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,
Robert Waterton IV. In 1391 he was appointed Master Forester at Pontefract Castle, and in that year accompanied Bolingbroke to the siege of Vilnius. He was with Bolingbroke when he returned to Vilnius in the following year. From 1392 he received a yearly fee from Bolingbroke of £6 13s 4d, and in 1398 Bolingbroke granted him an additional annuity of 10 marks. In 1399 he was Steward and Constable at Pontefract, as well as Constable at Tickhill Castle and Castle Donnington, positions which 'made him a dominant figure in the West Riding of Yorkshire and in north Nottinghamshire'. He remained in these