Nicholas’s father, Walter Chapman, expanded his property-holdings in Wootton Bassett by transactions completed in 1378 and 1389,
Wotton’s property qualification to represent Marlborough in Parliament consisted of a ‘barton’ he held there adjacent to the hall belonging to a putative kinsman, John Chapman. This was mentioned in a deed of June 1422, attested by Marlborough’s lord, Humphrey, duke of Gloucester.
From 1413 Wotton often appeared as an attorney at the assizes held at Salisbury, most notably on behalf of monastic houses in Wiltshire such as Bradenstoke priory and Malmesbury abbey,
Thereafter, Wotton was frequently engaged by Wiltshire litigants to be their spokesman in the common pleas, among them the bishops of Salisbury and Winchester, the abbot of Stanley and heads of the religious houses at Farleigh and Amesbury. In this capacity he remained active into the 1440s.
While busy on behalf of his clients, Wotton never neglected his own concerns, which focused on the steady accumulation of property. Some of this, situated in Somerset, came through his second marriage. His wife Isabel’s maternal ancestors, from the Braunche family, had held the manor of Frome-Faleise and the hundred of Frome, and although these particular holdings did not descend to her,
Wotton’s third wife brought him her dower and jointure from her previous marriage to Richard Pavele. He was quick to seize the opportunity presented by Pavele’s death: following the probate of Pavele’s will on 18 May 1430, he offered his services as proctor to the widowed Elizabeth so that she might be committed the administration of her late husband’s estate, and married her less than four months later. Together they occupied property on the south coast at Weymouth, but more importantly they held for Elizabeth’s lifetime the Pavele manor and advowson of Fairoak together with other lands in Somerset.
Throughout his career Wotton was a fierce litigant on his own account, bringing many suits against his debtors from Wiltshire and neighbouring counties, as well as pleas for trespass and under the statutes of labourers. These he continued to present in person at least until 1448.
In such suits Wotton was sometimes joined as plaintiffs by the feoffees he had put in possession of Westrop and Hampton, who included such prominent figures as Sir John Juyn j.c.p., Sir William Beauchamp* (the King’s carver), Walter Strickland I* and John Bird*, besides members of his family, Henry and John Wotton*. In November 1446 he obtained a royal licence for the surviving feoffees to put into effect a settlement of this manor whereby after his death it would pass to his daughter Elizabeth (the only child of his second marriage) and her issue, and his third part of Little Bedwyn and substantial holdings in Wootton Bassett further provided for her.
Agnes York died about that time. Her husband William was concerned about the legality of the settlement of Kingston Blount; he wanted Wotton’s feoffees to be examined by the chancellor to see if they knew of any ‘defaute, deseyt or mal engyne upon the makyng of the seides feoffement lees and remaynder or nay’.
