Gruffydd ap Cynan (c. 1055–1137) was a King of Gwynedd. In the course of a long and eventful life, he became a key figure in Welsh resistance to Norman rule. As a decendent of Rhodri Mawr, Gruffydd ap Cynan was a senior member of the princely house of Aberffraw. Through his mother Gruffydd had close family connections with the Danish settlement around Dublin and he frequently used Ireland as a refuge and as a source of troops. He three times gained the throne of Gwynedd and then lost it again before regaining it once more in 1099 and this time keeping power until his death. Gruffydd laid the foundations which were built upon by his son Owain Gwynedd and his great-grandson Llywelyn the Great.
According to the Life of Gruffydd ap Cynan, Gruffydd was born in Dublin and reared near Swords, County Dublin in Ireland. He was the son of a Welsh Prince, Cynan ap Iago, who was a claimant to the Kingship of Gwynedd but was probably never king of Gwynedd, though his father, Gruffydd's grandfather, Iago ab Idwal ap Meurig had ruled Gwynedd from 1023 to 1039. When Gruffydd first appeared on the scene in Wales the Welsh annals several times refer to him as "grandson of Iago" rather than the more usual "son of Cynan", indicating that his father was little known in Wales. Cynan ap Iago seems to have died while Gruffydd was still young, since the History describes his mother telling him who his father was. Gruffydd's mother, Ragnaillt, was the daughter of Olaf of Dublin, son of King Sigtrygg Silkbeard and a member of the Hiberno-Norse dynasty. Through his mother, who appears in the list of the fair women of Ireland in the Book of Leinster, Gruffydd claimed relationships with many of the leading septs in Ireland, including those of the Ua Briain. During his many struggles to gain the kingship of Gwynedd, Gruffydd received considerable aid from Ireland, both from the Hiberno-Norse at Dublin, but also those at Wexford, and also from Muircheartach Ua Briain.
Gruffydd made his first attempt to take over the rule of Gwynedd in 1075, following the death of Bleddyn ap Cynfyn. Trahaearn ap Caradog had seized control of Gwynedd but had not yet firmly established himself. Gruffydd landed on Anglesey with an Irish force, and with the assistance of troops provided by the Norman Robert of Rhuddlan first defeated and killed Cynwrig ap Rhiwallon, an ally of Trahaearn who held Llyn, then defeated Trahaearn himself in the battle of Gwaed Erw in Meirionnydd and gained control of Gwynedd. Gruffydd then led his forces eastwards to reclaim territories taken over by the Normans, and despite the assistance previously given by Robert of Rhuddlan attacked and destroyed Rhuddlan castle. However tension between Gruffydd's Danish-Irish bodyguard and the local Welsh led to a rebellion in Llyn and Trahaearn took the opportunity to counter attack, defeating Gruffydd at the battle of Bron yr Erw above Clynnog Fawr the same year.
Gruffydd fled to Ireland but in 1081 returned and made an alliance with Rhys ap Tewdwr prince of Deheubarth. Rhys had been attacked by Caradog ap Gruffydd of Gwent and Morgannwg, and had been forced to flee to the St David's Cathedral. Gruffydd this time embarked from Waterford with a force composed of Danes and Irish and landed near St David's, presumably by prior arrangement with Rhys. He was joined here by a force of his supporters from Gwynedd, and he and Rhys marched north to seek Trahaearn ap Caradog and Caradog ap Gruffydd who had themselves made an alliance and been joined by Meilyr ap Rhiwallon of Powys. The armies of the two confederacies met at the Battle of Mynydd Carn, with Gruffydd and Rhys victorious and Trahaearn, Caradog and Meilyr all being killed. Gruffydd was thus able to seize power in Gwynedd for the second time. He was soon faced with a new enemy, as the Normans were now encroaching on Gwynedd.
Gruffydd had not been king very long when he was enticed to a meeting with Hugh d'Avranches, 1st Earl of Chester and Hugh of Montgomery, 2nd Earl of Shrewsbury at Rug, near Corwen. At the meeting Gruffydd was seized and taken prisoner. According to his biographer this was by the treachery of one of his own men, Meirion Goch. Gruffydd was imprisoned in Earl Hugh's castle at Chester for many years while Earl Hugh and Robert of Rhuddlan went on to take possession of Gwynedd, building castles at Bangor, Caernarfon and Aberlleiniog.
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