By the year 1717, Stede Bonnet appeared to have settled into the life of the average landed Barbadian aristocrat. As the owner of 400 acres of working plantation, father of three, and husband of a notoriously captious wife, the twenty-nine-year-old’s future course was clear as the open seas.
Until, that is, it wasn’t.
In a brilliant display of midlife crisis and henpecked rebellion, Bonnet commissioned the construction of a ten-gun, sixty-ton sailing sloop (aptly named, in what must have been a nod to his marital strife, the Revenge), hired a crew of seventy swarthy seamen, and slipped off into the Barbadian sunset to become a pirate.
Like many in the occupation, Bonnet soon found himself the owner of a shiny new nickname, though chances are that his moniker, “The Gentleman Pirate,” was not coined entirely in compliment. With little knowledge of sailing, let alone the unwritten rules of high seas banditry, Bonnet wore his incongruity like a badge: his ship was purchased, not stolen, his men were paid wages, not booty, and his bedside manner still reeked of the polite society from which he came, a fact that left the aspiring pirate continuously befuddled by the lack of propriety among his new body of bedraggled peers.
In spite of these shortcomings, Bonnet’s first dip into the pool of piracy was surprisingly successful. Depending largely on the knowledge of his quartermaster (and the general willingness of merchant ships to humor those who hoisted the Jolly Roger), Bonnet made his way up the coast from the Carolinas to New York, rounding up and raiding the easy quarry of the well-traveled shipping lanes. Unfortunately, Bonnet’s somewhat misplaced confidence in his pirating chops increased in direct proportion to the plunder he collected. Having grown a bit big for his breeches, the dilettante picked a wildly injudicious fight with a fully-armed Spanish man-of-war, an experience that left his ship, his crew, and Bonnet himself all half dead.
Fortunately, it was around this time that Bonnet made the acquaintance of a particularly charismatic captain, one Edward Teach, better known as the dreaded pirate Blackbeard. Appealing to Bonnet’s wounded strength, pride, and aristocratic sensibilities, Blackbeard suggested that they strike up a partnership, offering to increase both their profits while relieving Bonnet of the weary task of managing a pirate ship. Delighted to have found another civilized soul, Bonnet took Blackbeard up on his offer, taking his rest in the comfortable quarters of the ships as they ploughed through the merchant lanes of the Eastern Seaboard. Unfortunately, when Bonnet pronounced himself fit to sail alone again, he found his crew less than thrilled at the prospect of leaving Blackbeard’s command and the wily pirate more than willing to indulge their desire to stay. Feeling bullied, betrayed, and in utter despair of ever understanding the nuances of pirate life, Bonnet wanted out.
Ever eager to lend a helping hand to his interminably dupable compatriot, Blackbeard stepped forward with a plan to help facilitate Bonnet’s early retirement, offering to stand guard over the men’s treasure while Bonnet traveled to the mainland to pursue a pardon from the governor. The grateful Bonnet agreed, but, upon his return from Bath, was shocked to find the Revenge robbed, his supplies stolen, and all but twenty-five sullen, marooned sailors vanished. Not surprisingly, Blackbeard was nowhere to be found.
Bonnet was in a bind. His pardon hinged on his renouncement of piracy, though with no food or provisions—and little chance of recouping the loss through legitimate means before the onset of the Atlantic hurricane season—he was left with little choice; he had to raise the black flag. Though Bonnet swore revenge on his perfidious friend, Blackbeard’s lessons were well learned: Bonnet was swift and brutal in his conquests, taking what he could use to fill his stores, patch his boat, or replenish his men, and burning the rest. When his reserves were filled, he made his way into the shallow, sheltered waters of the Cape Fear River to wait out the season.
Unfortunately, what made the isolated riverway the perfect hiding place also made it the perfect place for a trap. Shortly after dropping anchor, Bonnet spotted a ship making its way upriver and, never one to turn down easy pickings, dispatched a small party to capture it. As the men rowed closer, however, they realized that the swiftly approaching vessel was on no innocent river-cruise and its proximity no accident. Heavily loaded with weaponry and lawmen, the ship had come to take them in.
To Bonnet’s credit as a pirate, he fought a good, dirty fight. Despite being outnumbered three to one, he and his men resisted doggedly for hours, with Bonnet threatening to blow up every ship in Charleston Harbor—then his own—before being arrested and taken to Charleston. Upon arrival, the combination of the pirate’s blue blood and brigadier charm aroused such sympathy in the city’s people that there were rumors of riots in the streets in demand of his release. In spite of protestations, however, the Gentleman Pirate had finally come to the end of his journey. Just over a year after leaving his comfortable plantation home in Barbados to pursue the pirate life, Stede Bonnet marched to the center of White Point Gardens and, along with twenty-one of his men, was hanged.