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Owain‘s service to Arundel included taking part in the naval victory over the French in 1387 in which a wine fleet was captured. Such was the booty that the price of wine in England fell through the floor. He may well also have been involved in Arundel’s attack on the French coast a few months later.

Domestic trouble was, however, already brewing between Richard II and his baronial opponents, who may conveniently be called the Lords Appellant. Arundel was one of the prime movers of this group and arguably the most vocal of the King’s critics.

Some sources claim that Owain fought for the Appellants at Radcot Bridge (December 1387) and even that he did so as part of the retinue of Henry Bolingbroke, Earl of Derby. If he did so, this would be historical irony on an epic scale given that Bolingbroke was to become, as king, Owain’s most deadly enemy.

It is important to note that Owain was not some obscure Welsh backwoodsman. He would have known, and been known to, many of the most powerful men in the kingdom.

The Appellant triumph, although complete, did not last long. Richard II soon regained his power, but at first ruled moderately, under the influence of, among others, his uncle, Bolingbroke’s father, John of Gaunt, Duke of Lancaster. The political settlement imposed by the Appellants was largely left in place, but Richard itched to overthrow it and take his revenge, not least against Arundel – a man with whom Lancaster also had his quarrels.

By 1397, Richard was at last strong enough to impose his will. He had a new cohort of powerful aristocratic supporters around him. Arundel was arrested (along with the King’s youngest uncle, Gloucester and the Earl of Warwick.) Arundel, after a trial in Parliament, was beheaded in London. Gloucester was (probably) murdered. Warwick was sentenced to life imprisonment. All their lands were forfeited.

The lordship of Bromfield and Yale was merged with Cheshire to form King Richard’s Principality of Chester. This cannot but have caused local turbulence, not least because for many years the men of the two entities had been in the habit of raiding each other across their border. (A feature of Marcher lordships was that extradition between them was all-but-impossible, so cross-border crime was commonplace.)

Uncertainty was to continue. The King’s heir, given that he was childless, was Roger Mortimer, Earl of March. Mortimer was the great hope of Wales, for he was deemed sympathetic to the Welsh. Another descendant of Llywelyn ap Iorwerth, he was, pretty much uniquely for an English lord, praised in bardic poetry and hailed as a potential Son of Prophecy – a future king of Welsh blood. However, Roger was killed in Ireland in 1398, and King Richard’s intentions for the succession became rather opaque.

In the same year, Bolingbroke and Norfolk, having accused one another of treason, were banished. In 1399, Bolingbroke’s inheritance was forfeited following Gaunt’s death, and his banishment extended to life. King Richard then blithely departed to Ireland, taking with him all his most powerful supporters and much of their military potential.

As is well-known, Bolingbroke returned from exile and before long had deposed Richard II and installed himself as King Henry IV. This caused further turbulence. Bromfield and Yale and Chirkland reverted to Arundel’s son. Yet if there was anywhere in the kingdom where Richard was popular it was in Cheshire and Wales. An abortive rising against Henry flamed in Chester itself in January 1400, no doubt in connection with the Epiphany Rising.

What Owain thought of all these changes we cannot know. They can only have filled his life with uncertainty, that’s for sure. Perhaps, like Brer Rabbit, he ‘lay low and said nuffin.’ This would have been the obvious course for a middle-aged man of moderate prosperity who lacked a powerful patron to protect him.

Unfortunately, his quarrel with Reginald, Lord Grey de Ruthin, now flared. The details are elusive, but it seems to Grey disputed the ownership of part of Owain’s land. Mutual threats and legal action followed, but Grey had the advantage of being an English lord, and the further advantage of being one of Henry IV’s supporters. If Owain could get no satisfaction from the royal law courts, it is perhaps not surprising. The surprise might have been if he had.

In September 1400, at Corwen, Owain gathered together a small band of followers, including his sons, his brothers-in-law, and John Trevor, the Bishop of St. Asaph. They descended on the town of Ruthin and sacked it. Owain declared himself Prince of Powys. The great rising had begun.