Wenyngton came from a family of Norman origins which had settled in England sufficiently recently for him still to be commonly known as ‘de Caen’. Normally resident at Dartmouth, he owned a number of tenements in the town, including an empty plot to the east of the Kingsway which he rented from Thomas Bosse and his wife Denise in 1443 for a term of 80 years at a rent of 6s. 8d. p.a. and 26s. 8d. p.a. thereafter. It was probably on this plot that later in the same year he set about constructing a new house, having first reached an agreement with the widow and sons of a neighbour, Robert Bolt, to defend their joint right to a watercourse running between the two houses against the town authorities.
Like many other Dartmouth men, Wenyngton was a shipowner also active in trade. His business activities extended across England, as the debts he was owed by merchants from as far away as Great Yarmouth in Norfolk and Hamble in Hampshire indicate, and his ships also frequently crossed the Channel.
In spite of repeated petitions to the chancellor, there is no suggestion that Wenyngton was ever taken to task for his activities, which were in any event far from unusual for a man like him. Indeed, neither the men of Dartmouth nor the government took a particularly severe view of Wenyngton’s actions. In 1445 he was elected bailiff of Dartmouth, and just two years later he was chosen mayor of the town. From early in 1447 he also held office under the Crown as searcher of ships and subsequently as a customer in the ports of Exeter and Dartmouth. Equally, Wenyngton enjoyed cordial relations with his fellow burgesses, for whom he regularly attested deeds, or acted as a feoffee,
Yet, the expedition did not go as the Council had intended. Far from protecting English and neutral shipping from pirates and hostile privateers, within a short time of putting to sea Wenyngton’s small force seized the neutral Bay fleet, consisting of over 100 mainly Dutch and Hanseatic vessels, and brought them back to Southampton in triumph. Wenyngton’s own written account of the confrontation, sent to Daniell, survives and suggests that this turn of events was brought about to a large degree by the Dartmouth captain’s own wounded pride. Having encountered the Bay fleet while patrolling the Channel according to his brief, Wenyngton hailed their captains and ordered them to strike their sails. In doing this, he was exercising a right which had been first claimed by Edward III for all English sovereigns, but which was understandably not recognized by the towns of the Hanseatic League. Consequently, the Germans refused to comply with Wenyngton’s demand. Indignant at this perceived slight, the English commander threatened to force them to do his bidding, but as the neutral ships heavily outnumbered his own vessels the foreigners merely laughed at his threats. They found themselves, however, unable simply to evade the English flotilla, which engaged its enemy. Fighting continued all day, and according to Wenyngton’s version of events the Hanseatic fleet bombarded his ships with as many as 1,000 cannon balls, as well as innumerable other missiles, killing and wounding a number of his men. Yet on the second day, a wind started up which enabled the English ships to prepare to ram their opponents, and this manoeuvre caused the Germans to surrender, rather than risk being sunk. Wenyngton successfully escorted the captured fleet to port, but the damage the Hansards had done to his own ships was considerable: he assessed it at as much as £2,000 and in high dudgeon demanded that all the ships and goods should be permanently forfeit. As far as the captive sailors and merchants were concerned, failing other instructions from the King and his Council, he was ‘avesyd, and all my feleschyp, to droune them and slee them’.
Whatever motivated Wenyngton’s attack on the neutral fleet, it triggered a major diplomatic crisis. The towns of the Hanseatic League whose ships had been seized were incensed at this unwarranted attack by a fleet sent to sea for their protection, particularly as the goods of the Dutch and Flemish merchants which had also been taken were speedily restored, leaving the Esterlings as sole victims. The High Master of the Teutonic Order, whose town of Danzig had accounted for 14 of the largest of the captured ships, immediately ordered the arrest of all English merchants and their goods within his territory, as did the duke of Burgundy.
Meanwhile, after a spell in the Isle of Wight, from where he wrote to Daniell on 25 May, Wenyngton may have attended the final session of the Parliament, held at Winchester for a month from 16 June. At home at Michaelmas he renewed an earlier settlement of his property on prominent trustees.
Before long, the unrest blew over, and far from being charged with his unwarranted attack on the Bay fleet, the only proceedings Wenyngton faced concerned private, and by comparison relatively minor, quarrels. Thus, a commission of oyer and terminer appointed in late July 1450 was instructed to investigate his earlier attack on a local gentleman, Walter Reynell* of Malston. Wenyngton was accused of assaulting and imprisoning Reynell at Dartmouth, refusing to set him free until he agreed in writing to cease all litigation against his captor and consented to arrange the release of one John Purchas, who was held prisoner by his associate John Lake. By the time of the appointment of the justices of oyer and terminer, Reynell had been liberated and himself headed a further commission charged with Wenyngton’s arrest.
In spite of his earlier association with Henry VI’s courtiers, Wenyngton seems to have switched his allegiances to the Yorkist cause with some dexterity. It is quite possible that he had done so as early as 1455, for he served as customs collector throughout the period of the duke of York’s second protectorate. Certainly, his subsequent support for the house of York was more than nominal, for in February 1462 Edward IV granted him an annuity of £10 from the customs of Exeter and Dartmouth ‘for good and unpaid service to his great contentment’.
