Wyly apparently began his career as a royal servant in about 1352, and it was for good service that in January 1366 he was granted for life wages of 6d. a day from the issues of Wiltshire. He was probably already one of the four rangers responsible for the royal forest of Savernake. Certainly, by 1370 he had been promoted as deputy to the hereditary warden of the forest, Sir Henry Sturmy, an office in which he continued until his death. In the meantime, in 1378, his annuity had been confirmed by Richard II.
The headquarters of the Savernake forest administration was at Marlborough, and Wyly evidently lived in the town. Indeed, from the great royal barn there in 1376 he illegally carried off 1,000 slates worth 6s.8d. and other property worth 8s. Described as ‘farmer’ he contributed 1s. to the poll tax of 1379, as levied in Marlborough. All the same, it was perhaps because of his connexions with the influential Sturmys that he was returned for the borough to both Parliaments of 1388, for his attendance at the second of which Robert Warner (possibly still lieutenant of the castle) went surety.
In right of his wife, Agnes, Wyly occupied land at Calstone and nearby Quemerford, for which he paid 58s.4d. yearly to the Crown until 1386, the rent being then waived in recognition of his long service, said to be of 34 years’ duration. His wife also had possession of property in Cherhill and Avebury.
