Biographies & Memoirs

The Life and Tryals of the Gentleman Pirate, Major Stede Bonnet


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Major Stede Bonnet was living the good life by the age of 28. Bonnet was a wealthy, well-married father of three children, and the family lived on a 400-acre estate on the lush Caribbean island of Barbados.

Then Bonnet had a "humor to go a-pirating," and left it all behind...

Major Stede Bonnet enjoyed luxuries equal to those of the finest houses in London. "A Gentleman of good Reputation" and a "Master of a plentiful Fortune," he was given "the Advantage of a liberal Education," but the call of the sea-and perhaps more significantly, the push of his obligations as a father and husband-cast Major Bonnet onto an unlikely and deliberate course toward piracy.

Easily likable, by friend and foe, many would be drawn to Bonnet. In his two short years of piracy, Stede Bonnet would be mentioned alongside some of the New World's most notorious pirates, including Charles Vane, Robert Deal, "Calico" John Rackham, Israel Hands, Benjamin Hornigold, William Kidd, Mary Read, Anne Bonny, and the pirate to whom Bonnet would forever be connected, Edward Thatch (infamously known around the world as "Blackbeard"). Follow Major Bonnet through his improbable and exciting journey in the Golden Age of Piracy.

The Making of Major Stede Bonnet

It was 1688 in Barbados, a Caribbean hub that had matured, surviving early political divisiveness and unrest to later thrive as a wealthy society of sugar planters and traders. Navigation routes of the time had most vessels bound to the West Indies from Europe make landfall first in Barbados, the eastern-most island of the Caribbean. 

Being the windwardmost island of the Caribbean gave Barbados many advantages, thriving on early news reports, goods from Europe and, eventually, slaves, laborers and servants from Africa and elsewhere. Barbados also had a strategic military advantage, as winds blew across the region from east to west, making westward approach by ships slow and difficult.

Originally discovered by the Spanish in the early 1500s (Barbados appeared on Spanish maps as early as 1511), the small island was claimed by the Portuguese sometime between 1532 and 1536 when it was given the Portuguese name Los Barbados. An British historians assumed the name “no doubt relates to the Barbarity of the Country,” but conceded that “some weak people of this Island,” thought the name was derived from the “beards” of fig trees found on the island.   

An exploratory expedition was initially sent to the island in 1625  to determine its viability for settlement.  On February 17, 1627, the ship William and John landed on Barbados from England with eighty white settlers and ten African servants (slaves) for the purpose of settling the island as a proprietary settlement.

By 1639, an assembly of landowners was established on the island with annual election, making the Parliament of Barbados the third oldest legislature in the Americas (behind the Virginia House of Burgesses, now the Virginia General Assembly, and Bermuda’s House of Assembly).  An island council was also established, appointed first by the lord proprietor and later, in 1660, by the king.

Like the other colonies of the New World, early Barbados attracted a motley array of “offscourings,” from England, France, Holland, Scotland, Ireland and Spain, including adventurers, fortune-seekers, indentured servants, rogues and prostitutes.

In a 1655 journal entry, Henry Whistler, the master of Vice Admiral William Penn’s flagship (Penn was an English admiral and politician who served in the House of Commons from 1660 to 1670, and is better known as the father of William Penn, founder of Pennsylvania), described Barbados as “one of the Richest Spots of ground in the world and fully inhabited…,” going on to use more colorful language, 

This island is the dunghill whereon England doth cast forth its rubbage.  Rouges and whorse and suchlike people are those which are generally brought here.  A rogue in England will hardly make a cheater here.  A baud brought over puts on a demour comportment, a whore if handsome makes a wife for some rich planter.

These early settlers struggled to find viable, money-making crops for the island and grew tobacco, cotton, and indigo, among other things, on small family farms.

Major Stede Bonnet was born in 1688 in Barbados to Edward and Sarah Bonnet, and christened at Christ Church parish on July 29, 1688.  The Bonnets were affluent plantation owners and part of the original aristocracy of Barbados, with Stede born into the third generation of the Bonnets of Barbados. 

Thomas Bonnet, Stede’s great grandfather, was among the earliest inhabitants and settlers of Barbados.  Thomas Bonnet prospered on Barbados during the Barbadian “Sugar Revolution,” clearing portions of the Barbadian jungle to establish a plantation of over 400 acres, at least two homes (a townhouse on High Street in Bridgetown, and a plantation manor house in Christ Church).  The Bonnet plantation in Christ Church was among other large plantations created out of the consolidation of family farms.  

Early sugar production reaped huge profits for local Barbadian growers and the upper-levels of the island plantocracy flourished. Sugar production required significant labor, however, and the Barbadian aristocracy quickly turned to African slaves as a cheap labor source, establishing Barbados as the first black slave society in the New World.

Recognizing the need to formalize and institutionalize slave labor, the critical component for sugar production and wealth-generation, a 1636 political Barbadian political directive defined all Africans brought to Barbados as lifelong chattels (slaves). Later, in 1661, the Parliament of Barbados passed “the 1661 act for the better ordering and governing of Negroes,” consolidating the slave culture in a single statute. The 1661 act would serve as a model for later comprehensive slave laws in Jamaica and Antigua. Barbadian slaves would eventually be defined as real estate, attaching to the land on which they labored.

By the mid-1700s, British historians would already note Barbados’s value, providing that if Barbados “‘tis not the richest Spot of Ground in the World, ‘tis only because the Industry of the People is not enough encouraged.”

Edward Bonnet, Thomas’s younger son and Stede’s father, inherited much of the Bonnet estate upon Thomas Bonnet’s death in 1676. By the time of Stede’s birth in 1688, the economy and politics of the island of Barbados had matured, surviving early political divisiveness and unrest to thrive as a wealthy society of sugar planters and traders.

Edward Bonnet would manage the estate until his death in 1694, when Stede was only six years old.  With Stede’s mother, Sarah (Whetstone) Bonnet’s death not long after the death of Stede’s father, Stede was an orphan and the affairs of the Bonnet estate were taken care of by Stede’s guardian until he reached adulthood.   

Young Stede inherited and was raised on the bustling Bonnet estate with access and reign over 400 acres of sugarcane fields, two windmills, a cattle-driven mill, three servants (likely indentured whites from England, Scotland or Ireland) and ninety-four slaves.  From age eleven, until adulthood, Bonnet was raised by Jennet Whetstone, widow of former deputy secretary of Barbados John Whetstone. As he reached adulthood, Bonnet took over full responsibility for the Bonnet plantation.  

Bonnet’s continued use of slave labor on his plantation would have aligned him with other Barbadian aristocrats. Slavery was critical to the still-developing sugar plantocracy, and the profitable Barbados would ultimately provide the blueprint for future slave colonies in colonial America.

Barbadian slave-holders, like their successors, were known to be ruthless in securing the slaves for which they claimed title, and “had not yet learnt to govern their slaves by any other Ways than Severity.” Black slaves were even denied the benefit of Christian baptism, as “some more Scrupulous Overseers might not be willing to handle the Cat-a-nine-tails so often against their Fellow-Christians, as they would against Infidels.”

Enforced by a Barbadian militia comprised of land-owners, strict penalties were imposed on runaway slaves. Among those enforcement mechanisms was the “Cage,” an enclosure for runaway slaves located in the center of Bridgetown established by act of Parliament in 1688. 

Bonnet would be recognized as part of the Barbadian militia and given the title of Major.  Although some have exaggerated Bonnet’s status and rank into an assumption of significant military experience, his rank was merely bestowed upon him pursuant to a June 1652 Barbadian law that bestowed military titles upon the land-owning aristocracy. The title would be important to Bonnet, however, and history would assign “Major” to Stede Bonnet’s name for more than 300 years.

On November 21, 1709, twenty-one-year-old Bonnet married Mary Allamby, the sixteen-year old daughter of fellow plantation owner William Allamby, at the Cathedral of St. Michael in Bridgetown.  Allamby’s father, William, was another wealthy plantation owner and part of the Barbadian aristocracy.  Mary was his oldest daughter.  The Bonnets would live in Bridgetown, which also served as the seat of the assembly, for the next several years.

Stede and Mary would have had four children, three sons (Allamby, born on May 17, 1712, Edward, born September 24, 1713, and Stede, Jr., born on September 16, 1714) and a daughter (Mary, born in early 1717).  Stede’s first son, Allamby, died in early childhood (sometime before 1715).

Well-respected and part of the Barbadian elite, Stede was appointed and sworn in as a Justice of the Peace on January 24, 1716. Like other gentlemen of Barbados, Stede would have been “civil, generous, hospitable, and very sociable.” 

As plantation owners and masters, Stede and Mary would have lived like “little sovereigns” on their plantation. The Bonnets would have their servants of their household, and those of their fields. Their table would be spread with a variety of nice dishes and meals of beef, pork, veal, mutton and lamb, with second courses of turkey, geese, fowl, chickens, and fish (abundant in the small island colony).

 All sorts of sauces and relishes, including pickles and olives, would have been served with their meals, along with a variety of tongues, hams, anchovies, and caviar. Fresh breads and pastries, made with English flour, would accompany each meal, followed later by “admirable” desserts. 

Bonnet would drink primarily Madeira wine (either Malmsey or Vidonia), water, and lemonade made of “excellent Lemons, fine Sugar and Spring-Water.” All sorts of other wines, malt drinks and ciders from England would have been available to Bonnet and his friends. On special occasions Bonnet may have entertained with a local punch, mixing fresh lemonade with French brandy. Instead of using French brandy, Bonnet may have been like other “good Husbands,” manufacturing his own rum onsite. 

Their lifestyle would rival that of the nobility in England; with rich equipages, decked out in fine liveries, beautiful coaches and horses, and magnificent chairs, chaises and other conveniences for traveling from their plantation home into Bridgetown.

Stede and Mary’s dress was both fashionable and courtly, and their behavior would be the expected genteel and polite, even though they were Barbados, not London-bred. Nonetheless, Stede would have developed an “air” about him, having lived his whole life away from London, the center of the gentleman’s universe, having traveled outside Barbados very little, if at all, and like other “Country Gentlemen,” conversing always with his “Dogs, Horses, and rude Peasants...”

In short, the Bonnets and their Barbadian neighbors lived as plentifully as any in the world. They had everything necessary for a life of respect, pomp and luxury. But, try as they might, Stede and Mary would never be part of the London elite.

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. Perhaps Stede’s early life as an orphan 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 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. 

Following the 1688 revolution, often referred to as the “Glorious Revolution of 1688,” that ended the reign of James II and Catholic line of the Stuart dynasty over Britain, James supporters, referred to as Jacobites after the Latin rendering of James’s given name, Jacobus, refused to accept this revolution or the political establishment that followed. 

Following a series of riots across England in the fall of 1714 and the summer of 1715, English riot-leaders secretly negotiated with King James III for revolution while Jacobite Scots were encouraged by the disorder in England to begin secretly preparing an uprising that would restore both the Stuarts and an independent Scotland. King George I arrested the English leaders, but were not able to immediately quell the Scottish uprising.

As would become clear from future events, Stede Bonnet was a Jacobite sympathizer, and perhaps supporter. Barbados, in fact, had a history of Jacobite support and Bonnet would have grown up on the island being exposed to “too many have anything done which is really for the good of the King and his government.”

It is unclear, however, what Mary Allamby’s position (if she had one) on the rightful heir to the throne. If Allamby supported George I, Stede and Mary would have a significant political divide between the two. 

By the end of 1716, the twenty-eight year old Bonnet had enough of the good life and its related discontents.  Bonnet was struck with a “humor of going a pirating.”

For a historian and biographer, A General History presents the conundrum of history.  On one hand, Captain Charles Johnson’s A General History represents the most complete contemporary resource about pirates and their exploits, many of which have been corroborated by other contemporary accounts compiled by historians like Colin Woodard, Eric Jay Dolin and Robert E. Lee.

On the other hand, Captain Johnson’s A General History is unreliable, incomplete, and unwaveringly biased.  Published initially in May 1724, A General History brought tales of the carribean pirates across the Atlantic to England, shaping popular thinking about pirates forever.   

Nonetheless, as it relates to Bonnet, significant portions of A General History can be confirmed, or, at the very least, supported in spirit.  We will, therefore, refer back to A General History throughout Bonnet’s life story to provide facts, when possible, context, when appropriate, and colored commentary, when little else is available.

An apparently voracious reader with a fondness for books, Bonnet himself may have been inspired by books like the voyage narratives of the times, including competing narratives A Voyage to the South Sea, and Round the World, Perform’d in the Years 1708, 1709, 1710 and 1711, written in 1712 by Captain Edward Cooke, and A Cruising Voyage Round the World, written by Woodes Rogers (who would later become the first Royal Governor of the Bahamas and a famed pirate hunter).  

Cooke’s A Voyage to the South Sea, and Round the World, Perform’d in the Years 1708, 1709, 1710 and 1711 and Rogers’ A Cruising Voyage Round the World recount both captains’ accounts of their adventures from sailing around the world on a shared trip, under the command of Captain Rogers.  Both books include stories of adventure, privateering and capture, as well as more well-known tales, like the story of Alexander Selkirk, a mariner marooned alone on Mas a Tierra island after leaving William Dampier’s ship in the South Pacific for four years before discovery.  Selkirk’s story would serve as inspiration for Daniel Defoe’s 1719 classic, Robinson Crusoe. 

Earlier competing narratives, like Lionel Wafer’s A New Voyage and Description of the Isthmus of America, and William Dampier’s A New Voyage Round the World, published in 1697 may have further inflamed Bonnet’s wanderlust, along with Dampier’s second book, A Voyage to New Holland.  

Bonnet may have also read other contemporary tales of piracy, including The Successful Pyrate, a play by Charles Johnson (unrelated to Captain Charles Johnson author of A General History) based on the life of the “king of the pirates,” Henry Avery, published in 1713 and The Buccaneers of America by Alexander Exquemelin, translated and published in English in 1684.     

These books, combined with tales of piracy shared across Barbados by word of mouth and contained in the newspapers of circulation likely reminded Bonnet of his relatively sheltered lifestyle on the 166 square miles of Barbados.  Romantic tales of treasure, adventure and the endless immensity of the sea fed Bonnet’s longing to travel the world and seek out adventure, pushing back on the aristocratic society of status and hierarchy.

On December 13, 1716, Captain Godfrey Malbone sailed a small, Newport, Rhode Island-based sloop into the Barbadian harbor from South Carolina.  When he was approached by a local plantation owner who wished to purchase his sloop, Malbone would not have thought twice about the intentions or experience of its purchaser.

Malbone’s sloop presented the perfect opportunity to satisfy his longing for adventure on the sea (or to provide an outlet from the discomforts of his home life).  Bonnet bought Malbone’s sloop outright, perhaps with a portion of a L1700 (almost $400,000 in current dollars) loan he had recently taken out, commissioning a local shipyard to “fit out” the sixty-ton sloop at his own expense.  Modifications were made to ensure Bonnet’s new sloop could carry at least a dozen cannons and more than one hundred men, and to ensure that the sloop was equipped with the comforts a man of his status would expect, including a full library of books in his private quarters.

Bonnet may have been initially attracted to Malbone’s sloop because of its name, the RevengeRevenge was a common name for pirate ships, and resonated with Bonnet; the Revenge was Bonnet’s answer to those internal struggles that he had been dealing with; the Revenge was Bonnet’s retaliation against his home life, a lonely childhood, the loss of his first born son, and against feelings of mediocrity and accidie. 

Whether Bonnet explained the purchase to his wife, we do not know. Stede’s purchase of the Revenge may not have raised any suspicion at all. It was not uncommon, after all, for wealthier Barbadian landowners to have “Pleasure-Boats, to make their Tour of the Island in, and Sloops to convey their Goods to and from the Bridge.”

But, no records exist confirming that Mary knew anything of the time and money Stede was spending at the Barbadian harbor.  From Captain Johnson’s description of Mary’s nagging, we might assume Stede’s purchase was kept a secret. Much has 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.  But, it is likely 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, bi-polar disorder, or more likely, dementia, that evidenced itself in Bonnet’s behavior.  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. 

And, while it is true that it could be argued that almost all pirates show many of these symptoms, the reality is that Bonnet was not a pirate.  Bonnet was a man of some wealth and means, and while he had spent much of his life surrounded by the sea, he was a landsman.  It seems less likely that Bonnet’s piracy, as some historians have proposed, was “the mere extravagance of a wealthy planter wracked by tedium and oppressive heat, encouraged by family history.”  No, there is something more to Bonnet’s story that we may never uncover.

Bonnet had no “understanding [of] maritime Affairs,” other than what he may have read, but selected a proper sloop.  As Bonnet knew from his studies, sloops were favored by privateers and pirates because of its shallow draught and maneuverability.  Sloops were generally single-masted, front-and-rear-rigged boat with a short-standing bowsprit (the spar extending from the portion of the ship’s bow above water used to allow additional sail surface), or none at all, and a single headsail set from the forestay.  Sloops were relatively small (between 60 and 250 tons was typical) and suitable for most piratical tasks.

The Revenge gave Bonnet the means to escape Barbados, but now he would need a crew.

About the author

Jeremy R. Moss is a lawyer & lobbyist living in Alexandria, Virginia. An emerging author & historian, Jeremy's research is focused on piracy and maritime history. When not working or writing, Jeremy is a family man and can be found telling stories of adventure and buried treasure to his young sons. view profile

Published on September 15, 2020

Published by Koehler Books

50000 words

Genre: Biographies & Memoirs

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