The Pickering family had been lords of Oswaldkirk in Ryedale since the early fourteenth century, following the marriage of an earlier Richard Pickering (d.1349) to Joan, daughter and heiress of Nicholas Barton.2 VCH Yorks. (N. Riding), i. 549. This Richard was succeeded by his young grandson, another Richard, who was seemingly still the lord in 1383, although the pedigree from this point is unclear, and members of the family have been confused with those of another Pickering family, seated at Ellerton in the East Riding and Killington in Westmorland.3 Sheffield Archs., Copley mss, CD/382; CP40/482, rot. 434d; 489, rot. 411, where another Richard Pickering is named as the husband of ‘Orfama’, da. and coh. of Lyulf Stulle. Our MP may well have been the grandson of this second Richard, and the son of the John Pickering who held knight’s fees in Oswaldkirk and Ampleforth from William, Lord Roos of Helmsley in 1414. His mother may have been a member of the Hildyard family, for in his will of 1428, Robert Hildyard pardoned his ‘nephew Sir Richard Pickering’ a debt of six marks.4 CIPM, xx. 246; Test. Ebor. iv (Surtees Soc. liii), 12.
Although details are scarce, like many of his contemporaries the young Richard pursued a military career, if a relatively brief one. In 1417 he served in France under Richard Beauchamp, Lord Abergavenny, and in the summer of 1421, by which time he had been knighted, he was in the company of Ralph, Lord Cromwell, in the garrison at Harfleur.5 E101/50/9; 51/2, m 5. Thereafter, however, he made his career at home. The first recorded episode of that career was an unfortunate one. In either 1426 or 1427 his home manor at Oswaldkirk was attacked by the adherents of his baronial neighbour, John, Lord Greystoke. The attackers, mostly Greystoke’s tenants from nearby Hinderskelf, ‘beat, maimed and wounded an old lame man, walking on crutches’, and stole numerous cattle belonging to Pickering. Our MP began proceedings in common pleas and also sent a petition to the duke of Gloucester, as Protector.6 SC8/135/6703; CP40/666, rot. 146d. It is unclear whether these relate to two separate but remarkably similar attacks, or to the same incident. The plea roll clearly dates the event to 27 Feb. 1426, while the petition suggests a date in Feb. 1427. His plea directly to the duke takes on a greater significance in view of later evidence of a close connexion between the two men. Indeed, it may be that that relationship was already established, and thus explains why our MP was appointed to the duchy of Lancaster office of riding forester of Pickering in 1427 and then elected for Yorkshire to the Parliament which opened in September 1429.7 Somerville, i. 535.
Pickering’s attendance at that Parliament may also have been related to his appearance in connexion with the long-running dispute between another of Gloucester’s men, Sir John Keighley, and the prominent Lincolnshire esquire Walter Tailboys* over the Lincolnshire manor of Theddlethorpe. This dispute had rumbled on since 1425, but under bonds entered into on 1 Jan. 1431 to settle the matter, Keighley was to swear before Bishop Morgan of Ely, our MP and others that Tailboys was of good character, and that he had not brought about his indictment for felony.8 CCR, 1429-35, pp. 109-10. Pickering had no obvious connexions with Lincolnshire, but Tailboys had sat for that county in the same Parliament of 1429, possibly seeking election in order to further his case in this dispute, and it may be that either Gloucester procured Pickering’s election for Yorkshire to assist Keighley, or that his presence in the Commons led Gloucester and Keighley to look to him for support. Either way, his involvement in the dispute is not known to have extended further than the bonds of 1431.
In November 1431 Pickering was chosen as sheriff of Yorkshire, another event which may have owed much to support from Gloucester, and in January 1432 he was appointed to the North Riding bench, a position he would retain for the rest of his life. Later he benefited from a minor grant of royal patronage: on 8 Feb. 1439 he was granted a seven-year lease, at an annual rent of £10 3s. 4d., of certain herbage and agistment rights in the duchy of Lancaster lordship of Pickering.9 CFR, xvi. 71; CPR, 1429-36, p. 628; 1436-41, p. 594; DL42/18, f. 127v. Yet, for a man of his rank and apparent connexions, his appearances in the records are infrequent. The few surviving details relate to his dealings, both friendly and unfriendly, with neighbours. For instance, in the 1430s he witnessed transactions made by his neighbour Sir Edmund Darell*; at an unknown date he acted with his brother John and Sir John Constable*as a feoffee for John Hildyard (presumably a kinsman); and on 10 Aug. 1441 he witnessed a deed relating to the nearby manors of Cornbrough and Sutton on the Forest.10 Test. Ebor. iv. 12-13; CCR, 1435-41, pp. 467, 472. Less happily he was also the victim of further attacks on his property. In Michaelmas term 1440 he brought a suit in common pleas against a wide range of people regarding damage to his manor at Oswaldkirk, and in Trinity term 1441 he, together with Sir Thomas Percy, Sir William Eure* and John Caxton, complained of damage and thefts at their holdings in Newton by Wintringham.11 CP40/719, rot. 266; 722, rot. 255.
By that date Pickering’s health may already have been failing; he made his will on 1 Sept. 1441, and two days later he placed his lands at Oswaldkirk, Arnold, Riston and Rowton, together with the advowson of Oswaldkirk, in the hands of a group of feoffees headed by Sir John Constable. He died on the 11th, leaving his nine-year-old son John as his heir. Although news of his death seemingly reached Westminster by 14 Sept., when the writ de diem clausit extremum was issued, he was nevertheless re-appointed to the North Riding bench on 23 Nov.12 Harl. Ch. 55 A 43; CFR, xvii. 196; C139/111/49. Thanks to his earlier enfeoffment, his inquisition post mortem recorded only those lands he held in jointure with his wife, namely the manors of Lockton and Beadlam, held of the duchy of Lancaster honour of Pickering and Lord Roos’s castle of Helmsley respectively, as well as other lands in South Home, Great Barugh, Norton on Derwent, Sutton and Ampleforth, and a messuage and dovecot in Pickering.
In his will, Sir Richard asked to be buried before the altar of the Virgin Mary in Oswaldkirk church, where a tombstone which may have covered his grave still survives. He left bequests to various members of what was seemingly an extensive immediate family, including his brothers Robert, Hugh and Edmund (the latter presumably the man named to assist in executing the will), Cecily, widow of his deceased brother John, his sisters Joan (a nun in the Benedictine priory at Nun Monkton near York) and Maud (wife of John Dilcok, feodary of Tickhill), his sister Margery Horsman, and Margaret Sutton, presumably another married sister. He left a gown to the church at Oswaldkirk, but his only other bequests besides small sums to servants were of a gown and 6s. 8d. to Richard Thornton, another gown to Robert Thornton, the other assistant to his executor, and a horse to the lawyer, John Wenslawe. Pickering did not mention any children, and the remainder of his goods were left to his widow and executor Margaret. On 2 June 1445, Margaret had licence to marry Henry Banaster, a yeoman of the Crown, but he died in 1455, and on 26 Nov. that year she secured a royal pardon in which she was named as widow and executor of both her husbands. She appears to have remained a widow for many years, and was seemingly still administering property in Ingleton and Bentham as late as 1480.13 Test. Ebor. ii (Surtees Soc. xxx), 82; CP25(1)/281/160/11; Borthwick Inst. York, York registry wills, prob. reg. 2, f. 326 (administration granted 13 Feb. 1456); Somerville, i. 531; C67/41, m. 16; E40/8572. A Margaret Pickering, widow, was holding a court at Ingleton as late as 1506, but, while possible, it is unlikely that this was the same woman: SC2/211/68. Sir Richard’s heir, John, became a prominent local supporter of Richard of Gloucester, both as duke and later as King, but the Pickering family would gain greater prominence in the sixteenth century, when Sir William Pickering served as knight-marshal to Henry VIII, and his son, also Sir William†, was even seen as a potential husband for Queen Elizabeth. However, on his death in 1575 Oswaldkirk passed into the hands of his illegitimate daughter, and continued to be held by her descendants until it was finally sold in 1674.14 A.J. Pollard, North-Eastern Eng. 166; VCH Yorks, (N. Riding), i. 550.
As with most Yorkshire MPs of this period, insights into Sir Richard’s personal life and character are rare. However, some light may be shed by his association with one of his neighbours, Robert Thornton of East Newton, evidently a close friend who was named in his will, his final enfeoffment of Oswaldkirk and the jointure settlement of the majority of his other lands. Thornton was almost certainly the man responsible for producing an anthology of various books of the period, and while the provenance of these works are unknown, it is likely that Sir Richard and the wider Pickering family were the source of at least one book copied into the anthology, a medical tract Liber de diversis medicinis.15 G. R. Keiser, ‘Lincoln Cathedral Library MS 91: Life and Milieu of the Scribe’, Studies in Bibliography, xxxii. 158-79; idem, ‘More Light on the Life and Milieu of Robert Thornton’, ibid. xxxvi. 111-19. Moreover, there is significant circumstantial evidence to suggest that other works may have come from the priory of Nun Monkton, where Richard’s sister Joan was a nun, and others possibly from the rector of Oswaldkirk, explicitly mentioned in Thornton’s work. Other literary productions of this period can also be traced back to sources owned by the Pickerings of Oswaldkirk, and while not necessarily making the family any different to their contemporaries, it certainly gives the impression of a man, and a family, with a keen interest in the written word and its dissemination.