Rochester Castle built during Henry III's reign were never repaired; it has been suggested this was because by the 14th century, when considerable sums were being spent on repairs elsewhere in the castle, Rochester had fallen out of favour as a royal residence. As the castle's importance as a high-status residence waned, its role as a barracks and administrative centre came to the fore. The reign of Richard II (1377–1400) saw the investment of £500 in repairing the castle. This was in part in response to French raids on England's southern coast during the Hundred Years' War as England's fortunes in the
Hugh Waterton of Eaton Tregoz near Ross-on-Wye in Herefordshire, which by an inquisition taken after his death was found to contain castle buildings and a deer park of 144 acres. By 1377 he was one of Gaunt's retainers, and in 1399 an executor of his will. From the late 1370s he was also associated with Gaunt's son, Henry Bolingbroke, the future Henry IV, becoming a Privy Councillor and by 1386 was Bolingbroke's chamberlain. On 10 July 1386 he was among those who gave evidence in the celebrated case between Richard le Scrope, 1st Baron Scrope of Bolton, and Sir Robert Grosvernor as