Powys Wenwynwyn or Powys Cyfeiliog was a Welsh kingdom which existed during the high Middle Ages. The realm was the southern portion of the former princely state of Powys which split following the death of Madog ap Maredudd of Powys in 1160: the northern portion went to Gruffydd Maelor and eventually became known as Powys Fadog; while the southern portion going to Owain Cyfeiliog and becoming known, eventually, as Powys Wenwynwyn after Prince Gwenwynwyn ab Owain, its second ruler. Powys Wenwynwyn and Gwynedd became bitter rivals in the years that followed, with the former frequently allying itself with England to further its own aims of weakening the latter.
Princes of Powys Wenwynwyn
1160–1195 Owain Cyfeiliog married a daughter of Owain Gwynedd and abdicated in 1195.
1195–1216 Gwenwynwyn ab Owain
Gwenwynwyn seized the cantref of Arwystli in 1197, when he was aligned with England. Following the marriage of Llywelyn the Great and Joan of England in 1208, warfare broke out once more between Gwenwynwyn and Llywelyn. In 1212 Gwenwynwyn's ancient royal seat at Mathrafal was destroyed and he was evicted from his territories. He changed allegiance again and was restored to his realm in 1215, making a new capital at Welshpool. In 1216 he was defeated in battle with the forces of Llywelyn and fled to England, where he died shortly afterwards. He was succeeded by his son.
Gruffydd ap Gwenwynwyn spent his youth in England, maintained by King Henry III of England. He did not return to Wales until 1241 after the death of Llywelyn and when he was invested with the lordships of Arwystli, Cyfeiliog, Mawddwy, Caereinion, Ystrad Marchell and Upper Mochnant by Henry III. At some time before this he married Hawise, daughter of John Le Strange of Knockin. He transferred his allegiance back to Llywelyn ap Gruffudd in 1263 before returning to England's protection again after 1276, following a failed plot to murder Prince Llywelyn in collusion with his rival's own brother, Dafydd ap Gruffydd. His forces, commanded by his son Owain ap Gruffydd ap Gwenwynwyn, mobilised during the Welsh War of 1282–1283 with those of John Le Strange and Hugh le Despenser and it was their soldiers who ambushed and killed the last native Prince of Wales near Builth in 1282.
End of the Principality
Owain ap Gruffydd ap Gwenwynwyn allegedly surrendered the principality of Powys to Edward I at the Parliament held in Shrewsbury in 1283. In return for surrendering the principality he received it again from the king as a free Baron of England "sub nomine et tenura liberi Baronagii Angliæ, resignando Domino Regi heredibus suis et Coronæ Angliæ nomen et circulum principatus." The date should be accepted with reserve because Owen did not succeed his father in possession until 1286: it is possible that Owen was acting on behalf of his father, who was by then an old man. From about that time the former princely family began using the Normanised surname "de la Pole" instead of Welsh patronymics. The name derives from Pool, his principal town.
The Lordship of Powys
After the Statute of Rhuddlan in 1284 all of the other old princely titles in Wales also ceased to exist; and henceforth, with the exception of the Kingdom of Scotland after 1344, the English Crown did not recognise the title of "prince" or "king" in any native dynasty other than their own. However the principality continued as a marcher lordship. The ruling family of Powys survived in the children and remoter descendants of Gruffydd ap Gwenwynwyn, henceforth known as the de la Pole family, who lived in the newly built Powis Castle. In 1293 Owen de la Pole died and was succeeded by his son Griffith de la Pole, who died without heirs in 1309. The lordship was then inherited by his sister Hawise "Gadarn", rather than to the male heirs. She died in 1349 and on the death of her husband John Charleton, 1st Baron Cherleton in 1353, the lordship passed to their children and thence out of native Welsh hands.
Joyce Charleton of Cherleton, wife of John Tiptoft, 1st Baron Tiptoft, whose daughter, also Joyce, carried the Tiptoft portion of the Cherleton inheritance to the family of her husband Sir Edmund Sutton of Dudley, which their grandson John Sutton, 3rd Baron Dudley, "Lord Quondam", sold to his nephew, the 3rd Baron Grey of Powis, circa 1538.
Beyond the Marcher Lordship
The Laws in Wales Acts 1535–1542 abolished the feudal rights of the Lords of Powis and saw the territory of the Lordship of Powis almost entirely incorporated within the new county of Montgomeryshire. However the lordship continued to exist as a great landed estate.
Edward Grey, 3rd Baron Grey of Powis.
Edward Grey of London, his illegitimate son, sold the lordship to his kinsman Sir Edward Herbert in 1587.
Sir Edward Herbert, a blood relative of both descendant branches of the Cherleton Barony.
Sir William Herbert was created Baron Powis in 1629.
had several brothers, whom he enfeoffed as his feudal tenants with lordships within his own lordship. However none of them left children except William de la Pole, who had the lordship of Mawddwy, comprising that parish and most of Mallwyd. Descendants of the ancient princes of Powys were lords there for several generations, until the lordship passed to an heiress and then was divided between four coheiresses. One of these coheiresses, Elisabeth de Burgh, married Sir John Lingen and their descendants still exist today. Certain genealogical sources have claimed that Owen de la Pole had other sons, including an alleged William de la Pole, who succeeded to the lordship on Owen's death in 1293. Some have sought to identify him with the father of William de la Pole, who may possibly also have been called William, but whose name is not certainly known. However the link is most improbable, the merchants' surname probably being derived from a place near Hull. William de la Pole and his brother Richard were successful merchants from Hull, who rose to become royal financiers under Edward II and Edward III, William's son Michael being created 1st Earl of Suffolk.