Drury was almost certainly a local man, related to the namesake, John Drury, esquire, who witnessed a deed at Sandwich in 1417. He was perhaps the son of the Portsman Henry Drury, who in 1421 claimed exemption from the parliamentary subsidy in Eastry hundred,
It was not until December 1435, when he was first chosen to the ranks of the jurats, that Drury appeared in the Sandwich records. Thereafter he was a permanent feature among the town’s governing elite. Drury quickly made an impression in the town and within three years of his first election he was a chosen as one of the keepers of the keys to the common chest, as well as being a candidate for the mayoralty. On 12 Dec. 1438 he attended his first meeting of the Brodhull, a duty he repeated on six other occasions before his first mayoralty, and in July 1439 he was chosen as one of the Ports’ bailiffs to the annual Yarmouth herring fair.
It is not clear whether Drury actively sought the mayoralty of Sandwich, although his name was put forward as one of the three candidates from whom the jurats made their choice on more occasions than any of his colleagues. He was an unsuccessful candidate in 1443 and 1445, but meanwhile, in May 1445, he was one of the four barons of the Port chosen to carry the canopy at the coronation of Queen Margaret.
On 6 Dec. 1456 Drury was once again chosen as mayor, and as such he travelled to another meeting of the Brodhull eight days later.
Little more evidence survives of Drury’s private affairs. He was a resident of St. Peter’s parish, while his property outside of the town allowed him to claim gentle status and he was styled as such in proceedings before the Westminster law courts.
