By the end of 1283, King Edward I of England had completed his conquest of Wales, crushing the ambitions of Llywelyn ap Gruffydd—remembered as Llywelyn the Last—to unite the fragmented Welsh principalities under a single native ruler. Edward dismantled the power of the Welsh nobility, brutally scattering his opposition, eliminating many of its leaders. Yet one notable figure remained: Gruffydd ap Gwenwynwyn.
Often overshadowed by more iconic names such as Llywelyn the Last and Owain Glyndŵr, Gruffydd ap Gwenwynwyn is frequently remembered as a traitor—the Welsh prince who aligned himself with the English crown at a pivotal moment in his nation’s struggle to preserve its independence.
Medieval Wales was never a unified state for long. It was a patchwork of competing principalities and lordships, including Gwynedd, Powys, and Deheubarth. On occasion, a particularly capable ruler—usually through military strength—could rise above the rest and temporarily unify the Welsh rivals. Llywelyn the Last was the final Welshman to claim the title ‘Prince of Wales,’ but his struggle for unity was far from universally supported. His opponents included not just the encroaching Anglo-Norman lords but also fellow Welsh nobles, whose jealous rivalries and ambitions proved just as formidable to Llywelyn’s rule.
A late medieval depiction of King Alexander III of Scotland on the left with Llywelyn, Prince of Wales on the right as guests to King Edward I of England at the sitting of an English parliament.
Gruffydd ap Gwenwynwyn has long been painted with the same brush. An enemy to the Welsh nationalist cause for betraying Llywelyn’s vision of a united Wales, he is vilified as an Anglophilic traitor. But history—particularly medieval history—is rarely so clear-cut.
As his patronymic name reveals, Gruffydd ap Gwenwynwyn was the son of Gwenwynwyn, Prince of Southern Powys. For three generations, Powys had been divided into two distinct entities: Powys Fadog in the north and Powys Wenwynwyn in the south—which roughly corresponded to the area of modern-day Montgomeryshire.
Gruffydd’s path to power was far from straightforward. In 1216, his father renounced his allegiance to Llywelyn the Great of Gwynedd—arguably the most formidable Welsh ruler in history. This defiance cost Gwenwynwyn dearly; he and his family were forced into exile, and Gwenwynwyn died not long afterward.
Fatherless, Gruffydd was raised by his Anglo-Norman mother, Margaret Corbet, in Ashford, Derbyshire. Immersed in Anglo-Norman culture, he likely spoke more French than Welsh and was shaped by the customs and politics of the Anglo-Norman nobility. Yet he never fully abandoned his Welsh identity.
Gruffydd remained in exile for 25 years. Only after the death of Llywelyn the Great, and through the intervention of King Henry III of England, was Gruffydd restored to his ancestral lands. In 1241, he returned to Southern Powys and ruled with relative stability—aside from the turbulence of Dafydd ap Llywelyn’s brief uprising against the English crown—for the next sixteen years.
However, this peace was shattered by the rise of an ambitious new ruler in Gwynedd, Llywelyn the Last. In 1257, Gruffydd refused to bow to Llywelyn in his quest to unify the Welsh, and once more found himself in exile. He later negotiated his return to Powys, and in 1263, resumed power as Llywelyn’s vassal. For a time, the two worked together, focusing on harassing the Marcher lordships that threatened their grip on Wales.
A 1606 version of Humphrey Llwyd’s 1573 map of Wales, Cambriae Typus Edited by Peter Kaerius.
Gruffydd’s importance in the Welsh principality is evident in his role in the Treaty of Montgomery in 1267—an agreement between Llywelyn and King Henry III that marked the height of Llywelyn’s power. Gruffydd topped the list of witnesses to this treaty, emphasizing his status as Llywelyn’s most important vassal. Yet cracks began to appear in their alliance as Llywelyn’s rule became increasingly autocratic, marked by suspicion and a tightening grip on his allies.
By 1273, Gruffydd felt increasingly suffocated by Llywelyn’s growing interference in Mid Wales. Crucially, the construction of Dolforwyn Castle—a military and economic threat just a stone’s throw from Gruffydd’s seat of power, Powis Castle—was the final straw. Dolforwyn symbolized Llywelyn’s dominance over the other Welsh princes and threatened to divert trade from Welshpool, a market town Gruffydd had spent decades developing. These pressures ultimately led Gruffydd to take drastic action: an attempt on Llywelyn’s life.
Though the plot was foiled by bad weather, Llywelyn remained unaware of the attempt. He was, however, still suspicious that his Powysian vassal was working against him. In 1274, at a sham trial at Dolforwyn—and without explicitly stating why—Llywelyn stripped Gruffydd of some of his territories and took his eldest son as a hostage. Later that year, Gruffydd refused to appear before Llywelyn in North Wales and fled to England. Backed by the English crown, Gruffydd launched relentless raids into Powys, aiming to erode Llywelyn’s hold on the lands he once ruled.
In 1277, war broke out between King Edward I and Llywelyn, and Gruffydd was restored to his lands. While Llywelyn was forced to submit, peace was short-lived. Llywelyn’s brother Dafydd, who had once aided Gruffydd in the plot against Llywelyn, sparked a fresh rebellion in 1282, reigniting war between Gwynedd and the English crown. That same year, Gruffydd found himself standing on the opposite side of the battlefield from Llywelyn near Builth Wells, where the Prince of Wales met his end. With his death, the final hopes for Welsh independence were extinguished for nearly 120 years.
Even some of the most respected historians have overlooked Gruffydd’s story, often mentioning him only in the context of his conflicts with Llywelyn. This oversimplification contributes to a skewed portrayal of medieval Wales, casting it in stark black-and-white terms: Welsh versus English, freedom fighters versus occupiers. In reality, Gruffydd ap Gwenwynwyn’s loyalty to the English crown was driven less by ideology and more by political survival. Last Man Standing attempts to examine Gruffydd’s life in as much detail as the sources allow, to fully understand what influenced him to oppose Llywelyn’s united Wales. After all, as historian David Stephenson once concluded, “To charge those who resisted subjection to Gwynedd with acting as traitors is to accept without demur the Venedotian claim to dominance and at the same time to misunderstand one of the most powerful dynamics of medieval Wales.”
To safeguard Powys’s independence, Gruffydd had little choice but to align himself with his powerful Anglo-Norman neighbors. He wove his fate into the intricate and ever-changing politics of the Welsh Marches. This was hardly unique to Powys. Many of Wales’ most renowned rulers—such as Rhys ap Gruffydd and Llywelyn the Great—also sought to soothe their relationship with the English crown in order to stave off military incursions. Gruffydd was neither the first nor the last Welsh ruler to find himself caught between a commitment to Welsh independence and the pragmatic necessity of collaborating with Anglo-Norman powers to preserve his proud dynasty’s hold on Powys.
By marrying into the Marcher nobility, Gruffydd secured a foothold in the volatile, competitive political landscape of the borderlands. His union with Hawise Lestrange positioned him as a more integrated and accepted figure within the Anglo-Norman establishment. This, in theory, made him less vulnerable to both rival Welsh princes and the ambitions of the marcher lords. Gruffydd was already the product of a Cambro-Norman marriage, and with his own union into marcher society, he was uniquely positioned to thrive in both Anglo-Norman and Welsh environments. This came to his aid time and again throughout his life, particularly by the end of 1283.
Perhaps most crucially, the fraught relationship between Powys and Gwynedd meant that Gruffydd remained deeply suspicious of Llywelyn the Last’s true intentions, and Llywelyn always suspicious of his vassal. While the idea of uniting Wales under a single banner may seem noble, the petty Welsh principalities were unwilling to accept those they regarded as equals to be their overlords, further complicating any efforts at unity. Centuries of violent competition to be the head of Welsh leadership fostered a climate of distrust and reluctance to cooperate for the ‘greater good.’ It was only with Edward I’s conquest of Wales that the Welsh nobility and its people threw aside their regional differences. Only with the destruction of the petty states did all unite under the banner of Owain Glyndŵr’s rebellion (1400–1415). Only then was it truly apparent that Wales had overcome its long-standing divisions.
Last Man Standing: Gruffydd ap Gwenwynwyn, Prince of Powys shines a light on the important, yet often overlooked history of Powys. Once a principality that played a critical role in defending Wales against the Normans, it was eventually overshadowed by Gwynedd’s dominance in the 13th century. By reexamining Gruffydd’s actions through the lens of his personal and political context, the book invites readers to reconsider his legacy—not simply as a villain, but as a figure shaped by survival and circumstance. He was, after all, the last man standing in the centuries-old struggle between Wales and England.
C I Leah is a native Powysian and studied Welsh History at Aberystwyth University, where he developed his specialism for Medieval Welsh history. After qualifying as a history teacher, he is now based in South Wales.
You can get a copy of Leah’s new book, Last Man Standing: Gruffydd ap Gwenwynwyn, Prince of Powys from Amazon.com | Amazon.ca | Amazon.co.uk
By C.I. Leah
By the end of 1283, King Edward I of England had completed his conquest of Wales, crushing the ambitions of Llywelyn ap Gruffydd—remembered as Llywelyn the Last—to unite the fragmented Welsh principalities under a single native ruler. Edward dismantled the power of the Welsh nobility, brutally scattering his opposition, eliminating many of its leaders. Yet one notable figure remained: Gruffydd ap Gwenwynwyn.
Often overshadowed by more iconic names such as Llywelyn the Last and Owain Glyndŵr, Gruffydd ap Gwenwynwyn is frequently remembered as a traitor—the Welsh prince who aligned himself with the English crown at a pivotal moment in his nation’s struggle to preserve its independence.
Medieval Wales was never a unified state for long. It was a patchwork of competing principalities and lordships, including Gwynedd, Powys, and Deheubarth. On occasion, a particularly capable ruler—usually through military strength—could rise above the rest and temporarily unify the Welsh rivals. Llywelyn the Last was the final Welshman to claim the title ‘Prince of Wales,’ but his struggle for unity was far from universally supported. His opponents included not just the encroaching Anglo-Norman lords but also fellow Welsh nobles, whose jealous rivalries and ambitions proved just as formidable to Llywelyn’s rule.
Gruffydd ap Gwenwynwyn has long been painted with the same brush. An enemy to the Welsh nationalist cause for betraying Llywelyn’s vision of a united Wales, he is vilified as an Anglophilic traitor. But history—particularly medieval history—is rarely so clear-cut.
As his patronymic name reveals, Gruffydd ap Gwenwynwyn was the son of Gwenwynwyn, Prince of Southern Powys. For three generations, Powys had been divided into two distinct entities: Powys Fadog in the north and Powys Wenwynwyn in the south—which roughly corresponded to the area of modern-day Montgomeryshire.
Gruffydd’s path to power was far from straightforward. In 1216, his father renounced his allegiance to Llywelyn the Great of Gwynedd—arguably the most formidable Welsh ruler in history. This defiance cost Gwenwynwyn dearly; he and his family were forced into exile, and Gwenwynwyn died not long afterward.
Fatherless, Gruffydd was raised by his Anglo-Norman mother, Margaret Corbet, in Ashford, Derbyshire. Immersed in Anglo-Norman culture, he likely spoke more French than Welsh and was shaped by the customs and politics of the Anglo-Norman nobility. Yet he never fully abandoned his Welsh identity.
Gruffydd remained in exile for 25 years. Only after the death of Llywelyn the Great, and through the intervention of King Henry III of England, was Gruffydd restored to his ancestral lands. In 1241, he returned to Southern Powys and ruled with relative stability—aside from the turbulence of Dafydd ap Llywelyn’s brief uprising against the English crown—for the next sixteen years.
However, this peace was shattered by the rise of an ambitious new ruler in Gwynedd, Llywelyn the Last. In 1257, Gruffydd refused to bow to Llywelyn in his quest to unify the Welsh, and once more found himself in exile. He later negotiated his return to Powys, and in 1263, resumed power as Llywelyn’s vassal. For a time, the two worked together, focusing on harassing the Marcher lordships that threatened their grip on Wales.
Gruffydd’s importance in the Welsh principality is evident in his role in the Treaty of Montgomery in 1267—an agreement between Llywelyn and King Henry III that marked the height of Llywelyn’s power. Gruffydd topped the list of witnesses to this treaty, emphasizing his status as Llywelyn’s most important vassal. Yet cracks began to appear in their alliance as Llywelyn’s rule became increasingly autocratic, marked by suspicion and a tightening grip on his allies.
By 1273, Gruffydd felt increasingly suffocated by Llywelyn’s growing interference in Mid Wales. Crucially, the construction of Dolforwyn Castle—a military and economic threat just a stone’s throw from Gruffydd’s seat of power, Powis Castle—was the final straw. Dolforwyn symbolized Llywelyn’s dominance over the other Welsh princes and threatened to divert trade from Welshpool, a market town Gruffydd had spent decades developing. These pressures ultimately led Gruffydd to take drastic action: an attempt on Llywelyn’s life.
Though the plot was foiled by bad weather, Llywelyn remained unaware of the attempt. He was, however, still suspicious that his Powysian vassal was working against him. In 1274, at a sham trial at Dolforwyn—and without explicitly stating why—Llywelyn stripped Gruffydd of some of his territories and took his eldest son as a hostage. Later that year, Gruffydd refused to appear before Llywelyn in North Wales and fled to England. Backed by the English crown, Gruffydd launched relentless raids into Powys, aiming to erode Llywelyn’s hold on the lands he once ruled.
In 1277, war broke out between King Edward I and Llywelyn, and Gruffydd was restored to his lands. While Llywelyn was forced to submit, peace was short-lived. Llywelyn’s brother Dafydd, who had once aided Gruffydd in the plot against Llywelyn, sparked a fresh rebellion in 1282, reigniting war between Gwynedd and the English crown. That same year, Gruffydd found himself standing on the opposite side of the battlefield from Llywelyn near Builth Wells, where the Prince of Wales met his end. With his death, the final hopes for Welsh independence were extinguished for nearly 120 years.
Even some of the most respected historians have overlooked Gruffydd’s story, often mentioning him only in the context of his conflicts with Llywelyn. This oversimplification contributes to a skewed portrayal of medieval Wales, casting it in stark black-and-white terms: Welsh versus English, freedom fighters versus occupiers. In reality, Gruffydd ap Gwenwynwyn’s loyalty to the English crown was driven less by ideology and more by political survival. Last Man Standing attempts to examine Gruffydd’s life in as much detail as the sources allow, to fully understand what influenced him to oppose Llywelyn’s united Wales. After all, as historian David Stephenson once concluded, “To charge those who resisted subjection to Gwynedd with acting as traitors is to accept without demur the Venedotian claim to dominance and at the same time to misunderstand one of the most powerful dynamics of medieval Wales.”
To safeguard Powys’s independence, Gruffydd had little choice but to align himself with his powerful Anglo-Norman neighbors. He wove his fate into the intricate and ever-changing politics of the Welsh Marches. This was hardly unique to Powys. Many of Wales’ most renowned rulers—such as Rhys ap Gruffydd and Llywelyn the Great—also sought to soothe their relationship with the English crown in order to stave off military incursions. Gruffydd was neither the first nor the last Welsh ruler to find himself caught between a commitment to Welsh independence and the pragmatic necessity of collaborating with Anglo-Norman powers to preserve his proud dynasty’s hold on Powys.
By marrying into the Marcher nobility, Gruffydd secured a foothold in the volatile, competitive political landscape of the borderlands. His union with Hawise Lestrange positioned him as a more integrated and accepted figure within the Anglo-Norman establishment. This, in theory, made him less vulnerable to both rival Welsh princes and the ambitions of the marcher lords. Gruffydd was already the product of a Cambro-Norman marriage, and with his own union into marcher society, he was uniquely positioned to thrive in both Anglo-Norman and Welsh environments. This came to his aid time and again throughout his life, particularly by the end of 1283.
Perhaps most crucially, the fraught relationship between Powys and Gwynedd meant that Gruffydd remained deeply suspicious of Llywelyn the Last’s true intentions, and Llywelyn always suspicious of his vassal. While the idea of uniting Wales under a single banner may seem noble, the petty Welsh principalities were unwilling to accept those they regarded as equals to be their overlords, further complicating any efforts at unity. Centuries of violent competition to be the head of Welsh leadership fostered a climate of distrust and reluctance to cooperate for the ‘greater good.’ It was only with Edward I’s conquest of Wales that the Welsh nobility and its people threw aside their regional differences. Only with the destruction of the petty states did all unite under the banner of Owain Glyndŵr’s rebellion (1400–1415). Only then was it truly apparent that Wales had overcome its long-standing divisions.
Last Man Standing: Gruffydd ap Gwenwynwyn, Prince of Powys shines a light on the important, yet often overlooked history of Powys. Once a principality that played a critical role in defending Wales against the Normans, it was eventually overshadowed by Gwynedd’s dominance in the 13th century. By reexamining Gruffydd’s actions through the lens of his personal and political context, the book invites readers to reconsider his legacy—not simply as a villain, but as a figure shaped by survival and circumstance. He was, after all, the last man standing in the centuries-old struggle between Wales and England.
You can get a copy of Leah’s new book, Last Man Standing: Gruffydd ap Gwenwynwyn, Prince of Powys from Amazon.com | Amazon.ca | Amazon.co.uk
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