Hugh Denys of Osterley (c. 1440 – 1511) was a courtier of Kings Henry VII and of the young Henry VIII. As Groom of the Stool to Henry VII, he was one of the King's closest courtiers, his role developing into one of administering the Privy Chamber, a department in control of the royal finances which during Denys's tenure of office also gained control over national fiscal policy. Denys was thus a vital player in facilitating the first Tudor king's controversial fiscal policies.
Denys was probably born at Olveston Court, Gloucestershire, c. 1440, the second son of Maurice Denys (d. 1466), Lord of the Manor of Alveston and Earthcott Green, Gloucestershire. His mother was Maurice's second wife, Alice Poyntz, daughter of Nicholas Poyntz of Iron Acton, Gloucestershire. The Denys family, formerly of Waterton, Bridgend in Coity Lordship, Glamorgan, had become established in Gloucestershire in 1380, on the marriage of Hugh's grandfather Sir Gilbert Denys(d. 1422) to Margaret Corbet, heiress of her brother William (d. 1377) to the Gloucestershire manors of Siston, Alveston, and Earthcott Green, together with the Hundred Court of Langley, as well as to Hope-juxta-Caus, Salop, and Lawrenny, Pembroke. That Hugh was a second son is suggested by his use of a crescent as a mark of difference in his armorials. The Heraldic Visitation of the Co. of Glos. of 1623, on the other hand, shows him as the third son.
Denys married very advantageously to Mary Ros (or Roos), the daughter and only child of Richard Ros(1429–1492), younger son of Thomas de Ros, 9th Baron de Ros (1406–1430), of Hamlake Castle, Helmsley in North Yorkshire. The latter had drowned in the River Seine while on campaign in France. Richard's mother was Eleanor Beauchamp (1407–1466), daughter of Richard de Beauchamp, 13th Earl of Warwick and Elizabeth Berkeley, daughter of Thomas 5th. Lord Berkeley. Mary's brother Thomas de Ros, 10th Baron de Ros (1427–1464) of Hamlake married Philippa de Tiptoft, sister of John Tiptoft, 1st Earl of Worcester and Constable of England to King Edward IV. Thomas de Ros, Denys's brother-in-law was an ardent Lancastrian and was attainted in 1461, and beheaded at Newcastle in 1464. Mary's aunt was Margaret de Ros who married firstly (c. 1452) William Lord Bottreux (d. 1462) of North Cadbury, Somerset. She married secondly in 1463 Sir Thomas Borough of Gainsborough, Lincolnshire. Because Margaret's mother Eleanor Beauchamp had married secondly Edmund Beaufort, 2nd Duke of Somerset, Margaret's stepbrother became Henry Beaufort, 3rd Duke of Somerset, Captain of the King's Body Guard in about 1463. In 1464 he changed sides, again, back to the Lancastrians, and was beheaded at the Battle of Hexham in 1464. Margaret's second husband Sir Thomas Borough was on the victorious Yorkist side at Hexham so possibly witnessed the beheading of his wife's stepbrother. At Denys's death Mary had borne him no children, and Mary went on to marry again, Sir Giles Capel. Mary's sister Eleanor Ros (1449–1487) married in 1469 Sir Robert Manners, Admiral of England who fought for Richard III at the Battle of Bosworth, from which marriage descended the Dukes of Rutland who inherited Belvoir Castle in Rutland from the De Ros family via Eleanor. Mary's nephew Edmund de Ros, heir of her beheaded brother Thomas, was restored in his barony by Henry VII on his accession in 1485, and resided possibly quite close to the Denys's at Elsinges, Enfield, Middlesex.