Like many of Plymouth’s representatives in the early years after the port’s enfranchisement, Hill was apparently a local man. His early career is difficult to distinguish from those of several namesakes active in the south-west in the reign of Henry VI, but it is possible that he was the Thomas Hill who in October 1430 was serving on La Trinite of Exmouth when the ship took a merchant vessel from Guernsey on its voyage from Brittany to the island.
In 1435 Hill was first named as a member of a royal commission to inquire into an act of piracy, and he was to receive a small number of similar appointments during the first half of the 1440s. His experience of both trade and seafaring made him a valuable asset to the government and in May 1443 he was appointed to the more important post of controller of customs and subsidies in the ports of Plymouth and Fowey, although he held this office for only five months before he was replaced by the Exeter merchant John Salter I*. At the end of 1444, Hill suddenly disappeared from public life, and did not return from obscurity until his sole return to the Commons in early 1449. It is possible that this disappearance was connected with an acrimonious dispute with Thomas Pylkington, a former customs collector at Plymouth, over a debt of £40. This dispute had seen Hill outlawed in London’s court of husting in June 1447, and by the following summer he found himself in the Fleet prison. He was released on bail, and for some months proceedings dragged on without conclusion. Technically, Hill was still an outlaw, and it may have been to avoid fresh imprisonment that he sought election to Parliament. Proceedings did not come to a head until the late spring of 1451, but the apparently collusive pleas entered by the parties confused the judges to such a degree that they deferred judgement for several further law terms.
In the interim, Hill had also fallen foul of no less a man than Thomas Courtenay, earl of Devon, whose free warren near Plymouth he was said to have violated, helping himself to the hares, rabbits, pheasants and partridges.
Hill’s troubles go some way towards explaining his failure to rise to the top of Plymouth society and to attain the mayoralty of the town, as well as his exclusion from Crown office. Indeed, it is possible that his economic fortunes had taken a turn for the worse, for in the autumn of 1455, when the influential Thomas Calwodlegh* brought an action for trespass against Hill and the leading Plymouth merchant John Page before the justices of King’s bench, Hill was styled a mere yeoman.
Nothing further is known of Hill’s career, but it is likely that the John Hill who was appointed to a royal commission to seize stolen goods at Plymouth in 1463 was a descendant or other kinsman.
