A lawyer and ‘gentleman’,
Denys began his career as an office-holder at Ipswich at the end of the 1420s. Appointed a j.p. in February 1428, in the following year he was one of the portmen who helped to make ordinances for the borough. In early 1431, he sat as an MP for the first time, and later that year he became treasurer of Ipswich, an office that he still held when elected to his second Parliament. He served at least nine terms as a bailiff of the borough, during the third of which he and his co-bailiff, John Caldwell*, were featured in a Chancery suit brought by Robert Smith, a local merchant. This concerned a debt of £9 13s. 4d. that John Smith, an Ipswich vintner, claimed from Robert in the borough court. Robert alleged that the debt was not his responsibility, since it arose from a tun of wine that Denys and Caldwell had sent him to John to buy.
Although busy at Ipswich, Denys pursued a parallel career at Westminster. By the early 1420s, he was acting as an attorney and surety in the court of common pleas, where he was still an attorney well over two decades later. Probably the most important of all of his clients was William de la Pole, earl of Suffolk, for whom he was attorney in several common pleas suits of the 1440s. In one of these cases, which came to pleading in Michaelmas term 1442, the earl succeeded in winning damages from John Jenney and his sons, William* and John*, for breaking into his warren at Benhall and ‘Blykkyng’ in east Suffolk. From time to time, Denys was himself a litigant in the same court, in connexion with debts others had contracted with him.
Not surprisingly for a lawyer, Denys was frequently a feoffee in Ipswich and elsewhere in Suffolk, and acted as such in a number of settlements concerning property at Harwich as well. One of those with whom he was associated as a feoffee was William Debenham, the man for whom he had stood mainpernor early in his career.
Denys was himself a landowner of some substance. Near Ipswich he possessed lands at Whitton and a manor in Sproughton and Bramford (probably acquired in the late 1430s), and by his death he also held two properties located further afield, the manor of ‘Ramsholthall’ in Ramsholt and the moiety of another manor at Whatfield.
Denys displayed his trust in Felawe by appointing him one of his executors. He died during his ninth term as bailiff of Ipswich, in the spring of 1464 and, on 12 Apr. that year, John Walworth† took over from him for the remainder of that term. In his will, made in the summer of 1460, Denys asked to be buried in the parish church of St. Margaret, near the sepulchre of his second wife, Ellen. He presented a cope to the same church, as well as 20s. towards its upkeep, in return for prayers for the souls of himself and his parents, and he left 40s. to each of the houses of the Dominicans, Franciscans and Carmelites in Ipswich. He also provided for three chaplains to sing in St. Margaret’s for three years, for the benefit of the souls of himself, Ellen and Joan, his first wife, and he requested prayers from the Austin nunnery at Campsea Ash, to whose prioress he left 6s. 8d. and to each of its nuns 40d. To his third and surviving wife, Margery, he awarded a life interest in his chief messuage and two closes in the borough, with remainder to his daughter, Elizabeth, when she attained her majority. He also directed that Margery should receive for life an annual pension of 16 marks, charged upon the issues of lands he held in the parishes of St. Mary at the Tower and St. Laurence, as well as £20 of money from his chest and various other items, including silver plate and half of all his household goods and utensils. He was largely even-handed towards his children, possibly because they had not all been born to the one wife. His son and heir, Thomas (like his daughter, still a minor), was to have his manorial properties in Ramsholt and Whatfield and a messuage in St. Mary at the Quay, when he reached his majority, but his manor in Sproughton and Bramford was destined for Elizabeth. He left property in St. Mary at the Tower and St. Laurence to another son, William, to take possession after Margery had died and he had come of age. Denys also provided for his bastard son, Henry, directing that he should have another messuage in St. Mary at the Quay if he attained his majority.
Apart from Richard Felawe, Denys appointed another Ipswich burgess, John Drayll, to act as his executor. In the event, Drayll did not long survive him,
