Although Rye’s background is obscure, it would appear that he came from Dover and is to be identified with the Roger Reye who was associated in 1392 with John Monyn in the completion of a grant of certain properties to the local priory of St. Martin. Certainly, he was later nominated on Monyn’s behalf as an arbitrator in a dispute with a widow from Canterbury. Initially holding little or no landed property by inheritance, quite early on in his career he purchased the manor of Eythorne together with the advowson of the church and land in Kingston, Nonington and elsewhere, although it seems to have been to marriage that he owed possession of other holdings, in Stalisfield.
Roger may have been the ‘Rye’ (whose first name is missing) admitted to Lincoln’s Inn in the early years of the century. At that stage in his career he established friendly relations with a fellow lawyer, Richard Baynard of Messing (the future Speaker), to whom he offered his services as a trustee of substantial estates in Essex and property in London, between 1403 and 1422.
Rye was admitted to the fraternity of Christ Church cathedral priory, Canterbury, on 19 May 1425. In his will, made on 21 Sept. following, he asked to be buried wheresoever it pleased the Holy Trinity; but his bequests especially favoured the parish churches of All Saints, Canterbury, and Stalisfield (including 20 marks towards building the latter’s nave), and he left instructions that a bowl was to be made into a chalice, ornamented with his shield of arms, for presentation to the church at Charing. The sum of £16 13s.4d.was set aside to pay for 2,000 masses to be said within a month of his death, for the welfare of his own soul and the souls of his parents and Seman Tonge. Each of his godsons bearing his name was to receive £1. Rye died before 2 Dec., the date of probate.
