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,
Gilbert Denys William Dennis in 1701, last of the male line. Following Gaunt's death in 1399, Denys joined the retinue of Edmund, Earl of Stafford(d.1403), and probably fought with the Earl in Henry IV's campaign against the Scots in 1400. In 1403 he was appointed by the King as constable of the late Earl of Stafford's Newport Castle, Monmouth, in charge of 80 archers and 40 lances, specifically to resist the rebellion of Glendower. Having been discouraged from attacking nearby Chepstow Castle, a far larger fortification, Glendower turned his force on Newport, which Denys's force was clearly unable to resist, for the