[3] His paternal grandparents were William Drury (d. 1558) and Elizabeth (d. 19 May 1575), daughter and co-heiress of Henry Sothel, Esquire, Attorney General to Henry VII[4] of Stoke Faston, Leicestershire, and Joan Empson, daughter of Sir Richard Empson.

He succeeded his father, Robert, in 1557 and his grandfather, Sir William Drury, in 1558, inheriting considerable land in Suffolk, including Hawstead Place, where in 1578 he entertained Queen Elizabeth I.

In 1581 he was elected MP for Castle Rising, Norfolk, in a by-election caused by the illness of Edward Flowerdew.

By 1588, through the influence of Lord Willoughby, then in command of English forces in the Low Countries, Drury had been appointed Governor of Bergen-op-Zoom in the Netherlands, which was threatened by the Spanish.

After being replaced as Governor by Thomas Morgan, a more experienced soldier, he was sent as colonel over 1000 men under Lord Willoughby to the assistance of Henry IV of France.