A Pirate’s Life: 6 Swashbuckling Medieval Pirates

Stephanie Schoppert - June 20, 2017

For about as long as there have been a means to sail the ocean there have been pirates. During the middle ages, nations did not exist as we now know them and power constantly changed hands from one group to another, it was a good time for pirates. There was no real effort to stamp out piracy. Merchants, seamen and landowners would often support the pirates because they made them rich while rulers and warlords had their own ships that might occasionally engage in piracy. If a pirate was caught by a country that was not his own he might be put to death but that was hardly a deterrent from those seeking untold riches upon the seas.

Eustace the Monk (1170-1217)

Eustace the Monk was born to Baudoin Busket a lord in Boulogne in 1170. He later traveled to Toledo, Spain where he studied black magic. After which he changed course and traveled to St. Samer Abber which was near Calais. It was there he studied to become a benedictine monk until he learned that his father was murdered. Evidence suggests that the murder occurred around 1190 and that by 1202 Eustace was the seneschal and bailiff of the Count of Boulogne. The position was not to last as Eustace and the count, Renaud de Dammartin got into a fight in 1204. Eustace was accused of mishandling his stewardship and so he fled and was then declared an outlaw.

While working for King John he sailed with his brothers and raided the Normandy Coast. They also created bases in the Channel Islands, even holding Castle Cornet for a time. He also took control of the island of Sark in 1205. He made the mistake of raiding English villages which caused him to lose the favor of King John for a period. But he regained favor when the King was once again in need of a pirate. In 1212 his relationship with King John soured for good and he turned against the English when English forces seized his bases. During the English civil war in 1215, he supported the rebels and even provided transportation to Prince Louis of France in order to help the rebels in 1216.

In 1217, Eustace the monk was still working to help the rebels and France by bringing reinforcements to Louis. However, he crossed the path of an English fleet that was sailing out of Dover. What ensued was known as the Battle of Dover. Eustace got the upper hand and destroyed his former allies until the English ships blinded the French men with lime. The English were then able to board the ships and defeat the French in melee combat. Eustace on his flagship and some of his other ships escaped but only until August 24^th when they were surrounded. In the Battle of Sandwich, Eustace was outnumbered and the English were able to board his flagship. They found him hiding in the bilges and beheaded him.

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William Kyd (fl. 1430-1453)

Many know of the famous Captain William Kidd who sailed the seas during the 17th century. But William Kyd was an English pirate who flourished starting in 1430. He operated out of Southwest England and sailed with immunity for nearly twenty years due to the support of corrupt customs officials. He first gets mention in 1431 as the master of balinger La Trinite of Exmouth. His name appears on a list of pirates that was published that year and it was known that in 1430 he was one of a number of pirates active in West Country and that he had seized a Breton ship off the coast of Guernsey. He continued to join forces with other pirates including William Aleyn. In 1433, he and William Aleyn, along with several other pirates were able to capture four ships that were carrying provisions bound for Rouen. Over the next few years sailing alone and with other pirates he established a bit of a reputation for himself.

In 1436, he was sailing into the harbor of Saint-Pol-de-Leon in Brittany and though he had eight barges and balingers with him, the Seynt Nunne caught his eye. The ship was under safe conduct by local authorities but that did not stop William Kyd from taking it for himself. He sailed away with the ship and took it to Plymouth along with £100 of goods belonging to Thomas Horewoord. It would be another decade of piracy before William Kyd did anything that was particularly of note since pirates were more or less accepted during the time. In 1448, he got attention by capturing the La Marie of London. The ship was bound for Flanders but he took command and sailed it to the Isle of Wight where he sold it.

In 1453, he got significant attention once again when he captured the biggest prize of his career The Marie of St. Andrews. When William Kyd sailed into Exmouth, the ship was noticed by a Scottish knight, Sir William de Kanete. He decided he wanted the ship for himself and went to Thomas Gille who was the controller of customs of both Exeter and Dartmouth. William de Kanete pretended he was the brother of the Bishop of St Andrews and that he was the true owner of The Marie.

William de Kanete conspired with Gille in order to get a commission for the delivery of the ship in which they would share the goods on board. They issued a complaint with the local authorities and a commission was granted. The ship was seized by authorities and then all the goods on board were given to William de Kanete. The paperwork and records for this event get extraordinarily complicated and there are even those who believe it was Kyd working with Gille to get the commission. Whatever came of his event it is the last time that William Kyd gets much mention in the historical record. What became of him after is unclear.

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John Crabbe ( fl. 1305 – 1352)

John Crabbe likely operated as a pirate prior to 1305 but that is the earliest record of his life of piracy. It is known that he was born in the town of Muide in Flanders and there is a 14th-century tower in the town where it is believed the pirate was born. He was also thought to be the older brother to Peter and Baldwin Crabbe and uncle to Crabbekin. In 1305, he attacked the Waardeboure of Dordrecht at La Rochelle when it was in the Bay of Biscay. He took all the cargo from the ship which was reported to include 150 tuns of wine and then he burned the ship and kidnapped all the men aboard. Reports say that his ability to capture the Waardeboure was largely due to the fact that he had a catapult built which could be fired from the deck of his ship.

In 1310, Crabbe’s life of piracy was continuing to flourish. He seized a ship with cloth, gold, silver and jewels. The goods belonged to Alice of Hainault who was Countess Marshal. King Edward II of England sent letters of complaint to Count Robert of Flanders for the goods and for subsequent goods stolen from merchant ships in 1311. Though some of Crabbe’s men were punished, Crabbe was never brought to justice nor was restitution made. Therefore in 1315, King Edward ordered that Flemish ships be seized and their goods sold in order to compensate the Countess.

In 1316, Count Robert allowed Crabbe to return and even made him admiral of a fleet of ships. At the time Flanders was being ravaged by famine and they were so desperate for food they were willing to turn to piracy. Crabbe seized merchant ships once again to deliver food to Flanders and once again, complaints came into Count Robert. Robert claimed he had no idea the whereabouts of the pirate but promised that his punishment would come on the wheel if he was caught. In 1318, Crabbe had settled in Berwick, Scotland and proved to be a strong ally to the town when the English tried to capture it. His defense of the town was praised.

In 1332, war broke out again and while Crabbe once again defended Berwick, things did not go as well for him. He was captured by the English and transported to England. In 1333 the English attacked Berwick again but this time Crabbe was in England and the Scots believed that he was assisting King Edward III and killed his Crabbe’s son. From then on Crabbe was pardoned by the English and made Constable of Somerton Castle. He gathered his own fleet and helped Edward III throughout the rest of the war and throughout the Hundred Years’ War that followed. He died in early 1352.

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Henry Paye of Poole (1364 – 1419)

Henry or Harry, Page or Arripaye was born around 1364 and grew up to be a privateer and smuggler. He was from Poole, Dorset and despite having a life as a notorious pirate he became a commander of the Cinque Ports fleet. He started his life on sea by leading naval raids along the coast of France and Spain. His attacks ranged from Normandy through the Bay of Biscay and Cape Finisterre. He was pivotal in helping to put down the Welsh revolts that were headed by Owain Glyndwr and defeating a French fleet that was dispatched in order to assist the rebels. He became a well-known and greatly feared pirate throughout the southern seas.

His life is remembered through stories of his exploits as a fearsome pirate sailing upon the Mary. His ship was licensed to carry pilgrims to Spain but instead, he used to ship to capture vessels and raid towns. He stole a treasured golden cross from the Finisterre church which was never recovered. He also burned down the walled city of Gijon. The reason for burning the town might have been personal as the Spanish city was the home of his known lover Countess Isabel. His actions against the Spanish sparked their anger and they sought brutal revenge against the hated pirate.

In 1405 a group of French and Spanish galleys made their way along the south coast when they reached Poole. They learned the town was the home of Arripaye the pirate and decided to destroy the town. Many were killed and the villagers were forced to flee, allowing the Spanish to burn the town to the ground. In 1407, Henry sought his revenge and led a fleet of 15 ships up and down the English Channel capturing French and Spanish cargo ships. Archives report 120 ships were captured all of which were loaded with valuable goods and massive quantities of wine. Henry brought all the ships to the people of Poole to compensate them for their suffering. Local tradition says that the town feasted for days on the proffered food and wine.

Few pirates have as many daring stories as Henry Poole. He was once captured by the French. He and his shipmates were being held on the deck of their ship by a small number of guards while the rest went below deck to search for treasure. However, Henry and his men broke free of their bindings and killed all the Frenchmen. He then took control of two French ships and sailed them up the Seine, using the French flag as a means to plunder several ships before making his way out to sea. He was eventually made Warden of the Cinque Ports and retired on a Royal pension. He died in 1419 and there is a memorial in Faversham Church in Kent where he was buried.

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Didrik Pining (1428-1491)

Didrik Pining was a notable German pirate who is believed to have been born around 1428 in Hildesheim in Germany. Hanseatic records place him as a privateer or a captain working in the service of Hamburg until 1468. He was tasked with hunting down and capturing English merchant ships in the North Atlantic Ocean. Pining and his partner Hans Pothorst were known by the Hanseatic League as “pirates who did much damage to Hanse towns.” He went into the service of Denmark until Christian I of Denmark and his son John of Denmark from 1468 till 1478. It was during this period that Pining and Pothorst are said to have been distinguished as “not less as capable seamen than as matchless freebooters.”

One of the main reasons that Didrik Pining is remembered today is because some believe that Pining and Pothorst researched North America twenty years before Christopher Columbus did. In the early 1470s, Pining was made leader of an expedition northward toward Greenland. He was with Porthorst and other Portuguese explorers on the long expedition. The expedition started in Bergen and then went through Iceland and continued on to Greenland and after which they discovered the “Land of Codfish” which is presumed to be Newfoundland or Labrador. In 1478 Pining was appointed Governor of Iceland which some argue was a reward for discovering the “Land of the Codfish.” The idea remains contested and debated among scholars.

From 1478 until 1481, Didrik Pining enjoyed his time as Governor of Iceland. In 1481, he was said to have “fared out of Iceland” but he was present at the funeral of King Christian I of Denmark. In 1484, he and his men were accused of having raped women and stolen money from farmers. the accusations did not stop him from becoming knighted in Norway and having a personal coat of arms which featured a grappling hook. It also did not prevent him from becoming governor over all of Iceland in 1489. His godson and nephew would succeed him in 1490. Throughout this period, he continued his life of piracy, patrolling the North Atlantic waters and playing a major role lint eh Anglo-Danish War. Hans Pothorst was always by his side through all of his sea-faring adventures.

In 1484, he captured three ships which he brought to King John of Denmark. After this, he joined John in Bergen where he was made admiral of the royal fleet. As part of his new position, he led the fleet to the island of Gotland and secured it for Denmark in 1487. Pining either died or was killed in 1491 somewhere around Finnmark or the North Cape.

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Klaus Störtebeker (1360-1401)

Klaus Störtebeker is credited as being Germany’s most famous pirate, despite this there are very few facts that are known about his life. His name, Störtebeker, is his surname and his nickname, as it has the meaning “empty the mug with one gulp” in Low Saxon. Apparently, the name was given to him because of his ability to empty a four-liter mug of beer in a single gulp. He was born in Wismar sometime around 1360 but he did not really start making a name for himself until 1398. He was part of the Victual Brothers and it was during their expulsion from the Baltic island of Gotland that Störtebeker first enters into public record.

In the years following the expulsion, Störtebeker and other pirates captured a number of Hanseatic ships with little care as to where they came from. Störtebeker was known to have a stronghold in Marienhafe, East Frisia starting in 1396. There is a tower at the Evangelical Lutheran Marienkirche in Marienhafe that still bears the name Störtebeker. With those being the only known facts about Störtebeker it is strange to think he has become so famous throughout Germany but much of that is attributed to the legend that surrounds him.

Legend says that in 1401 a Hamburgian fleet under the command of Simon of Utrecht crossed paths with Störtebeker’s force somewhere near Heligoland. Some stories suggest that Störtebeker’s ship had been sabotaged by a traitor who had poured molten lead into the links of the chain that controlled the rudder of the ship. Whatever was the case with the ship Störtebeker and his entire crew were captured. They were taken to Hamburg where they were put on trial for charges of piracy. Störtebeker and the 73 men in his crew were all sentenced to death by beheading. This is where the real legend of Störtebeker begins.

It is said that Störtebeker asked the mayor of Hamburg to spare as many of his men as he could walk by after being beheaded. The mayor was said to agree to the request and Störtebeker was beheaded. After his beheading, he was able to walk past 11 men before the executioner tripped him. The mayor still went ahead with the executions of the 11 men along with the rest of the crew. In a small bit of karma when the executioner was asked if he was tired after performing 73 executions. He replied that he could easily kill the entire Senate, he was sentenced to death and executed. The legend also says that after his execution, his ship was dismantled and it was found that the core of his masts were gold, silver and copper. The gold core was used to create the tip of St. Catherine’s church in Hamburg.

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