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Let us start at the top of the social hierarchy with a future self-proclaimed Prince of Wales and a man voted the 23rd greatest Briton of all time (Henry V came a lowly 72nd in the poll). This man has also been named the 2nd Greatest Welsh hero (behind Aneurin Bevan) and the Welshman of the Millennium.  This is, of course, Owain Glyn Dŵr, renowned for leading the Welsh revolt against Henry IV from 1400. [1]


Before his conversion to the cause of Welsh independence, Glyn Dŵr had given sterling service on behalf of the English Crown. This was a fascinating part of his career, and one on which the soldier project can shed some valuable light. In 1387 he fought at sea as an esquire in the retinue of the earl of Arundel, who led the expedition; and he was first in the list of esquires named on the muster roll for the follow-up campaign of 1388. [2] You can find these entries on the online database by searching for the firstname Owen, or the surname Glyndouerdy. The surname as given derives from one of his estates at Glyndyfrdwy, Merioneth, and the English variant, ‘Glendower’ is a product of his appearance in Shakespeare’s Henry IV. [3] The database throws up three entries: two for 1387, one from a retinue listing and the other from the muster roll;


The muster roll for 1387 showing Oweyn Glyndouerdy, the eighth esquire listed in the retinue of Richard Fitzalan, earl of Arundel (TNA E101/40/33 m.1, Crown Copyright).


and one for 1388, from the muster roll.  The entry on the muster roll for 1388 is, however, crossed through, as it appears that Glyn Dŵr did not turn up for the expedition in that year. [4]    In 1387 he served in Arundel’s retinue alongside two other interesting figures from Welsh history: his brother Tudor ap Gruffudd, [5] and Goronwy ap Tudor. [6] The latter came to a particularly nasty end after being captured at the beginning of the revolt in September 1400. He took part in the opening attack of the rebellion at Ruthin, in north-east Wales, and the four quarters of his body were later sent to Bristol, Ludlow, Hereford and Chester as a warning to the Welsh and possibly as reassurance to the English. [7] This attack was part of a more general rising in North Wales however, in which Denbigh, Rhuddlan, Flint, Holt, Oswestry and Welshpool were attacked, together with further risings in north-west Wales, including Anglesey. This initial rising was suppressed by a swift three week campaign led by Henry IV and a general pardon for North Wales was issued in March 1401. [8]


Further details on Owain’s career and loyalties are contained in a note by Anthony Goodman: ‘Owain Glyn Dŵr before 1400’.[9]   Goodman states that the future rebel served in Richard II’s expedition to Scotland in 1385; indeed, Glyn Dŵr testified to this in his deposition to the court of chivalry in the following year. [10]   Goodman goes on to suggest that he served in the retinue of Sir Degory Sais on this campaign. [11] This is quite likely as Owain had been associated with Sir Degory in a military capacity since at least 1384. Owain and his brother can be found on two muster rolls dating from that year, which show that they were serving in Sais’ retinue in the garrison at Berwick upon Tweed. On the online database you can find Owain by searching for Glyndourdo and Glyndouido in the surname field, and his brother Tudor by searching for Glynderdo. [12]


That Owain and his brother should have served with the Flintshire knight, must come as no surprise. Not only was Sir Degory Sais (lit. The English) the only notable Welsh commander on the English side following the resumption of the conflict with France in 1369, but both his origins and experience placed him geographically close to Owain and his estates. Both his father and brother had served Edward, the Black Prince as sheriff in Flint and Sir Degory’s status within the Welsh community was equally significant. In common with much of the administrative elite of North Wales, he was descended from Ednyfed Fychan (d. 1246), the steward (W. distain) of Llywelyn ap Iorwerth. [13]


What can we say about Glyn Dŵr’s other early military connection, to Richard Fitz Alan, earl of Arundel? That this was a significant relationship is suggested not only by Glyn Dŵr’s appearance in Arundel’s retinue on successive campaigns in the late 1380s, but also by comments made in two fifteenth-century chronicles, where Owain is named as one of the earl’s esquires.[14]   Goodman notes that the relationship between Arundel and Glyn Dŵr was founded on a shared locality, for they were neighbouring landholders in the Marches near to the border towns of Chirk and Oswestry.  This regional connection probably accounts for Glyn Dŵr’s service in Arundel’s retinue and parallels the geographic link between Owain and Degory.  Goodman believes that Arundel retained the services of Owain from at least 1385, and that he was possibly linked to the earl before this. If so, it is likely that Glyn Dŵr was one of the earl’s chief supporters during the Appellant crisis of the late 1380s, when the earl took up arms against Richard II’s favourites. In fact, Goodman speculates that Owain may have indented to serve the earl in peace and war, and that he therefore probably joined with the earl in his defiance of the king at the battle of Radcot Bridge (December 1387).


So what drove Owain to rebel against the new regime of Henry IV, given that his relationship with the earl of Arundel (and perhaps with the earl’s son Thomas) may have made him a natural supporter of the Lancastrian usurper?  It appears that Glyn Dŵr did not prosper under the new regime; indeed, he seems to have lost out in a dispute with one of his neighbours in north-east Wales, Reginald Grey, lord of Ruthin.  Reginald, like Glyn Dŵr, had served under Arundel at sea in 1387.  These rivals, therefore, had served together in a common cause on at least one occasion. [15]   Grey was a strong supporter of Arundel and also of Henry IV; and it would seem that the new king favoured his support over that of the Welsh esquire. It has been suggested, moreover, that Grey deliberately caused the rift between Henry and Glyn Dŵr by not delivering to the latter a summons for service in Scotland, which the king had issued!


The significance of the summons is perhaps beyond the scope of this piece, but it should be noted that Owain was descended from two of the pre-conquest princely lines; that of Deheubarth in west Wales and of the northern part of Powys counted himself among the ranks of the Barwnaid (Welsh Barons). [16] Holding their lands as tenants in chief (W. Tir Pennaeth) was partly conditional upon military service, a responsibility which had survived from before the conquest of Wales and which was still clearly acknowledged by the English as late as 1345. [17] Whether this was a factor in his later rebellion or not, it is clear that Owain was abundantly aware of his position and that military leadership was something which he expected, and which he did not experience in English service.


This sketch of a military career, taken mainly from the information contained in the online database, is illuminating.  It demonstrates that during the 1380s Owain and his supporters: served as soldiers in an English garrison force on the Scottish borders; fought on the expedition led by Richard II to Scotland in 1385; and took part in the royal expedition led by the earl of Arundel in 1387. When, later, Owain led a rebellion against the English Crown, he may well have used tactics taught to him as a soldier in an English army. It was by a cruel twist of fate, therefore, that Glyn Dŵr’s former companions in arms later featured prominently in the bid to quench his rebellion.


Adrian R Bell, Adam Chapman and David Simpkin

[1] See R.R. Davies, The revolt of Owain Glyn Dŵr (Oxford, 1997) for details of Owain’s subsequent career.

[2] For details on these campaigns see Adrian R Bell, War and the Soldier in the Fourteenth Century (Boydell, 2004).

[3] For Owain’s estates, see J. E. Lloyd, Owen Glendower/Owain Glyn Dwr (Oxford, 1931), pp. 9-16.

[4] The following information on soldiers has been taken from the AHRC-funded ‘The Soldier in Later Medieval England Online Database’,, accessed 20/11/07.  For 1387 we will use the muster roll reference, E101/40/33 to denote service on campaign.  Owain Glyn Dŵr, 1387: E101/40/33 m 1, listed as Oweyn Glyndou’dy, esquire, 48th in retinue of earl of Arundel and the 8th listed esquire.  1388: E101/41/5 m 1, listed as Oweyn Glyndouerdy, esquire, 33rd in retinue of earl of Arundel and the 1st esquire listed.  However, this entry is crossed at the side and crossed out.

[5] Search database for first name Tudor.  Tudor ap Gruffudd, 1387: E101/40/33 m 1d, listed as Tudor de Glyndore, esquire, 93rdin retinue of earl of Arundel.  Not listed next to his brother Owain, but is listed next to Gronw ap Tudour, see following note.

[6] Search database for surname Tudor; in common with most Welshmen of this period this is a patronym rather than a fixed surname. Owain himself would be Owain ap Gruffydd Fychan (Owain son of Gruffydd the younger) for example.  Goronwy ap Tudor , 1387: E101/40/33 m 1d, listed as Grono ap Tudour, esquire, 94th in retinue of earl of Arundel.  Listed next to Tudor de Glyndore, see above note.

[7] Davies, Owain, p. 103.

[8] Calendar of Patent Rolls, 1399-1401, pp. 451-2.

[9] Anthony Goodman, ‘Owain Glyn Dŵr before 1400’, Welsh Historical Review, 5 (1970-71), p.67-70.

[10] The Controversy between Sir Richard Scrope and Sir Robert Grosvenor in the Court of Chivalry, A.D. MCCCLXXXV-MCCCXC, ed. N.H. Nicolas, 2 vols (London, 1832), i, p. 254 for Owain and p. 260 for Tudor.

[11] For the retinue of Sir Degory Seys, 1385: Lewis, ‘The Last Medieval Summons’, p. 17, listed as Seys, Degory, knight, retinue consisted of 9 soldiers, including 3 esquires and 6 archers.

[12] 1384, E101/39/39 m.1, listed as Owen Glyndourdo and Tedyr Glynderdo; E101/39/40 m.1, listed as Owen Glyndouido and Tedyr Glynderdo.

[13] A. D. Carr, ‘A Welsh Knight in the Hundred Years War: Sir Gregory Sais’ Transactions of the Honourable Society of Cymmrodorion (1977), pp. 40-53.

[14] Euliogium Historiarum sive Temporis, ed. F.S. Haydon, III (Rolls Series, 1863), p. 388; John Capgrave, Liber de Illustribus Henrics, ed. F.C. Hingeston (Rolls Series, 1858), p. 110.

[15] Search database for surname Grey.  Sir Reginald Grey, 1387: E101/40/33 m 1, listed as Sir Reginald de Grey, 9th in the retinue of earl of Arundel.

[16] A. D. Carr, ‘An Aristocracy in Decline: The Native Welsh Aristocracy after the Edwardian Conquest’ Welsh History Review 5(1970-1), pp. 103-129.

[17] J. G. Edwards (ed.) Calendar of Ancient Correspondence Concerning Wales (Cardiff, 1935), 245-7.