The new town of Winchelsea had been founded on a hill-top site by Edward I in the 1280s, following the destruction of the original town by stormy seas. The following half-century was a period of prosperity, but thereafter Winchelsea declined. By 1342 its population had shrunk noticeably, and the widespread destruction done by the French, when they captured and sacked the town in 1360 and again in 1380, led to further decay. In 1384 Winchelsea was said to be so desolate that it was difficult to discover who owned vacant plots and tenements; and its revenues were certainly so diminished as to affect the remaining townspeople’s ability to pay the farm due to the Crown and to provide ship-service. The steps then taken to encourage repopulation were limited in their effect, and the government eventually had to accept that the site was too large for full habitation and adequate defence. Of necessity, in 1415 Henry V, convinced of Winchelsea’s importance as a ‘frontier of the King’s enemies’ and ‘as it were, a key’ to that part of the south coast, granted 600 marks for its fortification with walls built on a shorter perimeter. Notwithstanding its adversities, Winchelsea continued to be the leading port in east Sussex, even though efforts were regularly needed to keep the channel between it and the sea open to shipping. Although it had ceased to be a head port for the collection of customs after 1378, thereafter being merged with Chichester for this purpose, it was still allocated resident deputies to the chief butler (an office to which townsmen were on occasion appointed), and in practice the Chichester area was divided, sometimes leaving a Winchelsea man to manage its eastern half.2

Winchelsea had shared its early history with its neighbour Rye: both were originally held by Fécamp abbey and developed together from being member-ports or limbs of Hastings into ‘ancient towns’ enjoying fully equal status with Hastings and the other Cinque Ports. Down to 1358 the two towns had even been combined for administrative purposes, under a single bailiff appointed by the Crown. Thereafter, they were less closely linked in this way, each having its own bailiff. The one at Winchelsea was in our period generally a royal servant allowed to hold the office as a sinecure.3 The bailiff presided with the mayor in the town courts and collected their profits, along with burgage rents, harbour dues and market tolls, to the King’s use or, as was later to be the case, his own. The town’s semi-independence was enforced, however, by the rule that the bailiff could not assume control until he had been sworn and admitted by the mayor. The latter was elected yearly in a common assembly held on Easter Monday, and it was he who chose 12 jurats from the most ‘prudent’ of the townsmen, to act as his assistants. He was given an annual fee of £4, and one of his chief responsibilities was to pay into the Exchequer certain issues (which might amount to as much as £14), apparently as a contribution to the fee farm which had been due from the town since its foundation. If the election of the mayor had ever been a democratic affair, it certainly ceased to be so after 1435, when an oligarchical tendency prevailed. Following a failure to elect a new mayor at Easter 1433, ‘propter discordiam communitatis’, and the occurrence two years later of ‘magna diversitas et murmuracio’, it was decided that future elections should rest with the jurats and a newly established common council of 36. This latter body was also empowered to give assent on the commonalty’s behalf to the levying of local taxes and the promulgation of ordinances, and it seems likely that it also took over the role of the common assembly in the election of Members of Parliament.4

To the 20 Parliaments of the period for which returns for Winchelsea have survived, the town elected 25 individuals, one of whom remains unidentified. The majority, 17, were returned not less than twice, those making the most appearances being William Skele I and Roger atte Gate, who both secured election eight times. Matthew Goldyve and John Salerne II had represented other of the Cinque Ports (Rye and New Romney, respectively) before they sat for Winchelsea, and John Tamworth was to be elected for Hastings after his parliamentary service for Winchelsea had ended. The barons of Winchelsea apparently preferred to send as their representatives men who already had some experience of the workings of the Commons: in 12 Parliaments one Member, and in six more both Members, were qualified in this way. Re-election to consecutive Parliaments occurred at least four times (in 1386, February 1388, January 1397 and 1419).

All 24 of those identified held property in Winchelsea, and the majority evidently resided there for much of the time. Indeed, most of them came from families long established in the town, and some, such as the Fynches, the Skeles and Thomas Thunder, carried on a tradition of parliamentary service. Winchelsea produced no such wealthy merchants as Edward I may have hoped for when he refounded it. Its typical parliamentary barons were engaged in a modest way in importing wine and other produce from France and Spain; and several of them owned ships which they used for the carrying trade or fishing (on occasion also indulging in piracy in the Channel). Nearly all of them owned a little land in the surrounding countryside; and as the port declined, so did agriculture form an increasingly large supplement to their incomes from trade. Indeed, John Salerne II, his son-in-law William Catton, and the two Vincent Fynches all became landowners of consequence in east Sussex. Vincent Fynch I, whose income from land (mainly acquired by other members of the family earlier in the 14th century) exceeded £30 a year, attained armigerous rank, and was considered to be of sufficient standing to be appointed as escheator and then sheriff of Surrey and Sussex; while his son, Vincent Fynch II, went on to secure election as knight of the shire for the latter county. But men such as these did not dominate the parliamentary representation of Winchelsea. For the most part seats in Parliament were shared fairly equably among the leading townsmen. Indeed, there was a greater chance of becoming an MP than there was of being made mayor, for between 1386 and 1422 the mayoralty is only known to have been occupied by a dozen men. All but one of these mayors represented the town in the Commons at some stage in their careers, although only three of them had done so before their first term of office. Not surprisingly, there are only a few instances (in five Parliaments of the period—January 1390, 1393, 1407, 1410 and 1417) of a current mayor being returned: namely, Skele, Arnold, Salerne, atte Gate and French.

Most of Winchelsea’s bailiffs of our period were absentees, but two of them—Robert Fishlake (bailiff 1399-1410) and William Catton (bailiff 1413-31) — did settle in the town and secure election as its MPs. Fishlake, who came from Dover, sat in Parliament in 1407, but failed to take root at Winchelsea, preferring to return to his home town when his bailiffship ended. By contrast, Catton, a royal retainer of East Anglian origin, married into a local family and achieved some standing in east Sussex. When returned to Parliament by Winchelsea in 1414, 1417 and 1421, Catton was also engaged in the demanding office of clerk of the King’s ships, closely involved in the organization of Henry V’s invasions of France, and this, coupled with his connexions with such prominent figures about the King’s person as Henry’s last treasurer of the Household, Sir William Phelip*, and his executor (Sir) William Porter II*, might well have been a significant factor in his elections. Certainly, after his retirement from regular royal service, even though he retained the bailiffship of Winchelsea for the rest of his life, Catton was never re-elected to the Lower House.