The family of Chertsey had been settled at Broxbourne in Hertfordshire since the late thirteenth century, and the manor of ‘Baas’ there descended to our MP’s father John.
What prompted Chertsey to move away from Hertfordshire in the early 1430s to live in Kent is unclear, although family financial difficulties may have been the cause. It is possible that he was drawn to Rochester through an undocumented kinship with Thomas Chertsey† (fl.1433), the ostler who had represented the city in Parliament in 1406 and 1410.
Having settled in Kent, Chertsey established himself in Rochester, where in October 1440 he was elected bailiff. The manner of his election and his activities during his official year are obscure, although during his term of office in June 1441 he was appointed to a royal commission to investigate the capture by two English-owned ships of a Breton vessel laden with a valuable cargo of wine and salt. His fellow citizens engaged his services in their property transactions. After the end of his bailiffship he was party to a grant to Thomas Cotyng* of five tenements in St. Clement’s parish, of which he, John Potager* and Thomas Glover had been enfeoffed.
By this time Chertsey’s first wife had died, and in 1443 he and his second wife formally relinquished possession of some of the lands and rents in Woolwich and elsewhere which Edith had brought him.
Although Chertsey’s association with Slegge was a close one, he does not seem to have been implicated to any great extent in the kind of misdemeanors that brought Slegge notoriety in 1450 during his term as sheriff of Kent and member of the circle around James Fiennes*, Lord Saye and Sele. Even so, Chertsey thought it prudent to purchase two pardons on 7 July 1450, just a few days after Fiennes had been put to death by Cade’s rebels. In one of these pardons he was called ‘of Headcorn’, in the other ‘of Rochester’.
In the late 1450s Chertsey continued to be involved in the affairs of Rochester bridge, and in 1456-7 he was appointed as one of the auditors of the bridge wardens’ accounts. The following year he was paid by the wardens for his expenses attending upon their business.
Chertsey’s status within Kent apparently rose under the new regime. In May 1461 he was appointed to a commission of array for the county, the first such appointment of his career. His professional association with Rochester bridge probably continued to the end of his life. In 1463-4 he was again appointed to audit the wardens’ accounts; by 1468-9 he was a member of the bridge council, the governing body which administered its extensive estates in Kent and London; and in 1466 and again in 1469-70 the wardens made extraordinary payments in return for Chertsey’s advice on specific legal matters.
Chertsey made his will on 25 Mar. 1474. He asked to be buried in St. Andrew’s cathedral, Rochester, next to his first wife. There, his executors were to erect ‘a convenient stone of marble with a Remembraunce of Imagey thereon’ of himself, his late wife, his current wife and all their children. The prior and monks of Rochester cathedral priory were left money to provide for his soul. Chertsey also left 6s. 8d. for the ‘payntyng’ of the shrine of St. William of Perth within the cathedral, as well as a bequest to the local hospital of St. Bartholomew. The remaining bequests were to his descendants and sons-in-law. To Elizabeth Bamme, his eldest daughter, he left five marks and his ‘Book of the Pater Noster’, and to her son Edmund (his godson and grandson) 20s. and his grammar books; while to his youngest daughter, also called Elizabeth, and to his younger son, Andrew, he left £20 and £10 respectively for their marriages on condition that they would be ‘guyded and governed’ by his widow. To one son-in-law, John Bamme, he left five marks and his ‘litle fair boke of oold statutes’, while his bequests to the other, the goldsmith Richard Massy (husband of his daughter Marion), were less straightforward. He noted that Massy had already received £20 as a marriage portion, and now left him 20 marks more. Finally, he appointed his wife, son William and sons-in-law Bamme and Massy as his executors. Chertsey was dead by the following 8 June when probate was granted.
Before too long the executors fell out. Massy petitioned the chancellor to complain that although Chertsey had promised him 50 marks on his marriage to Marion of which 20 marks was still outstanding, his co-executors refused to pay him. In their defence they claimed that Chertsey’s bequest had been conditional on Massy entering recognizance to leave Marion double the amount she brought him to the marriage if she outlived him.
