Of obscure parentage, Hilling came from a family of limited means and standing, and was for much of his career styled a mere yeoman.
In spite of his apparently modest status, by the early 1440s Hilling was of sufficient status to be included among the local men commissioned to investigate an act of piracy off the Devon coast. It is probable that he owed this appointment at least in part to an aristocratic patron, Thomas Courtenay, earl of Devon, lord of the borough of Plympton Erle where Hilling resided by this date.
If it had been the earl of Devon’s intention in packing Parliament to strengthen opposition to the court circle and above all to Henry VI’s chief minister, William de la Pole, duke of Suffolk, he was only partially successful. While de la Pole was impeached, exiled, and ultimately murdered, Courtenay’s grievances against his regional rival William, Lord Bonville*, and his ally, the newly-minted earl of Wiltshire, remained unaddressed. Courtenay thus withdrew to the south-west to plot other ways of settling his personal scores. In the autumn of 1451 he led an army into Somerset and Wiltshire and laid siege to Bonville in Taunton castle, until persuaded to withdraw by the duke of York. Early in the following year, Courtenay was once more on the move, this time evidently with York’s full acquiescence. By the beginning of February he had once again gathered his armed retainers and marched eastwards, while his supporters staged uprisings in several Devon towns, including Plympton Erle. In the event, at Dartford York allowed himself to be duped by the blandishments of the lords about the King, now led by the duke of Somerset. York’s leading allies were placed under arrest and the rising collapsed. Yet, while the leaders were held in captivity for some time, their more junior supporters were allowed to purchase royal pardons. Among those who did so later in 1452 was Hilling, whose part in the events of 1451-2 is otherwise obscure.
It seems, however, that he learnt his lesson, for there is no evidence to suggest that he took any part in the fresh violence stirred up by the Courtenays in 1454-5, unless the charges of robbery that his old enemy Uglowe brought against him and a group of associates in the autumn of 1455 were in some way connected with the disorder fomented by the earl’s sabre rattling at that time.
In the interim, there were other disputes. In 1456 Hilling sued a local blacksmith for his negligence in trying to cure one of his horses which had resulted in the animal’s death.
Perhaps on account of his longstanding service to the Courtenays, Hilling secured no further Crown office after Edward IV’s accession, although he was occasionally empanelled on local juries.
By the mid 1470s Hilling had apparently moved into the city of Exeter’s extramural parish of St. Sidwell.
