Eustace the Monk: Without doubt the worst medieval pirate you've never heard of
Monastic, mercenary, mage - a truly fantastical tale of the Middle Ages.

One of my favourite childhood comfort films when I’m feeling down is Disney’s supernatural swashbuckling series: Pirates of the Caribbean. From the moment I saw the first film, all my primary school playground games revolved around pretending to be the drunken trickster Captain Jack Sparrow. We’d fashion sabres from fallen twigs and proudly duel ourselves silly until we were caught by the classroom bell summoning us back to dreary reality. When I aged only a little further, I quickly graduated to living out my piratical fantasies on the family computer. My ever-tolerant parents purchased for me Bethesda’s little-known 2003 video game tie-in with the movies and I spent hour upon hour plundering my way through the pixilated ‘Golden Age of Piracy’, quaking in fear at the game’s super-creepy skeleton soldiers I had nightmares over. The point to this intro is to say that the pirate myth, the freedom-loving plunderer with no master but the sea, has always had a deep impact on me. It is with this nostalgia for my carefree childhood that I relished first learning about the merry pranks and crude sometimes magical tales of Eustache the Monk in John Brunton’s Rogues, Rebels and Mavericks of the Middle Ages.
Like Disney’s theme-park ride inspired films, The Romance of Eustace the Monk is at times colourful and taking artistic liberties as it is based on real world history. Although the Romance stretches the limits of belief, the adventures of this outlaw, who bafflingly performed the contradictory paths of pirate captain and Benedictine monk, are attested with other documentary evidence in the form of close rolls, patent rolls, and charters. What we can establish amidst the myth is that the man was born around the year 1170 in the Boulonnais region of northern France as the younger son of a noble, most likely Bauduin Busquet. In his youth, Eustace (or Eustache) likely received the standard knightly training to be expected of his breeding. The Histoire des Ducs de Normandie makes reference to him as one of many the ‘chevailiers de Boulenois’. So how Eustace transformed from an up-and-coming knight of the realm to the most famous pirate of his day, the scourge of the English Channel, is a story so wild it needs to be further told… (Disney? Robert Eggers? Are you listening?)
Translated from the original Old French, the Romance paints an image of Eustace as a deeply dark if comic Rasputin-type of figure. Having learnt necromancy and sorcery in Toledo he returns to France as a ‘black monk’. His pact with the devil taught him a thousand magic tricks and how to scare his fellow cloistered Benedictines by reciting the psalter backwards. The Abbot of Saint-Samer Abbey labeled him a demon for his unruly behaviour, encouraging disobedience, gambling and theft. His devilish deeds included making the monks fast when they should’ve had lunch, going barefoot when they ought to have worn shoes, and making them swear during their prayers.
But moving beyond this PG version into the harsher ratings, the Romance has Eustace getting up to some very naughty tricks indeed. This supposed man-of-God cross-dresses as a prostitute, magics a tavern’s customers into nude frenzies, and shape-shifts into wild beasts. Amongst the more comic adventures there are sinister episodes where he brutishly saws off the tongues of his enemies and takes personal delight at tormenting and hanging spies.
The question has to be asked, how could such a rogue end up in the monk’s habit? Some have speculated that the historical Eustace became a monk on a personal whim. I too feel the same impulsive pull of purpose and seeking of structure that cloistered life could bring and equally the pulls of adventure. However, rather more realistically in Eustace’s case, it was common practice in this time for a lord to confine a troublesome person into monasteries. Could it be then that Eustace was simply an untameable rapscallion and hell-raiser who never sought to don the habit which became his moniker? We know that he only stayed in the convent for a year. His father was murdered in 1190 and perhaps Eustace felt the need to take his vengeance out upon the world or, and more likely for this avaricious brigand, he wanted to claim his rightful inheritance.
Eustace returned to secular life for a short stint of civic duties as seneschal and bailiff for the Count of Boulogne, Renaud de Dammartin. However, not one to stomach authority, he soon found himself quarrelling with his master after accusations of mismanaging his position (and considering his reported temperament his guilt is perhaps likely). His lands were quickly seized and he was driven out of France as an outlaw but not before Eustace set fire to some of the Count’s property in retaliation.
With nothing for him in his homeland, Eustace and his band of brothers resorted to pirating. Throughout his newfound nautical career this sword-for-hire found himself swapping sides from the employ of King John of England to his nemesis the King Philip II of France. Starting in 1205, King John - ‘lacklanded’ for the loss of the old possessions to France - gave Eustace command of a fleet to raid and cause havoc along the Normandy coast. This Eustace did with relish, establishing bases for his plundering in the Channel Islands. This was partly at the behest of King John, but Eustace certainly at his own piratical interests in mind. The small island of Sark soon became a sort of Tortuga in the Dover Strait. It was the launch pad for this venture-capitalist’s rapid seizure of wealth from unexpecting merchant vessels. (I’m suddenly mindful of Monty Python’s Crimson Permanent Assurance which you need to watch.)

Not being one for loyalty, Eustace flew under his own colours and soon turned his indiscriminate sword to raid English coastal villages too. This forced King John to reluctantly outlaw him although this didn’t last long as the situation with his French geopolitical rivals soon meant he needed Eustace’s services once again. Becoming the most feared sailor in the Channel this sea-monk was soon the stuff of legend. Parents warned their children that if they did not behave Eustace would come for them and in the night, steal them away and force them into his service or perform some other ungodly magic on them.
In 1212 Eustace switched sides to aide his native Frenchmen. The Romance implies this is because Eustace’s long-time enemy, the Count of Boulogne, allied himself with King John and set the two against each other, resulting in the burning of Eustace’s daughter. Eustace raided Folkestone in retaliation and English troops stormed and seizing his bases in the Channel Islands. Subsequently, Eustace soon found himself embroiled in the First Barons’s War, ferrying the French armies under Prince Louis across the Channel in 1216.
A year later, Eustace was conducting a regular reinforcement mission to Louis when his fleet met that of the English under Hubert de Burgh, sailing out of the Port of Dover. A bloody and watery battle followed, Eustace bringing chaos to his old allies until powdered lime intended for the English met unkind winds and blinded his own men (an original weapon of mass destruction). The English boarded Eustace’s vessels and defeated his pirate band in the ensuing melee. Whilst Eustace initially escaped, his ship was surrounded by Philip d’Aubigny’s English fleet of Cinque Ports ships on 24th August 1217 in the Battle of Sandwich.
Eustace, the coward and yellow-bellied cad that he was, hid in his ship’s darkest and deepest parts. When he was inevitable found he begged for his life, offering vast sums, only for the English to refuse (they probably had enough of his tricks). They simply gave him the choice of site of the ship’s rail or the side of the trebuchet as his place of execution. The chronicler Matthew Paris in his account of Eustace’s demise does not say which he chose but depicts his brutal beheading. His head is then said to have been taken to Canterbury were it was placed on a lance and paraded in triumph throughout the southern English coast. A land he once terrified now rejoicing that this perennial pain-in-the-backside was no more.
Whilst his pirate brothers survived him, their retreat to Sark and the other Channel Island bases did not last long for the Treaty of Lambeth returned the islands to English control who quickly ejected them to exile to wherever those forgotten by history go.
Whatever the truth of Eustace, (the fact is hard to decipher from fiction), the Romance has it that Eustace was commanded by the devil to hurt as many people as possible and wage war on Kings and counts alike. This he did to no avail. His deeds went beyond simple practical jokes on monkish brothers or polite pirating as the tale depicts him in a very dark and dastardly light, labelling him at one of his lowest moments as “that fake monk of a pissing whore”. Yet despite his evil, reading the Romance it strikes me he’s almost a Flashman-esque anti-hero. He’s no Robin Hood, as he’s certainly not motivated with noble intent, but he’s an outlaw we root for regardless. He almost fits into that lovable rogue mould we’ve come to love in Jack Sparrow or Hans Solo, if weren’t for the murdering and pillaging.
So my advice, to the budding directors out there, or young pirate enthusiasts as I once was, is to read The Romance of Eustace the Monk and prepare to be both disgusted and thrilled but wanting more in equal measure.
Further Reading:
John Brunton, Rogues, Rebels and Mavericks of the Middle Ages, (Stroud, Gloucestershire: Amberley Publishing, 2022)
Glyn S. Burgess, Two Medieval Outlaws: Eustace the Monk and Fouke Fitz Waryn, (Cambridge: D. S. Brewer, 1997)
Maurice Keen, The Outlaws of Medieval Legend, (London: Routledge, 1987)
Further Gaming:
Pirates of the Caribbean, (Bethesda Softworks, 2003), [on PC]
This was a fun read! I actually came across Eustace (not in-person) when I was writing my dissertation many years ago, so it's great to see a more detailed breakdown of his biography and what we actually know from records. I also had no idea he was the subject of a romance, let alone such a wacky one! Your conjectures re. his early life, why he was sent to a monastery and why he left (/was expelled?) are also interesting and credible.
Eh, in the oldest tales we've got -- *Robin Hood And The Monk* for instance -- Robin Hood could be a pretty hard character, too.
There's a whole slew of ballads where Robin tries to rob someone poor, gets beaten, and recruits the man. What happens when the man can't beat him doesn't make it into the ballads.