It has been conjectured that the William Gaynesford returned for Bletchingley was a different person from the man elected in 1449 as a knight of the shire for Surrey.
As a younger son William could not expect to inherit a large part of the family estates in Surrey, and he initially invested in property elsewhere He it was who established a branch of the family at Cowden in west Kent, and together with another fellow of his Inn, William Moyle II*, he acquired land at Westerham in 1439
Even so, Gaynesford’s participation in affairs in Essex was limited. He was never appointed to a royal commission there, and only rarely acted as a trustee for landowners in that county. Indeed, his closest associations remained in Surrey during the 1440s. Property at Lingfield seems to have been settled on him at the time of his marriage, and this included the manor of Blockfield which descended in his line of the family. In November 1446 he was described as a ‘gentleman of Lingfield’ in a royal pardon obtained by both him and his wife, and his connexion with that part of south-east Surrey was reinforced by his employment by the local magnate Sir Reynold Cobham (d.1446), lord of Sterborough, who chose him as an executor. Like his father he assisted Cobham’s widow in transactions regarding her estates and in particular for the endowment of St. Peter’s College in Lingfield.
Shortly after his father’s death Gaynesford attested the shire election in Surrey, for the first of three times. Two years later he and his elder brother John made their initial appearances on the county bench, with William being named on the quorum. He was also appointed to the first of numerous ad hoc royal commissions, not only in Surrey but also in Sussex, where he similarly served on the bench, albeit for a shorter period. His growing standing in the latter county during the 1440s had been helped by strong links with Bartholmew Bolney*, a fellow member of Lincoln’s Inn, for whom he acted as a feoffee.
Gaynesford’s association with Thomas Hoo was particularly striking, for as well as acting alongside him on behalf of the Wakehursts, he became involved in the complicated arrangements made for the administration of the will of Hoo’s half-brother, Thomas Hoo I*, Lord Hoo and Hastings, who died in February 1455. In May, Thomas obtained confirmation of his possession of the lordship, barony, honour and rape of Hastings, in a transaction which included Gaynesford and his elder brother John as trustees. In November 1461 the surviving trustees, including Gaynesford, conveyed the estates to Edward IV’s friend William, the new Lord Hastings, in accordance with a royal grant. In the meantime, Hoo had chosen our MP as one of the feoffees of his manors of Roffey and Horsham.
Gaynesford’s administrative career had seemingly been little affected by the political turmoil of the late 1450s and early 1460s which culminated in the deposition of Henry VI and the accession of Edward IV to the throne. As early in the new reign as 16 Mar. 1461 he was appointed to a commission of array in Surrey, and he was reappointed as a j.p. in that county for another three years. His abilities as a lawyer were still much sought after: in October 1461 he and a family friend John Ellingbridge*, described as ‘literates’, were among those granted the sequestration of the affairs of Tanridge priory which was experiencing severe financial problems. Two years later he was named as supervisor of the will of Joan, wife of Richard Bruyn* (a lawyer who like his father had served the duke of Buckingham), which was proved in December 1463.
Seeking to put their own affairs in order, in the spring of 1453 Gaynesford and his wife Joan had placed her inheritance in Essex in the hands of trustees, headed by his brother Nicholas. Doubtless, their intention was to safeguard it from royal wardship, as is clear from the purchase by the trustees of a pardon for acquiring Ashwell without licence, for this pardon was dated 14 June that year, a mere 11 days after Joan’s death.
