The Cheyne family had been established in Kent since the end of the thirteenth century, but acquired what would become their principal residence, Shurland on the Isle of Sheppey, by marriage in the early fourteenth century.
In 1441 John’s father died and, along with his mother, he served as executor of his will. By this stage he had already married Eleanor, the daughter and heiress of Sir Robert Shotesbrooke, the noted soldier and diplomat. The match had probably been made in 1439, as in November of that year property in Harbledown near Canterbury was settled on a group of feoffees, including Shotesbrooke and William Cheyne, to the use of John.
Cheyne’s other important connexion was with the Fiennes family, to whom he was related through his paternal grandmother, Margery Cralle.
His connexion with James Fiennes may explain Cheyne’s election to the Parliament of February 1449. The parliamentary representation of Kent during the 1440s was dominated by Fiennes, his kinsmen and friends, and on this occasion Cheyne was elected alongside Fiennes’s son-in-law, William Cromer*. Despite this, however, there is no evidence that Cheyne had been a partisan of Fiennes in the politics of the 1440s. He had not been present at any of the other Kentish elections during the 1440s, nor had he close links with any of the other men in Fiennes’s circle (with the exception of the Household man John Warner*).
An alternative explanation for Cheyne’s election to Parliament was his business and legal entanglements in London and Westminster. Around the time of his election he was a defendant in a debt case brought by a London goldsmith, John Wynne, in the court of common pleas. His election may have been motivated by the prospect of enjoying the parliamentary privilege of freedom from common law process. This suit eventually resulted in Cheyne being outlawed for his failure to appear and it was not until Michaelmas term 1449 that his outlawry was reversed.
It was undoubtedly Cheyne’s kinship by marriage with Edmund Beaufort, duke of Somerset, and his links with London that led to his appointment as victualler of Calais in 1451. He appears to have remained close to Somerset from then until the latter’s death at St. Albans in 1455, and in June 1453 he stood as surety when the duke received custody of the Warwick lands following the death of Anne, daughter and heir of Duke Henry.
The job of victualling Calais clearly accounted for most of Sir John’s time and energy during the 1450s. Although he continued to be appointed to ad-hoc commissions in Kent throughout the decade and remained on the bench, he does not appear to have attended the sessions of the peace after July 1452.
It was against this background of the difficult task of supplying Calais that Sir John was pricked sheriff of Kent on 4 Nov. 1454. Indeed, his shrievalty would see Calais matters come to the forefront at the parliamentary election over which he presided at Rochester in July 1455. On the 5th of that month the King’s council wrote to Cheyne warning him that ‘we be enfourmed there is besy labour made in sondry wises by certaine persones for þe chesyng of the said knightes’ and that the peaceful proceeding of the election was threatened. He was ordered to observe the statutes concerning parliamentary elections and report any malefactors to the council.
Like Clifton, by the mid 1450s Cheyne had proved himself an indispensable figure in the administration of Calais and Kent. Thus, he was not replaced when the earl of Warwick took custody of Calais and its fortresses in the summer of 1456. Nevertheless, he appears to have spent much of that year and the remainder of the 1450s in Kent, being appointed to numerous commissions and, in August 1457, being among those who led the mobilization of the county following the French raid on Sandwich. The following December he was among the commissioners appointed to assemble the archers granted as part of an innovative subsidy in the Parliament of 1453.
The following year saw the outbreak of open hostilities between the Crown and the Yorkist lords. On 12 Oct. 1459 the latter fled England in disarray after the desertion of Andrew Trollope’s contingent of soldiers from Calais at Ludford Bridge. The earls of Warwick, Salisbury and March retired to Calais, while York himself fled to Ireland. Cheyne remained in Kent and appears to have allied himself alongside his friends, Clifton, Kyriel and (Sir) Thomas Brown, with the Lancastrians. On 3 Dec. he was replaced as victualler of Calais by Nicholas Hussey, another man associated with the Lancastrian court, but no reasons for his replacement are apparent. A week later he was commissioned to muster the force that Lord Rivers was putting to sea at Sandwich to defend the Channel. On 15 Jan. 1460 a Yorkist force led by John Dynham and John Wenlock* raided Sandwich, reclaiming Warwick’s ships and capturing Rivers and his son. Cheyne, like Clifton, appears not to have been at Sandwich at this time (perhaps forewarned by news from his contacts in the Calais garrison), and the following day he was appointed to a commission of array in Canterbury, presumably a belated attempt to resist the invaders. Two months later he was named on a commission of oyer and terminer to hear indictments relating to the raid on Sandwich.
A possible explanation for Cheyne’s hesitation to commit fully to the Lancastrian cause may have been his links with the Scott family. By November 1457 he was mortgaging property to John Scott†, a kinsman of his, probably in order to meet debts incurred through the victualling of Calais, and around 1460 he and the other feoffees of the London draper, Thomas Winslow II*, settled property in Romney Marsh on Scott, John Fogg† and others.
Little evidence remains of Cheyne’s activities during the 1460s. It is possible that he divided his time between Kent and Berkshire, for it appears that his father-in-law had by then settled the Berkshire manors of Woodhay, Enborne and Compton on him and his wife. In the pardon of 1462 he was styled as ‘of Woodhay’ as well as of Eastchurch. Before he died he settled these Berkshire manors on one of his younger sons, John, who still held them at the time of his own death in 1499, and entails ensured that they continued in this junior line of the family.
Cheyne died on 20 June 1467. An inquisition post mortem held at Ospringe on the following 30 Oct. is now badly faded and the value of his lands in Kent, concentrated on the Isle of Sheppey and Romney Marsh but also including the manor of Bilsington near Ashford, is not known. The latter had been acquired by the grant of Joan, widow of Sir William Brenchelse, j.c.p., and her feoffees in 1453. Sir John’s heir was named as his second and eldest surviving son, William, then aged 27 (the eldest son, Roger, had predeceased him).
