Sheriff, Herefs. 18 Nov. 1386-7, 21 Oct. 1391-18 Oct. 1392.
Escheator, Herefs., Glos. and adjacent marches 30 Nov. 1388-15 Nov. 1389.
Commr. of inquiry, Herefs., Glos. Nov. 1388 (lands of Sir Simon Burley), Glos. May 1389 (wastes on estates of Caen abbey), Herefs. Feb. 1391 (wastes Lire abbey), Dec. 1391 (Burley lands); arrest (adherents of Walter Brut), Sept. 1393, Apr. 1394.
Thomas Oldcastle came of a family long established at Almeley, near Kington, though as a younger son he did not inherit its estates. By the end of 1382, however, he had made a valuable marriage, to Alice, heir of his neighbour, Sir John Pembridge. (Since she was also the widow of his cousin, Edmund de la Bere, an episcopal dispensation had to be obtained before the union could take place.) In her right Thomas was to enjoy possession of the manor of Eyton by Leominster, together with property at Burghill and elsewhere in Herefordshire, as well as the castle and manor of Boughrood and Trewern, near Builth in Radnorshire.
Oldcastle first appears in the records in 1378, when he stood surety at the Exchequer for Ralph Maylock, proctor of the alien abbot of Lire, then granted custody of the abbey’s English lands. His fellow mainpernor was the Hereford lawyer, Richard Nash, with whom he was apparently closely associated in various ways. Other friends of theirs among the Herefordshire gentry included (Sir) Kynard de la Bere, Philip Holgot and Thomas Walwyn II, and as all of these were retained at one time or another by the Mortimer earls of March, it seems likely that Oldcastle himself was already of that affinity. They formed an inseparable group: Nash and Holgot were, by 1385, trustees of Oldcastle’s Radnorshire lands, and in 1389 Oldcastle, Nash and Walwyn became co-feoffees of an estate at Lower Bullingham, Herefordshire. Holgot, Oldcastle and de la Bere, furthermore, took on the trusteeship of Nash’s property in and around Hereford, and in 1398 Holgot and Oldcastle acquired a similar interest in estates in Shropshire and Herefordshire on behalf of Isabel, widow of Sir John Eynesford.
Oldcastle was first returned to Parliament in 1390, in company with his kinsman, (Sir) Kynard de la Bere, and while at Westminster (on 26 Jan.) the two men acted as mainpernors for the grant to Sir Thomas Peytevyn of custody of Newcastle Emlyn, Carmarthen. A month later (but still during the parliamentary session) Oldcastle provided securities when de la Bere obtained a royal lease of an estate in Warwickshire. Later in the same year he was appointed an executor of the will of another relative, Simon Burley, canon of Hereford. In July 1392, together with de la Bere and Thomas Walwyn, Oldcastle received a royal licence to amortize certain lands in Canon Frome, Herefordshire, it being their intention to endow a chantry in the parish church. By the time of his second return to Parliament he had been made a member of the council of Bishop Trefnant of Hereford, and in 1394 he acted as an arbitrator in a dispute concerning episcopal rights in Malvern chase, Worcestershire. That summer he was appointed an attorney for his neighbour, Sir Robert Whitney I, a harbinger of the royal household, who was then going to Ireland to prepare in advance for the arrival of Richard II’s army, and in the following September he performed the same service for other Herefordshire gentlemen (including Thomas Clanvowe and Sir Walter Devereux) who were joining the same force. Nothing is known of his activities in England during the next two years, save that in 1396-7, if not before, he was employed by Thomas Beauchamp, earl of Warwick, as steward of the marcher lordship of Gower. In May 1397 he was ordered by privy seal letters to appear before the royal council, along with Thomas Walwyn and James Nash (son of his old friend Richard). The reason for their summons is unknown, but three weeks later Oldcastle and Nash were both nominated as attorneys for Sir John Cheyne, about to sail for Ireland. In the following July, nevertheless, Thomas himself (together with his nephew, (Sir) John Oldcastle, and Walwyn) received royal letters of protection covering their own absense in the province for one year in the retinue of Roger, earl of March, the King’s lieutenant. Walwyn and Thomas Oldcastle probably both returned to England with the earl in January 1398, and on 3 Apr. following they were among the 28 knights and esquires who were each ordered, on pain of £200, to appear before the King and his Council at Easter. Once again, the reason for the summons is not stated, but a significant number of those called had been associated with Richard’s enemies, the former Lords Appellant (in Oldcastle’s case the now banished earl of Warwick), and it seems likely that the King required tangible proof of their loyalty. Then, too, Richard’s growing suspicions of the motives of his heir presumptive, the earl of March, doubtless had something to do with it. Nothing further is heard of Oldcastle after this, and by January 1400 his widow had married John Merbury.
Oldcastle’s will is no longer extant, but in 1404 Merbury entered into a bond with his chief executor for the fulfilment of its provisions. Thomas’s son and heir, Richard (who later by marrying Elizabeth, widow of Richard Ruyhale, acquired property in Worcestershire), was to have his armour, and money was left for the marriages of his daughters, Wintelan (later wife of Sir Robert Whitney II), Isabel (later wife of Walter Hakluyt) and Joan. A further sum of £200, in the hands of Thomas Walwyn, was also to be devoted to his daughters’ upkeep. The remainder of the testator’s goods were to be divided between his widow and the children, save for £28, which was to be spent on masses for the souls of his parents and Sir John Clanvowe, and ten marks, which was to be distributed among the poor, privately and without ceremony. This disavowal of funeral pomp, reminiscent of the language used in the testaments of several lollard sympathizers, provides the only suggestion that Thomas was in any way involved in the heresy of his nephew, Sir John Oldcastle, and several of his other acquaintances. On the contrary, his earlier connexions with the Church give every impression of conventional orthodoxy. 1