Although Skydemore never achieved the wide-ranging influence of his father, he was, as one of the leaders of a strong Lancastrian faction in Herefordshire in the 1450s, an important figure. His early career is obscure for it cannot be distinguished from that of his elder brother and namesake. The latter died relatively young: on 21 Oct. 1418 the administration of his goods was granted to his father.
Aside from this foray abroad (or perhaps forays if he rather than his brother served under Bourgchier), Skydemore’s early career was dominated by his efforts to make good his claim to his maternal inheritance in Herefordshire. His title was contested by his maternal great-uncle, an elderly King’s esquire, Robert Brut of Thorney (Nottinghamshire). In a petition presented to the chancellor late in the reign of Henry V Brut claimed that his paternal grandfather, Sir Thomas Brut, had entailed the manors of Grove, Chanstone (in Vowchurch), Tretire and Westhide and other Herefordshire lands in tail-male, and that he had been seised under that entail until the previous 24 Nov. (probably 1421) when Sir John Skydemore, our MP and John Weston†, a lawyer, had disseised him. On 12 Feb. 1422, as a result of this petition, the parties appeared before the royal council, and the lands were committed to an important local figure, John Merbury*, pending a conciliar decision on ownership. In the meantime, on the following 6 Apr. our MP’s father found surety of the peace in £500 to Brut.
In the early 1420s Skydemore and other members of his family became involved in the violent campaign conducted by John Abrahall* against John, Lord Talbot. He was among those indicted, before the Herefordshire j.p.s headed by Talbot himself, for having on 26 Mar. 1423 brought 1,000 men to Michaelchurch and Gillow (near Grove) with the intention of killing Talbot and his younger brother, Sir William Talbot. For want of a better explanation these disturbances may have been a reaction on the part of the old Talbot affinity against its new lord. Sir John Skydemore had been steward of Archenfield under the new lord’s late brother, Gilbert, Lord Talbot (d.1418), and Abrahall was receiver-general to Gilbert’s widow, Beatrice. Yet whatever the causes of the dispute, it quickly lost its intensity. In any case, our MP himself was probably only peripherally involved. He was not named in the petitions presented against the rioters in the Parliament of October 1423 (although his kinsman George Skydemore was). Despite the seriousness of the charges, he was able to purge himself of the King’s suit by making a fine of two marks in Michaelmas term 1428.
Skydemore’s hard-won maternal inheritance enabled him to play a part in local affairs as he waited to inherit the family patrimony. On 27 Aug. 1429 he attested the election of his father to Parliament; and by the mid 1430s he was acting as steward of Ballingham, a few miles to the north of Grove, for the priory of St. Guthlac, at a modest fee of 20s. p.a.
Skydemore may have been back in England in the next year, for on 1 Sept. 1438 he was nominated by James, Lord Berkeley, as one of his feoffees in the advowson of Slimbridge (Gloucestershire).
Early in 1445 Skydemore was elected to represent the county in Parliament in company with Sir John Barre*, with whom he had fought in France under the duke of York.
Skydemore’s services were much in demand, partly no doubt because of his relative wealth but perhaps also because the bulk of his lands lay on the politically sensitive border between England and Wales. In the early 1440s Humphrey Stafford, duke of Buckingham, granted him an annuity of ten marks. He went on to hold office as steward and receiver of the duke’s great lordship of Brecon, although he was removed in 1451, seemingly for failing to punish cattle-rustlers and other offenders.
On 18 Jan. 1449 Skydemore was again elected to Parliament, on this occasion with his brother-in-law, Fitzharry, and at the end of the year he was named as sheriff of Herefordshire.
Later, on 3 Apr. 1452, Skydemore was the beneficiary of a politically sensitive grant. The Crown committed to him keeping of a moiety of the castle of Ewyas Lacy and a moiety of a moiety of lordship there to hold during the minority of George, son of the Lord Abergavenny whose potential claim to the lordship of Abergavenny had troubled Henry Beauchamp. This grant was made on the contentious understanding that Ewyas Lacy, as part of the Despenser inheritance, was subject to division between the young George (who claimed a moiety through his mother, Elizabeth, daughter of Isabel Despenser by her first husband, Richard Beauchamp, earl of Worcester), and his cousin, Richard Neville, earl of Warwick (who claimed the whole inheritance in right of his wife, Anne (Isabel’s daughter by her second husband, Richard Beauchamp, earl of Warwick). This grant marks Chancery’s acceptance of George’s claim and must have been unwelcome to Warwick, who moved to secure his own grant of the keeping of the moiety of Ewyas Lacy claimed by his cousin. This was granted in April 1453, but, on the following 21 July, a new grant was made to Skydemore. By this date the Neville earl was coming to identify himself with the Yorkist cause, and thus this second grant, at least when viewed retrospectively, identified Skydemore with York’s opponents.
This raises the question of Skydemore’s sympathies as civil war threatened in the 1450s. No county was more riven by faction than Herefordshire in that struggle, and there were reasons why Sir John should have identified himself with York. Not only had he twice served under the duke in France, but he had no reason to love York’s rival Edmund Beaufort, duke of Somerset, who had, in the early 1430s, unjustly supplanted his father in his Welsh offices. To be balanced against this, however, his father had risen to prominence in the county through service to the house of Lancaster, and he himself, although no longer steward of Brecon, was an annuitant of the duke of Buckingham, a leading loyalist magnate. Further, he had close family ties with committed local Lancastrians, notably his brother-in-law, Fitzharry, and the powerful Welsh esquire, Gruffydd ap Nicholas, whose daughter had married one of his sons.
In these circumstances, it was natural that, when, in April 1455, the Crown summoned two men from each county to a great council, the choice, in respect of Herefordshire, should have fallen upon Skydemore and Fitzharry.
Soon after, the threatened civil war broke out in earnest and Skydemore took an active part. In company with Fitzharry and other Herefordshire Lancastrians, he was with the Lancastrian army that provoked a smaller one led by Yorkist lords into inglorious flight at Ludford Bridge on the night of 12 Oct. 1459. On the following day he travelled to Hereford to participate in a hastily convened parliamentary election (the writs of summons had been issued only four days before). In the light of events at Ludford Bridge, the gathering at the county court was a remarkable one. Skydemore was there with his son, Henry, and brother, William, and other local Lancastrians, but so too were several Yorkists, including the duke of York’s receiver-general, John Milewater. The three obvious candidates were Skydemore himself, Fitzharry and Barre, and it was the latter two who were returned. On the day after the Parliament ended, Skydemore was named to the county’s commission of array, and in the following spring he was appointed to two important commissions, the one of oyer and terminer in the Welsh and marcher lordships of the Yorkist lords, and the other to seize various of those lordships into the King’s hands.
The Yorkist victory at the battle of Northampton in July 1460 created a very different situation. Skydemore’s earlier connexion with York may have provided him with an opportunity to reconcile himself with the new government, yet reconciliation was not the course he chose to pursue. He was with the army commanded by Jasper Tudor, earl of Pembroke, which was defeated by the earl of March at the battle of Mortimer’s Cross on 2 or 3 Feb. 1461. The antiquarian, William Worcestre, who visited Herefordshire in 1479, reported the deaths of Skydemore’s sons, James and Henry, the one in the battle, the other by execution immediately afterwards, and remarks that Sir John was also present at the battle, noting, seemingly gratuitously, that he had 30 servants, perhaps to emphasize the high standing of the family. His list of those who died is unreliable – Henry lived until 1489 – but it may that he is correct in the case of James, who makes no further appearances in the records.
For what happened next in Skydemore’s eventful life, there survives his own account, presented to the Parliament of 1472 as he sought to secure the restoration of his estates.
In these circumstances, it is difficult to share Skydemore’s sense of injustice at the manner which he claimed to have been treated in the first Parliament of the new reign. He said that he had, ‘by synystre labour’ been ‘put in the comyn bylle of atteyndre’, but when the Commons learnt from Herbert and Devereux that they had promised him his lands and goods on the surrender of Pembroke castle, they removed his name from the bill. Similarly, a special bill to attaint him was disallowed by the Lords on the same grounds. Yet, he went on to claim, at the end of the Parliament, after many lords and knights of the shire had departed, ‘by marvelous pryvat labour’, a bill signed by the King was brought before the Commons, ordaining that Sir John should forfeit his lands (although not his life and goods and that he should not ‘hurt in his persone by ymprisonement or jeopardie of his lyfe’). In his petition of 1472 Skydemore presented all this as a clear case of unfair treatment. Far more probably, it represents the conclusion of a period of negotiation that ended unfavourably for him. After a period of debate, it was deemed that, quite reasonably, Herbert’s pardon should extend to his life and goods, but not to his lands. There are also some indirect grounds that Herbert himself shared this view. On 20 Feb. 1462 our MP’s forfeited lands were granted in tail-male to Herbert’s brother, Sir Richard, a grant repeated three years later. This can be interpreted in two ways: either Lord Herbert was at best indifferent to Skydemore’s restoration, or the grant to his brother gave him reason to do nothing to support his restoration.
There is no evidence of where Skydemore spent that decade. Part of his lands may have remained in the hands of his wife and he perhaps stayed with her in relative poverty in his native county. He does not again appear in the records until the Readeption, when he was restored to the bench in Herefordshire. No doubt had Henry VI maintained the throne he would have secured a formal restoration to his estates. As it was, that restoration came anyway. His support for the Readeption, probably merely nominal, had not been enough to compromise him further in the eyes of the Yorkists. In the Parliament which met on 6 Oct. 1472 he presented the petition alleging the unjust repudiation of the promise he had been made on the surrender of Pembroke castle and asking for restoration to his lands. He was, it seems, pushing at an open door. The death of the royal grantee, Sir Richard Herbert, at the battle of Edgcote in 1469, leaving a minor as his heir, had removed a potential obstacle. None the less, it is still noteworthy that the attainder was reversed on generous terms, in that the rival claim of Herbert’s son, William, was specifically repudiated. The exemption granted to William, in the Act of Resumption of 1473, specifically excluded the Skydemore property, as did a grant made in favour of Sir Richard’s widow, Margaret, in May 1475, just after our MP’s death.
Soon after this complete restoration, Skydemore did what he had been prevented from doing by the cloud hanging over him, that is, contract a marriage for his grandson and heir-apparent, Thomas, son of his dead son, James. The bride was Margaret, daughter of a Welsh esquire, Morgan ap Jankyn ap Philip, and the terms on which the match was made, embodied in an indenture of 20 Nov. 1473, were highly favourable to her family. The entire Skydemore estate, valued at £120 p.a., was to be settled on the couple in jointure: the manor of Kentchurch and other lands to the yearly value of £20 were to pass to them immediately and the rest was to come to them on the deaths of Sir John and his wife. In return Morgan was to pay only £100. The probability is that the bride had something to recommend her which is undisclosed in the contract, most probably she was a widow with lands from an unidentified first husband.
By this date Skydemore was already an old man, at least as old as the century, and he could gratify himself that he had lived long enough to oversee the family’s recovery occasioned by his adherence to Lancaster. Worcestre, on his visit to Herefordshire in 1479, noted that he had died about three years before and that he was the ‘most valiant’ of his family. Writs of diem clausit extremum issued out of Chancery on 3 May 1475 in respect of his estates in that county. No inquisition was taken by which his death might be dated more precisely, and it may be that none was taken because all his land was in the hands of feoffees.