Buccaneers of Brittany

Bounded to the north by the English Channel, to the south by the Bay of Biscay and to the west by the Atlantic Ocean, Brittany has some 2,900km (1,800 miles) of coastline peppered with estuaries, busy ports, small harbours and naval bases. The sea has always played an important part in the life and soul of Brittany; from the arrival of the early Christian saints in their stone boats to the departure of hundreds of vessels carrying men to join the Free French Forces in England in the final days of June 1940.

Maritime activities such as fishing and international trade were always key parts of the Breton economy. The peninsula was located on the main sea routes between the big trading nations of Spain, Portugal, England and the Netherlands; in the 16th century, there were 123 significant working ports in Brittany and many, such as those of Saint-Brieuc and Brest expanded into international hubs. The region also benefited from the expansion of France’s colonial empire and navy: the ports and shipyards at Saint-Malo, Brest, Nantes and Lorient were constantly improved; the latter was also headquarters of the French East India Company. A significant proportion of Brittany’s non-agricultural workforce were thus employed building, servicing and victualling its shipping industry.

With such a strong mercantile heritage, it is not surprising that Bretons came to constitute a leading component of the French navy and also played an important role in the colonisation of New France and the West Indies. Some of these Breton sailors – women and men – have left their mark on history.

The Lioness of the Sea

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.

Battle of Auray

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 IV de Clisson, was captured. He was subsequently exchanged for the 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. Towards the middle of the following year, de Clisson and a dozen other Breton nobles were invited to attend a tournament in Paris; here they were 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.

Execution of Olivier de Clisson

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, she raised a small army and began attacking French forces in Brittany; 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 eastern Brittany and after a brief sojourn in the north west of the region, eventually re-group with loyal Bretons in England.

Finding land attacks impractical, she acquired and outfitted three ships; painted deathly black and carrying blood red sails, and would personally lead her Black Fleet from her flagship, My Revenge. Her fleet scoured 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 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 is northern coast and it is said that, at times, she even sacked coastal settlements. At the request of the King Philippe VI, Pope Clement VI unsuccessfully petitioned England’s King Edward III to put an end to the actions of this “Breton tigress”. 

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.

Jeanne de Belleville

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. 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.

It was not just the French 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 the French and now considered them his. In 1349, the King 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 weeks later by his wife; a rather comfortable end for a pirate whose actions had once earned her the sobriquet ‘Lioness of the Sea’.

Medieval pirates

Throughout the Middle Ages, the sea was widely regarded as an area beyond rules and treaties; a wilderness outside the law. As such, the concept of piracy was vague and ill-defined and became especially opaque when rulers granted official sanction authorising men to raid the shipping of an unfriendly nation or recalcitrant noble.

The Governor of the Sea

Jean de Coatanlem, from the north coast town of Morlaix, is perhaps the most well-known Breton privateer of the late medieval period although his services at sea were licenced in support of the King of France rather than his nation’s sovereign. He seized a number of well laden English and Flemish merchant vessels in the English Channel from 1475 onwards and invested his prize money in new ships. Within a decade, his flotilla included about ten ships of between 150 to 250 tons and a large number of smaller boats from 30 to 80 tons.

There are stories that claim he mustered his forces to save his town when the port was raided by three English pirate ships in 1484 and that after defeating the raiders, he launched a punitive attack on the English port of Bristol, destroying large parts of the city and taking several notable hostages.

Unfortunately, contemporary records are unable to confirm these events as they are first noted in a family deposition to a French tax investigation in 1539, claiming exemption from taxes due to the noble status inherited from a grandfather, Nicolas de Coetanlem. We do know that 1484 was the year that de Coatanlem entered the service of the King of Portugal whom he served with great distinction until his death in Lisbon in 1492; his exploits defending Portuguese shipping against the pirates of the Barbary Coast having earned him the title ‘Governor of the Sea’.

De Coatanlem’s nephew, Nicolas, was one of the Breton ship-owners most frequently employed by King Henry VII of England to transport men, weapons and supplies to his forces supporting Duchess Anne of Brittany in her battles with France in 1489-91. De Coatanlem’s services were rewarded with a licence to import, under Crown protection, goods into England duty free.

de Coatanlem

The 15th century voyages of exploration and discovery, coupled with advances in navigation and cartography, quickly brought about vast changes to the fortunes and outlook of many nations. For the kingdoms of Europe, command of the sea was now no longer a case of protecting borders but of projecting influence and expanding opportunities for profitable trade. The distances and natural hazards involved in transacting such endeavours were great and many men, of all nations, saw opportunities for personal enrichment by helping themselves to the fruits of others.

The nomenclature surrounding such adventurers is rich and varied, particularly when the words thief or robber are all that are really required but a whole range of other descriptors have been used, such as Gentlemen of Fortune, Privateers, Freebooters, Corsairs and Filibusters to describe men, and it was usually men, who attacked and plundered targets with the approval of a state’s authority. Sometimes, that approval was deliberately vague and sometimes was conferred by a minor official completely out of touch with his government’s wishes; but it was nonetheless approval of sorts.

Pirates were essentially outlaws who attacked the shipping and settlements of all nations with no real pretence of serving under any flag but their own and risked the gallows in the event of capture. The term buccaneer was often used to describe both pirates and privateers. Often, the differences between pirates and privateers were, at best very subtle, and, at worst, a matter of subjective interpretation. Distinctions are further clouded by the fact that many men drifted between legitimate privateering and outright piracy and vice versa.

The practice of manning and arming private vessels to attack rivals’ ships is an ancient one and continues, in parts of the world, to this day. In Europe, over time, this practice was formalised with the awarding of privateering commissions or ‘letters of marque and reprisal’ that granted named individuals licence to seize the king’s enemies at sea and share the proceeds between the privateers and the Crown. Vessels and cargo seized by the privateers were sold at officially sanctioned auctions, with the Crown typically taking between 10 and 20 per cent of the proceeds and the ship’s captain and his investors receiving the remainder. It could therefore be a highly lucrative enterprise. For the ship-owners and the men who financed such expeditions, fitting out privateers was an expensive business; the ship had to be supplied with stores of victuals, powder, shot and other equipment. It was also crucial that the captain could be trusted to declare all his plunder and not trade too much on his own account.


The Golden Age of Pirates of the Caribbean

Born into a minor noble family in central Brittany in August 1661, Anne Dieuleveult is one 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 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. 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 17th 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 known as 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 18th 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.

Legend has it 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 legend but we do know that the couple married in July 1693.

Laurens de Graff pirate

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.

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 battle. De Graff now transferred his flag to the newly captured, 40-gun vessel, San Francisco.

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.

Capturing a ship

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. 

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 quarrels about the division of the spoils.

De Graff now seems to disappear from the records and is not noted in 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.

Anne Dieuleveult

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.

Duguay-Trouin privateer

Licensing privateers during periods of war was widespread in Europe between the 16th and 18th centuries, representing a cheap and low-risk way of striking at your enemy. It also carried the benefit of gnawing away at their foreign trade and perhaps forcing them to divert resources into protecting their merchant ships or actively patrolling for privateers.

From Teenage Corsair to Vice-Admiral of the Royal Navy

Born into a wealthy ship-owning family in the major privateer port of Saint-Malo in 1673, René Trouin aka Duguay-Trouin turned his back on the career in the Church that had been marked out for him and took to sea aboard a local privateering vessel at the age of 17. He was obviously a natural sailor and was given his own command the following year and successfully plundered many English cargo ships plying the Channel during the ongoing Nine Years War. 

His skill in naval warfare brought him to the attention of the navy who gave him command of a 36-gun frigate in 1692 but his luck ran out when he was captured by English warships off the Scilly Isles in April 1694. However, the resourceful officer escaped and was home in Saint-Malo by the end of June. The following year and in command of a 48-gun warship he captured an English warship after a two day running battle. A feat he surpassed in 1697 with the capture of a 15-ship Dutch convoy off Bilbao, earning himself a commission as a captain in France’s Royal Navy just as the Nine Years War concluded.

There was precious little peace in Europe at this time and five short years later the conflict known as the War of the Spanish Succession broke out. It was during this period that Duguay-Trouin enjoyed his greatest successes; his scattering of a great Portuguese convoy in 1706 and the seizure of hundreds of vessels over the next few years saw him ennobled in 1709.

In September 1711 he led an expedition of 15 ships, a mixture of naval warships and privateers, against Rio de Janeiro. His fleet stormed into Rio’s harbour and after a series of engagements, secured the town nine days later. After looting the city and the 60 cargo ships at anchor within the bay, Duguay-Trouin demanded a large ransom to spare the city’s buildings, eventually receiving 610,000 cruzados. When his fleet, now augmented by two captured Portuguese warships, departs in November, they leave behind a devastated city but the expedition proves a disappointment for his investors, particularly as two of his largest and most heavily laden ships were lost with all hands (over a thousand men) on the journey home. Further promotions followed his return and Duguay-Trouin successively commanded the naval forces at Saint-Malo and Brest, being appointed Lieutenant-General of the Naval Armies in 1728.

Surcouf corsair
Robert Surcouf

King of the Corsairs

Like Duguay-Trouin, Robert Surcouf was also born into a ship-owning family in Saint-Malo who hoped that he would enjoy a life in the Church but young Surcouf had other ideas and ran away to sea. At 16, he enlisted aboard a slave ship that plied the routes between the Horn of Africa, Pondicherry, Mauritius and Madagascar; surviving a shipwreck in the Mozambique Channel in 1790 in which 400 slaves, chained below decks, perished. Despite the 1792 ban on slave trading, Surcouf continued his ghastly activities until 1795 when he took command of a privateer in Mauritius, capturing five British merchant vessels over the course of the year even though he had been refused a letter of marque by the Governor of Mauritius.

After a brief sojourn in France, in February 1798, Surcouf left Nantes in command of a 14-gun privateer and an official letter of marque. After re-supplying in Mauritius, he set out to hunt on the busy trade routes of the Indian Ocean, capturing some 17 British, Dutch, Portuguese and American merchant vessels before returning to Mauritius in February 1800. He set out again in April and, over the course of a year, captured a further 8 British, American and Portuguese merchant ships. Surcouf returned to France in April 1801 where his exploits were much acclaimed; in May 1802, he was awarded the Legion of Honour upon the founding of the Order.

In March 1807, he once again set out from Brittany in pursuit of prey and prizes in the Indian Ocean, capturing 13, predominantly British, merchant vessels during this, his final cruise. In July 1808, his ship was requisitioned into naval service and he was forced to purchase a damaged de-commissioned naval frigate for the journey home to Saint-Malo. He arrived safely, along with an estimated haul of 8 million francs, in February 1809 but his ship sank at harbour the day after he arrived. Surcouf never put to sea again but used his considerable fortune to expand the family business, outfitting almost a dozen privateers and, after 1815, a score of merchantmen. He died peacefully at home in 1827.


For over three centuries we have been entertained by the adventures of fictional and fictionalised pirates and privateers from John Silver to Jack Sparrow but the Roman statesman and philosopher Cicero would not have welcomed such romanticism; to him “a pirate is not included in the list of lawful enemies but is the common enemy of all; among pirates and other men there ought be neither mutual faith nor binding oath“.

Published by Bon Repos Gites

Enjoying life in Kalon Breizh - the Heart of Brittany.

38 thoughts on “Buccaneers of Brittany

    1. Many thanks for your really kind words – much appreciated! She sounds quite a lady doesn’t she? So many of the bits that I’ve read about her have really exaggerated what’s known from contemporary sources but I really don’t think her tale needs embellishment. To have survived all that was thrown at her, esp as a woman in those days, and to have died peacefully in comfort, in old age, surely achievement enough 😉


    1. Thank you!! Glad that you enjoyed it 🙂 She was married when but a child herself (12/13) and it’s said that she took her infant sons to see their father’s head on the spike at the city gates to swear vengeance. We’ll never know what’s true or French propaganda now though.

      Liked by 1 person

  1. Amazing essay. The story of Dieuleveult and de Graff is quite comic, isn’t it?

    Reading this post makes me remember a book I read several years ago, about the sea people, sea tribes, and sea kings from centuries ago around the sea of Celebes, north of Indonesia. The author also writes about the concept of pirates, privateers, corsairs, and bucaneers. This post has enriched my knowledge about those seafarers. I just knew the term “bucaneer” was originated in Tortuga.

    Thanks for this wonderful post. 🙂

    Liked by 1 person

    1. Many thanks for your kind words!! I’m pleased you enjoyed it 😉 Yes, I’ve read about the pirates in that part of the world too! Sadly, there were an awful lot of them about! Stay Well!


  2. The mariners have me intrigued as my family on my father’s father’s side were marine engineers and came from Dartmouth and Kingswear. His first word was “boat” and so was my father. The women pirates are fascinating as well. I keep coming back to read some over to process. Another great post!

    Liked by 1 person

    1. What wonderful feedback – thank you so much. It’s great if a story can evoke memories!! Dartmouth is gorgeous and if I recall has its own cast of privates and privateers to run alongside the town’s legitimate maritime heritage 😉


  3. A great post, as usual. Your research is meticulous. I particularly liked the stories of Jeanne de Belleville and Anne Dieuleveult. They were strong women indeed.

    Liked by 2 people

  4. Great story telling and I’m particularly impressed by my fellow country women, the Tigress of the Sea and Dieuleveult (God wills it). A very appropriate name!


    1. Thank you for saying so – it is very appreciated. Yes, those two were obviously strong women! Dieuleveult was her family name but you will read in some places that it was the title bestowed upon her by her adoring crew. 😉


  5. I’ve always found it fascinating when I encounter pieces of information about Brittany when I read royal non-fiction and fiction. Calais features heavily too, but as much as it’s never explained, I understand France’s impact on the British monarchy.

    Dear Lord, punishment for treason was especially brutal. One day I’ll look up why this was the case.

    It’s interesting to learn more about de Montfort! In England, we actually have a university named de Montfort university!

    Liked by 1 person

    1. Yes, it’s fascinating how inter-connected Britain, France and Brittany are. For so long, the crown of England held more territory in what is today’s France than the Frankish king! Calais being one of the last territories on the continent to be lost.
      De Montfort ‘s family is a confusing one but typical of the era – marriages and alliances of convenience. Today, we would call them power-hungry power brokers 😉

      Liked by 1 person

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