Cary family Margaret Holleway, daughter and heiress of Robert Holleway. Sir John Cary's eldest son, Sir Robert Cary (died c. 1431) of Cockington, Devon, was 12 times MP for Devon. At some time after 1350 the Cary family acquired the manor of Cockington, in Devon, which they made their principal seat. Certainly according to Pole, Robert Cary held Cockington during the reign of King Henry IV (1399–1413). He was an esquire in the households of King Richard II (1377–1399) and of the latter's half-brother John Holland, 1st Duke of Exeter (c. 1352 – 1400). He married as his first wife Margaret Courtenay,
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