6 despicable pirates from history

As world trade burgeoned in the age of colonial expansion, valuable cargoes were transported across the world's oceans, providing vast opportunity for piracy on the seas. Writing for History Extra, Eric Jay Dolin presents six of history's most despicable buccaneers who plundered the seas, from the ports of the American colonies to the Indian Ocean…

Captain Edward Teach, better known as 'Blackbeard', a pirate who plundered the coasts of the West Indies, North Carolina and Virginia. (Photo by Hulton Archive/Getty Images)

The Golden Age of piracy (c1680s–1726) was the most dramatic era of maritime marauding the world has ever known, a period which at its peak saw as many as 4,000 pirates a year wreaking havoc across the Atlantic and Indian oceans. The age of colonial expansion meant that huge quantities of valuable cargoes were being shipped over vast ocean areas and, as European navies were reduced, many experienced sailors who were out of work turned to piracy.


Pirates had an enormous impact on the American colonies. In the early years of the period, there was a warm and financially lucrative acceptance of pirates. When the so-called Red Sea Men plundered Mughal ships in the Indian Ocean in the late 1600s, for instance, they were welcomed in the colonies because the wealth they brought back significantly bolstered local economies.

However, by the 1710–20s, when pirates began focusing their attacks on colonial shipping to the Americas, they were viewed not as commercial angels but as dangerous raiders who posed a grave threat to trade. One early 18th-century chronicler claimed that the merchants of Great Britain “suffered more by” the “depredations” of pirates between 1716 to 1726 than they suffered at the hands of France and Spain during the War of the Spanish Succession (1701–14). The pirates’ relationship with the colonies eventually ended in a bloody war against the seafaring criminals, punctuated by hundreds of pirate hangings throughout the Atlantic world.

Map of Algiers, c1700. It was here that Icelanders, including Ólafur Egilsson, were sold into slavery. (Culture Club/Getty Images)

Pirates made their way into popular literature in the late 17th century where they were transformed into mythical figures. One account that sparked public imagination was A General History of the Robberies and Murders of the most notorious Pyrates, published in 1724 under the pseudonym Captain Charles Johnson. For many years it was thought that Daniel Defoe (of Robinson Crusoe fame) was the actual author of A General History, and that Charles Johnson was just a pen name; but subsequent scholarship strongly points to the mysterious Johnson as being the true scribe.

It was Robert Louis Stevenson’s Treasure Island, first published in 1883, that gave us our modern-day image of a pirate, an image which has been replicated in countless films and books since its publication. Most have heard of Blackbeard and Captain William Kidd, two of the most famous pirates of the Golden Age of piracy. But there were many other pirates, whose names are less familiar but whose despicable deeds are often just as riveting. Here are six of the lesser-known, yet still fascinating pirates from that storied era…


Dixie Bull

In the summer of 1632, fur trader Dixie Bull was traveling along the coast of Maine, USA when disaster struck: a small group of Frenchmen had stolen his shallop [a light sailing boat]. Enraged, Bull hastily commandeered another vessel and gathered a force of 15 armed men to exact revenge on the French. Having no luck in that pursuit, and short on supplies, Bull resorted to piracy. He and his men ransacked two English vessels and attacked a settlement called Pemaquid on the coast of Maine, gaining fame under the name ‘the dread pirate’.

Illustration showing 16th-century french pirates – or 'filibusters'– attacking an American town via the sea. (Photo by Culture Club/Getty Images)
Illustration showing 16th-century french pirates – or ‘filibusters’– attacking an American town via the sea. (Photo by Culture Club/Getty Images)

Over the next couple of months there were periodic sightings of Bull and his men, who apparently had renounced piracy in fear of the fatal punishment that awaited them if they were caught. To make it clear that they wanted no more trouble, the pirates sent a letter to the governors of all the English colonies and plantations “signifying their intent not to do harm to any more of their countrymen, but to go to the southward, and to advise them not to send against them; for they were resolved to sink themselves rather than be taken”.

Bull and his men were never heard from again, and what happened to them remains a mystery. One contemporary account claimed that Bull’s crew “fled eastward”, most likely to French settlements in Canada, and “Bull himself got into England; but God destroyed this wretched man”. Others believe Bull joined the French, or that Indians killed him.


Thomas Tew

During the North American conflict known as King William’s War (1688–1697), in which New England colonists launched attacks on French colonies, many colonial governors gave letters of marque [letters authorising privately owned ships, or ‘privateers’, to capture enemy merchant ships] to men who had no intention of fighting the enemy French. Instead, these crews planned to attack Mughal ships in the Indian Ocean. Since England was not at war with the Mughal Empire, however, attacks on Mughal shipping were, by definition, pure piracy. This fact didn’t bother colonial governors in the least. They not only lined their pockets when issuing fake letters of marque, but they (as well as any investors in the ‘privateering’ cruise) also expected the pirates to return to the colony from which they departed to share the treasure and pay off debts.

In 1691, Thomas Tew (a Rhode Islander by birth) accepted a commission from Bermuda’s governor for a privateering venture to Africa, to take a French fort located on the Gambia River at Gorée. He found backers to provide him with a vessel – the 70-ton sloop Amity – and set off. Yet instead of attacking the French, he and his men sailed to the Indian Ocean, plundered a Mughal ship, and returned to Newport, Rhode Island. They returned with enough treasure so that each of his men walked away with from £1,200 to £3,000 – while Tew collected two to three times that amount.

A relief portrays patrons of a Roman tavern. (Photo By DEA / A. DAGLI ORTI/De Agostini/Getty Images)

Tew wanted to retire, but his men convinced him to return to the Indian Ocean for another round of piracy, and this time Tew purchased a fake privateering license from New York governor Benjamin Fletcher for £300. Commission in hand, Tew returned to Newport in early November, where the Amity was being readied for the voyage. Word of Tew’s plans had spread far and wide, in no small measure because of his boasting, and a great array of men flocked to the wharf to sign on as crewmembers, brilliant images of treasure no doubt firing their imaginations.

Tew should have quit while he was ahead. When he attacked a Mughal ship quite capable of defending itself near the mouth of the Red Sea the following year, the Amity – and Tew – got the worst of it. According to one account, a cannon ball ripped into Tew’s midsection, disemboweling him. After he was killed, his men gave up the chase and sailed to Madagascar. With the Amity in bad shape, and a slow sailer even under the best of conditions, the crew set off down the coast, where they found another vessel and commandeered it. These remnants of the Amity’s crew continued their pirating, never again returning to New York.


Thomas Pound

On August 10 1689, Thomas Pound and 12 armed associates launched their piratical career by capturing a fishing vessel out of Salem, Massachusetts, called the Mary. In subsequent months, the pirates plundered a number of ships in Massachusetts’s waters, and traded the Mary for a bigger and more powerful ship, the Goodspeed.

In late September, Massachusetts’s governor ordered a vessel, manned by 20 soldiers, to bring Pound and his men to Boston to face justice, using deadly force to “subdue” them if necessary. A captain named Samuel Pease was put in charge.

Pease found his quarry in Tarpaulin Cove, off Naushon Island, and he demanded that the pirates “strike to [the] King of England”, but Pound was not cowed. Standing on his quarterdeck, he flourished his sword, and barked across the water: “Come aboard you dogs, and I will strike you presently.”

No sooner had Pound issued this bellicose invitation than the shooting began. Pound took a musket ball to the arm, and one just under the ribs, while Pease was struck in the arm, the side, and the thigh. An hour after the first shots were fired, the soldiers swarmed onto the Goodspeed, getting off one good volley, and then using the butts of their muskets to mercilessly beat the pirates into bloodied submission. When the smoke cleared, four pirates were dead, and most of the rest were wounded, while five of the soldiers were injured. Pease would later die of his wounds.

The men of the Goodspeed were brought to trial in 1690 on charges of piracy and murder, and although 14 of them were found guilty and sentenced to be hanged, for reasons that are not clear, only one was executed.

A 1646 engraving of John Lilburne behind bars. The outspoken critic of successive governments spent half his life imprisoned or in exile. (Photo by Rischgitz/Getty Images)


Lewis Guittar

At the end of April 1700, the French pirate Lewis Guittar sailed into Chesapeake Bay, between Maryland and Virginia, on the La Paix (Peace), capturing several merchant vessels. Then, the HMS Shoreham captained by William Passenger appeared on the horizon. Pandemonium broke out on the pirate ship: 50 prisoners were hustled down into the hold and La Paix was readied for battle. Passenger was relishing the coming engagement, boasting that “this is but a small fellow, we shall have him presently.”

For hours, the two ships pummeled each other with broadsides [cannons on the sides of the ships] – and firing muskets and pistols when within range – but the La Paix was ultimately outgunned. Guittar surrendered – but he had one more trick up his sleeve: using the 50 prisoners as bargaining chips. He ordered his men to lay a trail of gunpowder leading to the ship’s magazine, and then forced one of the prisoners to swim to the Shoreham to deliver the following ultimatum: “Tell the commander in chief if he will not give me and my men quarter and pardon I will blow up the ship and we will all die together.”

Virginia governor Francis Nicholson, who was on board the Shoreham, agreed to grant the pirates quarter [the right to be taken prisoner instead of instant death] and refer them to the mercy of the king. In the end, 26 pirates were killed during the battle, and about half that number was injured, eight of whom would later die of their injuries. Four lay dead on the Shoreham, with many more injured.

Guittar and the rest of his men were shipped to England, where the king, feeling unmerciful, put them on trial. Ultimately, Guittar and more than 50 of his crew were found guilty and executed.


Edward Low

Edward Low started his piratical career in 1721 in the Caribbean. Over the next few years, Low blazed a path of destruction, becoming, according to one contemporary account, “the most noted pirate in America” – and certainly the most vicious. He seemed to relish torturing and killing his victims. When the captain of one boarded ship had the temerity to cut the rope holding a bag of gold coins, so that it fell into the ocean rather into the pirates’ hands, Low killed the man – after cutting off his lips and roasting them in front of his eyes. Then, Low killed the captain’s entire crew of 32 people.

On another occasion, when Low seized casks of wine and brandy from a captured vessel, its captain asked if Low would be so kind as to write a sentence or two stating that he had taken the liquor, so that the owners wouldn’t think that the captain had dishonestly sold it and pocketed the profits. Low cheerily agreed, and said that he would be right back with what the man requested. A few minutes later, Low returned with two loaded pistols, and “presenting one at [the captain’s] bowels”, he told the petrified man that this “was for his wine, and discharged it”, and then he pointed the other pistol at the captain’s head, saying this one is “for your brandy” and fired.

Although one of Low’s ships was captured by a British naval ship, and 26 of the pirates on board were hanged in Newport, Rhode Island, Low continued to plunder ships until the spring of 1724, when he suddenly disappeared from the historical record.

Engraving from 'The History and Lives of the most Notorious Pirates', showing pirates boarding a vessel in the West Indies. (Photo by Culture Club/Getty Images)
Engraving from ‘The History and Lives of the most Notorious Pirates’, showing pirates boarding a vessel in the West Indies. (Photo by Culture Club/Getty Images)

John Phillips

John Phillips and four other men became pirates during the summer of 1723, stealing a schooner off Newfoundland and christening it the Revenge. They proceeded to plunder more than 30 vessels up and down the American coast. In late March 1724, Phillips overpowered a Virginia ship, whose captain, John Mortimer, refused to hand over his valuable geese and hogs. This infuriated Phillips, leading to a yelling match between the two, which quickly escalated when Mortimer, apparently a brave but reckless man, grabbed a handspike and struck Phillips, who drew his sword and ran Mortimer through, killing him.

Phillips forced many men to become pirates against their will, and that was his ultimate undoing. A few of the forced men – including John Fillmore (the great-grandfather of Millard Fillmore, the 13th president of the United States), Edward Cheesman, Isaac Lassen, and Andrew Harradine – began to quietly conspire to rise up when the time was right. That time finally came on April 18, 1724, about 40 miles southeast of Cape Sable, Nova Scotia.

The prisoners were doing some repairs on the ship, when one of them gave the signal. Cheesman jumped up and grabbed the nearest pirate, pitching him overboard. A split second later, Lassen grabbed Phillips’s arm, while Harradine reached for an adze [a cutting tool similar to an axe] and brought it down on the captain’s head, instantly killing him. In the meantime, Fillmore dispatched another pirate with a broadax, while the coconspirators lunged at the gunner and flung him over the rails. The remaining pirates, seeing the force arrayed against them, gave up.

Harradine piloted the pirate’s ship and remaining crew to Boston, carrying the severed heads of Phillips and his boatswain in a barrel full of salt. The subsequent trials of Phillips’s remaining men resulted in four being found guilty. Two were given a reprieve and the other two were hanged on 2 June 1724.


Eric Jay Dolin lives in Marblehead, Massachusetts. This article is based on his recent book, Black Flags, Blue Waters: The Epic History of America’s Most Notorious Pirates (WW Norton, £21).