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In January 1402 near Ruthin , Owain Glyndwr captured his arch-enemy Reginald de Grey, 3rd Baron Grey de Ruthyn.
Reginald de Grey was responsible for issuing and enforcing royal demands in the Northern March and was in a long-running legal dispute with Glyndŵr, claiming a tranche of Glyndwr's land as his own. Under King Richard II the case had been found in favour of Glyndŵr, but on the usurpation of King Henry IV, Lord Grey seized the land.
Glyndŵr responded in law early in 1400 but his case was not granted a hearing, instead it was asked of Glyndŵr that he grant Lord Grey further concessions. de Grey also delayed summoning Glyndŵr's quota or levy of men for the king's service in Scotland until the last moment, making it impossible for Glyndŵr to respond as requested or even send an explanation for his absence. Such an act as refusal or failure to respond to an order of the King was deemed a treasonous act and Glyndŵr's estates were deemed forfeit until he could prove his loyalty or receive due punishment.
On 18th September 1400, Owain took up arms, burned Grey's property and for three days ravaged the coutryside of Flintshire and Denbighshire, but on 24 September, Glyndwr's forces were encircled at Welshpool and defeated. de Grey now invited Glyndŵr to a reconciliation meeting, but arrived with a large force and attempted to capture Glyndŵr. Glyndŵr escaped with his life and went into hiding, but this confirmed him as a traitor in English eyes and King Henry confiscated the estates of his supporters.
The rebellion spread and by 1402 it was gathering momentum. Lord Grey was captured by Glyndŵr's forces in an ambush near Ruthin in January 1402. A ransom of 10,000 marks was asked for him and Lord Grey was asked to swear an oath never to bear arms against Glyndŵr again. King Henry IV sent eleven knights to treat with Glyndŵr and then complied with the ransom. Lord Grey would then have been expected to repay the amount over time as best he could and any outstanding debt would be borne by his family.