Owain Glyndŵr, The Last Prince of Wales (Part 2)

August 23, 2021

Owain Glyndŵr, The Last Prince of Wales (Part 2)
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The Welsh have risen!

Owain Glyndŵr's rebellion has swept across the the British Isles.
As Welsh apprentices abroad down their tools and return home to heed the call, The Prince Of Wales secures an alliance with one of the most powerful Monarch's in Europe.

Meanwhile, a charismatic English Prince takes over the reigns of government from his bumbling father; and approaches the rebellion with a cunning new plan....

The epic conclusion to the story of Welsh national hero, Owain Glyndŵr.



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  • Discovered By The Enemy’ by Jordan Winslow
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  • Music by Drawing the Sky by Eugenio Mininni
    From: https://mixkit.co/

  • Music licensed to Anthology Of Heroes Podcast by Fesilyanstudios

  • Music: The Victory Of Heroes by Shane Ivers - https://www.silvermansound.com
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Hello, you've just tuned in to part 2 of the story about the Welsh hero, Owain Glyndŵr.

In part 1, we walked through the history of Welsh rebellions against England and the increasingly

harsh rule of its current king, Henry IV.

We covered Glyndŵr's rise to prominence and ended the episode with the capture and

ransom of his hated rival and neighbour, Baron Grey.

If you haven't already, I'd recommend listening to that episode to get some context.

Still here?


Here's the final part of Owain Glyndŵr, the last Prince of Wales.

As 1401 drew to a close, Glyndŵr tried and failed to besiege the fortress of Canaffan

in northern Wales.

Remember at the start when we talked about the English iron ring around northern Wales?

Well, Canaffan Castle was the diamond in that ring.

I've put a few pictures up on our website and Instagram I took while visiting there.

It's one of the most formidable castles I've ever seen and without siege weapons

and cannons, it's little wonder why Glyndŵr's siege failed.

Nevertheless, the siege became famous as during it, Glyndŵr raised his iconic golden dragon

banner for the first time.

The banner was the very same used by the mythical figure Uther Pendragon, the father of the

legendary King Arthur.

The use of this powerful ancient symbol was fantastic propaganda and I'll be adding

a picture of the banner to our website and socials.

By choosing this image, Glyndŵr was styling himself as the successor to these mythical

figures of old.

He was drawing a parallel between himself and the original inhabitants of the land before

the Normans arrived in the 12th century.

Building on this sentiment, he had letters sent to the King of Scotland and a few Irish

chieftains hoping to secure an alliance.

Like his banner, the language used in the letters harks back to their common ancestors.

One line says, quote, your most noble ancestor and mine was the first crowned king who dwelt

in this realm of England, which of old times was called Great Britain, end quote.

And throughout all the correspondence, he refers to himself humbly as, quote, your simple

cousin, end quote.

Letters to the French king penned in Latin were also sent, but these took a more my enemy

is your enemy kind of vibe.

There is also speculation that the envoys were sent in secret to Henry Hotspur, whose

frustration with the king was growing by the day.

Even now, Hotspur had still not been provided with any funds to defend the borders and was

also forbidden from making any concessions of peace towards Glyndŵr.

It's likely that these two men came to a mutually beneficial agreement, we'll say.

This becomes evident as going forward, we see a noticeable drop in the involvement of

Hotspur in suppressing the rebellion.

And we also see that his properties are coincidentally left untouched by Glyndŵr's men when

he comes raiding.

With Hotspur keeping quiet, the king sent another royal expedition into Wales, determined

to stomp out the growing rebellion before it reached the south coast where the majority

of English industry was centered around.

Sir Edmund Mortimer was put in charge of a large body of men around 2000 all up.

The Mortimers were a big deal, their families claim to the throne was even stronger than

King Henry's, but so far they had served the new regime loyally.

By now, Glyndŵr had many seasoned military men under his command, men who had fought

in France, Scotland and even further abroad.

These men knew the land and knew the enemy.

Glyndŵr split his forces, around 1500 men, into two groups concealing one in a dense

forest behind the battlefield.

Mortimer likely thought that the 700 he initially encountered was all Glyndŵr could muster

based on previous engagements.

As the heavier English soldiers charged down into the Welsh ranks, Glyndŵr and his men

held the line, waiting for the English troops to fully commit to the attack.

And when Glyndŵr was convinced they were, he gave the signal.

From the trees behind, the other half of the Welsh army charged into the British flanks

and rear.

Just when it looked like things couldn't get any worse for Mortimer, a large contingent

of his archers defected.

Welshmen who had been pressed into service against their countrymen turned an open fire

on the English troops they had just marched into battle with.

The Battle of Brynglass, as it's known, was an absolute disaster.

Glyndŵr's army, no, the Army of Wales, had steamrolled the king's best and brightest

in a pitch battle.

There was no way to claim that this was an isolated rebellion from a few barefoot Welsh


This was now a full-blown war of independence and it was only gaining momentum.

Sir Edmund Mortimer was captured with both him and Glyndŵr expecting a tidy ransom,

considering the man's position.

But to the shock of both of them, the king completely ignored the request.

After jumping to attention to pay Lord Grey's ransom, the complete indifference as to whether

this nobleman lived or died was a huge slap in the face to Mortimer.

While the king was indeed broke, he probably hoped that Mortimer, with his superior claim

to the throne, would languish in a Welsh prison and eventually expire, taking his claim to

the grave.

But Glyndŵr was too crafty for that.

Mortimer was of sound military mind of high birth.

If the king didn't want him, he would keep him.

The two men buried the hatchet and Edward Mortimer became part of the family, literally,

marrying Glyndŵr's daughter, Catrin.

With this victory on the open field, Glyndŵr's popularity went international.

Welsh apprentices all over England downed their tools and heeded the call to return

home, spurred on by the English king's increasingly harsh laws on people of Welsh descent living

in England and abroad.

In a way, King Henry IV was the best recruiter Glyndŵr could have asked for.

By constantly chipping away at the livelihood and chances of advancement, the choice to

side with Glyndŵr was an obvious one for the common man.

But by 1404, he was no longer simply Owen Glyndŵr.

Understanding the need to legitimize his rebellion, he called a Welsh parliament, the first of

its kind.

With representatives from all over Wales, France, and even Spain, Glyndŵr spoke passionately

about his vision for an independent Wales, the Wales of old, before the Norman invasion

subjugated them, and a separate Welsh church in communion directly with Rome.

Owen Glyndŵr was crowned Prince of Wales, an ancient title that had been usurped by

the British, with the last Welsh Prince of Wales almost 150 years ago.

As the parliament concluded, everyone's spirits were soaring as they looked towards

the future.

But over in England, there already was a Prince of Wales, the king's son, and perhaps his

only trump card, Prince Hal.

If you've binge-watched every series on Netflix during the pandemic, you've probably

seen the movie, The King, that features a moody young man decimating the French army

at the Battle of Agincourt.

Well, this is about the very same prince, about a decade or so earlier.

His real name was Henry, but we've already got enough Henrys in the story, so I'll

stick with Hal.

Hal was everything his father wasn't.

He was pious, handsome, and brave, a model of every virtue a medieval prince should be.

He was a natural leader who, even as a teenager, inspired loyalty from his men in the heat

of battle, and although he was as single-minded in his goals as his father, he was not as

stubborn and bloody-minded about reaching them in a specific way.

If diplomacy could achieve the same result as a long, costly war, he would pursue that


But at this point, the young prince was in a particularly dark place indeed.

After constantly being denied the funds to pay for defense against Glyndon, but still

being forbidden to make a truce with him, Hotspur had raised his banners against the

king in rebellion, and Prince Hal had been sent to deal with him.

In a particularly bloody battle, both he and Prince Hal had been badly injured by arrows

to the face.

Hotspur had died, and Prince Hal had only survived thanks to a skilled surgeon who managed

to remove the arrowhead from deep within his cheek.

Hal was on the mend, but for now he was out of action.

The death of Hotspur was a blow to Glyndor, but when one door closes, another opens.

Here in France, the king began to see just how unstable England was.

Behind the scenes, Glyndor had worked to form a three-part alliance with Hotspur's father

and his hostage-turned-son-in-law, Edward Mortimer.

Both these men were from powerful old families and could call on a huge amount of support

from their local districts.

A plan was concocted to depose King Henry IV and subdivide England between the three

of them, with Wales being recognized as a true independent country led by Glyndor.

With a parliament, a monarchy, and now what looked to be agreed borders, Glyndor was looking

more and more like a ruler of a sovereign nation, and the French king eagerly agreed

to an alliance with him, presenting the Prince of Wales with a brilliant set of armor as

a token of their friendship.

Glyndor had just secured the support of one of the most powerful nations in Europe.

As state-of-the-art French siege equipment and professional troops disembarked on the

coastline of Wales, Glyndor's rebellion went truly nationwide.

After the horror of King Henry, castles now began to fall to the Welsh menace.

If you'll remember from earlier, the Iron Ring of castles was conceived specifically

to halt rebellions exactly like this, but there was no contingency plan for what would

happen if the castles themselves were taken.

The idea that the Welsh could achieve a degree of professionalism on this scale had been

inconceivable to the English parliament and king.

With droves of veteran Welsh archers and French siege technicians now under his command, towns

and cities surrendered en masse, and castles on the English border made separate treaties

with Glyndor, paying his army to spare their possessions.

Though a few of the larger castles like Caernarfon, which we referred to earlier as the Diamond

of the Iron Ring, held out, Wales was now almost entirely under Glyndor's control.

The king would launch numerous punitive expeditions, but in an almost supernatural way, almost

as soon as men would cross a border, the moody Welsh weather turned against him.

And if the torrential rain didn't douse the men's spirits, the Welsh longbowmen hiding

in the trees did.

Spirits soared for Glyndor and his men, who were not only gaining independence but also

vast troves of wealth through the surrender of rich English lords.

But although Glyndor and his men had no way of knowing it, this was to be the apex of

the Welsh Free State.

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

Hello, I'm Patrick.

And I'm Will.

And this is the Cloak and Dagger podcast, where we explore the bloodiest assassinations

that changed the course of history.

From the shores of feudal Japan to the streets of Dallas, Texas, we've got poisoning, shootings,

stabbings and even a mummified garrotting.

So settle in, put your feet up and prepare to dive into the bloody mess which we call


With Prince Hal having recovered from his arrow wound, he began to take a leading role

in the Welsh campaigns.

If you plotted the rebellion on a line chart from an English perspective, it would be a

sharp V-shape with the uptick starting with the prince's involvement.

Favoring a peace with France and determined to stop the royal coffers hemorrhaging cash,

he opened up negotiations regarding marriage to the French king's daughter.

With the possibility of a royal heir, the French appetite for war with England, which

was already fading, cooled.

Slowly the troops that Glyndőr had begun to rely on for his sieges trickled back home.

Immediately he realized what this would mean for the rebellion and did everything he could

to try and re-secure French aid, even pledging allegiance to their pope.

Yeah, at this point in history there were two popes, one for France and one for everyone


After this, things began to turn.

The reports from battles in 1405 are incomplete and not too reliable, but it looks as if some

medium-sized battles were lost by Glyndőr's lieutenants.

With only a few scattered castles and bastions being controlled by the English, it's believed

that his lieutenants assumed these would be manned only by a few men, while in reality,

now that there were so few safe areas in Wales, the remaining garrisons were bristling with

grizzled defenders who had nowhere to run and defended the garrisons like their life

depended on it, which it probably did.

As the fickle loyalty of the population began to waver after these losses, Prince Hal started

another expedition into Wales, but with a very different tone to his father's burn-rape-and-pillage

style invasion.

The prince recognized his father's error in how he handled the rebel lords.

Rather than doubling down on anti-Welsh rhetoric or declaring them traitors, Hal lured many

men back to the English cause by amnesties and pardons.

All of a sudden many men who had taken up arms against the English king due to his increasing

ly harsh rules now had another option.

It's worth remembering that Wales was not a wealthy nor populous country and it had

been locked into a state of war with England for now five years.

Glyndŵr's appeal for an independent Welsh state was becoming less appealing as the farmers,

crafters, innkeepers and soldiers that made up his army began to dream of peace.

In an effort to keep the veil of legitimacy on his Folgering rebellion, Glyndŵr held a

second parliament and, though representatives from Wales were present, there was a noticeable

lack of foreign dignitaries.

If the backdrop to the first parliament was excitement and hope, this one was gloom and


But Glyndŵr fought on.

His lieutenants were sent to all corners of Wales to try and reignite the fading embers

of Welsh nationalism, but it was no good.

Word of Prince Hal's pardons had spread to many prominent lords and many of the men who

had become the backbone of Glyndŵr's military council began to turn back to King Henry and

his charismatic son.

Prince Hal further streamlined the process, offering a simple system where an ordinary

Welshman who had served in Glyndŵr's army could pay a fine at one of the local garrisons

in exchange for amnesty.

And with this, many of the rank and file troops too began to melt away.

With South Wales and many of the border districts slowly returning to English rule, Hal set

his sights on the stubborn north-west of Wales.

The north-west had always been the most difficult to subdue, I mean the Iron Ring was built

there for a reason.

Aware that these men would not surrender their loyalty so easily, the prince set up a naval

blockade around the island of Anglesey.

As we said earlier, Anglesey is the most north-west area in Wales and is separated from the mainland

only by a thin strip of water.

Due to its flat land, it was an ideal place for farmland and with Hal cutting it off from

the mainland, the price of food began to rise throughout the war-ravaged realm.

The Tudor brothers, who were the island's ruling family, fought back with everything

they had.

But for the same reason the land was ideal for farming, it was not ideal for guerilla


Glyndŵr once again did not fail to grasp the seriousness of the situation, sending further

envoys to France pleading for the support of their navy to break the blockade.

But the moment had passed.

While the French alliance to Wales was a core part of the rebellion, to France it was a

policy that could and did change based on the whims of the king.

The Tudor brothers gave it their best but soon, Anglesey, the breadbasket of north Wales

went dark.

As severe winter brought more problems for Glyndŵr who was already struggling to feed

his troops, news from France sunk his spirits even further.

France and England had agreed upon a truce and King Henry had demanded the dissolution

of the French-Welsh alliance as part of the treaty, and they had accepted.

The slim hope of France re-entering the war was gone.

In 1407, Prince Hal and his retinue pummelled Aberswith Castle, one of the most formidable

still held by Glyndŵr's men.

Through grit and determination, the men of Wales repelled the numerically superior English

army but at a great cost.

With the English army temporarily retreating, the Welsh commander in charge of the garrison

asked Glyndŵr's permission to discuss terms of surrender with the English.

Glyndŵr responded bluntly that if the man dared give terms, he would have his head.

Glyndŵr tried to consolidate his power base to the areas where he enjoyed the most popularity,

but by now English supply lines had been fully restored.

Supplies, siege weapons and men flowed in like a tidal wave from the west coast, south

coast and from across the border, but still he would not give in.

Making his presence known, he marched his dwindling band of men across the countryside,

sacking any villagers that had forsaken his cause.

In a way, he had come full circle.

Reduced to only a handful of men, he did as much damage as he could at carrying away whatever

loot was left in the desolated villages, but this time he found no receptive ears to the

Welsh Free State, only sullen and tired men, women and children who yearned for peace.

In 1407, Glyndŵr lost his last two remaining allies.

The dream of subdividing Britain between the Perses, the Mortimers and himself was put

to bed after each of them was decisively defeated by the King in separate engagements.

Not long after, one of Glyndŵr's last castles was recaptured by Prince Hal and within it

was Glyndŵr's wife and many of his children, who were taken back to England in chains and

locked away in the Tower of London.

The dream was dead, but Glyndŵr had one last right hook to swing.

In 1410, with the last of his supporters, including the Tudor brothers, the last Prince

of Wales headed deep into English territory, one last raid to make the English bleed.

There was no baggage trains in tow for the loot this time, no one was intended to return.

But even this failed to make a dent.

The English border towns were heavily defended and whatever was left of Glyndŵr's army

was defeated or killed, including his most loyal man, Rhys Tudor, who had been with him

since the beginning.

Rhys was dragged back to London before being hung, drawn and quartered.

This raid was the last verifiable sight of Glyndŵr in the flesh.

After this, Prince Hal removed himself from Wales to focus his attention elsewhere.

There were bigger fish to fry now.

Sporadic fighting lingered in isolated areas for the next few years and in 1412 Glyndŵr

captured a Welsh lord and successfully ransomed him back to the English king.

The letter was to be the last confirmed correspondence with Glyndŵr, who at this time was probably

around 53 years old.

After this, the man who was once the bane of England, the man who only a few years back

had declared himself the true Prince of Wales to the adoration of crowds, just disappeared.

There are few occurrences in history when a man as famous as Glyndŵr could simply vanish,

and it speaks volumes that even in post-war ravaged Wales, where the population would

have been desperate for money, no one sold him out.

Glyndŵr's disappearance is full of rumours and myths, just like his life was, but one

particular story stood out for me above all the others.

It goes like this.

On a dark and stormy night, a well-dressed gentleman and a servant arrive at the castle

of a local lord in southern Wales.

The gentleman asks in French if he could trouble the manor lord to rent a room for the night.

The lord, impressed with how the man carries himself, agrees and welcomes him into his


Assuming that he's a foreigner of high birth, the lord asks him to stay a few more nights

and the mysterious visitor agrees.

Over the next few nights, the manor lord tells the gentleman how he has heard rumours that

O Englandor is in the area, telling him he sent out many riders to capture this criminal

and that he doesn't care if he's returned to him dead or alive.

The gentleman listens quietly, agreeing that it would be good if someone was to catch O

Englandor, if anyone was able to.

After four nights and three days, the gentleman and a servant depart from the castle.

As he turns to leave his gracious host, O Englandor shakes the hand of the manor lord,

looking him dead in the eye and telling him, quote, O Englandor, as a sincere friend, having

neither hatred, treachery, nor deception in his heart, gives his hand to Sir Lawrenceburg

Rose and thanks him for the kindness and gentlemanly reception which he and his friend experienced

from him at his castle and desires to assure him on oath, hand in hand and hand on heart,

that it will never enter his mind to avenge the intentions of Sir Lawrence towards him,

end quote.

As he watched O Englandor disappear back into the night, Sir Lawrence was dumbstruck and

for the rest of his life did not recover the use of his voice.

As I said, almost completely untrue, but a great story and an analogy for the elusiveness

of Glyndŵr even when most of the country was searching for him.

In 1413, Henry IV, the man whose blatant nepotism and anti-Welsh rhetoric had fueled Glyndŵr's

rebellion 13 years ago, died.

His dynamic and now famous son, Prince Hal, stepped up formally to become King Henry V.

With his obstinate father out of the way, the new king continued the trend of pardoning

those involved in Glyndŵr's rebellion, even offering to pardon Glyndŵr himself as well

as his one remaining son.

This was done as King Henry prepared for a large military campaign in France and perhaps

speaks to the fact that maybe he believed Glyndŵr was still capable of rousing the support

of the Welsh into rebellion, which obviously would have caused major problems if he was

abroad with the majority of his army.

But Glyndŵr, whatever he was, would have none of it.

Either distrustful of the king's intentions or, even now, unable to let the dream die,

he refused.

Nothing is certain, but it seems like he died not long after.

To this day, no one knows what the last years of the great O Englandor's life looked like.

Many stories talk about him eking out an existence in the cave around his old ancestral lands

in northern Wales.

Another story has him passing his last few years as a friar on one of the estates of

his daughter.

And another follows a similar vein to so many heroes we've covered on this show, that

he turned to stone, ready to awaken in the time of Wales' greatest need and retake

his country.

The Glyndŵr Rising, as it's become known, was the last great rise of Welsh nationalism

against English dominion.

In a way, it was made possible through King Henry IV's tone-deaf diplomacy towards Welsh

people almost as much as it was through Glyndŵr himself.

Many times when the rebellion was gaining momentum, the king completely disregarded

options that may have cooled tempers of leaders like Glyndŵr or the Tudor brothers.

Instead, his insistence on unabated punishment pushed many men who may have wished to remain

neutral into Glyndŵr's court.

But in a strange way, Glyndŵr would have the last laugh when around 70 years later, at

the Battle of Bosworth Fields, a king of Welsh stock would find himself on the throne.

The very same hardened Tudor brothers of Anglesey, who opposed English dominion until the very

end, would go on to give us England's most well-known king, the famous womaniser and

Church of England founder, King Henry VIII.

During my time in northern Wales, I noticed many small landmarks still pay homage to Glyndŵr's


Most are just small markers, a plaque commemorating a battle, or a cave where he hid, or a flag

on a hill.

But whatever they are, Glyndŵr's legacy is there if you know where to look.

To me, the most memorable experience was driving down a quiet country road and spotting Glyndŵr's

gold and white banner that could be seen peeking out of an old pub, his memory still preserved

six centuries later.

In BBC's 2002 poll of The Hundred Greatest Welsh Heroes of All Time, Glyndŵr came in

at number 2.

But even more impressive, in the same poll for The Greatest Britons of All Time, Glyndŵr

came in at number 23, beating Stephen Hawking, King Henry VIII and William Wallace, clearly

showing that the respect for this man was not just confined to Wales.

He was also immortalised when he was made into a major character in the Shakespearean

play King Henry IV Part 1, which was written about 180 years after the event.

Che Guevara, the famous Argentinian revolutionary, also apparently drew inspiration from the

stories of Glyndŵr's guerrilla tactics.

But for me, I found Glyndŵr's legacy summed up most poignantly by T.P.

Ellis in his book A Story of Two Parishes, where he wrote, quote,

He passed away like a mist on his own mountains, with his mission unfulfilled.

No man knows when he died.

No man knows where he was laid to rest.

There is no monument to him, save for the memory enshrined in his people's hearts.

May it live there forever, a greater soul, a nobler spirit, never dwelt among these mountains.