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Owain Glyndŵr (Owain Glyndyfrdwy, Owain of the Valley of the Dee) was, on his father's side, heir to the dynasty of Powys Fadog. On his mother's side, he represented what was left of the claims of the descendants of the Lord Rhys of Deheubarth.

The male line of the Gwynedd dynasty became extinct with the death of Owain Lawgoch in 1378. Thereafter, to the extent that a Welsh claimant to the title of Prince of Wales did exist, it was Owain Glyndŵr. Born in about 1350, Owain held at Glyndyfrdwy near Corwen, and Sycharth near Chirk, remnants of the patrimony of his ancestors.

Glyndŵr was a man of the borderland. Sycharth is only a mile from the English border. His family lived under the shadow of the great marcher aristocrats, the Fitzalan lords of Chirk and Oswestry.

Owain married into a leading Marcher family. He spent time in London and in the army of the King of England; indeed he could appear to have been the epitome of an assimilated Welshman.

Yet he was clearly well versed in the legendary lore of his people. The poets delighted in the hospitality of Sycharth and they, being deeply versed in genealogy, seemed to be grooming him for the role of the deliverer of the Welsh. Shakespeare's portrait of him in Henry IV combined these two facets of his character with great skill.

The year 1399 saw the dethronement of Richard II and the seizure of the throne by Henry IV - the lord of Brecon, Monmouth, Kidwelly and Ogmore - although Edmund Mortimer, the leading lord of the March, had a better claim to be the heir of Richard II.

In the early years of his reign, Henry had difficulty in consolidating his authority and was opposed by leading magnates, including the Mortimers and the powerful Percy family of Northumberland. Many of the Welsh gentry had close links with Richard II, and the usurpation weakened their allegiance to the English crown.

The immediate spark for revolt seems to have been the king's unwillingness to mediate fairly in a dispute between Owain and his neighbour, Reginald Grey of the Ruthin marcher lordship. On 16 September 1400, a group of Owain's supporters proclaimed him Prince of Wales at Glyndyfrdwy. They attacked English settlements in north-east Wales and then melted away into the mountains.

Nothing then happened until his allies, the Tudor family of Anglesey, occupied Conwy Castle at Easter 1401. A few months later, Owain defeated a force on Pumlumon, and enthusiasm for him became apparent over much of Wales.

The king led several campaigns against him, but his orthodox strategy made little headway against Owain's guerrilla tactics. His campaigns were hindered by such appalling weather that some believed Glyndŵr had influence over the elemental forces of nature.

In an act of frustration, parliament passed the Penal Code, which prohibited the rebellious Welsh from gathering together, gaining access to office, carrying arms and dwelling in fortified towns, with the same restrictions being imposed upon Englishmen married to Welsh women.