Hill’s career is difficult to distinguish from that of a number of namesakes. It does, however, seem likely that the man who represented Totnes in 1431 was a merchant with trading interests and connexions throughout Devon. He was ordinarily resident at Dartmouth, where he owned extensive property, including seven messuages and 20½ acres of land, both in the town and at nearby Totnes, which he settled on feoffees in 1422.2 CP25(1)/45/79/2. Six years earlier, in 1416, he had been in dispute over some of these holdings with John atte Worthy, an influential Totnes burgess.3 JUST1/1531, rot. 14.
The wealth which he acquired both from these holdings and through his mercantile enterprises, along with the standing this prosperity brought him, was probably instrumental in securing his return to the Commons. Yet, on occasion Hill fell foul of the law. In 1415 he had deemed it necessary to take the precaution of procuring a royal pardon,4 C67/37, m. 32. and ten years later he found himself summoned into the court of common pleas under an accusation of having some years previously assaulted Joan, the wife of the Dartmouth merchant Thomas Bukke. Ultimately, the case was determined before the Devon assize justices who found Hill guilty and condemned him to pay damages of £10. It is not clear whether Hill ever paid the sum, for the royal justices at Westminster resolved to verify the original judgement and proceedings continued.5 CP40/658, rot. 480.