Chiselden’s parentage and early life are obscure, but he was probably related to the Joan Chiselden to whom he confirmed various parcels of land in Somerset in 1414-15.
The identity of Chiselden’s first wife is uncertain, but she appears to have been coheiress to the lands of John Wyke of Wick in Wells, which manor the couple settled on Joan Chiselden’s putative sister, Agnes, and her husband John Goundenham in 1415 in return for an annual rent of £10. Within a few years this rent may have fallen into arrears, for it is likely that this was the debt of £10 for which Chiselden sued Goundenham at some point before 1421.
By the time of Henry VI’s accession Chiselden had become associated with the influential William, Lord Botreaux, and it was clearly in his patron’s interest that he was returned to Parliament for the Cornish borough of Liskeard in 1423 alongside the baron’s own kinsman, William Botreaux I*.
By this date, Chiselden’s first wife had died, for by the end of 1424 he had remarried, taking as his second wife one Agnes, the widow of a Wells burgess. Her status allowed for Chiselden’s admission to the freedom of the cathedral city without payment of the customary entry fine of gloves. The prominent Richard Setter alias Milers* stood surety. There was, however, clearly another reason for his admission, for on the very same day he was elected to his second Parliament as the city’s representative, explicitly ‘nihil percipiendo nisi victualia’.
Although Chiselden normally resided in Wells, he maintained professional contacts in Cornwall and in the later 1420s stood surety in the Westminster law courts for various men from that county. In the spring of 1431 he was ordered to be outlawed, for one of his clients had failed to appear in the court on the appointed day, but the sheriff of Cornwall returned that he had died before the process of outlawry had been completed.
