The Wakehurst family had lived at Ardingley since the early 13th century. It is uncertain precisely when the manor of Wakehurst itself passed to Richard: between 1404 and 1411 he was conducting a suit (possibly collusive) for land there against John Wakehurst (either his father or elder brother), but John remained in possession at least until 1415. In that year Richard acquired other property in Ardingley and elsewhere. Some time earlier he had taken possession of land and rents at East Grinstead and Worth, also in Sussex, while in the neighbouring county of Surrey he already held property at Lingfield and, together with his wife, had acquired in 1409 the manors of Throwle and Bysshe Court. In later years Wakehurst was to become owner of Ockley, while the manors of Dixter and Gatecourt, which belonged to his wife’s family (the Etchinghams) came to him and Elizabeth by virtue of a complicated arrangement made with her kinsmen.
Wakehurst’s career as a lawyer began by 1400, and before long his evident ability, especially in the area of the law which related to land tenure, attracted him to a wide clientele among the gentry of south-east England. In those early years he often acted as a mainpernor in the Exchequer and Chancery, doing so on behalf of a former duchy of Lancaster bailiff, for the alnager of Surrey and Sussex, and for successive farmers of the estates of Seés abbey and Cogges priory. In 1404 he assisted Sir Philip St. Cler to complete the legal formalities for his purchase of a manor in Ospringe, Kent, and by St. Cler’s will he received a small bequest for travelling expenses while paying the testator’s debts. He was to continue to be employed as a feoffee of the St. Cler estates for the next 20 years. One of his closest associates in the early 15th century was Sir William Burcester, who named him as a trustee of his lands and executor of his will (1407), making him responsible for settlements of property on his widow and children, and for providing himself with an annuity of £1 for life from the estate.
There can be little doubt that, of all Wakehurst’s distinguished clients, the most important in the context of his election to Parliament in 1413 was Thomas Fitzalan, earl of Arundel. He had entered the service of the earl at least two years earlier, having been already so well versed in Arundel’s affairs as to be named in September 1411 as one of his attorneys at home while the earl was in Burgundy on a royal embassy. Wakehurst’s successful candidacy for Henry V’s first Parliament followed within weeks of Earl Thomas’s promotion to the treasurership of the Exchequer. Like other of the earl’s retainers he soon benefited from the patronage dispensed at Westminster: not long after the Commons were dismissed he shared with William Ryman the valuable farm of the estates of the alien abbey of Seés. Early in 1415 Arundel made him his co-feoffee of certain Fitzalan lands, and then, in May that year, when making preparations to join the King’s expedition to France, he appointed him among the trustees of his lordships in Surrey and Sussex for settlement on the Countess Beatrice in jointure. The trustees received final instructions as to how to dispose of the property in the will made by the earl that August. Wakehurst’s trusteeship ensured his continued involvement in the administration of the Fitzalan estates for several years after the earl’s death; and he also took on additional tasks to assist the countess, for whom he provided securities in Chancery in 1417, and in whose interests he served on a royal commission concerned with property in Shropshire in 1424.
In the course of his long career Wakehurst had several dealings with Sir Thomas Sackville II of Buckhurst, an association which culminated in the marriage of Sackville’s son and eventual heir, Edward, to his daughter Margaret. (In the 1440s both Wakehurst and his son, another Richard, acted as trustees of the estates in which Margaret Sackville enjoyed jointure.) A second daughter, Anne, married the Surrey MP John Gainsford (d.1460), forming a connexion which was strengthened further by the marriage of Gainsford’s sister to Anne’s brother, Richard. The latter died shortly before November 1454, when his aged father was still alive.
Wakehurst’s will, made on 3 Jan. 1455, contained bequests to the churches of Ardingley and Robertsbridge abbey, the Austin priors at Rye, and the hospitals of St. Mary of Bethlehem and St. Anthony in London. He was re-appointed as a j.p. that April, but died before 23 Aug., when the will was proved. A month later Chancery issued a posthumous royal pardon addressed to him in connexion with a transgression in his trusteeship of the Cobham estates.