Oliver was a kinsman, perhaps nephew, of the wealthy Bridport merchant William Mountfort*, whose property he inherited and to whom he referred in his will as ‘my master’. He appeared in 1433 with his father as a feoffee of Mountfort’s land in Southtown Dartmouth in Devon, of which they were confirmed in possession two years later by Sir Humphrey Stafford*, Sir William Bonville* and others. Further transactions established William Oliver as Mountfort’s principal heir, not only to this estate, but also to his considerable holdings in Dorset. These, although concentrated on Bridport, also included several properties situated on the coast at Weymouth, Melcombe, Smallmouth and Wyke,
To his Mountfort inheritance Oliver added yet more property in Bridport, for instance acquiring a tenement in West Street from the widow and son of Philip Brice† in 1440. Five years later the cofferers and wardens of lands belonging to the town demised to him, his wife and their son John for term of their lives a house in ‘Kyllyngeslane’, and at the same time he purchased land there known as ‘Mortehay’. To these holdings he subsequently added more buildings in East Street and West Street.
While his inheritance from Mountfort is well documented, there is no evidence to date precisely when William came into his patrimony in Devon, although it is clear from the claims later made by his daughters that he was the main heir to Thomas Oliver’s property. Even so, it was in Bridport that he made his career, initially as an apprentice to Mountfort, who had prospered through supplying the King’s ships with cordage. A few surviving bonds, given to Oliver by men of Bridport and Somerset, a merchant of St. Germans, Cornwall, and the widow of Robert Wenyngton* of Dartmouth, provide only a hint of the extent of his trading activities.
Oliver’s private transactions reveal that, like his father, who had once asked the duke of Bedford to be a trustee of his land, he too established contacts with magnates, albeit these relations were not necessarily amicable. In 1439, not long after he inherited the landed possessions of William Mountfort, his title to a messuage and land in Wyke Regis and a moiety of the ferry of Smallmouth was challenged by one of the most powerful landowners in the region, Richard, duke of York. On 6 June that year he and two friends were bound in £40 to abide by the award of four of the duke’s legal counsel. The outcome is not clear, but a later deed (now damaged) shows that in the mid 1440s he placed the same disputed properties in the hands of none other than William de la Pole, marquess of Suffolk, Ralph, Lord Sudeley, then treasurer of England, and other feoffees including Sir James Butler, afterwards earl of Wiltshire. There seems little doubt that he was seeking their protection against the claims of the duke.
In the last year of his life Oliver was in receipt of an annual fee of 20s. for his services as receiver of John Newburgh’s manor of Bradpole, so he evidently remained busy to the end. Throughout his career he had been actively involved in the affairs of the various fraternities in St. Mary’s church in Bridport, of which he and his wife were members, and he frequently provided pledges for newly-appointed wardens.
Oliver’s daughters had trouble obtaining the land which their father had purchased from John Bettiscombe, since, as a suit in Chancery in 1482 showed, the aged Bettiscombe had enfeoffed his son Robert in the property to hold to the use of Oliver and his heirs and to complete the sale, but Robert refused to relinquish possession. In reaching a decision favourable to the women the chancellor relied on testimony provided by Richard Pylle, Oliver’s servant of over 40 years’ standing, who understood that a marriage had been proposed between Bettiscombe’s son John and one of them. Further testimony was added by Richard Bulle, a merchant from Winchester who by that date had married Oliver’s widow. Bulle said she had told him that Oliver had paid £32 for the disputed land, as well as giving Christine Bettiscombe her annuity; and it was also reported that Oliver had paid £20 to the abbot of Cerne to whom Bettiscombe had mortgaged the property.
