The earlier biography correctly distinguishes the careers of the MP and his more important namesake of Shavington in Shropshire,
Of the MP’s status as a lawyer, there can be no doubt. It is implied by the small payments made to him and several known lawyers by John Mowbray, duke of Norfolk, in the course of a legal action pending at Coventry in 1427-8;
Early in his career Chetwynd was involved in his family’s violent dispute with the Poultneys of Poultney in Leicestershire. On 2 Oct. 1411 he allegedly joined his older brother, Richard, and his brother-in-law, William Purefoy, in assaulting James, son of Sir John Poultney†, at Misterton. Thirteen months later the three assailants entered into a bond, in the massive sum of £1,000, to abide arbitration in the dispute, but the matter was not resolved for, early in the next reign, the Poultneys were implicated in an assault on our MP’s brother, Richard.
The death of Chetwynd’s uncle, Sir Philip Chetwynd, on 10 May 1444 promised to transform the prospects of himself and his issue. This transformation had been promised for some time, but had recently been threatened by Sir Philip’s second marriage to a woman many years his junior, namely Joan, daughter and coheiress-presumptive of William Burley I*. Not only did this give the knight renewed hope of issue, but, even if this hope was frustrated, provision made for Joan’s widowhood was likely to delay significantly the descent of part, perhaps a large part, of the inheritance to John Chetwynd or his issue. Her prospects as an heiress ensured that she could claim a generous settlement, and on 28 June 1442 the two principal manors of the Chetwynd patrimony, Ingestre and Grendon, were settled on her and her new husband.
Chetwynd must have viewed this development with dismay, and it is not surprising that frustration should have prompted him to wage a campaign against Joan in the wake of Sir Philip’s death. Immediately, he sued the executors for a chest containing charters, one of which, judging from a later action, was a deed of entail. He added to the pressure by bringing an assize of novel disseisin against her in respect of the manor of Grendon. Soon after, he resorted (or, at least, he was later accused of having done so) to more direct action: he is said to have broken into her closes and houses at Grendon, Ingestre and elsewhere in the summer and autumn of 1444.
If, however, Chetwynd’s task in undermining Joan’s rights was difficult in the immediate aftermath of Sir Philip’s death, it was soon to become very much more so. Late in 1444 or early in 1445 she protected herself by marrying Thomas Lyttleton, a well-connected apprentice-at-law who was later to enjoy a famous legal career. In Easter term 1445 Chetwynd set out the basis of his legal claim, suing an action of formedon against the new couple for the manor of Ingestre and other property in Staffordshire on the basis of an entail in tail-general upon his paternal grandparents, Philip and Alice Chetwynd. He also advanced an additional claim, asserting that the feoffees who had settled the jointure on Sir Philip and Joan did not have seisin. If either claim could be proved then Joan could have had her dower but not her jointure.
As it was, however, Chetwynd was soon forced on the legal defensive. Before the justices of assize at Warwick on 17 July 1447 the Lyttletons won damages and costs of £40 against him for his alleged entry into Grendon, and they sued further actions against him for other alleged entries in Staffordshire.
Chetwynd died while legal action was still pending. He last appears in the records at the end of Easter term 1450, as he vainly pursued an action of attaint against the jurors who had ruled against him in 1447, and he probably died before the next law term.