Constituency Dates
Herefordshire 1437, 1442, 1453
Family and Education
2nd s. of Sir John Oldcastle† (d.1417) of Almeley, Herefs. and Cobham, Kent, by his 1st w. Katherine, da. of Richard ap Ievan (d.1416); bro. and h. of John Oldcastle (d.1420). m. by Jan. 1438, Elizabeth, da. of Sir Walter Devereux† of Weobley, Herefs., by Agnes (d.1436), da. and coh. of Thomas Crophill of Weobley; wid. of John Milborne (d.1436) of Tillington, s.p.
Offices Held

Attestor parlty. election, Herefs. 1450.

Commr. to distribute allowance on tax, Herefs. May 1437, Mar. 1442, June 1453; of inquiry July 1443 (lands of John Abrahall*), July 1446 (lands of Henry Beauchamp, duke of Warwick), Dec. 1453 (escapes of prisoners); gaol delivery, Hereford castle Feb. 1450, May 1452;1 C66/471, m. 22d; 475, m. 31d. to treat for loans, Herefs. Dec. 1452; of array Dec. 1459.

J.p. Herefs. 28 Nov. 1456–8.

Address
Main residences: Almeley; Tillington, Herefs.
biography text

On 14 Dec. 1417 Sir John Oldcastle, the heretic and traitor, was hanged and burnt at St. Giles’s Fields, his estates having already been forfeited to the Crown.2 The Commons 1386-1421, iii. 866-9. He left two sons, John and Henry, to repair the family’s ruined fortunes and restore its honour. John died within a few years of his father, and Henry succeeded him in what little remained to the family. This consisted of a small estate, the inheritance of their maternal grandmother, at Bledlow, Princess Risborough and Aston Sandford in Buckinghamshire, valued at a paltry six marks p.a. in 1416.3 CFR, xiv. 334; CIPM, xx. 674; CCR, 1413-19, p. 396. Our MP’s future depended on securing restoration of the Oldcastle patrimony in Herefordshire, and, given the rarity of permanent forfeitures at this date, his hopes of success were good. They were, however, slow to be realized, perhaps, in part at least, because of his youth.4 His er. bro. was born c.1397: CIPM, xx. 674. He does not appear in records until 28 May 1427, when he sued out letters of protection as about to proceed to Ireland in the retinue of John, Lord Grey of Codnor, the newly-appointed royal lieutenant there. He may have been recommended to Grey’s service by his Herefordshire neighbour, Sir Roland Lenthall, the husband of Grey’s sister, Lucy, with whom his association was, judging by later evidence, close.5 CPR, 1422-9, p. 409. Much later, Lenthall named our MP as one of his executors: CP40/780, rot. 305d.

Oldcastle’s indirect service to the Crown through the King’s lieutenant in Ireland was probably intended to demonstrate his loyalty, and in 1429 he petitioned the King and council for restoration of his father’s forfeited estates. Making his case on the legal immunity against forfeiture enjoyed by entailed lands, he claimed that when his father was indicted for treason in 1414 he held the manor of Almeley, near the Welsh border, with other scattered holdings (principally in Hereford), in fee tail and not, as an inquisition held in 1418 had found, in fee simple. The Crown responded, on 14 July 1429, by issuing a commission of inquiry to various members of the local gentry, headed by Sir Robert Whitney*. The commissioners were slow to act, not sitting until the following April, but their findings gave Oldcastle nothing to complain of, wholly vindicating his title. Perhaps this proves no more than that the facts cited in the petition were true; even if they were not, however, the jurors were probably inclined to put the interests of one of their own above those of the Crown. It may also be relevant here that Whitney was the husband of Henry’s cousin and potential heir, Wintelan, daughter of Thomas Oldcastle†, and thus had a vested interest in the restoration.6 CPR, 1422-9, pp. 546-8; CIMisc. viii. 36. Whether suspicion about the validity of the findings prompted further delay cannot be known, but the government resisted acting upon them. Not until 2 July 1432, after a further jury verdict in his favour, did the Crown finally accept the fact of the entail and formally restore Oldcastle to his own.7 CPR, 1429-36, pp. 177-8; Feudal Aids, ii. 416; KB27/682, rex rot. 28; E159/209, brevia Mich. rot. 6d. None the less, these formalities discharged, he came into an estate sufficient to place him among the better-endowed gentry of his native shire. Only a small part of the Oldcastle lands, those that had not been entailed, remained in royal hands, but in 1444 he was able to secure their restoration by royal grant.8 CPR, 1441-6, p. 249.

Oldcastle was quick to make his presence felt in the county, falling into dispute with his near-neighbours, the de la Beres of Kinnersley. The cause of the quarrel is lost, but it may be that Sir Richard de la Bere was unhappy to see his neighbours survive their treason.9 He had been named to the comm. of inquiry of 1429, but had not sat: CIMisc. viii. 36. At all events, the quarrel, although brief, was violent and serious. On 21 Sept. 1432 Oldcastle and his adherents allegedly broke into one of Sir Richard’s houses at Kinnersley and assaulted his servants. Since Sir Richard claimed as much as £1,000 in damages for this offence, it must have stood outside the ordinary run of trespasses endemic amongst landed society, and the dispute soon escalated. A year later, on 20 Sept. 1433, Sir Richard and his son, Kynard*, allegedly led an attack upon our MP at the same place, imprisoning him for a day and a night, and, more seriously, killing one of his men.10 KB27/692, rots. 3d, 75; 694, rot. 66. The death, probably a manslaughter arising out of an armed clash, provided Oldcastle with a chance to discomfort his enemies. If the testimony of the de la Beres is to be believed, he resorted to subterfuge to do so, prevailing upon one of the county coroners, Richard Gambon, to act fraudulently. After an initial attempt to secure an indictment at the scene of the murder had failed, Gambon took another, empanelling a jury, described in one Chancery petition as adherents of Sir John Oldcastle, and in another as ‘Walshmen and other nosed for lollardery’. The result was the indictment for murder of several of the servants of the de la Beres, and that of Sir Richard and his wife, Elizabeth, as accessories. Oldcastle then added to the pressure, demanding damages of £400 against the de la Beres for the events of 20 Sept.11 C1/11/171; KB27/691, rot. 6; 692, rot. 3d; 693, rex rot. 4d. This, however, appears to have marked the end of the active prosecution of the suit. The suits for damages were allowed to lapse, and on 5 Mar. 1436 those indicted at the contentious inquest were acquitted.12 KB27/694, rot. 66. Indeed, by 1440 Oldcastle and Kynard de la Bere had so resolved their differences as to co-operate in an act of lawlessness. If the complaint to the chancellor is to be believed, they joined together at the head of a large body of armed men, broke into a house in Gloucester and took goods worth 100 marks belonging to Thomas Woodward, one of the Gloucestershire tax collectors, but there is no evidence to give this alleged offence a context.13 C1/12/1; C244/30/139.

By this date Oldcastle had added to his estates by marriage to the widow of his neighbour, John Milborne. The marriage had taken place by 10 Jan. 1438, when the couple are alleged to have abducted the widow’s baby son, Simon Milborne (b.1435), from the custody of her nephew, Walter Devereux I*, who unsuccessfully claimed the wardship as overlord of some 40 acres in Tillington.14 CP40/709, rot. 308. Elizabeth was a good match, for she brought from her first marriage an interest in the Herefordshire manors of Tillington and Munsley and in addition property in Gloucestershire and Lincolnshire.15 C139/81/31; CCR, 1435-41, p. 75; CP40/727, rot. 588. With the lands he held in her right, Oldcastle became a figure of greater account. In the subsidy returns of 1450-1 he was assessed on an annual income of £40, making him one of the richest of those taxed, and it curious that he had not been among the men distrained to take up knighthood in 1439. None the less, with his new resources came a larger part in county affairs. His first election to Parliament on 5 Jan. 1437 may post-date his marriage; and a further return to Parliament came on 30 Dec. 1441.16 E179/117/64; C219/15/1, 2.

Soon after, Oldcastle was drawn into another controversy. In the autumn of 1443 he sat with Thomas Bromwich* as royal commissioners to inquire into the estates of John Abrahall, his fellow Herefordshire MP in the Parliaments of 1437 and 1442. The findings of that inquiry – that Abrahall had died seised inter alia of the manor of Eaton Tregoes – threatened the title of two other leading gentry of the county, Thomas Fitzharry* and his brother, Richard.17 CPR, 1441-6, p. 201; CIPM, xxvi. 74; KB27/734, rot. 36. In a petition presented to the chancellor in the following January, our MP gave a lurid account of the Fitzharrys’ outraged reaction. Having melodramatically warned Oldcastle that men would die if the inquiry’s findings were returned into Chancery, they assaulted him when he insisted the inquiry would be returned; then, after they had been indicted before the county j.p.s for this assault, they threatened that both the inquiry and indicting jurors would be cut up, ‘as smalle as haukes mete’, a threat that was very much current when the petition was presented.18 E28/71/54. The indictment was taken on 13 Jan. 1444, and the petition was presented before the end of that month: KB9/245/113. There is more than a coincidental correspondence of wording between the two documents, and there is reason to be sceptical about the allegations against the Fitzharrys. Suspiciously, it was Oldcastle, although not then a j.p. himself, who delivered the indictment into King’s bench. What interest Oldcastle had in the matter, beyond that of royal commissioner, is not known, but his role was not a disinterested one. In Trinity term 1444 Richard ap Harry claimed that, before the issue of the commission, he had retained our MP at a fee of 40s. to be of his counsel in the matter of the manor, only to have his counsellor betray to Abrahall’s widow a possible flaw in his title. Moreover, another inquiry soon found that the Fitzharrys had reasonable grounds for their resentment, returning that the findings of Oldcastle’s inquisition were untrue.19 CP40/734, rot. 472; KB27/734, rot. 36. All in all, it is not an episode from which our MP emerges with credit.

Soon afterwards, Oldcastle was involved in a much less well documented quarrel, but here he appears more as victim than aggressor. In a petition to the chancellor, probably to be dated to the mid 1440s, he complained that Walter Hakluyt, and his son, Richard, had assembled 1,000 men to prevent him attending the manorial court of John Talbot, earl of Shrewsbury, at Archenfield, where he had an assize of novel disseisin pending against Richard and Richard’s wife, Maud. Forewarned of this hostile gathering, he had sent an attorney to the court to excuse his absence, but the attorney had been assaulted by the Hakluyts, and now no juror dared appear to decide on the matter. No evidence survives to give this petition a context; it was, however, a dispute between kin. Walter was the husband of our MP’s cousin, Isabel, daughter of Thomas Oldcastle, and after our MP’s death Henry Hakluyt, perhaps Richard’s son, made claim to the un-entailed part of the Oldcastle inheritance.20 C1/16/112; 28/22.

The later part of Oldcastle’s career can only be very partially reconstructed. He was one of 21 of the county’s gentry who benefited from the liberality of the Beauchamps – by June 1446 he was in receipt of an annuity of ten marks – but the premature death of Henry, duke of Warwick, in that month, meant that the connexion had no long term significance. It is, however, possible that he had employed the influence of the young Beauchamp, a friend of the King, in securing the grant in fee of the un-entailed part of the Oldcastle inheritance made to him on 18 Feb. 1444.21 E368/220, rot. 122d; CPR, 1441-6, p. 249. On 20 June 1447 he sued out a pardon, described as ‘of Tillington’; on 24 Oct. 1450 he was named as an attestor to the county election for the only time in his career; and at the next election, on 10 Mar. 1453, he was elected by attestors including his stepson, Simon Milborne.22 C67/39, m. 41; C219/16/1, 2.

In the crisis of the late 1450s Oldcastle’s political sympathies seem to have lain with the Lancastrians. He was certainly, despite his wife’s kinship with the leading Yorkist family of Devereux, no friend of the strong Yorkist faction in his native county. His wife’s great-nephew, Walter Devereux II*, having been indicted in the spring of 1457 for, among other things, hanging six of the citizens of Hereford, claimed damages of £1,000 against him for maintaining an appeal sued by the widow of one of the victims; and actions brought by Oldcastle himself, on unrelated matters, against allies of Devereux, argue to the same purpose. In Michaelmas term 1457 he sued Thomas Monnington† for close-breaking at Almeley, and in Easter term 1460 he brought a bill of debt against Devereux II’s brother-in-law, James Baskerville†.23 KB146/6/36/1; 38/3; KB27/789, rot. 40. What else is known of his career in the late 1450s is consistent, or at least not inconsistent, with adherence to the Lancastrian interest. He was belatedly added to the commission of the peace in November 1456, when the Lancastrians were in control of government, and his exclusion two years later is not to be interpreted in political terms. He was one of five removals, among whom were two prominent royalists, (Sir) William Catesby* and Thomas Acton*. Nor is there anything to be read into the fact that he sued out general pardons in 1456 and 1458, nor into his indictment before the royal commissioners of the spring of 1457 for having illegally given livery to four tradesman of Hereford in August 1455. Even though the indictments overwhelmingly concerned the offences of the Yorkists, several of the county’s gentry, including Lancastrian supporters, were indicted for illicit retaining. Further, Oldcastle’s Lancastrian loyalties are confirmed by his appointment to the commission of array issued at the close of the Coventry Parliament.24 C67/41, m. 2; 42, m. 22; KB27/784, rex rot. 34d; CPR, 1452-61, pp. 559, 666-7.

It must, however, remain an open question whether these Lancastrian sympathies were translated into active support during the civil war of 1459-61. Since Oldcastle disappears from the records after Easter term 1460, when he brought his bill against Baskerville, it is possible that he met his death at the battle of Mortimer’s Cross, fought in Herefordshire in February 1461. Yet it is more likely that he died peacefully. He was prominent enough for his death in battle to have left a trace on the records, particularly as the antiquary, William Worcestre, made a list, as early as 1479, of the Herefordshire notables who fell at Mortimer’s Cross. At all events, there is no reason to doubt the statement of a later antiquary, John Leland, that Oldcastle was buried in the Dominican friary at Hereford, a popular choice for burial among the county gentry.25 William of Worcestre, Itins. ed. Harvey, 202-5; J. Leland, Itin. ed. Toulmin Smith, ii. 67.

Oldcastle left no children. His common-law heir was John Norris, infant son of John Norris* by Eleanor, daughter and heir of our MP’s sister, Maud (d.1457), and Roger Clitheroe of Ash-next-Sandwich in Kent. Our MP, however, seems to have had no connexion with her family, and to have felt free to adopt his stepson, Simon Milborne, as his heir. That he did so is implied by two later conveyances: in 1469 the manor of King’s Caple (probably the lands our MP had been granted by the Crown in 1444, in other words, the un-entailed part of the Oldcastle estate) was settled upon Milborne in fee; and on 12 Mar. 1485 John Norris released to Milborne all his right in the manor of Almeley and the other entailed lands restored in 1432.26 CP25(1)/83/57/8; CP40/892, cart. rot. 1. There were, however, rival accounts of our MP’s intentions. In a petition to the chancellor in the early 1460s, Thomas Bromwich claimed that Oldcastle had instructed his feoffees, headed by Milborne, to convey the manor of King’s Caple to him or to our MP’s cousin, Eustace Whitney, or to both of them, on the payment of 80 marks; that, although Whitney was not interested in purchasing the manor, he was ready to do so; but that the feoffees refused to relinquish their estate. Another cousin of our MP, Henry Hakluyt, told a different story, again in a petition to the chancellor: he asserted that Oldcastle had told his feoffees, among whom was Bromwich, to convey the manor to Hakluyt in fee. These complaints are probably to be seen as mainifestations of jealousy at Milborne’s adoption.27 C1/28/22; 29/141.

Author
Alternative Surnames
Oldecastell
Notes
  • 1. C66/471, m. 22d; 475, m. 31d.
  • 2. The Commons 1386-1421, iii. 866-9.
  • 3. CFR, xiv. 334; CIPM, xx. 674; CCR, 1413-19, p. 396.
  • 4. His er. bro. was born c.1397: CIPM, xx. 674.
  • 5. CPR, 1422-9, p. 409. Much later, Lenthall named our MP as one of his executors: CP40/780, rot. 305d.
  • 6. CPR, 1422-9, pp. 546-8; CIMisc. viii. 36.
  • 7. CPR, 1429-36, pp. 177-8; Feudal Aids, ii. 416; KB27/682, rex rot. 28; E159/209, brevia Mich. rot. 6d.
  • 8. CPR, 1441-6, p. 249.
  • 9. He had been named to the comm. of inquiry of 1429, but had not sat: CIMisc. viii. 36.
  • 10. KB27/692, rots. 3d, 75; 694, rot. 66.
  • 11. C1/11/171; KB27/691, rot. 6; 692, rot. 3d; 693, rex rot. 4d.
  • 12. KB27/694, rot. 66.
  • 13. C1/12/1; C244/30/139.
  • 14. CP40/709, rot. 308.
  • 15. C139/81/31; CCR, 1435-41, p. 75; CP40/727, rot. 588.
  • 16. E179/117/64; C219/15/1, 2.
  • 17. CPR, 1441-6, p. 201; CIPM, xxvi. 74; KB27/734, rot. 36.
  • 18. E28/71/54. The indictment was taken on 13 Jan. 1444, and the petition was presented before the end of that month: KB9/245/113. There is more than a coincidental correspondence of wording between the two documents, and there is reason to be sceptical about the allegations against the Fitzharrys. Suspiciously, it was Oldcastle, although not then a j.p. himself, who delivered the indictment into King’s bench.
  • 19. CP40/734, rot. 472; KB27/734, rot. 36.
  • 20. C1/16/112; 28/22.
  • 21. E368/220, rot. 122d; CPR, 1441-6, p. 249.
  • 22. C67/39, m. 41; C219/16/1, 2.
  • 23. KB146/6/36/1; 38/3; KB27/789, rot. 40.
  • 24. C67/41, m. 2; 42, m. 22; KB27/784, rex rot. 34d; CPR, 1452-61, pp. 559, 666-7.
  • 25. William of Worcestre, Itins. ed. Harvey, 202-5; J. Leland, Itin. ed. Toulmin Smith, ii. 67.
  • 26. CP25(1)/83/57/8; CP40/892, cart. rot. 1.
  • 27. C1/28/22; 29/141.