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Leader of a Welsh revolt against English rule

In 1400 Owain Glyndŵr, a descendant of several Welsh royal dynasties, had a dispute with a neighbouring English lord that resulted in Glyndŵr claiming his title of Prince of Wales, which instigated the revolt against English rule. In response to the uprising, discriminatory penal laws were implemented against the Welsh people; this deepened public unrest and significantly increased support for Glyndŵr across Wales. In 1404, after a series of successful castle sieges and several battlefield victories against the English, Owain gained control of the country and was proclaimed by his supporters Prince of Wales in the presence of French, Spanish, Scottish and Breton envoys. He summoned a national parliament, where he announced plans to reintroduce the traditional Welsh laws of Hywel Dda, establish an independent Welsh church, and build two universities. Owain formed an alliance with King Charles VI of France; in 1405 a French army landed in Wales to support the rebellion. Under Owain Glyndŵr's leadership, an internationally recognised independent Welsh state was briefly established. It lasted for five years until February 1409, when English forces captured Owain's last remaining strongholds of Aberystwyth Castle and Harlech Castle, effectively ending his territorial rule in Wales. Glyndŵr refused to surrender to the new king Henry V, ignoring two offers of a pardon from the monarch. He retreated to the Welsh hills and mountains with his remaining forces, where he continued to resist English rule by utilising guerrilla tactics. This continued until Owain disappeared in 1415, when one of his supporters, Adam of Usk, recorded that he died of natural causes. He was the wealthiest Welshman in Wales before his downfall. Despite the large bounty placed on him by the English crown, Glyndŵr was never betrayed or captured, and in Welsh culture he acquired a mythical status alongside the likes of Cadwaladr, Cynon ap Clydno and King Arthur as a folk hero awaiting the call to return and liberate his people – "Y Mab Darogan" ('The Foretold Son'). In William Shakespeare's play Henry IV, Part 1 he appears as the character Owen Glendower as a king rather than a prince.

Owain Glyndŵr was born in 1354 in the northeast Welsh Marches (near the border between Wales and England) to a family of uchelwyr – nobles descended from the pre conquest native Welsh royal dynasties – in traditional Welsh society. This group moved easily between Welsh and English societies and languages, occupying important offices for the Marcher Lords while maintaining their position as uchelwyr. His father, Gruffydd Fychan II, hereditary Tywysog (Prince) of Powys Fadog and Lord of Glyndyfrdwy, died sometime before 1370, leaving Glyndŵr's mother Elen ferch Tomas ap Llywelyn, a woman with an accent from Ceredigion (Deheubarth), a widow when he was still a boy. Owain Glyndŵr was a direct descendant of several Welsh royal dynasties, including the princes of Powys via the House of Mathrafal through his father. Through his mother, he was also a descendant of king John and the kings and princes of Deheubarth as well as the royal House of Dinefwr, the kings and princes of Gwynedd including Llywelyn ab Iorwerth, and their cadet branch the House of Aberffraw. The young Owain ap Gruffydd was possibly fostered at the home of David Hanmer, a rising lawyer shortly to be a justice of the King's Bench, or at the home of Richard FitzAlan, 3rd Earl of Arundel. Owain is then thought to have been sent to London to study law at the Inns of Court. However they may have married at an earlier date in the late 1370s, according to sources. They started a large family and Owain established himself as the squire of Sycharth and Glyndyfrdwy. Glyndŵr joined the king's military service in 1384 when he undertook garrison duty under the renowned Welshman Sir Gregory Sais, or Sir Degory Sais, on the English–Scottish border at Berwick upon Tweed. His surname Sais, meaning 'Englishman' in Welsh, refers to his ability to speak English, not common in Wales at the time. In August 1385, he served King Richard II under the command of John of Gaunt, again in Scotland.

In the late 1390s, a series of events began to push Owain towards rebellion, in what was later to be called the Welsh Revolt, the Glyndŵr Rising or (within Wales) the Last War of Independence. His neighbour, Baron Grey de Ruthyn, had seized control of some land, for which Glyndŵr appealed to the English Parliament. Lord Grey had stature in the royal court of Henry IV. The law courts refused to hear, or the case was delayed because Lord Grey prevented Owain's letter from reaching the King. On 16 September 1400, Owain Glyndŵr instigated a 15 year Welsh Revolt against the rule of Henry IV of England. Using guerrilla tactics, the Welsh troops inflicted a series of defeats on the English forces and captured key castles across Wales, rapidly gaining control of most of the country. News of the rebellion's success spread across Europe, and Glyndŵr began to receive naval support from Scotland and Brittany. He also received the support of King Charles VI of France, who agreed to send French troops and supplies to aid the rebellion. In 1403 a Welsh army including a French contingent assimilated into forces mainly from Glamorgan and the Rhondda Valleys region commanded by Owain Glyndŵr, his senior general Rhys Gethin and Cadwgan, Lord of Glyn Rhondda, defeated a large English invasion force reputedly led by King Henry IV himself at the Battle of Stalling Down in Glamorgan. hence why Glyndŵr is often also viewed as a Robin Hood figure. Sources state that Glyndŵr was under threat because he had written an angry letter to Lord Grey, boasting that lands had come into his possession, The deposed king, Richard II, had support in Wales, and in January 1400 serious civil disorder broke out in the English border city of Chester after the public execution of an officer of Richard II. These events led to Glyndŵr's formally assuming his ancestral title of Prince of Powys on 16 September 1400 at his Glyndyfrdwy estate. This included such plans as building two national universities (one in the south and one in the north), re introducing the traditional Welsh laws of Hywel Dda, and establishing an independent Welsh church. There were envoys from other countries including France, Scotland and the Kingdom of León (in Spain). In the summer of 1405, four representatives from every commote in Wales were sent to Harlech. Machynlleth may have been chosen due to its central location in Wales and the recently acquired possession of three nearby castles: Castell y Bere, Aberystwyth Castle and Harlech Castle. The current Parliament House (Senedd dy) in Machynlleth is associated with the 1404 parliament but the present building is more recent. Local tradition has it that the stones used came from the original 1404 building.

In February 1405, Glyndŵr negotiated the "Tripartite Indenture" with Edmund Mortimer and Henry Percy, Earl of Northumberland. The Indenture agreed to divide England and Wales among the three of them. Although negotiations with the lords of Ireland were unsuccessful, Glyndŵr had reason to hope that the French and Bretons might be more welcoming. He dispatched Gruffydd Yonge and his brother in law (Margaret's brother), John Hanmer, to negotiate with the French. The result was a formal treaty that promised French aid to Glyndŵr and the Welsh. The immediate effect seems to have been that joint Welsh and Franco Breton forces attacked and laid siege to Kidwelly Castle. The Welsh could also count on semi official fraternal aid from the Duchy of Brittany and from Scotland. Scots and French privateers were operating around Wales throughout Owain's war. Scottish ships had raided English settlements on the Llŷn Peninsula in 1400 and 1401. In 1403, a Breton squadron defeated the English in the Channel and devastated Jersey, Guernsey and Plymouth, while the French made a landing on the Isle of Wight. By 1404, they were raiding the coast of England, with Welsh troops on board, setting fire to Dartmouth and devastating the coast of Devon. 1405 was the "Year of the French" in Wales. A formal treaty between Wales and France was negotiated. On the continent, the French pressed the English as the French army invaded the English Plantagenet Aquitaine. Simultaneously, the French landed in force at Milford Haven in west Wales and attempted to capture Pembroke Castle before they were bought off. The combined forces of French and Welsh marched through Herefordshire and on into Worcestershire to Woodbury Hill. They met the English army just ten miles from Worcester.

By 1405, most French forces had withdrawn after politics in Paris shifted towards peace, with the Hundred Years' War continuing between England and France. On 31 March 1406 Glyndŵr wrote a letter to be sent to Charles VI of France during a synod at the Welsh Church at Pennal, hence its name. Glyndŵr's letter requested maintained military support from the French to fend off the English in Wales. Glyndŵr suggested that in return he would recognise Benedict XIII of Avignon as the Pope. The letter sets out the ambitions of Glyndŵr for an independent Wales with its own parliament, led by himself as Prince of Wales. These ambitions also included the return of the traditional law of Hywel Dda, rather than the enforced English law, establishment of an independent Welsh church as well as two universities, one in south Wales, and one in north Wales. Following this letter, senior churchmen and important members of society flocked to Glyndŵr's banner and English resistance was reduced to a few isolated castles, walled towns, and fortified manor houses. Glyndŵr's Great Seal and a letter handwritten by him to the French in 1406 are in the Bibliothèque nationale de France in Paris. This letter is currently held in the Archives Nationales in Paris. Facsimile copies involving specialist ageing techniques and moulds of Glyndŵr's seal were created by the National Library of Wales and presented by the heritage minister Alun Ffred Jones to six Welsh institutions in 2009. The royal great seal from 1404 was given to Charles IV of France and contains images and Glyndŵr's title – Owynus Dei Gratia Princeps Walliae – 'Owain, by the grace of God, Prince of Wales'. Glyndwr cited himself as the “Prince of Wales” and noted his “right of inheritance” in these letters. He would also have known, from his experience at the High Court of Chivalry (Scrope v Grosvenor) in 1386, that in bearing a coat of arms the same as those of Llywelyn ap Gruffydd, he was signalling a family blood line connection.

During early 1405 the Welsh forces, who had until then won several easy victories, suffered a series of defeats. Glyndŵr's brother, Lord Tudur ap Gruffudd, a commander during the war, died at the Battle of Pwll Melyn in May 1405. English forces landed in Anglesey from Ireland and would over time push the Welsh back until the resistance in Anglesey formally ended toward the end of 1406. As late as 1414, there were rumours that the Herefordshire based Lollard leader Sir John Oldcastle was communicating with Owain, and reinforcements were sent to the major castles in the north and south. On 21 December 1411, the King of England issued pardons to all Welsh except their leader and Thomas of Trumpington (until 9 April 1413, from which Glyndŵr was no longer excepted). In his book The Mystery of Jack of Kent and the Fate of Owain Glyndŵr, Alex Gibbon argues that the folk hero Jack of Kent, also known as Siôn Cent – the family chaplain of the Scudamore family – was, in fact, Owain Glyndŵr himself. Gibbon points out a number of similarities between Siôn Cent and Glyndŵr (including physical appearance, age, education, and character) and claims that Owain spent his last years living with his daughter Alys, passing himself off as an ageing Franciscan friar and family tutor. There are many folk tales of Glyndŵr donning disguises to gain an advantage over opponents during the rebellion.

The Owain Glyndwr Hotel in Corwen is a historic inn. An earlier building had been a monastery and church dating from the age of Glyndŵr in the 14th century, although the current building mostly dates from the 18th century. The waymarked long distance footpath Glyndŵr's Way runs through Mid Wales near to his homelands. As well as in North Wales, in the capital, Cardiff is the Owain Glyndwr pub on St. John Street in the city centre. At least two ships and one locomotive have been named after Glyndŵr. In 1808, the Royal Navy launched a 36 gun fifth rate frigate, She served in the Baltic Sea during the Gunboat War where she participated in the seizure of Anholt Island, and then in the Channel. Between 1822 and 1824, she served in the West Africa Squadron (or 'Preventative Squadron') chasing down slave ships, capturing at least two. Owen Glendower, an East Indiaman, a Blackwall frigate built in 1839. In 1923, a 2 6 2T Vale of Rheidol locomotive was named after Glyndŵr. The locomotive is still operational and was one of a few used by British Rail until it was privatised. Following Glyndŵr's death, he acquired mythical status as the hero awaiting a call to return and liberate his people in the classic Welsh mythical role Y Mab Darogan ('The Foretold Son'). Glyndŵr came second to Aneurin Bevan in the 100 Welsh Heroes poll of 2003/2004. Stamps were issued with his likeness in 1974 and 2008, and streets, parks, and public squares were named after him throughout Wales. There is a campaign to make 16 September (Owain Glyndŵr Day), the date Glyndŵr raised his standard, a public holiday in Wales, including by Dafydd Wigley in 2021. Many schools and organisations commemorate the day, and street parades such as Gŵyl y Fflam ('Festival of the Flame') are held to celebrate it. On 16th September 2023, a portrait of Owain Glyndwr was unveiled at Sycharth by the artist, Dan Llywelyn Hall. The portrait was made in support of a campaign to restore the motte and bailey of Sycharth. An annual award for achievement in the arts and literature, the Glyndŵr Award, is named after Glyndŵr. From 2008 to 2023, Wrexham University was known as (Wrexham) Glyndŵr University in his honour. Despite adopting its new name without Glyndŵr in 2023, the university maintains links with the Owain Glyndŵr Society for one of its annual top graduate awards. Glendower Residence, at the University of Cape Town in South Africa, was named after Owain Glyndŵr. The residence was opened in 1993 having previously been the Glendower Hotel. The hall of residence houses 135 male students. Glyndŵr's personal standard (the quartered arms of Powys and Deheubarth rampant) began to be seen in Wales on commercial products, and also flags used at games and other sporting events.

Owain married Margaret Hanmer, also known by her Welsh name Marred ferch Dafydd, daughter of Sir David Hanmer of Hanmer, early in his life. efn|According to Lloyd, Owain and Margaret had five sons and four (p. 211) or five (p. 199) daughters: Glyndŵr's daughters Janet and Margaret married respectively Sir John de Croft and Sir Richard Monnington, in Herefordshire. Owain's sons were either taken prisoner or died in battle and had no issue. Gruffudd, born about 1375, was captured by the English, confined in Nottingham Castle, and taken to the Tower of London in 1410. He died in prison of bubonic plague in about 1412. Maredudd, whose date of birth is unknown, was still living in 1421 when he accepted a pardon. Little is known about Madog, Thomas, and John. Owain had additional illegitimate children: David, Gwenllian, Ieuan, and Myfanwy.

Some sources allege that Glyndwr's royal ancestor from the Kingdom of Gwynedd as a Prince of Wales was Llywelyn ap Gruffudd. Llywelyn supposedly does not have any living descendants from his childless daughter named Gwenllian. However, he was in some instances documented to have had another daughter named Catherine by his wife Eleanor de Montfort. Professor Sir J E Lloyd said: "There is no evidence that Llywelyn had any daughter but Gwenllian, born in the last year of his life and after his death confined for the rest of her days as a nun of the order of Sempringham". Lloyd’s assessment has been reciprocated by other Welsh historians. Glyndwr was descended from the grandfather of Llywelyn ap Gruffudd, Llywelyn the Great.