Born in about 1100, Owain ap Gruffudd of Gwynedd - Owain Gwynedd - is considered as one of the foremost monarchs of Gwynedd as, by the end of his reign he ruled most of Wales. A typical prince prince of his day, he was both warlike and powerful.

Upon the death of their father Gruffudd ap Cynan in 1137, his three sons, Cadwallon, Owain and Cadwaladr shared his kingdom – as was the Welsh custom.

The two foremost princes of the day, Owain Gwynedd in the north and Gruffudd ap Rhys  in the south carried Wales through these difficult days. Both were acutely minded of the problems they faced – rival Welsh kingdoms fighting each other, Marcher lords forever seeking new lands in Wales and extending their power and, of course, the ever intrusive, richer and more powerful neighbour, England.

1157 saw Henry II (Stephen's successor) lead an invasion of Gwynedd supported by Owain's exiled brother, Cadwaladr. Owain fought back, with his forces ambushing the English army at Ewloe; the English were thoroughly routed with the King of England only just evading capture. However, Owain was eventually forced to come to terms with Henry, and was required to render homage to Henry. In the politics of the day Owain often had to yield - but he never lost the initiative and was soon acting with complete independence.

Henry invaded again in 1164(65) but was met by an alliance of all the Welsh princes, led by Owain and including Rhys ap Gruffudd - yr Arglwydd Rhys - which led to the successful capture of Basingwerk and Rhuddlan castles by the Welsh alliance. Little other fighting took place as torrential rain forced the English army into retreat. Infuriated by his failure, Henry mutilated many of his Welsh hostages including two of Owain's sons and blinding Maredudd, son of yr Arglwydd Rhys..

Henry II never invaded Wales, or challenged Owain again.

Owain Gwynedd died a powerful, successful ruler whose later years were marked by peace and the building of  structures to enforce both state and church in his own lands. Sadly after his death in 1170, his sons of which he had 5 by two marriages, also a number of illegitimate sons, fought amongst each other for supremacy in the kingdom leading to chaos in the realm. One of his sons, Iorwerth Drwyndwn was the father of Llywelyn ap Iorwerth - better known as Llywelyn Fawr (Llywelyn the Great) - who was to put an end to the feuding.
 

Native Princes of Gwynedd / Wales
Monarch	Birth	Reign
Rhodri Mawr	circa 820-878
Hywel Dda	circa 880 - 950
Grufydd ap Llywelyn	circa 1007-1063
Grufydd ap Cynan	circa 1055 - 1137
Owain Gwynedd	circa 1080	1137-1170
Llywelyn Fawr  (the Great) - Llywelyn ap Iorwerth	1173	1199-1240
Dafydd ap Llywelyn	1212	1240-1246
Llywelyn Ein Llyw Olaf  (the Last)  - Llywelyn ap Gruffudd	circa 1223	1246-1282
Owain Glyndwr	circa 1349	1400 - 1404