'That great magician, damn’d Glendower'

By Andrew-Paul Shakespeare

Owain Glyndwr sketch by William Blake
Owain Glyndwr sketch by William Blake

So anguished the seething between nations, the women of Bryn Glas emasculated the dying English littering their slopes. Have you never heard of it? Never of the battle of Hyddgen? The capture of Conwy? The sack of Cardiff? The last Welsh Prince of Wales?

History is written by the victors. But for ten long years, the reign of Henry IV shook with assaults from the west, the north and the south, a furious campaign of fire and fury; of parliaments, alliances, kings and the pope, which threatened the very existence of the English kingdom.

But unless you live in Wales, you’ve probably never heard of Owen, of the Glen of Dee Water (referring to the River Dee that empties into the Irish Sea by Chester), or Owain Glyndefrdwy in his own language; Owain Glyndwr for short; Owen Glendower as Shakespeare rendered it.

The Unlikely Revolutionary

He had spent a lifetime achieving nothing much. He had married well, to the daughter of a prominent judge, Sir John Hamner. He had served with distinction in wars against the Scots. He had acquired two good houses: Glyndefrdwy and Sycharth, the latter being a goodly pile with a deer park and a fish pond; and several chimneys, which was quite something in those days. In his forties, the autumn of medieval life, he looked forward to a comfortable and companionable retirement, and his hospitality was noted.

Wales had seen two centuries of strife, but it was peaceful now. Edward I had bankrupted England building a “ring of iron,” a series of castles to keep the troublesome Welsh under his thumb, and passed a plethora of laws to ensure Welsh money would flow inexorably into English pockets, but Glyndwr was doing well; neither mighty nor rich by English standards, but comfortable by the subjugated standards of the Welsh.

Had Richard II remained king, Glyndwr would no doubt have died contentedly and anonymously. But Richard was deposed and quietly murdered in 1399, and Glyndwr became the biggest thing in Wales since Jesus.

A Disorderly Neighbour

In theory, at least, Wales was administered by both English and Welsh laws. In practice, Reginald de Grey, lord of Ruthin in north Wales, a stone’s throw from Glyndwr’s estates, was a law to himself.

In the 1390s, Grey had attempted to annex a portion of Glyndwr’s land, and been embarrassed when the law had upheld Glyndwr’s claim. But Henry Bolingbroke was a personal friend of Grey’s, so when he crowned himself Henry IV, Grey tried his luck again, and this time, Glyndwr could not even get a hearing, dismissed with a contemptuous snort: “What do we care for barefoot rascals?”

Emboldened, Grey decided to help himself to the entirety of Glyndwr’s property. As baron, one of his duties was to administer the king’s demands for men whenever a military expedition was planned. Henry now planning a campaign against Scotland, Grey declined to inform Glyndwr until it was too late to explain his absence. Glyndwr was assumed to be a rebel, and Grey was only too keen to fulfil his duty to punish Glyndwr in the king’s name by seizing Glyndwr’s estates.

A Rebellion Launched

It was the moment the slumbering Welsh dragon awoke to breathe fire across the whole country. Glyndwr raised his standard in Corwen, one of the villages on his misappropriated estate that today hosts his statue.

Resentful Welsh flocked from all the valleys about. Each of the massive Welsh royal castles had its own walled cantonment in which lived all the carpenters, masons, blacksmiths, farriers, butchers, bakers, accountants, lawyers and everybody else necessary for the functioning of the castles; leading prosperous if sometimes nervous lives, amid a hostile countryside that didn’t even speak the same language.

How nervous is indicated by the mightiness of Conwy’s well-preserved wall: 30 feet high, 24 feet thick, with three gates and twenty-two towers.

9th September 1400, was market day in Grey’s walled cantonment in Ruthin. Two hundred and fifty Welshmen infiltrated the milling crowds of colonists. At the appropriate signal, they threw off their disguises, whipped out their weapons, and commenced randomly slaying the crowds of English all about them. The thatched roofs needed only a brief touch of a torch to erupt into flame. Within minutes, the piles of English corpses were being roasted by the conflagration.

Ruthin, scene of the slaughter of the English, 9 September 1400
Ruthin, scene of the slaughter of the English, 9 September 1400

The Welsh moved rapidly through the north-east. Within a fortnight, most of the English colonies had been sacked, the survivors fleeing or cowering inside castle walls. In the north-west, Glyndwr’s cousins, the Tudors (ancestors to the royal dynasty) swore allegiance. As word spread through England, Welsh labourers dropped their tools, and Welsh students their books, swarming westward.

Henry IV’s army was in Newcastle, hundreds of miles from Ruthin. It would take days for the news to reach him, and weeks to divert to the Welsh borders. But although he had proposed dealing firmly with the Welsh, on north Wales’ abrupt gradients, there was hardly a Welshman to be seen. Henry’s army burned the impoverished huts and looted what little the peasantry had left behind, but of people to hang, rape and terrify, there was barely a soul.

And the rain! The long, grey, stormy autumn drenched the army, froze them to the bone, soaked the firewood, rusted the weapons and sucked wagons down to the axles in sodden ground churned into a quagmire by thousands of squelching feet.

Exhausted, cold, wet, fed up and sick, the English column muttered whether Glyndwr was some kind of sorcerer – “that great magician, damn’d Glendower,” Shakespeare called him – controlling the very elements against them, as they dragged pointlessly over the gradients to Llanfaes, Anglesey.

Pillaging the monastery that housed the Tudors’ family graves presumably provided some satisfactory booty for the soldiery, but probably much of that was dropped when the returning column was ambushed by Rhys ap Tudor and fled behind the walls of Beaumaris Castle.

King Henry tried to look commanding: he took a handful of prisoners back to Shrewsbury with him, so he could magnanimously release them again; he declared Glyndwr’s estates confiscated and delivered to the Earl of Somerset, despite having no authority to enforce his will.

He appointed his fourteen-year-old son, Henry of Monmouth, the future Henry V, to take charge of Wales, assisted by the legendary Henry “Hotspur” Percy, son of the powerful Earl of Northumberland. But as the country’s most-wanted outlaw that Christmas held a great winter festival at his estate a dozen miles from the English castle of Chirk, a brazen challenge that nobody dared accept, there was no disguising that the Welsh had won, the English had been soundly kicked out, and Henry IV humiliated.

The English presence in north Wales reduced to little more than a few forlornly defiant castles in a smouldering landscape.

Henry IV
Henry IV

Henry IV was not an incompetent general, but his expertise was confined to pitched battles and clashing armies. Of this Welsh warfare, a battle against terrain and weather as much as people, where an action might consist of nothing more than a volley of arrows appearing from nowhere to take down a dozen of his soldiers, of this war of eternal, nerve-jangling vigilance against an unseen enemy, he was clueless.

Capable though he was in his field of expertise, he lacked the brilliance that his son would display in the campaign to Agincourt. That brilliance now drove Henry of Monmouth to issue the order that would slowly win the war: a general pardon to all Welsh who would surrender, excepting Glyndwr and the Tudors.

Throughout the winter, in London, not even the king could dissuade Parliament from enacting a raft of legislation intended to awe the Welsh with English power.

Some of the new laws were intended to discourage the Welsh movement. Many were simply vindictive, intended to reduce the Welsh to the status of peasants with no prospects of advancement. The practical result was to eliminate the middle ground between king and rebel. Welshmen seeing their livelihoods evaporate in England were presented with the choice between ruin, and Glyndwr.

In Anglesey, the Tudors plotted. Conwy Castle’s ruined state remains today an awe-inspiring vision, silhouetted against the twisted peaks of Snowdonia. Gleaming white, perched above its walled town, banners streaming and adorned with coats of arms, it had been planned from the start as a royal seat of power, and its sumptuous royal apartments had hosted both Edward I and Richard II.

Conwy Castle
Conwy Castle

The Taking of Conwy Castle

Perched atop a rock that impeded siege engines and undermining, its eight towers and high walls were impregnable. It was captured intact within a few minutes on April Fool’s day.

April 1st 1401 was Good Friday. The garrison had gone to mass in the parish church, leaving the entire castle manned by two gatekeepers. The gate was approached by the castle’s carpenter, with a couple of assistants, who insisted on the necessity of completing an outstanding task.

Once admitted, the carpenters drew daggers and stabbed the astonished gatekeepers, admitted Gwilim ap Tudor and forty followers, then pulled up the draw bridge. The garrison emerged from church to find their castle bolted and barred against them, its new garrison hooting and dancing on the ramparts, baring their bottoms at the bewildered English.

In reality, conditions in the castle were a disappointment. A century of peace had engendered the garrison’s complacency. For all the walls’ mighty appearance, the food stores were rotting, the weaponry missing and defective, the ammunition depleted, providing a less-reliable bastion than anticipated.

None the less, Henry Hotspur, arriving with several hundred men and some primitive canon whose effect was probably mostly psychological (they could only be fired safely once an hour, but having never been used before in Wales, were probably the loudest, most-terrifying noise any Welshman had ever heard), was aware of the impossibility of assaulting the fort and, although the siege would destroy the town, immediately commenced negotiations.

Within three weeks, a surrender had been agreed, involving a pardon for all involved, including the Tudors. The king’s ratification was assumed would be a formality.

Hotspur was wrong. In a fit of fury, not only did Henry IV insist that at least some of the Welsh forfeit their lives, but, since the loss of the castle had happened on Hotspur’s watch, Hotspur should pay the crippling costs of the siege.

In truth, the war was crippling England’s treasury, not least because it was no longer receiving Wales’ annual tribute of 60,000 pounds, but, in high dudgeon, Hotspur resigned, returning to his estate in northern England. All the chroniclers of the time wrote that he held a secret interview with Glyndwr en route, although how, why and what the conclusions were is impossible to say.

For the Welsh inside the castle, the king’s response was a catastrophe. Lacking the resources for a long siege, the months dragged into hunger, into desperation, and finally surrender on June 24th, on condition of a pardon for the Tudors and four-fifths of their followers. How those eight were selected, we don’t know.

We do know that they were set upon as they slept, bound, and summarily shoved out of the gate to be taken away and hanged. Gwilim ap Tudor and his remaining followers were permitted to flee to the hills.

Notwithstanding the Tudors’ ultimate defeat, news of the capture of such a prestigious fortress electrified Wales. Glyndwr himself had done little throughout the winter and spring. It is assumed he was travelling, sounding out the districts most likely to support an expansion of the rising.

With little English booty left in the north, he now raised his banner in the mountains outside Aberystwyth. Hundreds, now including men of rank and noble birth, flocked to him. Many more rose up in naked banditry to pillage English settlements around Carmarthenshire in Glyndwr’s name if not with his authority.

The Battle of Mynnydd Hyddgen

For the settlers, there was no relief, no protection except inside a castle’s walls. It fell to Flemish colonies in the Gower peninsula, near Swansea to mount a pre-emptive expedition.

Despite surprising Glyndwr at his camp at Mynnydd Hyddgen, and outnumbering his force by three to one, Glyndwr had the advantage of height, and archers battle-hardened in recent wars.

Lightly armoured against the thousands of darts falling on them, their comrades falling in heaps around them, it was a few minutes before the decimated Flemish fled. It was then a small matter for Welsh horsemen to chase and cut them down.

Mynnydd Hyddgen
Mynnydd Hyddgen

Through the summer, Glyndwr swept through the south and centre of the country, ravaging the lands of all – English and Welsh – who failed to join him: burning, stealing, no doubt raping with abandon, even capturing occasional undermanned castles such as New Radnor, whose sixty-strong garrison Glyndwr hanged from the ramparts.

Other than the Franciscan orders, which generally supported Glyndwr, ecclesiastical institutions were ransacked relentlessly. Panic gripped the English borders, abbots and squires scribing heart-rending petitions for support. With little time or money, Henry might well have hesitated, but the king had to be seen defending his people, or else what was the point of him?

Tenuous as his crown was at the best of times, he hastily assembled new levies, marching into Wales with inadequate provisions and preparations. Again, the Welsh disappeared, the fields stripped, the barns bare, the pastures devoid of livestock.

His army ravenous, miserable and murmuring, Henry targeted Strata Florida Abbey at Ystradfflur, suspected of supporting Glyndwr perhaps solely on the grounds that Glyndwr hadn’t got around to pillaging it yet.

For two days, his army got riotously drunk on the abbey’s wine stores, then, when the booze was all gone, plundered it, stealing even the sacred vessels from the high altar. The monks they didn’t hang were turfed into the street.

Until now, the weather had been unseasonably mild. As Henry’s column turned east, the heavens opened to lash them once again into a sodden hell, regularly interrupted by hit-and-run attacks that whittled down their numbers.

Time and again, Henry tried to lure Glyndwr into battle.  Every time, Glyndwr slipped away, but Henry’s spirits were lifted when a man of Cayo, Llewelyn ap Gruffudd Fychan, promised to lead them to Glyndwr’s hideout.

Day after day, the army struggled, hungry and frozen, after him, through the sucking quagmires and swollen torrents, through gales and downpours, through sudden flurries of arrows and small parties appearing from nowhere to stab a dozen soldiers and then vanish again, until suspicious Henry confronted Llewelyn.

Llewelyn replied that he had two sons serving with Glyndwr, and stretched forth his neck for decapitation. The apoplectic king had him quartered as well, but there little disguising that he had wasted time and a great deal of money harrying an already-harried land, failed to relieve any of his beleaguered castles, and enhanced Glyndwr’s reputation at the expense of his own.


No English speaker was safe more than a bow shot’s distance from a castle’s wall, but master of guerrilla warfare though Glyndwr was, he was given a sharp reminder of the limits of his authority that autumn when he attempted to storm Caernarfon Castle, losing three hundred men in the failure.

The rising had reached stalemate: Glyndwr, lord of the country; Henry, king of the castles; neither having the resources to press his advantage. Insouciantly wintering again on his estate within walking distance of English castles, Glyndwr turned his attention to unfinished, personal business.

Taunted by a little party of Glyndwr’s men, Reginald de Grey sallied forth with a band of supporters, chasing them out of sight of his stronghold, suddenly to be surrounded and cut to pieces by an overwhelming force of Welsh.

Grey was taken to the depths of Snowdonia, far from any prospect of rescue, and imprisoned uncomfortably in Dolbadarn Castle. King Henry was doubtless livid to receive a huge ransom demand, but borrowed the money, ensuring the financing of Glyndwr’s movement for years to come.

De Grey was ruined, impoverished, shamed into swearing an oath never again to bear arms against Glyndwr, his house destroyed and now a peacock-adorned ruin attached to an hotel – named after Owain Glyndwr!

Dolbadarn Castle, where both Grey and Mortimer were held for ransom
Dolbadarn Castle, where both Grey and Mortimer were held for ransom

At the same time, Glyndwr was seeking to apply pressure to Henry’s stretched government. Letters to the king of France and to the Irish chieftains were intercepted, but the Scots responded by pouring south across the border into England.

Breton raids devastated the Channel Islands and Plymouth. French buccaneers landed on the Isle of Wight. Glyndwr attacked still-unravaged Herefordshire. Hotspur’s family, the Percys, were able to hold the Scots at bay, but the bankrupt king was dependent on whatever he could borrow to finance yet another hungry and underpaid expedition into Wales.

The Battle of Bryn Glas

Perhaps reluctant to invite further ridicule upon himself, Henry this time entrusted the command to Edmund Mortimer, lord of Chirk. Seeking a confrontation with a Welsh encampment, Mortimer led his army along the Lugg valley to the hill of Bryn Glas, where the Welsh commander, Rhys ap Gethin, had divided his numerically inferior force. As Mortimer slogged up the steep gradient through a hail of arrows, bodies crumpling to the left and right, the hidden part of Rhys’ army appeared behind him to assault his rear.

Confused, and with nowhere to retreat, the English were slaughtered, pinned by arrows, limbs sliced off, ghastly gashes leaking blood. The wounded howled amid the corpses to little effect. The women who gathered to rob the bodies in the twilight castrated the dying as they begged for help.

Among the captured was Edmund Mortimer: the king’s nephew, Henry Hotspur’s brother-in-law, and one-time supporter of Richard II. The king’s refusal to pay Mortimer’s ransom was not unreasonable. Having recently paid ten thousand marks for Reginald de Grey, and as bankrupt and dependent on borrowing as he was, was Henry IV to finance both the English and the Welsh war efforts?

But Hotspur would not understand why the king forbade his offer to ransom Mortimer personally. “You are a traitor,” the king declared: “You would succour the enemies of myself and my kingdom!”

“I am no traitor,” protested Hotspur, outraged: “but faithful and speak in good faith!” Henry whirled out his sword. “Not here!” yelled Hotspur: “But on the field of battle!”

Owain Glyndwr's Coat of Arms
Owain Glyndwr's Coat of Arms

The battle of Bryn Glas terrified the south-eastern regions of Wales. Wales’ most-heavily anglicized districts had been half-hearted supporters of the uprising, at best.

Glyndwr fell upon Abergavenny, sacked Usk, and burned the cathedral and bishop’s palace at Llandaf, and captured Newport and Cardiff Castles. The Grey Friars of Cardiff alone, he spared, although when they appealed for the return of the books and chalices that they had stored in the castle, he refused. The friars should have kept them in their priory, he reasoned. When he captured the castle, he captured its contents also.

Besieged by want of money, with his viceroy in Ireland reduced to penury, with forty thousand Scots swarming across his northern border, overwhelming the Percys’ capacity to resist, with Breton corsairs devastating the Channel Islands and Plymouth, further French landing on the Isle of Wight, still others landing in Wales to join Glyndwr for further, unsuccessful attempts to seize Caernarfon and Harlech Castles (with the support of the Tudor brothers, who clearly no longer felt a need to worry about the king’s pardon), Henry determined to deal with Glyndwr once and for all, to crush the Welsh finally with overwhelming power. In August, three armies – one hundred thousand men – assembled at Chester, Shrewsbury and Hereford, plunging into the heart of Wales.

Henry Strikes Back

Never within living memory had Wales seen such a storm. Amid thunder and lightning, the heavy, black clouds lashed the English columns, swelling rivers, submerging fords, sweeping away bridges. The royal tent was flattened one evening, the posts striking the king himself, who escaped uninjured solely because he happened to be wearing armour at the time.

Sinking into the marshes that passed for roads, unable to cook over the pathetic wisps of heatless smoke that emerged from the drenched firewood, numerous died of exposure, convinced of Glyndwr’s awesome powers of sorcery. Within a few days, having scarcely seen a Welshman, the bedraggled columns gave up the quest and turned for home. As Shakespeare wrote: 

Three times hath Henry Bolingbroke made head
Against my power. Thrice from the banks of Wye
And sandy-bottomed Severn have I sent
Him bootless home.

Who were the “barefoot rascals” now?

Returning to his castle at Berkhamstead, Henry did have the consolation of learning that Hotspur had defeated the Scots through a combination of miraculous luck and brilliant tactics at Homildon Hill, and captured the Earl of Douglas, worth a fabulous ransom that Henry, conspicuously devoid of any Welsh prisoners worth ransoming, coveted. His command, against all medieval custom, that all their Scottish prisoners be surrendered to him was, for Hotspur, the last straw.

Things could hardly have looked rosier for Glyndwr. Mortimer, abandoned to his fate in the depths of Snowdonia, had already switched sides. Some of the English border counties had given up resisting, preferring to pay protection money to dissuade Glyndwr from further attacks.

The Welsh castles’ resistance was on the verge of collapse, some having already fallen, and some others reduced to garrisons of little more than a dozen; the constable of Dynefor Castle wrote that his men were fainting with hunger; Henry of Monmouth was meeting his daily expenses by selling a small stock of jewels, and writing desperate letters to his father warning of mass desertions should his men remain unpaid much longer; so great was the terror of Glyndwr throughout England that as far east as St Alban’s, the monks supplicated the Almighty for salvation from the accursed Welsh.

In July 1403, the king was in council, having just approved £1000 for Henry of Monmouth (a drop in the ocean for an army of thirty thousand). He had just finished speaking of his “beloved and loyal cousins” fending off the Scots when he received the news that his beloved and loyal cousin Hotspur had abandoned the northern border and was marching south with all his Scottish prisoners to join Glyndwr.

On the evening of July 20th, Hotspur arrived at the gates of Shrewsbury with fifteen thousand men, but there was no sign of the Welsh. The message having failed to get through, Glyndwr, with ten thousand, was a hundred miles away in Carmarthen.

The Battle of Shrewsbury

The Battle of Shrewsbury must rank as one of the great “what if” moments of British history. Had the opposing armies been more closely matched, how different the history of the British Isles might have been. As it was, Hotspur was killed (Henry of Monmouth was nearly killed with an arrow through his right cheek, causing such terrible scarring that, as Henry V, he was uniquely among British monarchs, painted in left profile), and his Scottish army cut to pieces.

The news spelled disaster for Glyndwr. Not only had the major part of his alliance been destroyed, but with it, his reputation for invincibility. No sorcerer after all, this Welshman, but thoroughly human, and beatable.

He tried to recover some of his prestige by returning to what he was good at; raiding Herefordshire, penetrating as deep as Leominster, and extorting money to leave them alone. Henry tried to capitalise on his son’s triumph by organising a quick and cheap charade masked as an expedition, but premised on an assumption that the Welsh would disappear again.

Making no effort to track them down, he arrived in Carmarthen in record time, issued a few proclamations but did nothing to relieve the castle’s deprivation, and was back in England four days later.

Before he had even returned to London to triumphal acclaim, Glyndwr was sweeping back through Glamorgan and Cardiff, exacting terrible vengeance upon the backsliders there, and early the next year, 1404, two glittering jewels, the king’s own castles in Harlech and Aberystwyth finally yielded, incapable of further resistance. Harlech’s garrison had been whittled to just sixteen.

Henry of Monmouth had burned Glyndwr’s houses, but Henry IV had bequeathed two of his own, far grander than Glyndwr’s had ever been.

A New Welsh State

But what Glyndwr desperately needed was to replace Hotspur’s support. Previous overtures to England’s old agitator, the king of France, had achieved lukewarm assistance. Glyndwr now adopted the trappings of statehood, adopting Harlech as a royal residence, and organising a parliament at Machynlleth, which held a formal coronation.

A royal seal was carved, depicting Glyndwr seated on a throne, and on May 10th, 1404, he signed a formal proposition of alliance to the French king, Charles VI, signed “Owen, by the grace of God, Prince of Wales.”

The treaty was signed two months later, covenanting each to support the other in the event of attack by “Henry of Lancaster” (Charles VI had never recognised Henry as king of England), but there was no commitment to a campaign of aggression. Notwithstanding the endless raids on the borders, Glyndwr had given up designs on England. He had already achieved as much as he was likely to.

Glyndwr's parliament house in Machynlleth
Glyndwr's parliament house in Machynlleth

Henry was scarcely better off. Finding money to finance another expedition was out of the question. The Earl of Warwick mounted a small expedition in the king’s place, inflicting a defeat on the Welsh at Mynnydd Cwmdu, but when lack of provisions forced their return east, the Welsh fell upon them at Graig-y-Dorth, between Chepstow and Monmouth, the corpses of Warwick’s retainers littering the wayside right up to the gates of Monmouth Castle, where the battered column took refuge.

Over Christmas, Henry left Windsor Castle for Eltham, leaving the Earl of March, the child who would have inherited the throne from Richard II had Henry not usurped it, in the care of Lady Despenser, owner of Caerphilly Castle until Glyndwr had captured it.

Having secretly had duplicate keys made, Lady Despenser spirited the child to waiting horses, and was miles away before word even reached the king. They were in Gloucestershire, a day’s journey from Glyndwr’s territory, before they were overtaken and, following a brief but bloody fight in which several were killed, returned to London.

Lady Despenser confessed to a plot to kill the king, in which she implicated her brother, the Duke of York, but the duke vehemently protested his innocence.

Lady Despenser appealed for a champion to defend her honour. A minor courtier of little reputation threw down his gauntlet before the portly and obviously unfit duke. Instead, the king threw the lot of them into the Tower. Perhaps surprisingly, he soon forgave all of them, except the locksmith who made the duplicate keys. His hands were chopped off.

At the start of 1405, Glyndwr ruled unchallenged over a desert of cinders, except for a few hard-pressed castles. The people who manned his armies were probably supportive on the whole, but those who had failed to loot suffered very real hardships: their homes and farms destroyed, their crops and livestock gone, all means of providing social welfare – the alms, the hospitals, the schools – devastated with the abbeys. It was the year it all went wrong. 

In April, the Welsh plans for the coming year’s campaigning were leaked to Henry of Monmouth. In May, 8000 Welsh fell upon Grosmont, outside Monmouth, the third-largest city in Wales after Abergavenny and Carmarthen. It would never recover.

In the nineteenth century, it was still possible to trace the lines of the streets through the turf. Today, Grosmont is a village of a few hundred. The seventeen-year-old to the throne responded by despatching a massive force from Hereford that surprised the Welsh and slaughtered 800 of them.

Grosmont, once the third largest city in Wales
Grosmont, once the third-largest city in Wales,
devastated by Glyndwr's raid

Disaster at Usk

Glyndwr himself rushed to intercept the fleeing Welsh and try to reverse the defeat by attacking Usk Castle. Reinforced and strengthened, it held. As the realisation dawned that the castle would not be reduced that day, the Welsh fell back into the surrounding woodland; perhaps to give up and retreat; perhaps to build siege machines for a renewed assault.

The defenders burst forth, laying into the disorganised Welsh and pursuing them until 1500 bodies scattered the ground for miles beyond the castle.

Among the dead was Owain Glyndwr’s brother, Tudur, who bore such a strong resemblance that the body was briefly believed to be Owain’s, until it was pointed out that it lacked a defining skin tag on the left eyelid.

For the first time, Welshmen began turning in their weapons, accepting the king’s pardon, in large numbers. It was becoming clear that Owain Glyndwr was not one to free Wales, but a glorified bandit; one who had been remarkably successful, and wrecked the country and the livelihoods of the people in the process.

After five years of guerrilla warfare, it was becoming clear to all that pitched battles would be necessary to force Henry IV to relinquish his hold, and, with occasional exceptions such as Bryn Glas, Glyndwr did not have the resources to win those.

Glyndwr persisted in the belief that French help could yet turn the tide. One hundred and forty ships set sail from Brest, landing as many as five thousand cavalry, men-at-arms, crossbowmen and archers in Tenby, although lack of water had meant that many of the horses died en route.

They started with an assault on Haverfordwest, although failing to capture the castle, so proceeded successfully against Carmarthen Castle, but the French had been promised booty, and found slim pickings in an already plundered land.

Faced with their discontent and the threat of their simply packing up and going home, Glyndwr marched his ten thousand Welsh and five thousand French into England again, laying waste to the renegades of Glamorgan on the way.

Woodbury Hill - The Beginning of the End

At Great Witley, ten miles from Worcester, in August 1405, the quest for Welsh independence ground to a halt. On Abberley Hill, Henry’s large if threadbare army was arrayed in potent battle positions. The Franco-Welsh army took up defensive positions in an iron-age hill fort on what is still known locally as Owen’s Hill.

Between them lay a mile-wide valley ideal for a battle, but Henry was determined to prove a point to the French, the Scots, and above all to the Welsh.

For eight days, the two sides stood in full battle array, ready for a showdown that never happened. If Owen wanted a fight, he would have to take the initiative, and Henry was determined to prove that he didn’t dare. So the two armies faced off for a week, until Glyndwr’s food rations depleted. He must have realised the game was over when he turned his people around, and trudged home.

Woodbury Hill, where Glyndwr's dream of Welsh independence ended
Woodbury Hill, where Glyndwr's dream of Welsh independence ended

Certainly, his French did, and promptly quit, empty-handed. Henry tried to capitalise on his success with yet another expedition to relieve Coity Castle, near Bridgend.

Same old story: the heavens opened and the Welsh vanished until Henry turned back, and then his column was mercilessly harried; but this served to emphasise that hit-and-run attacks on the rear and the baggage was the best that Glyndwr could achieve. His reputation, even among his own people, was as ruined as his country.

He tried to brazen out the crisis, playing up his role as a crowned Prince of Wales. For thirty years, there had been two popes, the Church of England aligning itself with the pope in Rome. Probably never especially devout, Glyndwr offered the allegiance of the Church in Wales to the pope in Avignon, in hope of reviving French support. None the less, another letter to the French king achieved little.

Dividing the Country

A covenant was signed between Glyndwr, Mortimer and Henry Hotspur’s father, agreeing to carve up England and Wales between them, but few saw it as more than grandstanding.

Proposed division of England and Wales between Glyndwr, Percy, and Mortimer
Proposed division of England and Wales
between Glyndwr, Percy, and Mortimer

Piece by piece, Glyndwr’s regime fell apart. The Vale of Tywi surrendered in the face of famine engendered by seven years’ war. Anglesey, always a tower of support for Glyndwr, was captured by troops released from service in Ireland.

A thousand men in Flintshire appeared before the justiciar and submitted to a communal fine. Glamorgan, never the most enthusiastic, affirmed its allegiance to the king, only to be once again ravaged by Glyndwr’s supporters, when the chiefs preferred to burn their barns and castles, and flee across the Severn rather than face their wrath. Not that this saved them when an English expedition passed through two years later.

The English Attack

Little is known of Glyndwr’s movements in 1407, but surviving letters suggest a sense of depression among his friends. In England, having the whip hand was building a movement to dowse the rebellion conclusively; only this time, having confidence of success.

Hundreds of knights and archers applied to join, with cannons and great stores of munitions. The Forest of Dean and the woods along the Severn were chopped down for siege engines. Initially delayed by plague, Henry of Monmouth drove the expedition into Glamorgan in June 1408, and through south Wales all the way to capture its largest city, Carmarthen, finally to relieve its castle.

By winter, Aberystwyth Castle, the glittering jewel that Glyndwr had invested so much time, effort and money to capture, surrendered to Henry. The following February, Glyndwr’s royal seat at Harlech, also surrendered. Mortimer had been killed during the siege.

Glyndwr’s wife, daughters and grandchildren were captured and taken to the Tower of London, never to be heard of again.

Glyndwr and his small band of devotees took to the hills again, and remained a problem for a time. They even mounted another raid on Shropshire, although it went badly wrong, with the Tudor brothers, Rhys and Gwillim, they who had captured Conwy Castle, both dead as a result.

By 1410, Glyndwr was a hounded pariah, cursed by contemporaries who had seen their livelihoods and country destroyed for nothing, and anti-Welsh legislation more repressive than ever.

In 1413, Henry IV died, and Henry of Monmouth was crowned Henry V. Impoverished Welsh applied in droves to join his invasion of France, eager for plunder to improve their living standards, and five hundred Welsh archers distinguished themselves at the Battle of Agincourt (although the French side included a handful of Welsh irreconcilables).

The same French king who had assisted Owain Glyndwr now married his daughter to the young English king with the horrible facial disfigurement, acquired in battle against the cause of Glyndwr.

Deprived on their Anglesey estates, the third Tudor brother, Maredudd (whose role in the war appears to have been minimal) moved to London. His son, Owen, married Henry V’s widow. Their son was Edmund Tudor. His son was Henry Tudor, who launched another Welsh rebellion in 1485, and met Richard III at Bosworth.

Unlike Glyndwr in Worcester, Henry Tudor dared take the initiative, won, was crowned Henry VII, and finally repealed the anti-Welsh legislation. In the early sixteenth century, Wales was annexed to England, and granted Parliamentary representation for the first time.

The End

Of Owain Glyndwr’s end, nobody knows. Henry V offered him a pardon in 1415, but he was apparently too proud to accept. His son, Maredudd ap Owain Glyndwr, also refused the pardon, but accepted another in 1421, suggesting that his father was, by then, dead.

It has been suggested that Owain Glyndwr lived in secrecy with his daughter, the wife of the sheriff of Hereford, but this is merely one rumour among numerous concerning the wanderings of his last days.

With all the prominent Welsh dead, imprisoned or impoverished, peace returned to Wales, and the countryside slowly recovered.

Among the as-yet-unborn, Glyndwr became revered, almost a saint; the patron saint of Welsh nationalism, perhaps: a name for pubs and hotels, a star of folklore, a coat of arms to wave in parades, an invocation of historic grievance by the chippy. But the people he presided over lost everything in a decade of bitter struggle, and saw the regulations designed to keep them repressed rendered considerably harsher for two generations to come. In return, he gave them nothing.

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