Skydemore is one of the most interesting of the Herefordshire MPs of our period, with a long career as a soldier and important royal official, complicated by an embarrassing family connexion with Owen Glendower and by an apparently pronounced tendency to lawlessness. His parentage is somewhat obscure, but his family lands certainly centred on Kentchurch, on the Herefordshire-Monmouthshire border, near the Black Mountains.
In October 1393 Skydemore received authority to act as an attorney for the prior of Llanthony Prima, who was then going to Ireland, and in September 1394 he agreed to do the same for Sir Thomas Brut. In 1395 he married Alice, daughter of Owen Glendower, then still a loyal subject. Skydemore entered the royal service, as a ‘King’s esquire’, by September 1396, and in November following he obtained custody of an outlaw’s lands in Dorston, Herefordshire. A year later he was accompanied to his first Parliament by one of Richard II’s household knights, (Sir) Thomas Clanvowe, who may have been his uncle; and it seems very likely that he was the John Skydemore who later, by November 1398, served the King’s half-brother John Holand, duke of Exeter, as a member of his council. Holand had been promoted to the dukedom for his part in the prosecution of the Lords Appellant in the Parliament of September 1397; and Skydemore’s appointment during the parliamentary recess to seize their confiscated estates, leaves us in no doubt that he too had supported royal policies, in the Commons.
Even so, Skydemore’s most advantageous early connexion, as it fell out, was with the duchy of Lancaster, which he was serving as deputy steward of Brecon by 1393. Doubtless this stood him in good stead following the accession of Henry IV, whose Scottish expedition he joined in the autumn of 1400. On 28 May 1401, again as a King’s esquire, he was granted an annuity of 20 marks from the Mortimer manor of Mansell Lacy (then in royal hands), and two days later he received for life the stewardship of Kidwelly, the most important duchy office in west Wales. From October following he was also in command of Carreg Cennen castle, with a garrison of ten archers. By this time Owen Glendower’s revolt had become a serious threat to the stability of all Wales. As Owen’s son-in-law, Skydemore must have been in a difficult position, but he clearly remained loyal to the Crown, even when, in July 1403, the rebel leader overran Carmarthenshire and took Kidwelly. John retired to Carreg Cennen, and in a letter from there, dated 5 July, he described how, on the previous evening, he had met Glendower at nearby Dryslwyn castle, in order to obtain a safe conduct out of the area for his wife and her mother (Glendower’s own daughter and wife), a request which he refused. Skydemore seems, however, to have successfully defended Carreg Cennen, for it was still in English hands in September following. Skydemore’s family connexion with Glendower (and the defection of his kinsman, Philip Skydemore, to the rebels) was probably the basis of an accusation made against him in August 1405, it being then alleged that he had been secretly acting as Owen’s receiver-general. John Oke, a convicted cattle thief, affirmed that he himself had delivered to Skydemore, at various places in Wales and the marches between March 1401 and April 1405, contributions from Glendower’s English sympathizers amounting to nearly £7,000. The charge, however, was plainly disbelieved by the government, and Skydemore continued to hold important offices in Wales as long as the revolt lasted.
Meanwhile, Skydemore retained connexions with Herefordshire, his home county. In 1405 he became a feoffee, on behalf of Sir John Chandos, of a moiety of the manors of Wellington and Fownhope. He first served as sheriff in 1409, and shortly after the end of his term he attended the county elections to the Parliament of 1410, but it was not until November 1413 that he joined the local commission of the peace. He represented the county in both Parliaments of 1414 after an absence of 17 years.
Soon after his return from France Sir John began feuding with neighbours of his in Herefordshire. Their quarrel concerned the ownership of the manor of Longford, near Leominster, which Thomas Walwyn II (d.1415) had bequeathed by will to his executors, but which was also claimed by Walwyn’s former employer, Joan, Lady Abergavenny, apparently in association with Skydemore. On 11 Nov. 1418, so it was alleged, the latter invaded the manor with a ‘grand multitude’ of Welshmen, armed with swords, bows and guns, ‘en manere de nouvell insurreccion’, so that Walwyn’s widow and other executors had to petition the chancellor for redress. Malcolm Walwyn, a younger son of Thomas, seems to have gone further, for in June 1419 he was bound over in £900 to do no harm to Skydemore and also to appear before the Council when required. The following month a royal writ placed Longford in the hands of John Merbury, pending the settlement of the dispute, but its final outcome is not known. At about the same time, Sir John was engaged in another quarrel, this time on behalf of his son, John, who had married Margaret, heiress of Sir Thomas Brut, and was claiming in her right her family’s lands in Herefordshire, in the face of opposition from Sir Thomas’s cousin, Robert Brut of Nottinghamshire. In 1422 the matter came before the King’s Council which, deferring its decision, temporarily entrusted the property to (once more) John Merbury; and in April 1422 and again in July 1423, Sir John was required to give sureties not to harm Brut. This dispute seems to have been eventually settled in favour of young Skydemore.
Meanwhile, Sir John had been present at the Herefordshire elections to the Parliaments of 1419, 1420, 1421 (May) and 1423. In April 1422 both he and his son secured letters of protection in preparation for joining Henry V’s army in France, but it seems likely that they returned to England when the King died at the end of August. And, evidently, Sir John himself now turned his attention once again to South Wales: in February 1423 he was confirmed in his captaincy of Carmarthen and other offices, and in June following he was also re-appointed to the duchy of Lancaster stewardship of Kidwelly. Then, between 1424 and 1426, he discharged the duties of sheriff of Carmarthenshire, and in August 1425 the grant of the important duchy of Lancaster office of steward and constable of Monmouth and the Three Castles extended his influence to south-east Wales as well. He continued to represent Herefordshire in the House of Commons, doing so in 1426 and 1429.
Skydemore’s advancement no doubt owed something to his connexion with the Protector of England, Humphrey, duke of Gloucester, for whom he stood surety when, in 1425, the duke was granted custody of the estates of the Mortimers during the minority of the heir, Richard, duke of York. He was Duke Humphrey’s co-feoffee of the much-disputed manor of ‘Maudelyns’ in Hertfordshire, in 1427, too, although whether he was ever formally retained by him does not appear. Skydemore had other influential links. For example, in 1430 (along with Joan, Lady Abergavenny) he became a feoffee of estates belonging to her son-in-law, James Butler, earl of Ormond, for the purpose of effecting an entail in favour of her grandsons. Meanwhile, he had continued to extend his influence in west Wales, by obtaining in 1429 the farm of Dryslwyn and in 1430 sharing the custody of the Cardiganshire lands of a minor with Gruffydd Don, his deputy steward of Kidwelly, and the husband of his daughter, Joan. In April 1431 he was appointed a deputy justiciar in South Wales (during the absence of James, Lord Audley, the chief justiciar), and by this time he was also acting as steward of Anne, the countess of Stafford’s lordship of Cantrefselyf.
In 1433, however, Skydemore’s career suffered a disastrous reverse. His father-in-law, Owen Glendower, had disappeared in 1415, and local tradition maintained that the defeated rebel spent his last years in hiding at Sir John’s manor of Kentchurch, where he died in about 1417. Whether this was true or not, Glendower’s lands (confiscated when he first revolted) had by this time passed to Henry V’s cousin, John Beaufort, earl of Somerset, who, captured at Baugé in 1421, was destined to remain in French hands until 1438. Apparently encouraged by Beaufort’s captivity, Sir John advanced his claim, jure uxoris, to Owen’s estates, and in the spring of 1430 he attempted to have Glendower’s outlawry reversed by the King’s bench, only for a petition to be presented to the Parliament of 1431 (presumably in the Beaufort interest) to confirm the attainder instead. Skydemore and his wife, nevertheless, laid an official claim to Glendower’s principal manors of Glyndyfrdwy and Sycharth before the sheriffs of Shropshire and Merioneth, and went on to commence an action for restitution in the court of common pleas. When he attended the Parliament of 1433, his plans were countered by Somerset’s brother, Edmund, who acting on behalf of his imprisoned kinsman, successfully petitioned for confirmation of possession of the Glendower estates and for the total rejection of Skydemore’s claims. In a second petition, moreover, he invoked against Sir John the statute of 1402, which had ruled that no Englishman married to a Welsh woman might hold any office in Wales or the marches. In consequence, on 8 Aug., before the end of the first session, Skydemore was stripped of his royal offices in the principality and four days later he lost his duchy of Lancaster posts as well, all of them being at once granted to Edmund Beaufort. Evidently, his links with the duke of Gloucester carried little weight now that Gloucester’s brother, Bedford, had returned from France.
Skydemore did not long survive his misfortune. As a shire knight in the Parliament of 1433, he was commissioned in December that year to apportion in Herefordshire the rebate of the subsidy granted by the Commons, and in May 1434, in the same capacity, he administered to the local gentry the oath generally required by Parliament against maintenance of those breaking the King’s peace. However, he died before December 1435, when one of his annuities passed to his son-in-law, Gruffydd Don.