Skilling came from a line of lawyers. His grandfather, Michael Skilling, was ‘King’s attorney’ to Richard II,
The Skillings had settled at Rushall in the Avon valley in the early fourteenth century. In 1389 our MP’s parents granted at farm to the local parson substantial parcels of arable land and pasture for some 500 sheep, in return for an annual payment of 50s. Besides this they had more landed holdings in the same area, notably at Cholderton, Upavon and Netheravon, in Wiltshire, as well as across the Hampshire border at Shoddesden, which were entailed on them and their issue.
John Skilling was first recorded (as ‘the younger of Hampshire’) in December 1408 when he stood surety in £100 that he would bring the parson of Monxton into Chancery in the next Hilary term.
Skilling was elected for Ludgershall to the Parliament summoned to meet at Leicester on 18 Feb. 1426. The borough was only a very short distance from the family manors of Crawlboys and Shoddesden, so he must have been well known to the inhabitants. Yet he may also have owed his return to a connexion with the influential diplomat and former Speaker Sir William Sturmy*, who farmed the royal lordship at Ludgershall and was chief steward of Queen Joan’s estates in the region. Skilling’s father had had private dealings with Sturmy, and in his youth the MP himself appears to have been attached to the household of Sturmy’s younger daughter, Agnes – for he had been at Marsh on the Isle of Wight in 1407 when she had given birth to her son William Ringbourne*.
The date of Skilling’s marriage to one of the daughters of the Hampshire landowner Edward Cowdray, and the terms of their contract is not recorded, although it had taken place within a few months of his Parliament, for in December 1426 he and his wife were named in the settlement of the manor of Herriard and specified lands in Hampshire and Berkshire which Cowdray was to hold for life with successive remainders in tail to his sons and their heirs, and then to his two daughters.
Skilling took the generally administered oath against maintenance in Hampshire in 1434,
