Of the two John Cricklades active in Wiltshire in the period, it was on chronological grounds clearly the elder, the son of Thomas Cricklade, who represented two Wiltshire boroughs in the 1430s and 40s, rather than his younger namesake and nephew, the son of his brother Robert, who survived until 1470. Like Robert, John trained in the law, and the two men seem to have conducted a joint legal practice, frequently being named as alternative attorneys by litigants in the Westminster law-courts.
Although the Cricklades evidently spent much time at Westminster, they also maintained their position in their native part of Wiltshire. In the first 20 years of Henry VI’s reign a Cricklade sat in all but three Parliaments for either Calne or Cricklade, and between 1429 and 1435 John’s kinsmen Robert and William took both Calne seats. In 1433, the year of his own first return, John thus accompanied both of his relations to Westminster. Other local connexions are evident from an otherwise obscure dispute with the Calne mercer Thomas Harryes over a debt of 60s. at some point before 1443,
The extent of John’s own landholdings is difficult to gauge. It is clear that at various times in his life he acquired holdings in several parts of Wiltshire, but his evident industry in seeking to augment them by exchange, purchase and less salubrious methods makes it hard to be certain as to what he possessed at any one time. Thus, in February 1461 he exchanged an annuity of 13s. 4d. with the London merchant William York for pasture rights in ‘Pynellys’ and ‘Wodelond’ in Calne,
As a younger son, Cricklade had no certain expectations of succeeding to any of the family lands, but it seems that the premature death of his brother Robert, which left his nephew and namesake a minor, changed this. Robert had possibly predeceased their father, but was certainly survived by their mother, Alice, from whom the younger Cricklades derived the majority of their titles, until at least 1456. When she died, the heir, whose upbringing had been entrusted to the prior of Bradenstoke, was still under age, and his uncle, the elder John, headed the feoffees of his lands.
In the meantime, Cricklade had become entangled in a separate disagreement with the Berkshire landowner Thomas Beke* over holdings at Foxham, in the Wiltshire hundred of Chippenham. According to Beke’s version of events, he had enfeoffed Cricklade, along with Sambourne and another local esquire, John Mompeson*, of the property, with the intention that they should re-enfeoff him when required to do so. However, Cricklade had secured sole possession of the lands, had taken eight years’ worth of revenues, cut down and sold timber, and threatened Beke with death if he attempted to come near the property. Probably in connexion with the accusations of attempting to murder his nephew, Cricklade at this time found himself in the Fleet prison, but he eventually secured his acquittal of the charges brought by Beke through the good offices of the lawyer John Whittocksmead*, who gave evidence on his behalf.
The younger John Cricklade’s death in 1470 revived the struggle over his inheritance once more. Neither the childless elder John nor his sisters and their descendants were prepared to see their mother’s inheritance pass out of the family, and within a few years Edward Hungerford was back in Chancery to complain of the claim now staked by Cricklade in association with his sister Christine and his nephews Sambourne and Robert Warlond. At the same time, however, Hungerford evidently employed other means of persuasion, and in February 1472 commissioners headed by the royal justice William Lacon I* were appointed to investigate the offences he had committed against Cricklade.