoms of dementia align closely with Bonnet’s bizarre behavior. Loss of judgment, disinhibition, impulsivity, social misconduct, loss of awareness, interpersonal withdrawal, wanderlust, excessive joviality, sexually provocative behavior, and the use of inappropriate words of action are all behaviors that can evidence dementia.”

It’s possible, although early onset dementia usually rears its tragic head in people no younger than their 40s. What seems clear is that the mad major was running from something. By the time Bonnet smelt the salty sea and had his morose depression injected with adventure, he was hooked “like a dog to its vomit”, so his trial transcript put it. As Jeremy Moss makes abundantly and expertly clear, though, by the time he found an eternal peace at the end of a hangman’s noose, he’d taken his seat among the most famous captains of the golden age of piracy.

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