Although Sylton was a merchant, who imported wine and iron through the Sussex ports, on at least one occasion he was described, perhaps derogatively, as a ‘husbandman’.
Owing to deficiencies in the records of Winchelsea, the date of the first Parliament Sylton attended is uncertain. The Parliament of 1455 (for which returns do not survive) may be ruled out, as he attended a meeting of the Brodhull on 22 July during its initial session, and furthermore on that occasion he was chosen to be one of the Ports’ bailiffs at the herring fair at Yarmouth in the autumn – an unlikely appointment for a sitting MP. Rather, the Coventry Parliament of 1459 may have seen his introduction to the Commons. Sylton began the first of an impressive eight terms as mayor of Winchelsea at Easter 1462, and at the Brodhull of July 1463, during his second term, he was nominated with John Cobbey* of Hastings and Babylon Grantford* of Rye to be ‘solicitors’ to Edward IV for the new charter sought by the Ports.
During Sylton’s fifth mayoralty, that of 1475, he was appointed by the Crown as controller of customs in the port of Chichester, taking responsibility for the Sussex coast extending east to his home port, although he may not have acted in the office. Nevertheless, in May 1481 as the ‘King’s servant and yeoman of the Crown’ he was granted for life the office of bailiff of Rye, a post which from October that year he combined with that of customer at Chichester. Among the tasks assigned to him was the fitting out of The Agnes of Rye for her voyage to Rouen in October following, and arranging passage for a royal herald and another envoy sent by Edward IV as messengers to the duke of Albany. As Richard III confirmed Sylton in both the bailiffship and as customs’ collector, he remained in both posts until that King’s death.
Although after Bosworth Sylton lost his posts as bailiff of Rye, yeoman of the Crown and customer, he was reinstated in the last office in February 1489, while attending Henry VII’s third Parliament. At the Brodhull which met in January following, before the start of the final parliamentary session, he and the other barons were authorized to ‘labour’ with the treasurer and barons of the Exchequer regarding the Ports’ advocants. Matters more closely affecting Winchelsea came before the Brodhull of April 1491, relating to suits between its mayor and named men of the Port (including Sylton), and John Bradman of London, a merchant of the staple of Calais; and in the next year the assembled delegates discussed a withernam granted by Dover against Sylton’s home town.
Sylton last attended a Brodhull in April 1494,
