Oliver first comes to notice in May 1395, when he was attempting to recover a debt of £32 which had been promised to him in the previous year by a London apothecary. He had by this date set up in business as a grocer in the City, and was an active member of the Grocers’ Company for at least 30 years.
Oliver’s involvement in the affairs of John Chichele, the spendthrift son of his close friend, William Chichele, and the nephew of Henry Chichele, archbishop of Canterbury, shows how rich he had become in his later years. The grocer initially undertook to act as a surety for John, who was deeply in debt, but in 1417 he settled with Chichele’s creditors himself, on the understanding that the young man would reimburse him within the year. The archbishop then persuaded Oliver to wait longer for part of the money because of ‘the grete poverte that the same John Chicheley was yn’: a deficit of £300 remained unpaid during Oliver’s lifetime and it was left to the widow of one of his executors to sue for redress in the court of Chancery. She alleged that although Chichele had been advanced over £880 by the grocer, and had, moreover, been released by him from all forms of legal action, he on his part had persistently ignored his obligations despite a marked improvement in his financial circumstances. The outcome of the case is not known, but other evidence confirms that by September 1418 Oliver had indeed paid out at least £438 on Chichele’s behalf. Meanwhile, in June 1417, he advanced £20 towards the cost of Henry V’s second expedition to France. The loan, repayment of which was eventually assigned to him as a charge upon the wool subsidy to be collected after February 1420, places him among the wealthier citizens of London.
A substantial part of Oliver’s wealth was invested in property. According to the lay subsidy return of 1412, his holdings in the City brought him over £6 a year, an income far below that which he came to enjoy over the next decade. Shortly after the return was made, he purchased a tenement, four shops and annual rents of 64s. in the parish of All Hallows, Bread Street. By December 1414 the prior of St. Bartholomew’s hospital had leased to him certain cottages and gardens in the parish of All Hallows, London Wall, but no rent was actually paid until 1418, when Oliver settled his arrears. From the very beginning of the century, if not before, the MP seems to have lived in Bucklersbury, and it was here that he made his next significant acquisition. In November 1421 he took possession of a tenement called The Sarysenshede to the north of his own home in the City, together with two shops in the parish of St. Mary Woolchurch and other premises in the Walbrook which were rented out for a term of years by the prioress of Clerkenwell. All this property had previously belonged to Robert Chichele, who had settled it upon him as a feoffee at an earlier date. References to Oliver as the new owner confirm, however, that the conveyance of 1421 was in no way collusive, and there is, in fact, a distinct possibility that Chichele had either entered a mortgage on behalf of his impecunious son, or else had sold part of his estate outright to raise money for him. At all events, six years later, in February 1427, Oliver and two other grocers obtained seisin of a hostelry known as The Lambe and the Escheker on the Hope in the parish of All Hallows, Staining, being promised security of tenure by the mercer, Thomas Palmer, under substantial guarantees of £80.
Although he never held civic office, Oliver was clearly respected by his fellow Londoners. He often acted as a feoffee — on many occasions with the grocers Thomas Knolles, William Mitchell and Robert Chichele.
Oliver died between 19 Dec. 1432 and 8 Feb. 1433 and was buried in the church of St. Thomas Acon. He had promised some years before to settle certain property upon the church for the upkeep of a chantry and the maintenance of a boy chorister. Provision was made for this in the first of his two wills, but nothing appears to have been done about it, and the bequest became a matter for litigation. The mercer, Henry Frowyk, left money for the education and support of ‘Olivere’s Querester’ in 1453, so the grocer’s wishes appear finally to have been fulfilled. There were no children to inherit Oliver’s considerable estate: his second wife, Margaret, received 500 marks and most of his effects, while his other bequests came to more than £80.
