Eric Jay Dolin

Introduction -- Black Flags, Blue Waters

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At the end of April 1726, Captain John Green was finally ready to leave. The last of the food, water, and supplies had been hoisted aboard the Elizabeth, which was tied to a wharf in Jamaica’s capacious Kingston Harbor. Green and his sixteen-man crew were about to sail across the Atlantic to Africa’s Guinea Coast to pick up a cargo of slaves, the main labor source for the island’s cruel economy. Jamaica’s vast and lucrative sugar plantations brutally employed tens of thousands of slaves to do the backbreaking work of harvesting and processing sugar cane so that an ever-increasing number of people throughout the British Empire could sweeten their tea, coffee, and cakes—most of these consumers blissfully unconcerned about the horrors perpetrated to delight their palate. The death rate was so high on these plantations that the owners needed to continually replenish their supply of slaves to keep up with the growing demand for sugar. Without the services of men like Green and his crew, Jamaica’s economy would eventually grind to a halt.

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Not long after the Elizabeth departed from Jamaica’s crystal blue waters, the trouble began. Captain Green, and his first mate, Thomas Jenkins, quickly earned the enmity of the majority of the crew, who claimed that the two men had subjected them to “bad usage,” and treat ed them “barbarously . . . like dogs.” Twenty-seven-year-old boatswain William Fly channeled this anger and began plotting a mutiny. In the dead of night on May 27, when the Elizabeth was hundreds of miles from the American coast, Fly and his coconspirators decided it was time to strike.

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Just after one in the morning, Fly, who was standing watch, gave the signal. Tense with anticipation of the violence to come, he and four others strode across the main deck and approached Morrice Cundon, who was manning the helm. Fly leaned in close and whis- pered menacingly in Cundon’s ear, “Damn you, if you stir hand or foot, or speak a word, I’ll blow your brains out.” To drive his threat home, Fly lifted his shirt to expose the gun tucked into his trousers. Petrifed, Cundon watched as Fly climbed down the companionway to the captain’s cabin below, with crewman Alexander Mitchell following closely behind.

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Violently rousing the startled Captain Green from his bed, the two mutineers hauled the struggling officer to the main deck. As they were about to pitch him into the sea, he screamed, “For God’s sake, boatswain, don’t throw me overboard, for if you do I shall go to hell.” Relishing his new position of power, Fly coolly ordered the captain to repeat after him, “Lord have mercy upon my soul,” and then Fly, Mitchell, and a crewman named Winthrop threw Green over the rail. Reluctant to accept his fate, in a last-ditch effort the struggling captain grabbed hold of the mainsheet with a vise-tight grip. It was, however, only a momentary reprieve. As Green dangled above the waves, Winthrop swung a cooper’s broadax in a mighty arc, bringing it down on the hapless captain’s wrist, severing his hand and launching him into the deep.

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Their bloodlust still raging, the mutineers now searched for their next victim—Jenkins. Quartermaster Samuel Cole yelled to the mate, “Come out of your cabin you dog.” But Jenkins, who had heard Green struggling with his executioners just moments before, would not budge. Instead he pleaded, “For the Lord’s sake, save my life.” The mutineers hauled Jenkins out to the main deck, where Winthrop shattered his shoulder with his now bloody broadax, shouting, “He should go over after his commander!” as he threw the first mate overboard. Bobbing in the water, Jenkins called out, “For God’s sake, throw me a rope.” But there would be no help. The mutineers controlled the vessel, rechristening it Fame’s Revenge. Their reign as pirates had begun.

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After electing Fly captain the pirates set a new course for the American coast in search of prey. Fame’s Revenge, a two-masted, square-rigged vessel called a snow, was not particularly formidable, boasting just four cannons and two mounted swivel guns, but it was powerful enough to fulfill its crews’ criminal designs. Over the next few weeks, Fly and company, boastfully calling themselves “Gentlemen of Fortune,” plundered three merchant vessels between North Carolina and New Jersey, taking a number of prisoners along the way. The most important prisoner was William Atkinson, the former captain of the merchantman Bonetta, who had been hitching a ride to Boston on one of the now-captured vessels. Since Atkinson was quite familiar with the local waters, Fly gave him a choice— either pilot Fame’s Revenge to New England or the pirates would “blow his brains out.”

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A reluctant Atkinson took up the task, and around June 12, Fly ordered him to direct the snow to Martha’s Vineyard, where the pirates hoped to get water and wood. Atkinson, however, had other plans. He purposely missed the Vineyard, and Fame’s Revenge was well past Nantucket before Fly realized they were off course. Incensed by Atkinson’s deception, Fly threatened to kill him but thought better of murdering his best pilot. Instead, he let Atkinson continue, ordering him to set a new heading for the waters to Nova Scotia, where the New England fishing fleet was gathered. If everything went according to plan, once there, Fly would be able to discard Fame’s Revenge, a sluggish sailer, and upgrade to a better vessel, one that offered greater speed and agility.

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Even before he had intentionally veered off course, Atkinson had been scheming. He was eager for a chance to take the snow, and he had shared his inchoate plan with a few of his fellow prisoners. In fact, Atkinson had often thought about what he would do if pirates took one of his own ships, and he had vowed that if he were captured, he would “humor” the pirates “till he could see his opportunity to rise upon them.” All Atkinson needed was an opening.

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By the morning of June 23, Fame’s Revenge was on Browns Bank, about sixty miles south of Nova Scotia, and a favorite haunt of New England fishermen in search of the mighty cod. With their black flag—the universal symbol of pirates—raised aloft, Fly and his men quickly overtook the James, a fishing schooner out of Marblehead. But Fly wanted a faster vessel, so when another promising schooner hove into view, he placed the bulk of his crew on the James to hunt it down.

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Fly’s zeal for a faster vessel proved to be his undoing. Just three of his men remained on Fame’s Revenge, and only one of them was fit for duty; another was in irons on suspicion of mutiny, while the third had gotten into the liquor and was three sheets to the wind. At the same time, there were fifteen prisoners aboard, a few of whom were unshackled.

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Not long after the James departed on its piratical errand, Atkinson, who was at the bow of Fame’s Revenge, informed Fly that he saw another fishing vessel in the distance. Thinking that this might be the opportunity he was waiting for, Atkinson then pretended to see a few more vessels, and he excitedly told Fly that he would soon “have a fleet of prizes.” When Fly, who was on the quarterdeck near the stern, protested that he only saw one vessel through his spyglass, Atkinson bade him to come forward to take a closer look. In a move that proved Fly was neither a great pirate nor a good judge of men, he left his two loaded guns and sword on the quarterdeck as he joined Atkinson at the bow. Suspecting nothing, Fly sat on the windlass and took out his spyglass to scan the horizon.

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While Fly’s attention was thus engaged, Atkinson grabbed the unsuspecting and feckless pirate lord, pinioning his arms behind him. At that moment, two other prisoners, who had also committed themselves to rise up when the time was right, rushed forward and took hold of Fly, while Atkinson sprinted aft to retrieve one of Fly’s guns. When Atkinson rushed back to the bow, he pointed the weapon at Fly, coolly informing him that “he was a dead man if he did not immediately submit himself [to be] his prisoner.”

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Hearing the commotion, the only other pirate fit for duty rushed up the ladder and onto the main deck. Atkinson spun around, struck him on the head with the butt of the gun, and subdued the man with the help of another prisoner. Fly and his followers were soon in chains. With that, Fly’s short, bloody, and almost farcical career as a pirate captain came to an abrupt end.

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Atkinson immediately set a course for Boston. Meanwhile, the pirates on the James, shocked to see Fame’s Revenge leaving, chased it into the night. But the skilled sailor Atkinson was able to lose his pursuers in the covering darkness. Over the next few days, the men aboard Fame’s Revenge were subjected to Fly’s incessant ranting. He “cursed himself, and her that bore him,’ as well as “the very heavens, . . . the God that judged him, [and] all rovers that should ever give quarter to [or spare] Englishmen,” rather than put them to death upon capture. He also wished that “all the devils of hell would come and fly away with the ship”—a fate that he no doubt thought was better than that which awaited him in port.

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On June 29, Fame’s Revenge docked in Boston, the largest and most vibrant port in the American colonies. The shackled pirates were thrown into the town jail, a gloomy stone edifice with walls three feet thick and a massive oak and iron door, the keys to which were more than a foot long. The speedily convened Special Court of Admiralty ruled on July 5 that Fly and two of his men should be hanged for piracy, while the fourth, the drunkard and, as it turns out, a simpleton, was granted a reprieve.

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For a week after sentencing, the pirates were the talk of the town, and the intense focus of Cotton Mather’s ministrations. A third-generation Puritan preacher, and arguably the most famous man in the American colonies, Mather visited the condemned men and pleaded with them to renounce their crimes and repent before God. at was the only way, Mather argued, that they could “escape the Damnation of Hell” after their date with the gallows.

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The following Sunday, Mather preached a sermon at Boston’s Christ Church (the modern-day Old North Church), decrying the pirates’ heinous acts and glorifying the rule of an all-powerful and merciful God. Two of the pirates, who had succumbed to Mather’s entreaties and repented, were on hand to listen and serve as objects of pity for the parishioners filling the church’s pews. Fly, however, refused to attend, declaring that “he would not have the mob to gaze upon him.” Fly also cheekily told the earnest but long-winded Mather that he couldn’t repent and disavow the actions he had taken because he had no remorse, and would not “go out of the World with a lie in my mouth.” 

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Two days later, a cart was brought to the jail to transport the condemned to the place of execution at the harbor’s edge. Despite the fact that Fly, in a “sullen and raging mood,” had refused to eat for nearly a week, taking only an occasional drink, he was surprisingly energetic. According to a witness, “Fly briskly and in a way of bravery jumped into the cart,” while his two fellow convicts solemnly climbed aboard. Thousands of people lined the streets, eager to witness the procession of shame. Fly, Mather said, was intent to die “a brave fellow.” Holding a nosegay in his hand, Fly even complimented some of the spectators along the route. He “nimbly mounted the stage” set up under the gallows, and smiled at the assembled throng. en, his bravado fully on display, he reproached the hangmen for “not understanding his trade,” and proceeded to retie the noose so that it would function properly.

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Three local ministers offered prayers, and each of the pirates was given a chance to share his last words. Two of them took the time to pray and warn the spectators to avoid the sinful temptations they succumbed to, such as cursing, drunkenness, and Sabbath-breaking. When it came time for Fly to speak, Mather hoped he would finally admit his failings before God. But that hope was in vain. With the noose around his neck, Fly defiantly looked out upon his audience and said he “would advise the masters of vessels to” treat their men well, or risk having them mutiny like he had done. Despite Fly’s failure to accept responsibility for his actions, and his lack of remorse, Mather still had a small sliver of satisfaction. Just before Fly was to be sent swinging to face the “judgment to come,” he noticed that the pirate’s hands and knees were trembling. As well they should be, Mather must have thought, for the unrepentant soul has much to answer for in the next world.

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After the execution, the pirates’ bodies were rowed out to Nix’s Mate, a small island in Boston Harbor about five miles from the town, where Fly’s two associates were buried. But Fly, the director of this sad and tragic story, was “hung up in irons, as a spectacle for the warning of others, especially seafaring men.”

 

The warning was hardly necessary. Fly’s spectacular, bloody, and brief piratical campaign was the last gasp of the so-called Golden Age of Piracy, which started in the late 1600s. This was the most dramatic era of maritime marauding the world has ever known, when pirates wreaked havoc across the Atlantic and the Indian Oceans. It produced such iconic characters as Captain William Kidd and Blackbeard, along with thousands of other pirates whose names are less familiar, but whose despicable deeds are often just as riveting. So powerful is the pull of the Golden Age that, in most people’s minds, it is virtually synonymous with piracy.

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Much has been written about that time period, and this book adds to that literary lineage, but with a twist. Rather than focusing broadly on this era, Black Flags, Blue Waters zeros in on the history of the pirates who either operated out of America’s English colonies or plundered ships along the American coast. From the early 1680s to 1726, these pirates had an exceedingly close, often tempestuous, and frequently deadly relationship with the colonies. While this arrangement began with a warm and financially lucrative embrace, it eventually ended in a bloody war against pirates punctuated by scores of hangings from Boston to Charleston. Black Flags, Blue Waters explores the fascinating origins and nature of this volatile relationship, and in so doing reveals one of the most gripping stories of the American experience.

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Of course, America’s connection to piracy did not abruptly end in 1726 with the execution of Fly. Most notably, in the early to mid-1800s the United States vanquished both the Barbary pirates who harassed American ships o the coast of North Africa, and Spanish pirates who waylaid American shipping throughout the Caribbean and off the East and Gulf Coasts of North America. More recently, twenty-first-century Somali pirates have seriously disrupted not just American, but the world’s maritime commerce, by overpowering ships within striking distance of Somalia and holding them for ransom. The exploits of these and other pirates with an American connection, however fascinating, are beyond the scope of this book. Instead, what follows is a narrative and chronological history of America’s pirates during the Golden Age.

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At the core of Black Flags, Blue Waters are the pirates themselves, who made the fateful choice to attack and plunder on the high seas. But before one can talk about pirates, it is necessary to define the term and differentiate it from privateer. The word pirate first appeared in the fourteenth century and derives from the Greek, peiratēs, and the Latin, pīrāta, both of which broadly mean “to attempt, attack, assault.” More specifically, in the maritime context, pirates are people who steal at sea; they are the oceanic equivalent of land-based robbers.

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For as long as people have taken to the sea, there have been pirates. Every culture and country whose ships have dipped a paddle or oar into the salty brine, or raised a sail to harness the wind, has contended with what the Greek poet Homer called “sea-wolves raiding at will, who risk their lives to plunder other men.” Captain John Smith, the controversial English explorer and one of the founders of the Jamestown Colony in Virginia, had it right when he remarked, “As in all lands where there are many people, there are some thieves, so in all seas much frequented, there are some pirates.” And almost two thousand years before Smith, Roman historian and statesman Dio Cassius wisely observed, “There was never a time when piracy was not practiced, nor may it cease so long as the nature of mankind remains the same.” Ancient and modern history is replete with stories about the path of ruin that pirates left in their wake.

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Privateers, in contrast, are men who sailed on armed vessels owned and outfitted by private individuals who had government permission to capture enemy shipping during times of war. That permission was embodied in a “letter of marque,” a formal legal document issued by the government that gave the bearer the right to capture vessels belonging to belligerent nations, and claim those vessels and their cargoes as prizes. The proceeds from the auction of these prizes were, in turn, usually split between the privateers, the investors in the operation, and the issuing authority. Typically, governments used privateers as a means of amplifying their power upon the seas, especially when their navies were not strong enough on their own to wage war. More specifically, by attacking and hobbling the enemy’s maritime commerce and its naval forces, privateers could in inflict a savage economic and military blow designed to help ensure victory. In a nod to both the legality of privateering, and its more than passing resemblance to piratical behavior, some have called it “licensed” piracy.

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As numerous historians and writers have observed, the line between pirates and privateers is often exceedingly thin, to the point of sometimes being undetectable. Letters of marque can be of questionable legitimacy, and, by the same token, those people labeled as pirates might think that they are nonetheless acting in accord with the wishes, implied or stated, of the nations for which they are ostensibly fighting. Muddling matters further is the issue of perspective. Just as beauty is often in the eye of the beholder, one person’spirate may be another person’s privateer. For example, while a privateer with proper papers is viewed as legitimate by the sponsoring nation, those on the receiving end of the privateer’s attacks might well view the privateer as a pirate, the pejorative label only adding to the purportedly ignominious nature of the act.

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This book is about pirates, not privateers, although there is no doubt that some readers will argue that in a few cases the distinction is improperly drawn in one direction or the other. Nevertheless, the focus will be on what famed English jurist and politician Sir Edward Coke (1552–1634) called hostis humani generis, or the “enemy of mankind,” those ocean-borne outlaws who pillaged merchant vessels, usually without regard for the nationality of their victims, breaking the law and blazing a trail of terror on the high seas for private gain.

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At its most elemental, Black Flags, Blue Waters is about men acting like oceanic gamblers, playing the risky and sometimes fatal game of preying on merchant ships in search of treasure. Most pirates failed to achieve great financial success, and had brief careers that often ended in violent death. But that was not always the case. There were some, especially those operating out of the colonies prior to 1700, who were able to retire from piracy with their riches.

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This book is also a history of intimidation and, at times, extreme brutality. Pirates were almost always able to rely on the threat of force to get their victims to submit without violence, but when that approach failed, pirates were willing to fight for what they coveted. The bloodiest encounters, however, were generally not between pirates and their victims, but rather between the pirates and the forces sent to destroy them.

 

This is likewise a story of political intrigue and collusion. In the late 1600s, many colonists heartily encouraged and supported pirates, though such activities outed English law. Those colonists viewed pirates not as dangerous raiders, but as commercial angels, and as friends and family, who enabled the colonies to obtain the goods and money they so desperately desired despite the onerous trade restrictions put in place by the mother country. Some colonial governors went so far as to accept bribes and issue privateering licenses to pirates to give them the veneer of official respectability, even though the governors knew full well that the pirates had no intention of going after England’s enemies, but instead were heading to the Indian Ocean to loot ships carrying the riches of the Muslim world, and bring that wealth back home.

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Finally, Black Flags, Blue Waters is about crackdowns, punishment, and eradication. Reacting to the growing problem of piracy in the late 1600s, England launched political, legal, and naval initiatives that had considerable success in countering the pirate threat. But in the mid-1710s, piracy experienced a resurgence, and the number of pirates exploded. More than ever before they focused their depredations on British ships traveling along the coast of the American colonies. Once viewed by many colonists and their official represen- tatives in a favorable light, pirates were now increasingly viewed as mortal enemies who posed a grave threat to trade. Through a combination of legal, political, and military means, pirates were virtually eliminated by the middle of the 1720s, when Fly and his compatriots swung from the gallows.

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Aside from their actions, Black Flags, Blue Waters explores the question of why pirates pursued such a dangerous and violent life so far outside the legal and social norms of society. Pirates’ motivations are often difficult to discern, especially since we know little of most pirates’ early lives, and almost none of them put their thoughts on paper. Yet, the records of the era, complemented by modern scholarship, are rich enough to make for an absorbing analysis of what drove these men to sail “under the banner of King Death.”

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In the following pages, the reader will meet a rogue’s gallery of maritime plunderers. In addition to the infamous Kidd and Blackbeard, there is Dixie Bull, America’s first pirate; buccaneer extraordinaire Henry Morgan; Thomas Tew, whose success electrified the colonies; gentleman pirate Stede Bonnet, a man out of place; Edward Low, who relished torture and murder; and Samuel Bellamy, who acquired and then lost a treasure worthy of Midas.

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Pirates, however, are not the only dramatis personae who bring this story to life. They are joined by many others, including Edward Randolph, the acerbic English colonial administrator who viewed the pirate-supporting colonies with disdain; “King” Adam Baldridge, who served as ringleader of Madagascar’s most notorious pirate haunt; New York’s money-grubbing governor, Benjamin Fletcher; Lieutenant Robert Maynard, the man who proved that Blackbeard was not invincible; America’s “Robinson Crusoe,” Philip Ashton; and Captain Peter Solgard, who captured thirty-six pirates off Block Island in the summer of 1723.

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Pirates have long been among the most colorful and memorable celebrities in popular culture. Much of this has to do with the impact of books and movies that use pirates as a motif, such as Robert Louis Stevenson’s Treasure Island, and the 1935 film Captain Blood, which launched Hollywood idol Errol Flynn’s career. More recently, Disney’s Pirates of the Caribbean movie franchise, starring the flamboyant, sassy, and charismatic Johnny Depp as Captain Jack Sparrow, has generated a new pirate-mania, further cementing the hold that pirates have on the human psyche. No wonder, then, that pirate costumes are among the most popular donned on Halloween night, and International Talk Like a Pirate Day is observed by legions of devoted fans every September 19.

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Many people view pirates in a romantic light, but there was absolutely nothing romantic about them, other than the legends woven about their exploits after they were gone. That is not to say that pirates were boring. Far from it. While the pirates in the pages that follow can’t compete with the magnetic charms and witty repartee of Captain Jack Sparrow, they are compelling characters nonetheless. And the real story of America’s pirates is even more astonishing and fascinating than any fictional pirate adventure ever written or cast on the silver screen.