The Hiltons of Swine belonged to a cadet branch of the baronial family of Hilton, and are known to have settled in Holderness by the early 13th century. One local historian has described them as being ‘hardly less powerful and magnificent than the stately tree from which [they] sprang’; and they certainly exercised considerable influence in the East Riding. Sir Robert Hilton the elder twice became sheriff of Yorkshire as well as sitting as a j.p. He married one of his daughters, Denise, to her kinsman, William, 5th Lord Hilton, thus strengthening the alliance which already existed between them, while for his eldest son, the subject of this biography, he chose a wife from one of the leading families in Holderness. Robert Hilton’s marriage to Joan, the daughter of Sir Robert Constable of Flamborough, followed several years after that of his other sister, Maud, to Constable’s second son, John (d.1407), and it brought the two families even closer together. It also enabled Robert to establish a valuable connexion with the important Lincolnshire landowner, (Sir) Thomas Cumberworth, whose sister, Katherine, was married to Sir Robert Constable’s son and heir, Sir Marmaduke (d.1404), and who remained on close terms with the Hiltons throughout his life. When Joan died, in 1432, she left Katherine one of her most treasured possessions, unum librum de Romanse incipientem cum Decem Preceptis Alembes.
Quite early on in his career, Robert Hilton became attached to Thomas Percy, earl of Worcester, who, in February 1397, granted him the marriage and wardship of the young (Sir) Brian Stapleton, together with a rent of £20 p.a. with which to support him. Since Sir Robert Hilton the elder had himself recently married Sir John Godard’s widow, Constance, it made sense to marry the youth to one of Godard’s daughters, who duly became his wife. Unlike his patron, Hilton proved to be a loyal and committed adherent of the Lancastrian regime; and after Percy’s execution and forfeiture for treason in 1403 the award was confirmed by Henry IV. As early as 3 Nov. 1399, he and his brother-in-law, John Constable of Halsham, had acted as attorneys for the King when the latter delivered an estate in Holderness to his second son, Thomas of Lancaster; and just four days later royal letters patent authorized payment of £32 p.a. from the wool custom at Hull to Hilton, who was then retained for life by King Henry as an esquire of the body. He succeeded his father in, or shortly before, January 1401, and within a matter of weeks a knighthood was conferred upon him.
Hilton appears to have confined his attention to the business of local government during this period, although in about 1408 he agreed to act as a trustee for his nephew, William Constable of Halsham; and shortly afterwards he performed a similar service for the above-mentioned Sir Thomas Cumberworth. Although his administrative experience had hitherto been confined to Yorkshire, he became sheriff of Lincolnshire in 1414, and two years later he was returned to Parliament for the first time by the electors there. His younger brother, Sir Godfrey, was also beginning to establish himself as a member of the county community, and in May 1416 Robert went surety for him at the Exchequer as farmer of the manor of ‘Swynford’ in Harlaston, which formed part of his young stepson’s inheritance. Godfrey’s marriage to a wealthy Lincolnshire heiress and his subsequent election as a Member of the first Parliament of 1421 may well have owed something to Sir Robert’s influence. The latter was also made a feoffee-to-uses of the extensive Lincolnshire estates of John Skipwith’s son, Thomas; but, even so, he remained chiefly active in the East Riding, and all of his four later appearances in the Lower House were as a Member for Yorkshire. It was there, too, that he served no less than three terms as sheriff, being responsible during the second for the reception of certain hostages surrendered by James I of Scotland.
Hilton drew up his will in March 1429, and died at some point before 22 Dec. 1431, when it was proved. He was still in receipt of his annuity as a knight of the body to Henry VI, and was buried with befitting pomp in the ornate family chapel in Swine church. He made bequests well in excess of £100, as well as remitting half the annual rent of each of his tenants. His widow, Joan, who was chief of his executors, died within the following year, leaving their two daughters, Elizabeth and Isabel, to share the family estates between them, although their uncle, Sir Godfrey, enjoyed a life interest in the manor of Swine, which was conveyed to him in 1432 by Humphrey, duke of Gloucester, one of the principal trustees. Joan Hilton was clearly a woman with literary tastes, for in addition to the book which she left to Katherine Cumberworth, she also bequeathed unum librum de Romanse de Septem Sages to her niece, Margaret Constable.