Talbot paid maltolts in Holyngbroke ward, Romney, from 1381 until his death. As a Portsman he claimed tax exemption on land in the Kentish hundred of Worth.
When Archbishop Courtenay made Talbot bailiff of Romney in succession to Edward Middleton, he may have hoped, in replacing a stranger with a local man, to conciliate the townsmen, who had been seeking to subject the bailiff more strictly to themselves as a way of reducing the archbishop’s authority as lord of the town. But Talbot soon found himself at odds with his fellows: as early as February 1392 he was compelled to enter into a bond with the jurats to forfeit £40 to them if he ever gave decisions in the town court contrary to their judgement and to the customs of Romney. Although, following the archbishop’s intercession, this penalty was reduced to £10, Talbot was still held liable for a fine of £2 for certain trespasses he had allegedly committed against the town’s liberties during his first year of office. For a while conflict was avoided, and in June 1393, when he was being sued by Alice Letton, widow of Thomas Barbour of London, two ringleaders of an earlier confrontation with the archbishop, namely, William Holyngbroke and William Child, stood surety under pain of £200 for his appearance in Chancery. (The case apparently fell through, for on 3 July Alice gave Talbot a general release from all legal actions.) At Michaelmas Archbishop Courtenay leased to him for ten years his manor of Chene in Romney Marsh, at a rent of £40 a year. But in the last few months of Courtenay’s life, in 1396, Talbot’s troubles as bailiff of Romney re-emerged. In March that year four criminals broke out of Romney gaol, allegedly through his default, and as a consequence he was fined by the King. At the same time he fell foul of the archbishop’s steward, William Makenade, and on 6 June he had to give him a bond in 200 marks, probably in connexion with a lawsuit. It seems likely that he had lost Courtenay’s confidence, and may in any case have forfeited his office when Courtenay died the following month. (He had certainly done so by 12 Aug., by which date Richard Water of Canterbury had secured the bailiffship.) Nevertheless, Archbishop Arundel, Courtenay’s successor, permitted him to remain as farmer of Chene, where he retained the lease at least until October 1397, when Arundel suffered exile and forfeiture of his estates.
Following his dismissal as bailiff, Talbot evidently returned to favour among his fellow townsmen, for he was chosen by them as one of their representatives in the Parliament which acclaimed Henry of Bolingbroke as King. During the session he was present at Henry’s coronation among those barons of the Cinque Ports privileged to bear the royal canopy.