Nothing definite is known of Welywrought’s origins and parentage, but he probably descended from a family of this name who by the early years of the fifteenth century were tenants of the Holand earls of Huntingdon at Fremington.
The context for the suits brought against him that year by the Crown officials John Stopyndon and Robert Burton, and Richard Alrede, for debts of £100 and 100 marks respectively, has not been discovered,
Once the earl had been declared of age and had assumed his family’s traditional position in local society, the service to his noble master became central to Welywrought’s career. It was in his capacity as the earl’s steward that in 1439 he was called to give evidence in the dispute between Thomas Tremayne* and Nicholas Radford*, while three years later, in early 1442, he was one of the Courtenay retainers associated with the earl in the acquisition of the custody of the lands and heir of Sir William Bodrugan*, which in the event proved unprofitable.
Unquestionably, Welywrought’s return to the Parliament of November 1449 for the borough of Plymouth alongside another Courtenay servant, John Brigham*, was part of the earl’s deliberate policy to maximize the number of his supporters in the Commons. The sharply deteriorating military position of the English in Normandy had exacerbated the criticism of the policies of the King’s chief minister William de la Pole, duke of Suffolk, and Earl Thomas would before long align himself with the administration’s principal critic, Richard, duke of York. In addition, however, the earl also had a personal grievance: his regional rival Sir William Bonville* enjoyed the favour of the court, and in the spring of 1449 had been summoned to sit among the Lords as Baron Bonville of Shute. Whatever Courtenay’s plans for the meeting of Parliament were, he evidently made some effort to have his retainers returned to the Commons. The two Plymouth Members aside, the earl’s men took one each of the two seats for Totnes, Plympton Erle, Bodmin and Exeter, while the earl’s cousin, Sir Hugh Courtenay*, was returned as a knight of the shire for Cornwall and his servant Edward Potte* was elected at Truro.
In the autumn of 1451, the earl decided to settle his score with Bonville by violent means, and marched his armed retainers into Somerset and Wiltshire, before being made to retire by the duke of York’s intervention. Nevertheless, early in the following year Courtenay’s men were once more up in arms, and on this occasion the earl of Devon joined with York in his ill-fated attempt to force the King to dismiss the duke of Somerset as his principal minister, which resulted in the arrest of both magnates at Dartford in February 1452. It is not clear exactly what part Welywrought played in his master’s machinations, but he was outlawed and proceedings against him continued for some months, before he was able to plead the general pardon he sued out in August 1453.
It may be that the difficulties and delay in clearing his name had a salutary effect on Welywrought, who is not known to have participated in the fresh campaign of violence unleashed by the earl of Devon in the autumn of 1455. Although he was still associated with members of the Courtenay circle, he was increasingly kept busy in the London law courts, and by the summer of that year he was styling himself ‘of London’.
Rather less is known of Welywrought’s private affairs. In the autumn of 1435 he had become embroiled in a dispute between Richard Fortescue and John Serle alias Silverlock* over property in Plympton Erle that had formerly belonged to John Brackley†. Welywrought took Serle’s side in the disagreement, which in the summer of 1438 was submitted to the arbitration of John Fortescue* (Richard’s brother) and Walter Burell, but in spite of the potential conflict of interest that this choice of arbiters suggested, it was evidently Fortescue who refused to abide by the award made.
On 3 Feb. 1458 Earl Thomas died at Abingdon, aged just 44. It may be indicative of Welywrought’s sudden lack of a protector that (alongside another Courtenay servant) he immediately set about procuring a general pardon, which was granted on 24 May. Nevertheless he seems to have remained in the service of the earl’s son and heir, the murderer of the prominent lawyer Nicholas Radford, for in October 1460 he was among the jurors taking an inquisition post mortem at Tiverton, the earl’s seat.