Glyndŵr was born to a prosperous landed family in North-East Wales. He was part of the Anglo-Welsh gentry of the Marches. His father, Gruffydd Fychan II Hereditary Tywysog of Powys Fadog and Lord of Glyndyfrdwy, died some time before 1370 leaving his mother Elen ferch Tomas ap Llywelyn of Deheubarth a widow.
On September 16, 1400, Owain acted, and was proclaimed Prince of Wales by a small band of followers. This was a revolutionary statement in itself. Owain’s men quickly spread through North-East Wales. By September 19, the de Grey stronghold of Ruthin was attacked and almost destroyed. Denbigh, Rhuddlan, Flint, Hawarden, and Holt followed quickly afterward. On September 22 the town of Oswestry was so badly damaged by Owain’s raid that it had to be rechartered. By the 24th, Owain was moving south and sacked Welshpool. Simultaneously, the Tudor brothers from Anglesey launched a guerrilla war against the English. The Tudors were a prominent Anglesey family who were closely associated with Richard. Gwilym and Rhys ap Tudor had been captains of archers in Richard’s campaigns in Ireland. They quickly switched allegiance to their cousin, Owain Glyndŵr.
Henry IV, on his way north to invade Scotland, turned his army around and by September 26 he was in Shrewsbury ready to invade Wales. In a lightning campaign, Henry led his army around North Wales. He was harassed constantly by bad weather and the attacks of Welsh guerrillas. By October 15, he was back in Shrewsbury with little to show for his efforts.
In 1401, the revolt began to spread. The whole of northern and central Wales went over to Owain. Multiple attacks were recorded on English towns, castles, and manors throughout the North. Even in the South in Brecon and Gwent reports began to come in of banditry and lawlessness by groups calling themselves the Plant Owain — the Children of Owain. In May Gwilym and Rhys ap Tudor easily took Conwy castle while the garrison was at church. They were to hold out for more than six months until they negotiated its return for a sizable payment and free passage. Owain also scored his first major victory in the field. In June, at Mynydd Hyddgen in West Wales, Owain and his army of four hundred were camped at the bottom of the Hyddgen valley when fifteen hundred English and Flemish settlers from Pembrokeshire charged down on them. Owain rallied his army and fought back, killing 200 and making prisoners of the rest.
The situation was sufficiently serious for the King to assemble another punitive expedition. This time he attacked through central Wales. From Shrewsbury and Hereford, Henry IV’s forces drove through Powys toward the Abbey of Strata Florida. The Cistercian house was known to be sympathetic towards Owain and Henry intended to remind them of their loyalties and prevent the revolt from spreading any further south. After terrible weather and constant harassment by the Plant Owain he reached Strata Florida. Henry was in no mode to be merciful. After a two-day drinking session, he partially destroyed the Abbey and executed monks suspected of pro-Owain loyalties. However, he failed to engage Owain’s forces in any large numbers. Plant Owain harassed him and engaged in hit-and-run tactics on his supply chain but refused to fight in the open. Henry was forced to retreat. As he did so the weather turned. The army was nearly washed away in floods and Henry almost died when his tent was blown down. Wet, starving, and dejected, they returned to Hereford with nothing to claim for their efforts.
The English saw that if the revolt prospered it would inevitably attract disaffected supporters of the deposed King. They were concerned about the potential for disaffection in Cheshire and were increasingly worried about the complaints of the military governor of North Wales, Henry “Hotspur” Percy. The legendary warrior — son of the powerful Earl of Northumberland — complained that he was not receiving sufficient support from the King and that the repressive policy of Henry was only encouraging revolt. He argued that negotiation and compromise could persuade Owain to end his revolt. In fact, as early as 1401, Hotspur may have been in secret negotiations with Owain and other leaders of the revolt to attempt to negotiate a settlement. The core Lancastrian supporters would have none of this. They struck back with anti-Welsh legislation designed to establish English dominance in Wales. The laws actually codified common practices that had been at work in Wales and along the Marches for many years. However, they sent a message to many of those who were wavering that the English viewed all the Welsh with equal suspicion. Many Welshmen who had tried to further their careers in English service now felt pushed into the rebellion as the middle ground between Owain and Henry disappeared.
In the same year, Owain captured his arch enemy, Reynald de Grey in an ambush at Ruthin. He was to hold him for a year until he received a substantial ransom from Henry. In June Owain’s forces encountered an army led by Sir Edmund Mortimer, the uncle of the Lord of the March, at Bryn Glas in central Wales. Mortimer’s army was badly defeated and Mortimer was captured. It is reported that the Welsh women following Owain’s army killed the wounded English and mutilated the bodies of the dead, supposedly in revenge for plundering and rape by the English the previous year. Glyndŵr offered to release Mortimer for a large ransom but, in sharp contrast to his attitude to de Grey, Henry IV refused to pay. In response, Sir Edmund negotiated an alliance with Owain and married one of Owain’s daughters, Catrin.
It is also in 1402 that mentions of the French and Bretons helping Owain were first heard. The French were certainly hoping to use Wales as they had used Scotland as a base from which to fight the English. French privateers began to attack English ships in the Irish Sea and provide weapons to the Welsh. French and Breton freebooters were also active in Owain’s attacks.
1403 marks the year when the revolt became truly national. Owain struck out to the West and the South. Recreating Llywelyn the Great’s campaign in the West, Owain marched down the Tywi Valley. Village after village rose to join him. English manors and castles fell or their inhabitants surrendered. Finally, Carmarthen, one of the main English power-bases in the West, fell and was occupied by Owain. Owain then turned around and attacked Glamorgan and Gwent. The castle at Abergavenny in Gwent was attacked and burnt. Owain pushed on down to the coast and took Cardiff and Newport. Royal officials report that Welsh students at Oxford were leaving their studies for Owain and Welsh labourers and craftsmen were abandoning their employers and returning to Wales in droves. Owain could also draw on the seasoned troops from the English campaigns in France. Hundreds of Welsh archers and men-at-arms left English service to join the rebellion.
In the North, Owain’s supporters launched a second attack on Caernarfon Castle (this time with French support) and almost captured it. In response, Henry of Monmouth (the son of Henry IV and the future King Henry V) attacked and burned Owain’s homes at Glyndyfrdwy and Sycharth. The situation became much worse – Hotspur defected to Owain. Raising his standard of revolt in Cheshire – a bastion of support for Richard II – he challenged his cousin Henry’s right to the throne. His young protégé, Henry of Monmouth, then only 16, turned to the North to meet Hotspur. On July 21, Henry arrived in Shrewsbury just before Hotspur forcing the rebel army to camp outside the town. Henry forced the battle before the Earl of Northumberland had managed to reach Shrewsbury. Thus, Henry was able to fight before the full strength of the rebels was present and on ground of his own choosing. The battle lasted all day. When the cry went out that Hotspur had fallen, the rebels’ resistance began to falter and crumble. By the end of the day, Hotspur’s rebellion was over. Over 300 knights had died and up to 20,000 men were killed or injured.
In 1404, Owain captured and garrisoned the great western castles of Harlech and Aberystwyth. Anxious to demonstrate his seriousness as a ruler, he held court at Harlech and appointed the devious and brilliant Gruffydd Yonge as his chancellor. Soon afterwards he called his first Parliament (or more properly a “Cynulliad” or “gathering”) of all Wales at Machynlleth where he was crowned Owain IV of Wales and announced his national programme. He declared his vision of an independent Welsh state with a parliament and separate Welsh church. There would be two national universities (one in the South and one in the North) and return to the traditional law of Hywel Dda. Senior Churchmen and important members of society flowed to his banner. English resistance was reduced to a few isolated castles, walled towns, and fortified manors.
Owain demonstrated his new status by negotiating the “Tripartite Indenture” with Edmund Mortimer and the Earl of Northumberland. The Indenture agreed to divide England and Wales between them. Wales would extend as far as the rivers Severn and Mersey including most of Cheshire, Shropshire, and Herefordshire. The Mortimer Lords of March would take all of southern and western England and Thomas Percy, the Earl of Northumberland, would take the north of England. Most historians have dismissed the Indenture as a flight of fantasy. However, it must be remembered that in early 1404 things still looked positive for Owain. Local English communities in Shropshire, Herefordshire and Montgomeryshire had ceased active resistance and were making their own treaties with the rebels. It was rumoured that old allies of Richard II were sending money and arms to the Welsh and the Cistercians and Franciscans were funneling funds to support the rebellion. Furthermore, the Percy rebellion was still viable; even after the defeat of the Percy Archbishop Scope in May. In fact the Percy rebellion was not to end until 1408 when the Sheriff of Yorkshire defeated Henry Percy Earl of Northumberland at Bramham Moor. Thus, far from a flight of fantasy, Owain was capitalizing on the political situation to make the best deal he possibly could.
Things were improving on the international front too. Although negotiations with the Scots and the Lords of Ireland were unsuccessful, Owain had reasons to hope that the French and Bretons might be more welcoming. Quickly Owain dispatched Yonge and his brother-in-law, John Hanmer, to France to negotiate a treaty with the French. The result was a formal treaty that promised French aid to Owain and the Welsh. The immediate effect seems to have been that joint Welsh and Franco-Breton forces attacked and laid siege to Kidwelly Castle. The Welsh could also count on semi-official fraternal aid from their fellow Celts in the then independent Brittany and Scotland. Scots and French privateers were operating around Wales throughout Owain’s war. Scots ships had raided English settlements on the Llyn Peninsula in 1400 and 1401. In 1403 a Breton squadron defeated the English in the Channel and devastated Jersey, Guernsey and Plymouth while the French made a landing on the Isle of Wight. By 1404 they were raiding the coast of England, with Welsh troops on board, setting fire to Dartmouth and devastating the coasts of Devonshire.
1405 was the “Year of the French” in Wales. On the continent the French pressed the English as the French army invaded English Aquitaine. Simultaneously, the French landed in force at Milford Haven in West Wales. They had left Brest in July with more than twenty-eight hundred knights and men-at-arms led by Jean de Rieux, the Marshall of France. Unfortunately, they had not been provided with sufficient fresh water and many horses had died. They also brought modern siege equipment. Joined by Owain’s forces they marched inland and took the town of Haverfordwest but failed to take the castle. They then moved on and retook Carmarthen and laid siege to Tenby. What happened next is something of a mystery. The Franco-Welsh force marched across South Wales (according to local tradition) and invaded England. They marched through Herefordshire and into the Midlands. They finally met the English outside Worcester at the ancient British hill fort of Woodbury Hill. The armies viewed each other without any action for eight days. Then, for reasons that have never been clear, both sides withdrew. The Welsh and French withdrew back through Wales into the West. More French were to arrive as the year went on but the high-point of French involvement had passed. By 1406, most French forces had withdrawn after politics shifted in Paris toward the peace party. Even Owain’s so-called “Pennal Letter”, in which he promised the French King and the Avignon Pope to shift the allegiance of the Welsh Church from Rome to Avignon, produced no effect.
There were other signs the revolt was encountering problems. Early in the year Owain’s forces suffered defeats at Grosmont and Usk (Pwll Melyn). Although it is very difficult to understand what happened at these two battles, it appears that Henry of Monmouth or possibly Sir John Talbot defeated substantial Welsh raiding parties led by Rhys Gethin (“Swarthy Rhys”) and Owain’s eldest son, Gruffudd. The exact date and order of these battles is subject to dispute. However, they may have resulted in the death of Rhys Gethin and Owain’s brother, Tudur, and the capture of Gruffudd. Henry also showed that the English were engaged in more and more desperate tactics. Adam of Usk says that after the battle of Pwll Melyn, Henry had three hundred prisoners beheaded in front of Usk Castle. John ap Hywel, abbot of the Llantarnam Cistercian monastery, was killed during the battle of Usk as he ministered to the dying and wounded on both sides. More serious for the rebellion, English forces landed in Anglesey from Ireland. Over the next year they would gradually push the Welsh back until the resistance in Anglesey formally ended toward the end of 1406.
At the same time, the English were adopting a different strategy. Rather than focusing on punitive expeditions favoured by Henry IV, the young Henry of Monmouth adopted a strategy of economic blockade. Using the castles that remained in English control he gradually began to retake Wales while cutting off trade and the supply of weapons. By 1407 this strategy was beginning to bear fruit. In March, 1,000 men from all over Flintshire appeared before the Chief Justice of the county and agreed to pay a communal fine for their adherence to Glyndŵr. Gradually the same pattern was repeated throughout the country. In July the Earl of Arundel’s north-east lordship submitted. One by one the lordships began to surrender. By midsummer, Owain’s castle at Aberystwyth was under siege. That autumn the castle surrendered. In 1409 it was the turn of Harlech. Last minute desperate envoys were sent to the French for help. There was no response. Gruffudd Yonge was sent to Scotland to attempt to coordinate action but nothing was to come. The castle fell. Edmund Mortimer died in the final battle and Owain’s wife Margaret along with two of his daughters (including Catrin) and three of his Mortimer granddaughters were taken prisoner and incarcerated in the Tower of London. They were all to die in the Tower of London before 1415.
Owain remained at large but now he was a hunted guerilla leader. The revolt continued to splutter on. In 1409 or 1410, Owain readied his supporters for a last raid deep into Shropshire. Many of his most loyal commanders were present. It may have been a last desperate suicide raid. Whatever was intended, the raid went terribly wrong and many of the leading figures still at large were captured. Rhys Ddu (“Black Rhys”) of Cardigan, one of Owain’s most faithful commanders, was captured and taken to London for execution. A chronicle of the time states that Rhys Ddu was: “…laid on a hurdle and so drawn forth to Tyburn through the city and was there hanged and let down again. His head was smitten off and his body quartered and sent to four towns and his head set on London Bridge.” Philip Scudamore and Rhys ap Tudur were also beheaded and their heads displayed at Shrewsbury and Chester (no doubt to discourage any further thoughts of rebellion).
In 1412, Owain captured and later ransomed a leading Welsh supporter of Henry’s, Dafydd Gam (“Crooked David”), in an ambush in Brecon. These were the last flashes of the revolt. This was the last time that Owain was seen alive. As late at 1414, there were rumors that the Lollard leader, Sir John Oldcastle, was communicating with Owain and reinforcements were sent to the major castles in the North and South. Outlaws and bandits left over from the rebellion were still active in Snowdonia.
But by then things were changing. Henry IV died in 1413 and his son began to adopt a conciliatory attitude to the Welsh. Pardons were offered to the major leaders of the revolt and other opponents of his father’s regime. In a symbolic gesture, the body of Richard II was interred in Westminster Abbey. In 1415 Henry offered a pardon to Owain as he prepared for war with France. There is evidence that Henry was in negotiations with Owain’s son, Maredudd ab Owain Glyndŵr, but nothing was to come of it. In 1416 Maredudd was offered a pardon but refused. Perhaps his father was still alive and he was unwilling to accept the pardon while he lived. He finally accepted a pardon in 1421, suggesting that Owain was dead.