Background
He ruled southern Powys from 1195, having taken control following the death of his father Owain Cyfeiliog.
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Owain Cyfeiliog
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His possession of Powys Wenwynwyn brought him into conflict with Llywelyn the Great, ruler of Gwynedd, who was keen to extend his own jurisdiction over the whole of Wales. King John favoured Gwenwynwyn until a marriage alliance was made between Llywelyn and John"s illegitimate daughter. The two native princes then kept their distance until 1208.
As a result of Gwenwynwyn"s activities, John confiscated his lands and allowed Llywelyn to appropriate Ceredigion and Powys.
Gwenwynwyn did not get his territory back for two years, but his resentment towards the English led him into an alliance with Llywelyn, which lasted from 1212 until 1216, when John restored some of Gwenwynwyn"s property and the two Welsh princes fell out again. 1195 Becomes ruler of Powys Wenwynwyn
Gwenwynwyn hands Gruffydd over to the English
c.
1198 Raises a large army and besieges Painscastle. Gruffydd, released by the English, engages Gwenwynwyn with a large force and defeats him. c.
1202 Swears allegiance to Llywelyn the Great
1208 Arrested by King John and his lands annexed by Llywelyn. c.
1210 Freed by John and recovers his possessions. He accompanies John on his expedition into Wales. 1211 Takes up arms for Llywelyn. c.
1216 Deserts to John, pursued by Llywelyn who takes his lands, and takes refuge in Chester.
Llywelyn invaded Powys, and Gwenwynwyn is believed to have died or been killed that same year.
