Gaynesford was the eldest of three sons of John I, all of whom became fellows of Lincoln’s Inn like their father and sat in Parliament. Relatively little is recorded of his early career, a reflection primarily of his father’s high profile in their home county, manifested in service to the Crown as a royal commissioner and a j.p. of the quorum, and his prominence as an estates-steward and feoffee. It is striking that none of the three brothers were appointed to the Surrey bench until after their father’s death in 1450. An exception to this relative inactivity was the returns to Parliament in 1431 and 1433 of first William and then John II for the borough of Bletchingley. Their elections were almost certainly facilitated by their father, who was then steward of the Surrey estates of Humphrey, earl of Stafford, feudal lord of the manor and borough of Bletchingley.
The quarrel over the Wakehurst inheritance emerged several years after the death of Gaynesford’s first wife, for by the summer of 1447 he had married the widowed Katherine Stalworth, daughter of the Middlesex landowner Walter Green. This match took place against the background of the Gaynesfords’ succession to the manors belonging to their kinsfolk the de la Poyles. In 1438 the manor of Hampton Poyle in Oxfordshire had been settled on Robert Warner* for life, with reversion to the older John Gaynesford and his son, our MP, and this reversionary interest fell in after Warner’s death in the following year. The Gaynesfords were confirmed in possession of Hampton Poyle, together with the manor of Poyle in Surrey in the summer of 1440. The prospect that our MP would inherit the de la Poyle manors as well as his own family estates, made him a potentially lucrative catch in the marriage market, and one readily apparent to Walter Green, who had married the widow of Henry de la Poyle (d.1422). As part of the marriage settlement our MP obtained a royal licence enabling him to release his right in Hampton Poyle to his father, and for the latter to then settle the manor on him and his second wife in jointure.
Other property, including a messuage and some 500 acres of land at Horne in Surrey, had also been conveyed to Gaynesford by his father in the early 1440s. Such transactions enabled him to gain some experience of running the family estates. These were extensive and the cartulary begun by John I eventually came to contain copies of more than 200 deeds relating to their acquisitions in Surrey and Sussex. Even without the de la Poyle manors the Gaynesford inheritance of our MP was worth over £60 p.a.
Further commissions in both Surrey and Sussex followed, and Gaynesford was one of those appointed in May 1454 to arrest the troublesome Robert Poynyngs, alleged to have been the rebel Jack Cade’s sword-bearer. In March 1456 he shared with Thomas Acton* and others custody of the manor of Stanwell in Middlesex, which had formerly belonged to Miles Windsor, whose wife Joan, another daughter of Walter Green, was Gaynesford’s sister-in-law. Green, concerned for the interests of his young grandson Thomas Windsor†, guaranteed on their behalf payment of 200 marks for the wardship.
Unlike his father, Gaynesford did little to enlarge the family’s estates, and there is no evidence from the deeds or rentals contained in the family cartulary of any significant acquisitions made during the 1450s.
Gaynesford’s service as a j.p. and as a commissioner in Surrey continued, and from 1457 onwards he was regularly included on commissions of array, including that appointed in December 1459 following the attainder of the Yorkist lords at the Coventry Parliament. Evidently, he was considered to be loyal to the Lancastrian regime, which in April 1460 directed him to make inquiries into the escapes of prisoners from gaols in Surrey. It may have been the escalating crisis of the civil war, with the Yorkists poised to return in force from Calais, which prompted Gaynesford to put his affairs in order at that time. On 8 May he obtained the King’s licence to grant the manor of Poyle to a body of feoffees headed by his brothers,
Some uncertainty exists over his heir’s age in 1460, for while the inquisition recorded that he was at least 30 years old, Gaynesford’s will makes it clear that the younger John was not yet 24. A reference in the household book of John Howard* (later duke of Norfolk) from the early 1460s adds to the confusion with its note ‘to remember that Gaynesfordes sone, that dede is, is ward to my Lord Scales’.
