Owain Glyndŵr, The Last Prince of Wales (Part 1)

August 09, 2021

Owain Glyndŵr, The Last Prince of Wales (Part 1)
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We tell the story of Owain Glyndŵr, a Welsh nobleman who sparked a rebellion against the English king in the late 14th century.

Glyndŵr’s army was small, but determined, and they managed to win several key battles against the English. However, their ultimate goal was always to unite Wales and throw off the shackles of English dominion.

To this day Glyndŵr remains a lasting legacy as a symbol of independence and pride for the Welsh people.



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It's 1402. On a wet and cold morning in northern Wales Owain Glyndŵr (Owain Glendower) and a few supporters galloped at full pace away from Ruthin Castle. 

His sworn enemy, Baron Reynold Grey, hot on their trail.

Glyndŵr's siege had ended in failure, and his army, tired and sick, had melted away into the countryside, leaving him alone with just a few loyal men. 


Lord Grey, never one to waste an opportunity for glory, seized the initiative. This was his chance to capture the Welsh rebel once and for all. The history between these two men was long and bitter. Grey was a favorite of the King of England. He had been provided with choice lands on the borders of England and Wales, and was tasked with making the lives of his Welsh neighbors as difficult as possible. 


Over the years, through thievery and deceit, he had stolen everything from Glyndŵr his lands, his reputation and now he came for his life.


Now, with not a penny to his name, Glyndŵr and a few friends sped through the countryside, his banner; a brilliant golden dragon set against a white canvas, billowed in the wind. 


With the rain stinging his eyes, Glyndŵr spurred his exhausted horse forward. His ultimate gamble was coming up. 


The plan had to work.


 It just had to.


As the muddy, open fields of the countryside gave way to tree cover, he could hear Grey hot on his trails and gaining fast. Wheeling around the last corner. Glyndŵr arrived at the clearing and directed his horse around a bend and out of view. Grey and his men immediately saw it. They had rode straight into a trap. Dumbfounded, Grey scanned the treeline and realized it was brimming with enemy soldiers, their iron helmets giving away their positions in between the dark birch trees. 


Where had all these men come from so quickly?


“Trap!”  yelled Grey. But it was too late.


As he and his knights tried desperately to spin their horses around, they were shot full of arrows. Man and beast screamed out horribly as the razorsharp bodkin arrows tore through them. In a matter of seconds, Grey was the only one alive. 


Emerging from behind a thick tree Owain Glyndŵr walked calmly towards his rival and yanked him down, unceremoniously off his magnificent white horse. As the man who had cost him everything glared up at him covered in mud, nothing would be easier or more satisfying than ending his life. 


A quick flick of a knife and Glyndŵr would have the revenge he dreamt of.

But that was wasteful.

Despite all he had done to him, Grey was too valuable as a hostage. The baron was bound and shackled, and Glyndŵr dragged him to the edge of the clearing. A wry smile crept across the face of the Welshman as he watched his bound nemesis gaze upon his army. 


Nothing but a bunch of iron helmets bounced on wooden stakes.


You're listening to Anthology of Heroes, the podcast that takes you through the lives of national heroes of every country around the world.


and today's stories of a Welsh nobleman driven into revolt by a tyrannical English king who would ignite a slumbering sense of nationalism his countrymen shared. Something that England thought they had snuffed out long ago.


Tired of being second class citizens in their own country, thousands would flock to his golden white banner, determined to throw off the shackles of English dominion. His war would last over a decade, and at no point would he ever surrender or be betrayed by his people. And then, almost as fast as he rose, he would disappear from history, cementing his place forever in the hearts of Welsh people as a symbol of independence and pride. 


This is the story of Owain Glyndŵr, The Last Prince of Wales.




In the 14th century, something stirred beneath the streets of Wales throughout the population.


From the most meager peasant to the richest landowner, a bond connected people from all walks of life. This was not a physical thing, but a shared connection to a common culture, a culture that had been systematically and methodically eroded over the centuries by their English cousins. 


Wales was not England.

It had never been.

Since the time of Anglo-saxon kings, earth and stoneworks had been constructed as barriers to clearly show where England finished and Wales started. To the east of the boundary lay civilization, and to the west, Barbaris - at least that's how many English kings saw it.

As English influence waxed and waned over the centuries. Usually Welsh power would do the opposite. If England was strong, the independent Welsh kingdoms kept their heads down and maintained a low profile. But when England was weak, raiding into the richer border towns and vying for deals to increase their own power was the order of the day in Wales.


Since back in the 11th century, the North of Wales had been the target of English attention. At an enormous cost to the English king. A so-called Ring of Iron was constructed in the northwest of the country. The Ring of Iron was a collection of state-of-the-art defensive castles circling the Snowdonia region, a particularly rebellious part of Wales.

These castles were intended to be strongholds from where The King's representatives could project English power across the countryside. And in the event of widespread rebellion, they were designed to be impenetrable. 


A few generations later, another English king had his own idea of keeping down Welsh nationalism.


His new plan was more nefarious and long term. Slowly and systematically, he replaced the native rulers of southern Wales with men of his choosing, known as marcher lords. These lords, who now owed their position directly to the English crown, could be relied upon to keep down the northern Welsh kingdoms in the event of a rebellion. The hope was that over time, the Welsh language, culture and separate sense of identity would be swallowed up by that of England. But the Welsh did not go gently into that good night. 


Just a quick side note on place names.I really, really struggle with Welsh pronunciation.

Especially the cursed ‘double l’ sound, so I've generally stuck with English pronunciations of these names.


Anyway, over the next 400 years or so, talented and patriotic Welshmen rose and fell, all with lofty ideas for a united Wales. In the mid 12th century, Owain Gynedd became the first Welsh ruler to have his claim as Prince of Wales, recognized by the English crown. A century or so later, his grandson Llywelyn The Great was one of the leading barons who forced the English king to sign the famous Magna Carta, which limited the amount of power a king could project on his subjects, which still continues to be referenced in England today. 


So I know we've just flipped over quite a bit of history with quite a few names. If that felt like a bit of a high school lesson, my apologies.


But to understand today's story and the motivation behind the characters, it was important to do a bit of a deep dive. Summarized though, England had tried a variety of ways to stamp out Welsh nationalism with varying levels of success, depending on the king and political landscape.


For all the talk of nationalism, however, nothing about the early life of today's hero would lead you to think you would one day lead the greatest rebellion Wales would ever see.


Owain Glyndŵ was born around 1350 and grew up in a well off Anglo-Welsh family in the northeast of Wales. His family's land straddled the traditional borders of Wales and England. His family was one of the few that could trace their lineage back to the time before the Norman invasion some 400 years earlier. This kind of pedigree was completely ignored in English high society, but was held in higher acclaim in Welsh society. 


Bards and poets singing the deeds of one's ancestors was common practice for the Welsh elite, and all through his childhood, Glyndŵr would have heard minstrels retell the deeds of his long lost relatives. 


RR Davies, Oxford professor, describes this element of Welsh aristocratic society as a kind of secret to outsiders - quote:

“This was a part of Wales that the English official traveller would have barely skirted on his tours or in his consciousness; 


it was a secret Wales which was yet at the very heart of the experience and vision of the poet and their patrons.


Owain Glyndwr and his like (meaning other Welsh nobles) straddled these two worlds to a considerable degree”

End quote


Glyndŵr's father served the English King Richard II loyally. He and others like him were quite literally the eyes and ears of the king, fully integrated into Welsh society, they kept their king aware of rumors and rebellions that cropped up now and again. But sometime before Glyndŵr's 11th birthday, his father died and he was adopted by a lawyer of similar family pedigree. His name was David Hanmer. By all impressions, Glyndŵr settled in well with his new family, extending his social circle and even marrying his stepfather's daughter Margaret. They went on to have quite a brood, about five boys and around four girls. 


From the time Glyndŵr was around 18 to his early 30s there's conflicting reports about where he was and what he did, but as a member of Welsh nobility, it's highly likely that he served The King in a military capacity, mustering troops through his campaigns in Scotland, which was in rebellion at this time.
Glyndŵr and other landowners in Wales enjoyed a good deal of freedom under the rule of King Richard and rewarded him with their loyalty, keeping tax flowing into the kings coffers and troops into his army.
But the same could not be said for other parts of the country. As the 14th century began to draw to a close, the king was deeply unpopular with many of his nobles. Many saw him as a tyrant and were unhappy with his choice to make peace with France. Long story short, one of the leading nobles with a claim to the English throne out maneuvered the king, and by 1399, Richard II was locked away in the Tower of London and a new king sat on the throne. He was to be known as Henry the Fourth. To describe the kind of man Henry the Fourth was. I brought on Chris from History With Chris my go to for anything related to English monarchy:

Henry Bolingbrook was born on the 15 April 1367 at Bollingbrook Castle, Lincolnshire. Henry was the eldest son of John of Gorn and Blanche of Castile, and his father John was the third son of feigned warrior King Edward III, meaning John of Gorn was repelled to a position of significant power and control during the reign of his nephew Richard II. Richard was a notorious tyrant, and in 1388, Henry rebelled against his cousin before being exiled to the Continent for his treachery. In 1399, his father, John of Gaunt, died, but Richard denied Henry his father's gland and titles. Henry rebelled again. Later that year, Henry returned to England, quickly gathering support and set about capturing and removing his cousin Richard II from power. On 13 October 1399, Henry was crowned King Henry IV, and for the first time since Harold Godwinson in 1066, an English king made an address in English. Henry was the first English king since the Norman Conquest whose first language was English. France had been the language of court since the conquest. Henry wasn't raised to be a king. He was the son of a duke and never really meant to inherit the throne. Henry was able to get one group of people on side, and that was Parliament. Henry was able to get an act of Parliament to secure his legacy and his legitimacy. Henry's entire reign was filled with plots, rebellions and political upheaval, all centered around his dubious claims to the throne. Yes, he was a direct descendant of Edward III, but he wasn't even the next in line.


After Richard's death in January of 1400, Henry finally dealt with his political rival and cousin, Richard II. Richard's official cause of death was starvation, and it's impossible to know if Henry was involved. It's likely as Richard presented the biggest threat to his claim, as a year earlier, it was his way around. But the evidence is sketchy at best. But it's safe to say that Henry was probably at least pleased to know that his cousin had been killed. Glyndŵr  was able to use the king's paranoia against him, likely causing others to rebel. As well as the Welsh and his northern barons, Henry also had to deal with problems with the Church, specifically a group of dissenters known as the Lollards. Many men and women were burnt at the stake on the orders of Henry.


Henry V's entire reign seemed to be one long fight against his subjects and, for the most part, himself. Henry was a paranoid king, and for good reason. He'd usurped his cousin, taken a crown that wasn't meant for him, and didn't he know it?


Thanks for that, Chris.


The new king's reign was rocky. After foiling one assassination plot and clearly suspecting more, he pulled every trick he could to move those loyal to the previous king away from positions of power. 


Many of the nobles, even ones who had actually helped him gain the throne were not sparedhis ire. Lands were confiscated and positions were repealed. And because of this, if you look at a map of Wales and the governors of each region, you would see a lot of new names from 1397 to 1399. 


And it did not go unnoticed by the locals. 


As we said earlier, despite the fact that many men of English stock held power in Wales, cooperation from local lords, Welsh lords, was essential for things to run smoothly. RR Davies summarizes this tricky balancing act, by saying quote:


‘An essentially alien and absentee royal and aristocratic lordship depended for the weekly exercise of its power of governance, justice and revenue raising on the services and cooperation of the leaders of local welsh communities’ 


End quote


But in the blink of an eye, many of these absentee lords had built up connections with the community were gone. Replaced with men who didn't know and probably didn't care to know, the local community. 

Wales was a powder keg. The English just didn't know it yet.

 And the fuse was about to be lit.


 By this point in time, Owain Glyndŵr had grown into a successful and wealthy landowner in line with his birthright. But like half the world, he did not get along well with his neighbor, a man called Reynold Grey.
Baron Reynold Grey formerly, and Reginald de Grey First Baron Grey of Wilton- Ultra formally. 


Grey was of old English stock and he, like Glyndŵr, had enjoyed a good relationship with Richard II and had kept his hands clean in the rebellion and counter -rebellion of King Henry IV, so now enjoyed a good relationship with him too. On paper, the two men were fairly similar, except Glyndŵr was a mixed English and Welsh heritage, while Grey was English through and through. 


In the past, Glyndŵr and Grey had bickered over a piece of land they both believed they owned. The exact order of events that follows is up for a bit of debate, but generally the story goes that the matter was taken before Parliament and they ruled in Glyndŵr's favor. 


But now, a few years later, with a different king who favored Grey, the sneaky baron tried his luck again, and surprise, surprise, the Parliament overturned their previous ruling, forcing Glyndŵr to concede the land to Grey. 


The two men wrote a series of letters to each other threatening the destruction of the other's property. Yada, yada, yada, Grey kept the letters and then threatened to take them to the king…Standard neighbor drama, right? 


Not long after this, Glyndŵr's petition for the matter to be relooked out was thrown out of Parliament without them even reviewing it. A quote of questionable authenticity claims that when presented with Glyndŵr’s petition, the Parliamentarian stated, quote:


"What care we for barefoot Welsh curs?"


End quote.Barefoot being a reference to the supposed grimy conditions in which people from Wales lived. Whether or not this phrase was actually uttered, it did seem to be the sentiment felt by Parliament and the increasingly xenophobic king. 

Not long after this occurred, a mustering call was issued by the king for an invasion of Scotland. A mustering call was a demand sent to the major lords in the area to gather a number of troops for an upcoming war. And the sneaky old baron, who was meant to pass a message along to Glyndŵr, conveniently forgot until it was too late! To ignore a summons was treason. And treason meant land confiscation for Glyndŵr until he could plead his case against the very same Parliament that had now ruled twice against him.


Blood boiling with rage, Owain Glyndŵr was about to show the world exactly what a bunch of barefoot Welsh curves could do. 


But first, a quick message from one of our friends of the show.


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Glyndŵr and around 200 men took to the countryside, specifically the English countryside. For five days, English towns were sacked, buildings put to the torch, and its inhabitants scattered. Glyndŵr's power base lay in the northeast to Wales, but it didn't take long for the rebellion to spread to the northwest also. 


When he heard of the rebellion, Henry V was heading back from Scotland on the very expedition Glyndŵr was tasked to provide men with. The king diverted his army to meet the threat. But by the time he arrived, Glyndŵr's force had disbanded. All of his men had no wish to fight a pitched battle against a professional English army. Determined to punish the inhabitants who had rose up with Glyndŵr, Henry's army marched across northern Wales, sacking in burning towns that they deemed as rebel hotspots. 


The island of Anglesey, just off the northern Welsh coastline, copped it particularly hard. This island was home to an influential family who I'm sure you've heard of. 

The Tudors. 

That's right.


The very same family that would later give England its most famous monarch, Henry VIII.


The two Tudor brothers, Rhys and Gwilym, were relatives of Glyndŵr and, like him, they had no love for the new king. And because of this, when Glyndŵrs rebellion started, it was these two that roused the men of their community to follow suit. But like their cousin, they were not about to give pitched battle to a professional army. Instead, they picked off small groups of troops that had strayed away from the main army: scouts, foraging parties or anyone who broke off from the main group of the army were battered by constant guerrilla attacks by the combined forces of Glyndŵr and the Tudor brothers.


As the weather began to worsen, which it does regularly in Wales, The king and his army retreated back to the English border. With almost nothing to show for their efforts. The token force of English troops were left in some of the key fortresses in the northern countryside.

To calm the population down, general pardons were issued for all involved. Except for the Tudor brothers and Glyndŵr himself.


In Parliament later that year, a new set of restrictive laws were imposed to further curtail the freedom of the Welsh. With the passing of the bill, men of Wales were further restricted from purchasing lands or holding offices in any of the border cities. English citizens were also now unable to be convicted of a crime that took place within the border cities.
The message from the Crown to its Welsh subjects was clear: know your place and keep a low profile.


As far as the king was concerned, that was the end of it. But that wasn't the end of it, not by any stretch of the imagination.


Once the king's troops left, Glyndŵr's men emerged from their mountain hideouts again, ravaging the border towns. Meanwhile, in Anglesey, fury is at the desecration of their ancestral home and being left out of a general pardon, the Tudor brothers pulled a sneaky one at the large fortress in the city of Conwy. Knowing that they had no way of taking the fortress by force, the brothers and a group of men dressed up as carpenters and talked their way into the fortress, insisting they were coming to actually do some repairs.


I've included a picture I took when I went to Conway Castle on our Instagram and website, but safe to say this was a huge fortress once again thought to be impenetrable. The small group killed all the guards and barred the gates from the inside. The crafty brothers then negotiated the return of the castle in exchange for the pardon they had missed out on before. 


The commander in charge of the negotiation with the brothers was a man called Henry, nicknamed Henry Hotspur for his speedy cavalry charges.


Henry was from he incredibly rich and influential Percy family.

A family which also had claimed to the English throne.The brothers got their pardon, but over in London, once King Henry heard of Hotspur's truce, he overruled him and renegedon the pardon that Hotspur had already granted the brothers.


Eventually, the Tudor brothers and the king came to an agreement. But this continual pigheaded stubbornness, showed by King Henry to grant any concessions at all to the rebel leaders, served only to help the rebellion gain steam.
Despite Conwy castle being returned to the English, the men of Wales now knew that these seemingly invincible bastions of English power could be taken.


These gigantic stone barriers that for centuries had been a constant reminder of their own submission to the English crown now represented opportunity.


Glyndŵr's men rose from the shadows again.Decimating English townships and whatever token garrison The king had left behind.

But this time, properties belonging to his much hated neighbor, Baron Grey, were deliberately sought out and torched.

Anything of value Grey owned was methodically and very deliberately burnt to the ground: buildings, food stores, horses and cattle, Glyndŵr wanted the man destitute and broken.


Like he had made him.


More expeditions were sent to Wales, but they met the same fate as the earlier ones. The men that were fighting may not have had the armor, training or discipline but they knew the land and were well informed of the movements of English troops long before they arrived at their destination.


In response, the king doubled down even further on laws to restrict the liberty of the people of Wales. With each passing month, anyone of Welsh descent living lawfully in England was seeing their civil rights being chipped away piece by piece. 


They couldn't go on like this.


 Throwing their lot in with Glyndŵr was quickly becoming their only option.


 But even so, rebellions like this did have a tendency to burn themselves out after a few months. Oxford professor RR Davies speculates that with some imagination and clemency from the king, perhaps the whole rebellion could have been put to bed. Perhaps if Glyndŵr’s properties had been returned, then our story would end here.


But clemency was not something King Henry IV had an ample supply of.


A quirky, though likely untrue Welsh legend states that one night, as agents of the king searched for Glyndŵr, he was laying low in a valley in the mountainous region of Snowdonia. Emerging from a black night, a friend of his rode around the corner, saying that the king's men were hot on his trail and that he needed to leave right now!

With nothing but the clothes on his back, the middle aged Glyndŵr fled up into the mountains, but was spotted on the way by his pursuers! 


As the king's agents closed in around him from all sides, and with only a sheer rock face behind him, he did the only thing he could.




The peak was described as being 250 foot or 76 meters high and as steep as a chimney. But with no other options, he had to try. The dumbfounded English scouts could only watch as the marked man scrambled up the rock face and out of their clutches. 


Though this is probably a legend, the cave that he hid at the top is fairly well known by locals known as ‘Owain Glyndwr’s Cave’.


During my time in Wales, I tried my best to find it and I'll put the clues as to where it's meant to be on our website, but I had no luck. 


And just as a disclaimer: anthology of heroes podcast takes no responsibility for any injuries occurring trying to find this cave that may or may not exist!


As things began to heat up in the north, Hotspur wrote to the king several times, pointing out that many castles were in urgent need of repair and more men to man the walls.


Hotspur knew that there was a gathering storm at his doorstep and he was doing all he could to try and batten down the hatches in preparation.

But his plea was ignored, partly due to the dire finances of the English treasury, but also likely due to the man's claim to the throne. Despite keeping England's borders secured, Henry Hotspur was and would always be a threat to the king. Someone with a claim to the throne always was.


Hotspur spending his own capital to defend against Welsh rebels was good news for the King, weakening a rival and with any luck, stamping out the Rebellion at the same time.

While Hotspur's letters stressed the need for a peace with the Welsh, the king and his favorites would have none of it. Baron Grey was particularly vocal in Parliament that the war must continue. Furious at the mounting repair bill Glyndŵr was costing him, the Baron whispered constantly In the kings ear against any talk of peace or reconciliation with the Welsh.


…At least not before he had his revenge. 


In June 1 1401 Glyndŵr and somewhere around 300 of his followers were met by a large English host of around 1500 men. The battle had been a long time coming. Glyndŵr's men had harassed the invading force up and down the countryside.


His strategy seemed to be to slowly wear down the morale of the attackers while drawing them into a location of his choosing. Finally, in a muddy valley with an uphill advantage, the English army charged down and collided with Glyndŵr's militia. Though being outnumbered at least three to one, the Welsh troops were more nimble. Smaller Welsh ponies deftly skirted atop the marshy bog, while arrows shot from powerful Welsh longbows crisscrossed the field. 


It wasn't long before the professional army of the Crown was sent running back across the border.


Owain Glyndŵr had just won his first pitched battle...


 Glyndŵr knew his appeal was growing. Welsh students studying in Oxford had begun to drop their studies and head home to heed his call. But he needed to keep the momentum going. He needed something big, and more than anything, he needed money. And his old neighbor, Lord Grey, had a stack of it.


Hauled up in his castle at Ruthin, the Baron sat quietly as the countryside rose up in arms around him.


In a way, he was a sitting duck. Glyndŵr put his men put Ruthin castle to siege, but the Baron's disciplined household guards held firm against Glyndŵr's mob.


As the siege dragged on, the momentum began to melt away and many of Glyndŵr's followers gave up, losing interest now that the easy lightning raids had slowed down.


Lord Grey watched from his high walls as the army drifted off until only his despised rival and a few friends were all that remained. 


The opportunity was too good to pass up.


The ever elusive OEN Owain Glyndŵr was right there outside his fortress, with almost no army!


With possible advice from his household servants, who may have been supporting Glyndŵr, Grey and seven of his knights suited up and burst from the castle, speeding down towards Glyndŵr and his men.


Through the countryside, they chased them, their sturdier warhorses gaining more and more ground than the smaller Welsh ponies. But, as a legend goes, Glyndŵr had planned an ambush and was actually leading his old neighbor into a trap…


At the agreed upon location, a group of Glyndŵr’s archers waited…


Grey and his men sped around the corner, and in the tree line they spotted Glyndŵr's army, which were actually just iron helmets and uniforms stuck on wooden pikes.


But in the thrill of the chase and the misty Welsh forest, they looked every bit authentic. Grey and his knights tried to speed back out the way they came, but when they did, they ran into Glindor's real army:  the archers, who promptly killed all the knights save  Baron Grey himself. 


The origins of this story are spurious, of course, but the hill where this ambush apparently took place is known today as ‘Bryn Saith Marchogor Seven Nights Hill.


The capture of Grey, besides being immensely satisfying for Glyndŵr himself, won him a ton of propaganda points for his rebellion. Grey was soon ransomed back to the king, who, despite being flat broke, took loans to secure his release, with 110 silver marks being the recorded amount.


As part of the agreement for his release, Grey was made to swear before Glyndŵr to never take up arms against him.


 And even if he wanted to, the ransom was so incredibly steep that he never had the money to even try. 


Glyndŵr had broken Grey.


Both financially and politically. 


His family would never regain the status they once had.


 In one lucky afternoon, Glyndŵr had completely neutered his arch rival.


And he was only just getting started.


... And that is the end of part one of Owain Glyndŵr, the Last Prince of Wales. Tune into our next episode, where Glyndŵr's rebellion reaches its zenith before the timely involvement of a charismatic young English prince unravels it all…