Please enable JavaScript for this site to run correctly.



‘Anno 1403. In the fourth year of King Henry, in the month of May, Sir Walter Betterley, Steward of Ulster, a right valiant knight, was slain, and to the number of thirty other with him’. [1]


Sir Walter Bitterley appears only once in the current pilot version of the ‘Soldier in later medieval England’ database. This was in 1388, when he took part in the earl of Arundel’s expedition to France as an esquire in Sir John Darundell’s retinue. [2] By 27 January 1390, he was an esquire in the king’s household, and was granted lands, tenements and pastures in Cleeton and Farlow, Shropshire, for life, worth £10 per annum. His ancestors had apparently held these lands before. [3] In the following year, Walter was granted protection for one year to serve with the earl of Nottingham in the Calais garrison. [4]


By 26 April 1392 Walter was back at Westminster, where we find him obtaining a pardon for Richard Marsshall of Thornton, who had killed a man two years previously. On 13 December 1393, Walter did the same for John Jekkes of Pockthorpe, a Norwich tanner. [5] On 16 January 1394, together with Ralph Repyngton, clerk, Walter obtained temporary possession of the lands of Sir Nicholas Styuccle, together with the marriage of his heir, until the latter reached his majority. [6]


Walter subsequently participated in Richard II’s first expedition to Ireland, and was paid wages for himself and three archers from 7 September 1394 to 21 April 1395. [7] Along with several others, he was knighted by the king on the morning of 26 October 1394, prior to the English army launching an attack on Art MacMurrough’s stronghold in the “wood of Garrowkill”. [8] The Irish chieftain’s house was eventually taken and burnt in the presence of the king, but MacMurrough himself managed to escape. He later submitted to the earl of Nottingham, and on 7 January 1395, ‘in a field between Tullow and Newcastle’, acknowledged himself to be the king’s liege man. An indenture to this effect was witnessed by ‘Waltero Bytterly militibus’. [9] On 19 July 1395, at Leeds Castle, Sir Walter was retained for life by the king, who granted him 40 marks a year, payable from the Exchequer. [10]


Four years later, Sir Walter returned to Ireland with the king’s second expedition. Letters of protection for one year were issued at Westminster on 26 March 1399 and again on 5 April. [11] However, by July 1399, Sir Walter was back in England, leading a small retinue in the duke of York’s army, which had been raised to oppose Henry Bolingbroke’s return from exile. [12] York’s efforts were ineffective, and Sir Walter was subsequently arrested by the Lancastrian forces at Berkeley. [13] Bolingbroke claimed the throne as Henry IV and like many other knights of the royal household, Sir Walter soon became reconciled to the new regime. On 6 February 1400, the new king granted him £40 for life from the revenues of Shropshire, and on 18 March, Sir Walter, his men and his possessions, were granted letters of protection until midsummer, being ‘occupied on divers businesses of the king within the realm’. [14]   Later in the same year Sir Walter took part in the Henry’s unsuccessful expedition into Scotland. [15]


On 30 June 1401, we find Sir Walter engaged in a heated dispute with Sir John Colvylle of Dale over the right to bear arms on a field or, a fess, three torteaux in chief gules. He was represented in the Court of Chivalry by the clerical chronicler, Adam of Usk, who tells us that possession was refused to both men on that day. [16] Colville also participated in Richard II’s 1394 expedition to Ireland and in Henry IV’s 1400 expedition to Scotland. [17] He was also retained for life as a king’s knight on 4 December 1399. [18] What was the ultimate result of the dispute is not known. The Bitterleys seem to have borne the arms in question since the reign of Henry IIIthe Colvilles, no earlier than that of Edward II. [19]


When Henry IV sent his son Thomas of Lancaster to Ireland as lord lieutenant, Sir Walter went with him. Letters of protection were issued on 8 September 1401 for one year. [20] On 28 April 1402, Sir Walter was appointed deputy to Sir Edward Perrers, marshal of the army in Ireland, and on 8 November he was made seneschal of the liberty of Ulster, which was then in the king’s hands due to the minority of Edmund Mortimer, earl of March and Ulster. On the following day, Sir Walter was appointed Thomas’s deputy in Ulster, not only in the lands of the liberty, but also those of the church too. [21] Walter’s new position was no sinecure. Thanks to continual attacks by the Irish, the earldom of Ulster had contracted significantly since the Scottish invasions in the second decade of the fourteenth century. Carrickfergus, the liberty’s chief seat, subsequently became a frontier post, and Dublin could only be reached by sea. The Anglo-Norman castle was impressive, but the neighbouring town was protected only by an earthen rampart. [22]


On 20 February 1403, Sir Walter was named as one of Janico Dartasso’s attorneys in Ulster for one year. The other attorney was Thomas Thyngden, the liberty’s chancellor and treasurer. [23] The reason for Dartasso’s presence in Ulster in early 1403 is not clear, but he soon became heavily involved in the region, right up until the end of Mortimer’s minority. [24] Dartasso’s military experience was probably sorely missed, for we next hear of the death of Sir Walter, who was slain in May 1403, together with thirty other men. [25] One John Liverpool replaced him as seneschal of Ulster on 29 June 1403. Liverpool was also appointed the lord lieutenant’s deputy on the following day. [26]


Henry Marlborough, the contemporary Dublin-based chronicler, gives us no details of how, where or why Sir Walter’s death occurred, but this event can probably be linked with the destruction of Carrickfergus. [27] On 2 July 1403, following supplications from the mayor and three other burgesses, the town was excused its annual customs payment of one hundred shillings, so that it could be rebuilt, having been burnt recently by the ‘king’s enemies’. [28] Exactly who were the ‘king’s enemies’ is not clear. Sir Walter’s appointment as deputy six months previously, mentions ‘Scots and other enemies of the out-isles’, ‘English and Irish rebels’. The same combination, less the ‘English rebels’, is mentioned again in 1404 with regards to a subsidy granted by the Great Council held at Castledermot. [29] However, Marlborough also informs us that one Hugh Mac Giolla Mhuire, an Irishman, destroyed the Franciscan church in Carrickfergus prior to 1408, the year in which he was trapped and killed in the very same building by members of the Savage family. The latter were seeking revenge for deaths of their kinsmen, Patrick and his brother Richard, who were murdered in 1404 by one Adam Mac Giolla Mhuire after a ransom of two thousand marks had been paid. Patrick Savage, who previously served as seneschal of Ulster, may well have fallen into the Mac Giolla Mhuires’ hands as a result of Sir Walter’s defeat and death in the previous year. Richard was apparently acting as a pledge for his brother’s ransom. [30]


It is also perhaps noteworthy that an indenture was signed on 5 July 1403, apparently in Carrickfergus itself, in which John of the Isles, ‘lord of Dunevage and of the Glynnys’, acknowledged himself to be the king’s liege man and rendered service for his wife’s lands in the Glens of Antrim. Although John may have sacked Carrickfergus earlier in the year, it was probably not in his best interest to do so. John’s patrimony lay in the Western Isles of Scotland, and both he and his brother Donald, Lord of the Isles, considered themselves independent of the Scottish throne. They were certainly viewed as potential allies by the English king. John was already linked to the influential Savage family, through the marriage of his sister Christina, and he later entered into a marriage alliance with Janico Dartasso, through the double marriage of two of their children. By signing the 1403 indenture, John may well have been formalising his relationship with the English in Ireland, as well as seeking allies to defend his Ulster lands from his wife’s gaelicised Bisset relatives, the MacEoins. The latter would have considered female succession to their family’s patrimony unacceptable. [31]


However, whatever remedial actions were undertaken by John Liverpool in the summer of 1403, the English settlements in Ulster were under attack again in following year by ‘Mac Aonghusa, Mac Giolla Mhuire, and by Scotsmen’. [32] This resulted in James, earl of Ormond leading a punitive expedition to the north, paid for by extraordinary subsidies.  His success on this occasion was remembered by the inhabitants of Ardglass and Downpatrick with much affection a generation later. Much attention has been devoted to the 1404 crisis by Irish historians, but the fact that it was probably precipitated by the killing of Sir Walter Bitterley in the year before seems to have been overlooked. Indeed, Sir Walter is never mentioned. [33]


At the time of his death, Sir Walter owed the London goldsmith, Thomas Lamport, forty marks. Steps were taken on 13 July 1403 to recover this sum via the sheriff of Shropshire. The debt appears to have been a long-standing one, dating from 1398. [34]


We will perhaps never know why Marlborough gave Sir Walter the epitaph of ‘a right valiant knight’. His compliments are few and far between, but in this particular case he clearly thought it appropriate. However, from the evidence above, we can deduce that Sir Walter was a member of an old Shropshire family who tried to make good through royal service, the fees for which were probably his principal means of support. This factor alone, perhaps, explains his ready acceptance of regime change, following Richard II’s deposition in 1399. Indeed, his initial opposition during Bolingbroke’s invasion doesn’t seem to have been held against him. He was quickly rewarded by the new king and entrusted with important business. It also led to Sir Walter seeking his fortune with Thomas of Lancaster in the harsh environment of early fifteenth century Ireland. He ultimately failed, losing his life in the process, but the king’s council in Ireland clearly thought him capable of holding an important post in what was undoubtedly a perilous part of the country. Although their judgement was probably faulty, Marlborough’s epitaph suggests that Sir Walter’s reputation was redeemed perhaps through his valiant conduct in his final battle at Carrickfergus.


Randolph Jones

[1] The Chronicle of Ireland, by Henry Marleburrough; continued from the collection of Doctor Meredith Hanmer, in the Year 1571. (Dublin, 1809), p. 18.

[2] The National Archives (TNA) E 101/41/5 m.6, from the AHRC-funded database, date of access 17 December 2007. On this occasion, his surname appears as ‘Bytterley’ There are many variant spellings in the contemporary sources.  The other references in this article provided by the Soldier in Later Medieval England Team (Soldier Team) will be rolled into the online database in due course.

[3] Calendar of Patent Rolls 1388-92 (London, 1902), p. 182. Sir Walter appears to have been descended from one Stephen de Butterley. See Rev. R. W. Eyton’s, Antiquities of Shropshire, Vol. IV (London, 1857), pp. 267-370, for the manorial history of Bitterley down to 1324.

[4] TNA C 76/76 m. 14. I am indebted to the Soldier Team for providing this reference.

[5] CPR 1391-96 (London, 1905), pp. 47, 348.

[6] Calendar of Fine Rolls 1391-99 (London, 1929), p. 107.

[7] TNA E 101/402/20 f. 36r (Soldier Team).

[8] Edmund Curtis. ‘Unpublished letters from Richard II in Ireland 1394-5’, in Proceedings of the Royal Irish Academy, Vol. XXXVII, Part C (1927), p. 291.

[9] Edmund Curtis, Richard II in Ireland and submissions of Irish Chiefs (Oxford 1927), p. 85.

[10] CPR 1391-96 (London, 1905), p. 615.

[11] CPR 1396-99 (London, 1903), p. 514. Rymer, T. Foedera, Conventiones, Litterae etc., ed. A. Clarke, F. Holbrooke and J. Caley (4 vols, London, 1816-69), vol. 3, part 4, p. 160.

[12] He was given a prest of 25 marks on 12 July 1399: TNA, E 403/562, m. 15. He was a knight captain, but the number of men with him is not stated (Soldier Team).

[13] Douglas Biggs. Three armies in Britain. The Irish campaign of Richard II and the usurpation of Henry IV, 1397-99 (Leiden-Boston, 2006), p. 146.

[14] CPR 1399-1401 (London, 1903), pp. 195, 239.

[15] TNA E 101/42/35 (Soldier Team).

[16] Chris Given-Wilson, ed. and trans. The Chronicle of Adam Usk 1377-1421 (Oxford, 1997), pp. 133-5.

[17] Colville: Ireland 1394/5, TNA E 101/402/20 f. 35; Scotland 1400, TNA E 101/42/35 (Soldier Team).

[18] CPR 1399-1401, p. 77; Chris Given-Wilson, The Royal Household and the Kings Affinity (London, 1986), p. 288.

[19] J. Foster. Some Feudal Coats of Arms from Heraldic Rolls 1298-1418 (Bristol, 1984), pp. 43, 59.

[20] CPR 1399-1401, p. 511.

[21] Tresham, E. Rotulorum patentium et clausorum cancellariae Hiberniae (Dublin, 1828), 163, no. 137; 172, no. 16; 172, no. 21.

[22] Avril Thomas, The Walled Towns of Ireland, vol. 2 (Dublin, 1992), pp. 37-43.

[23] Rot. Pat. Claus. Hib., 174, no. 91; 160, no. 5.

[24] For Dartasso’s career see Simon Walker, ‘Janico Dartasso: Chivalry, Nationality and the Man-at-Arms’, History, 84, 273 (Jan., 1999).

[25] The Chronicle of Ireland, by Henry Marleburrough, p. 18.

[26] Rot. Pat. Claus. Hib., 167b, no. 73; 170b. no. 67; 170b, no 68.

[27] For details of Henry Marlborough’s career, see: New Oxford Dictionary of National Biography (Oxford 2004), Vol. 36, pp. 717-8.

[28] Rot. Pat. Claus. Hib., 170 b, no. 74. Samuel McSkimin: The History and Antiquities of the County of the Town of Carrickfergus (New Edition, Belfast 1909), p. 18.

[29] National Library of Ireland MS 4: Harris’s Collectanea de rebus Hibernicus Vol. 4, f. 114. Rot. Pat. Claus. Hib., 178, no. 77(c).

[30] The Chronicle of Ireland, by Henry Marleburrough, pp. 19, 20 and 23. G. F. Savage-Armstrong. A Genealogical History of the Savage Family in Ulster being a revision and enlargement of certain chapters of ‘The Savages of the Ards’ (London, 1906), pp. 53-55. Patrick Savage was seneschal of Ulster in 22 Richard II and 1 Henry IV. See National Library of Ireland MS 761, f. 297: Betham’s extracts from the pipe rolls of the Irish exchequer.

[31] National Archives of Ireland. 2/446/6 (1a 49 147), Ferguson MSS, Repertory to Memoranda Rolls Henry IV – Henry V. p. 54. K. W. Nicholls, ‘Anglo-French Ireland and After’, in Peritia, Journal of Medieval Academy of Ireland (1982), Vol. 1 p. 387-8. Simon Kingston, Ulster and the Isles in the Fifteenth Century. The lordship of the Clann Domhnaill of Antrim (Dublin 2004), p.166.

[32] S. O’hInnse, Miscellaneous Irish Annals 1114-1437 (Dublin, 1947), p. 174. The Scotsmen were probably gallowglass in the service of various Irish chieftains.

[33] H. G. Richardson and G. O. Sayles, The Irish Parliament in the Middle Ages (Philadelphia, 1952), pp. 155-6 A. J. Otway-Ruthven, A History of Medieval Ireland (New York 1980) p. 344. K. Simms ”The King’s Friend’: O’Neill, the Crown and the Earldom of Ulster’ in James Lydon (ed.) England and Ireland in the Latter Middle Ages (Blackrock, 1981), p. 219.  A. Cosgrove. ‘Ireland beyond the Pale 1399-1460’ in A Cosgrove (ed.), A new history of Ireland (Oxford, 1993), Vol. II, p. 574. Kingston, Ulster and the Isles, p. 47.

[34] TNA C 241/193.