The Last Prince of Wales: The Death of Llywelyn ap Gruffudd | History Hit

The Last Prince of Wales: The Death of Llywelyn ap Gruffudd

Image Credit: Public Domain

Wales had proven impossible to conquer after the Norman army had rolled across England with relative ease. The rugged terrain and fierce independence of the people had caused the failure of many campaigns to subdue them. The one problem was that the rulers of the regions of Wales were as often at odds with each other as with the English crown.


At the beginning of the 13th century, Llywelyn ap Iorwerth, King of Gwynedd in North Wales, married an illegitimate daughter of King John. By 1210, relations were worsening, and in 1215, Llywelyn sided with the barons that forced Magna Carta on John. In the following year he was able to use the problems in England to establish his own dominance over the other princes of Wales, a position he would retain until his death in 1240.

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Remembered as Llywelyn the Great, he was succeeded by his son Dafydd, who imprisoned his brothers Gruffydd and Owain. Both brothers were then handed over to Henry III of England as hostages.

Gruffydd died in 1244 trying to escape from the Tower of London by tying sheets together to climb out of his cell window. The makeshift rope broke, and Gruffydd fell to his death. The window he used was bricked up, but can still be made out today.

Gruffydd’s son Llywelyn supported his uncle Dafydd in the brutal fighting with the English that followed. When Dafydd died in February 1246, Llywelyn was able to claim his uncle’s lands and titles.

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A New Rivalry

On 14 February 1254, Henry made some provisions for his son Edward, the future Edward I, by making him Earl of Chester and giving him castles in Wales. In 1256, a long rivalry was begun when Llywelyn tried to expand his holdings by attacking Edward’s properties.

With the English unable to catch the Welsh and Llywelyn unwilling to risk a pitched battle, an uneasy peace was agreed. As Simon de Montfort, Earl of Leicester fell into dispute with King Henry in the 1260s, Llywelyn allied himself with the rebels, as his grandfather had done, to try and make further gains. Targeting Prince Edward’s lands again, the alliance fell apart when Edward concluded peace with the de Montfort family.

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At the Battle of Lewes on 14 May 1264, King Henry and Prince Edward were both captured by Simon de Montfort, who took control of the government. Llywelyn negotiated the Treaty of Pipton, which was sealed on 22 June 1265, and recognised Llywelyn as Prince of Wales in return for a payment of 30,000 marks.

Within two months, de Montfort was defeated and killed at the Battle of Evesham on 4 August, restoring King Henry and negating the Treaty of Pipton. Llywelyn’s continued resistance combined with ongoing problems in England forced Henry to negotiate the Treaty of Montgomery, finalised on 29 September 1267.

Llywelyn was recognised as Prince of Wales but was required to give homage to the English crown for his control of Wales and pay 3,000 marks a year. This peace would endure for the rest of Henry III’s reign.

Llywelyn ap Gruffudd paying homage to King Henry II. (Image Credit: Public Domain).

Rising Tensions

King Edward I succeeded his father in 1272 but was on crusade in the Holy Land. The task of running England was given to three barons, one of whom, Roger Mortimer, was a rival of Llywelyn’s on the Welsh borders. Mortimer backed an attempt to take Brycheiniog Castle from Llywelyn and conflict erupted again.

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Edward retained a strong dislike for Llywelyn, possibly holding a grudge stemming from earlier attacks on his lands. Edward would always have an abrasive relationship with London after the city had harassed his mother during a revolt against his father.

Llywelyn tried to revive his alliance with the de Montfort family by arranging a marriage to Simon’s daughter Eleanor, a first cousin of the king, despite the family’s fall from influence. Edward ordered the Prince of Wales to come to him on several occasions and renew his homage, but Llywelyn refused, claiming he feared for his life.

Edward I’s Invasion of Wales

In 1277, Edward took a large army into Wales after declaring Llywelyn a traitor. The king managed to march far into North Wales and sent a second force to Anglesey to seize the island and the harvest there. By November, Llywelyn was forced to agree to the Treaty of Aberconwy. He kept his lands west of the River Conwy but lost those to the east to his brother Dafydd.

Edward I, also known as Edward “Longshanks”. (Image Credit: Public Domain).

Although he kept his princely title after giving homage to Edward, Llywelyn lost control over the other rulers of Wales and with no mechanism to pass his overlordship to anyone else, the office of Prince of Wales would die with Llywelyn. The first part of Edward’s campaign to conquer and subdue Wales was completed by the construction of castles around Gwynedd, encircling Llywelyn’s dwindling power base.

In 1282, Llywelyn, now around 60 years old, found those Welsh princes who had been lured away by Edward looking to return to him to escape the uncomfortable grip of the English crown. Llywelyn’s brother Dafydd began an offensive, and though Llywelyn claimed he was not involved at all, he nevertheless offered his brother support. Edward’s new castle at Aberystwyth was burnt down, and Carrey Cennen Castle was taken.

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The king sought to repeat his success in 1277 by invading Gwynedd from the east and taking Anglesey. Luke de Tany quickly took the island and its harvest again, but then tried to cross the Menai Straights to attack Llywelyn without waiting for Edward. Alert to the threat, Llywelyn met the English force at the Battle of Moel-y-don on 6 November and drove them back into the sea.

Walter of Guisborough recorded that ‘The Welsh came from the high mountains and attacked them, and in fear and trepidation for the great number of the enemy, our men preferred to face the sea than the enemy. They went into the sea but, heavily laden with arms, they were instantly drowned.’

Llywelyn’s Downfall

Llywelyn moved south. At Builth Wells he was confronted by an alliance of English Marcher lords and Welsh princes. On 11 December, they fought the Battle of Orwin Bridge where the English cavalry and archers outmatched the Welsh spearmen.

Llywelyn was reported to have been absent when the battle began, negotiating with a local lord, but quickly returned when he heard the news. As he approached the fighting, Llywelyn was killed by an English soldier who had not recognised him.

Death of Llywelyn. Illustrations and photographs of places and events in Welsh history from a childrens book, ‘Flame Bearers of Welsh History’. (Image Credit: National Library of Wales, Public Domain).

It was the next day before his body was recovered. His corpse was decapitated, and the head sent to Edward before being placed on the gatehouse of the Tower of London. The gruesome trophy remained there for at least fifteen years.

Dafydd was captured in June 1483 and hung, drawn, and quartered. After that, Edward stormed into Gwynedd and stripped it of all royal regalia, destroying the position of Prince of Wales. He would later create his son Prince of Wales, a tradition that endures to this day, but Llywelyn the Last was Wales’s last native Prince of Wales.

Llywelyn ap Gruffydd statue. (Image Credit: CC).


Matt Lewis