Brittany’s Women Pirates

With its extensive coastline and key position alongside major trade routes, Brittany has long enjoyed a close relationship with the sea. However, it was not just the region’s fishermen and traders that commanded the waves; generations of Bretons long constituted the backbone of the French Royal Navy, playing a leading role in the colonisation of New France and the West Indies. Some of these Breton mariners have left an indelible mark on history while others are perhaps more famous for their misdeeds.

Breton pirates or privateers – there are legal differences between the two terms but the paths from one state to the other were well sailed in the murky waters of diplomatic niceties – such as Jean de Coatanlem, Duguay-Trouin and Robert Surcouf amassed great prestige and wealth from their buccaneering exploits on the high seas. Other Breton pirates are perhaps not as well known today as they once were and the adventures of two particularly remarkable women are well worth retelling here; stretching as they do from one of the bloodiest conflicts of Medieval Europe to the golden age of the pirates of the Caribbean.

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An element of the Hundred Years’ War, the Breton War of Succession (1341–1364) saw the House of Montfort, supported by the King of England, battle against the House of Blois, supported by the King of France, for the right to rule Brittany. The chief claimants were Jean de Montfort, half-brother of the last Duke of Brittany, and his niece, Joanna de Penthièvre, who was married to Charles de Blois, the French king’s nephew. After a protracted conflict, de Montfort emerged victorious after winning the decisive battle of Auray in 1364.

However, one of the war’s early battles took place under 14km (10 miles) away in the city of Vannes. Having declared for de Montfort within weeks of his brother’s death, control of the city changed hands through four devastating sieges in 1342. During the final siege, the Breton commander of the de Blois garrison, Olivier de Clisson, was captured. He was subsequently exchanged for the English Earl of Stafford and a relatively modest ransom which was seized upon by the de Blois camp as indicative of de Clisson having intrigued with the besiegers.

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Towards the middle of the following year, de Clisson and a dozen other Breton nobles were invited to attend a grand tournament in Paris; here they were promptly seized and imprisoned. De Clisson was accused of ‘several treasons and other crimes perpetrated against the king and the crown of France’ and summarily executed. To add insult to injury, his body was publicly humiliated; his corpse hung from a gibbet in Paris and his head displayed on a pike in the city of Nantes – outrages usually reserved for low-born criminals.

The treachery of the King of France, Philippe VI, consumed de Clisson’s widow, Jeanne de Belleville, who swore revenge. Selling her estates before they could be confiscated by the French king, she raised a small army and began attacking French forces in the Breton Marches; her wrath first falling on Château Thébaud whose occupants, including women and children, she slaughtered, leaving just two men alive to tell of the stronghold’s fate. The forces of France pursued her vigorously, forcing her to flee into Brittany and after a brief sojourn in the north-west of the region, to eventually re-group with Bretons in England.

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Finding land attacks impractical, she acquired and outfitted three ships; painted deathly black, flying blood red sails, and would personally lead her ‘Black Fleet’ from her flagship, My Revenge. Her fleet scoured the waters of the Channel and the north coast of France in search of targets; all French vessels whether warships or traders, were fair game but de Belleville did not play fair. She became renowned for her ruthlessness; killing entire crews and beheading nobles and anyone linked to the exercise of French authority, sometimes she was even said to have wielded the axe herself.

It seems she always left at least one survivor who was charged to tell the French king of her revenge. Her exploits clearly affected French maritime trade along its northern coast and it is said that, at times, she even sacked coastal settlements although there is no real evidence to support the latter charge. At the request of King Philippe VI, Pope Clement VI unsuccessfully petitioned England’s King Edward III to put an end to the actions of this “Breton Tigress”. 

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Some authors claim that de Belleville’s violent vengeance spanned some 13 years and that she continued to attack French shipping after the death of King Philippe IV in August 1350. However, this is unlikely for two reasons. Firstly, in late 1344, her flagship was wrecked after a battle with a French warship and in 1348 she married one of King Edward III’s military commanders, Sir Walter Bentley. Bentley had served in Brittany since 1342 and famously staged a night-time raid on the French forces besieging Vannes that year.

In September 1350, Bentley was appointed Governor or King’s Lieutenant in Brittany. During his tenure he forbade pillage and to help prevent the potential attraction to it, he secured increases to his soldiers’ pay – both unusual actions for a Medieval leader. An active commander, he lifted the sieges of Ploërmel and Fougeres in 1351 and took the war into France, raiding along the Loire valley and later led an outnumbered Anglo-Breton force to a bloody victory in the battle of Mauron where he was severely injured in August 1352.

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It was not just the forces of the French king that Bentley battled against; he and his wife had to deal with the machinations of Ralph of Cahors, the King’s Lieutenant in the adjoining province of Poitou, who had wrested control of de Belleville’s estates from France and now considered them his own. In 1349, the King of England ordered that the estates be returned to Bentley but after he was replaced as Governor in April 1353 he was instructed to transfer his wife’s estates as part of a treaty with the new Duke of Brittany. This Bentley refused to do and he was consequently imprisoned in the Tower of London while the King considered his case; eventually finding in his favour.

The Bentleys enjoyed great estates in Brittany and settled in the castle at Hennebont, west of Vannes. The Duke of Brittany seems to have borne no grudges against this medieval power couple because in January 1357, he granted them the Barony of La Roche-Moisan. Sir Walter died in December 1359, followed just weeks later by his wife; a rather comfortable end for a pirate whose actions had once earned her the sobriquet: ‘Lioness of the Sea’.

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Born into a minor noble family in central Brittany in August 1661, Anne Dieuleveult is another of the very few reputed female pirates. It is not known how she came to end up in the Caribbean; some have suggested that she was taken there from the north coast town of Morlaix by the man she subsequently married, while others believe that she was one of the contingent of Filles de Roi or ‘Daughters of the King’ – mainly impoverished young women who were provided with paid passage to New France in order to marry settlers and increase the population of the colonies. 

Dieuleveult is thought to have arrived on the island of Tortuga, off the northwest coast of Hispaniola, sometime before 1680. This was a settlement that owed its very existence to pirates and privateers who had, time and again, wrested it from Spanish over-lordship over the previous fifty years. From being a hideaway to careen ships, replenish fresh water supplies and hunt for game, the island was now home to a motley assortment of multilingual and multinational pirates, privateers, hunters, planters, traders, indentured servants and African slaves.

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The island gave birth to the word buccaneer as we now understand it and was an important base for pirates and privateers, being the home of the notorious confederation of buccaneers knows as the ‘Brethren of the Coast’. The majority of the island’s buccaneers were men from France, England and the Netherlands but there were also sizeable numbers of escaped slaves in their ranks. Life in 17^th century Tortuga was not for the fainthearted; deaths from disease and violence were commonplace and women, particularly those of European descent, were very scarce.

We do not know how Dieuleveult fared in her early years in the colony but she married another Breton, the former buccaneer Pierre Lelong in 1684. Lelong seems to have given up his career in piracy when he and a dozen adventurers settled Cap François (now Cap-Haitien), on the north coast of Hispaniola, in 1670, subsequently establishing successful plantations. (His settlement flourished and later became the capital of the colony of Saint Domingue which in the 18^th century was the world’s leading producer of sugar cane and an important hub in the slave trade.) In July 1690, just six years into the marriage, Lelong was killed in a brawl and Dieuleveult soon married another buccaneer, Joseph Chérel. The couple survived the capture and plunder of Cap Francois by Spanish forces in January 1691 but Chérel died during a brawl a few years later, leaving Dieuleveult a wealthy widow with two children to raise.

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Legend tells that she made quite an impression on the man who would become her next husband; notorious former Dutch pirate, Laurens de Graff. It was said that de Graff insulted Dieuleveult who promptly challenged him to a duel of honour; de Graff unsheathed his sword only to find himself facing a cocked pistol whereupon he remembered his chivalry and declared that he could not fight a woman. He was apparently so impressed that he made an immediate proposal of marriage. We will never know what truth lies in this tale but we do know that the couple married in July 1693.

De Graff was described by no less a judge than Henry Morgan as “a great and mischievous pirate” and seems to have enjoyed a long and lucrative career on the Spanish Main, Caribbean Sea and Gulf of Mexico. References to his exploits span over two decades: in March 1672 he was one of the leading figures in a pirate raid on Campeche in Mexico, taking the town and a merchant ship loaded with over 120,000 silver pesos. De Graff was known to often change his flag ship by upgrading to a stronger captured vessel and by 1679 commanded 200 men aboard his 28-gun frigate, Tigre. This he surpassed in 1682 with the bloody capture of the 240-ton Spanish Armada de Barlovento frigate, Princesa, along with the payroll for the Spanish garrisons on Hispaniola and Puerto Rico; over 120,000 silver pesos.

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The following year, de Graaf, now in possession of a privateering licence from the Governor of Saint Domingue, joined forces with two other privateers for an attack on the Mexican port of Veracruz; the combined party amounted to five large ships and eight smaller vessels with over 1,300 men. The town fell to the pirates after just thirty minutes and was plundered over the following days. Many of the townsfolk were tortured to reveal their treasures and a sizeable ransom was demanded for the freedom of the town’s 6,000 inhabitants.

A few months later, de Graaf led another joint enterprise preying on coastal traffic around the busy Colombian port of Cartagena. The Spanish Governor sent out three heavily armed ships to see off the pirate flotilla but the pirates chose to fight rather than flee and their audacity and superior seamanship saw them prevail in a bloody four hour long battle. De Graff now transferred his flag to the newly captured, 40-gun vessel, San Francisco.

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In July 1685, de Graaf joined his forces with another veteran pirate to create a flotilla of ten ships, six sloops and over a dozen smaller craft for a raid on the Mexican port of Campeche. After a protracted battle, including seeing off two Spanish relief columns that arrived five days after the initial assault, the town was taken but the spoils were disappointing. Over the next two months, troops of pirates ravaged the surrounding countryside in search of plunder while a hefty ransom was demanded for the town and its inhabitants but this time the Spanish Governor refused to pay. In their frustration, the pirates set the town ablaze and threatened their hostages. Met with another refusal to accede their demands, the pirates began their executions but de Graaf halted the slaughter before the death toll reached double figures. A strong Spanish squadron was despatched to bring de Graff to justice and after hunting for over six weeks finally tracked him down in the Gulf of Mexico. Despite being outmanned and outgunned, de Graff managed to outmanoeuvre and outshoot his pursuers in a battle that lasted all day.

Having become a French subject in 1685, de Graaf seems to have moved away from outright piracy to mixing privateering with an official position on the Governor of Saint Domingue’s staff and the outbreak of the Nine Years War in May 1689 found him serving at Cap François. This is likely the time that he first met Dieuleveult. In December 1689, de Graff began a five month blockade of the northern cost of Jamaica, capturing many English ships and plundering plantations along that coast. 

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At the end of June 1694, de Graff, with the dual role of buccaneer chief and King’s Lieutenant, was appointed Second in Command of a fleet of 22 ships, including naval warships and 3,200 men assigned for the invasion of Jamaica. At the end of the following month, he commanded the landing party of 1,500 men who overran the 250 men defending Carlisle Bay and plundered the area.

In retaliation, a joint Anglo-Spanish force crossed into French Saint Domingue towards the end of May 1695 and quickly brushed aside de Groff’s defenders, capturing Cap Francois and plundering the town and its surrounding plantations. In June, Port-de-Paix was blockaded and the town fell the following month; amongst the captives taken were Dieuleveult and her children. The invaders did not press their advantage and take the colony; international cooperation disintegrated over petty quarrels about the division of the spoils.

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De Graff now seems to disappear from the records and is not noted in the musters of the massive French invasion force that captured Cartagena in April 1697. Perhaps there were questions about his role in the defence of Cap Francois or the terms of ransom for his wife forbade action against her Spanish captors? Dieuleveult and her children were released in 1698 and returned to Saint Domingue. Upon the death of de Graaf in May 1704, his wife inherited a sizeable estate and successful sugar plantation and died at home in January 1710.

There are stories that claim Dieuleveult accompanied de Graaf on his buccaneering raids, fighting by his side and sharing command of his ship. Some elaborations even go so far as to say that she took part in the invasion of Jamaica in 1694 and that she took command of de Graaf’s flagship after he was killed during an attack on a Spanish ship, fiercely leading the crew in an ultimately unsuccessful fight. Alas, these stories are likely fictional; by the time of their marriage, de Graaf was no longer a buccaneer but an officer of the Crown and an independently wealthy one at that.

It is unclear when or where Dieuleveult died and perhaps that is just as it should be. Sometimes, remarkable lives lead to forgotten ends and what better way to end a pirate story than with the mist of a little mystery?