William Chester’s father, himself the son of a prominent burgess who died in 1471, served as bailiff and sheriff of Bristol. Chester became a whittawer and pointmaker, but his wealth—his goods were assessed at £90 for the subsidies of the period—suggests that, like his 15th-century ancestors and his own sons, he traded overseas. He converted three houses in the Broadmead into a residence abutting on to the Dominican Friary. This property he extended in 1540 by purchasing the site of the Friary, part of which he made into a bowling alley. In 1557 he acquired two tenements and land in Rodford in Westerleigh, nine miles from Bristol, at the same time that John Roberts, his son-in-law, purchased the manor.3Waters, 2-11; E. M. Carus-Wilson, Overseas Trade of Bristol (Bristol Rec. Soc. vii), 209; Bristol Wills (Bristol and Glos. Arch. Soc. xxiv), 203-4; APC, v. 358; Cal. Bristol Apprentice Bk. i. (Bristol and Glos. Arch. Soc. xxiv), 203-4; APC, v. 358; Cal. Bristol Apprentice Bk. i. (Bristol Rec. Soc. xiv), 146; E179/114/192, 205; LP Hen. VIII, xiii, xv; CPR, 1557-8, p. 332.
From May 1529,when Chester defended the town before the council in the marches, his name occurs frequently in the corporation records and numerous payments were made to him for visits to London. He took a prominent part in religious affairs at Bristol to the extent of being accused by reformers in 1539 as a ‘double knave’, sometimes with them and sometimes against them. Ten years later his labours were said to have quenched the disturbances following the first Act of Uniformity (2 and 3 Edw. VI, c.1) and to have secured pardon for citizens guilty of riot. Whatever his religious outlook it was as a leading citizen that he was elected to the Parliament of 1555; his role as a go-between with (Sir) Anthony Kingston and the corporation may have influenced his return. During the Parliament, Henry Sandyford, attached for a trespass in London, claimed privilege as his servant.4LP Hen. VIII, xii, xiv; Bristol AO, 04026/2/303, 6/40; 04027/52 p. 2 insert; CJ, i. 45.
Chester’s will is dated 2 Sept. 1558, only two days before his death. He left to the church of St. James, where he wished to be buried, a chasuble of green velvet and a cloth of tissue. His charitable bequests were few: an annuity for six poor people in the alms-house founded by a 15th-century kinsman and 40s.for the highways towards Westerleigh. Chester’s five houses in Bristol were left to his wife Maud for life. He bequeathed among his children a rich collection of gold and silver plate including standing cups, spice dishes, ale cups, and a nest of goblets. His heir was his son James, aged more than 30, who died in 1560.5PCC Chaynay; C142/128/99; Bristol and Glos. Arch. Soc. Trans. lx. 157-8.