Of high social status and impressive connexions, Cokesey was the last in the male line of an old Worcestershire family. The Cokeseys had held two of their manors in the county, those of Great Cokesey (from which they took their name) and Great Witley, since the mid thirteenth century and another, at Alderminster, since the later 1200s. By the fifteenth century, their main residence was the manor of Caldwall in Kidderminster, Cokesey’s birthplace, although they also held extensive estates elsewhere. Cokesey enjoyed a far fuller career than did his father, Walter, who succeeded his own father and namesake, Sir Walter Cokesey†, in 1405, but died aged just 23 in August 1407. In May 1409, the Crown acknowledged the right of Walter’s widow Maud to hold the manor of Lee in Lincolnshire and a moiety of that of Weston Turville in Buckinghamshire for her jointure. By that date she had found a new husband in John Phelip†, a household esquire of the prince of Wales. She died some time before September 1414 when the Crown granted Phelip, by then a knight, custody of the manor of Bickley and Shocklach in Cheshire, a property that she had held in dower. After Phelip died at the siege of Harfleur a year later, the manor passed into the hands of his executors for the duration of his stepson’s minority.
At his father’s death, Cokesey was a little over two years old.
By then George Brewes was no longer alive, for he had died at the end of December 1418. In the following April the King committed the keeping of the Brewes manors of Chesworth and Sedge Wick in Sussex to the late Sir John Phelip’s elder brother and executor, Sir William Phelip†, and others to hold until Hugh came of age. The grant was a matter of some controversy, because in 1422 two feoffees of the manors, Nicholas Carew† and the clerk John Bromsgrove, challenged it in a petition to the Crown. No doubt, Carew and Bromsgrove were not acting in Hugh’s interests, since by then he himself was already in dispute with Bromsgrove. In Michaelmas term 1421 a suit that the lawyer John Forthey* had brought on behalf of the still under age Cokesey came to pleadings in the court of common pleas. Forthey accused Bromsgrove of detaining a pyx containing charters and other documents relating to the Brewes lands, but Bromsgrove claimed that he had already surrendered the pyx to Cokesey.
Another four and a half years were to pass before Cokesey finally attained his majority, on St. George’s Day 1426. On the following 27 May he proved his age before the escheator in Worcestershire, and a day later the escheator and his counterparts in the other counties where the Cokesey and Brewes estates lay were ordered to take his fealty.
Some property also came to Cokesey in marriage, for his first wife was a coheir to the manor of Shifnal in Shropshire and the lordship of the town of Talgarth ‘English’ in Herefordshire. Formerly held by Sir Philip ap Rees (d.1369), these properties had passed to his daughter Elizabeth and her husband Sir Adam Peshale†. Peshale had survived both Elizabeth and his only child by her, and in Henry IV’s reign the Crown had granted the reversion of the ap Rees estates to Thomas Neville, Lord Furnival, a younger brother of Ralph Neville, 1st earl of Westmorland. In the event, Furnival had predeceased Sir Adam, meaning that after the knight’s death in October 1419 the ap Rees lands were divided between Furnival’s daughters and coheirs, Maud and Joan.
At the time of Sir Adam Peshale’s inquisition post mortem in November 1419, Cokesey was already a knight although still a minor.
Near the end of 1425, Cokesey was involved in yet more lawless behaviour, again in association with Talbot. In November that year the brothers-in-law raided the manor of Snitterfield, Warwickshire, a property belonging to Joan Beauchamp, Lady Abergavenny, at the head of an armed following. There followed an affray with Joan’s servants, during which Talbot’s brother Sir William Talbot was killed. Probably, there was a connexion between the raid and Talbot’s feud with Joan’s son-in-law James Butler, earl of Ormond, in Ireland, although it seems also to have enjoyed the tacit approval of her nephew by marriage, Richard Beauchamp, earl of Warwick, to whose authority in the Midlands she was posing a challenge. A year later, both sides agreed to refer the quarrel to the arbitration of John, duke of Bedford, who took recognizances of £1,000 from Joan and Talbot, to guarantee that they would abide by his award, in November 1426. In the following May, however, the Crown instituted a commission of oyer and terminer to investigate her complaint that Cokesey and a band of armed followers had broken into her houses and park at Snitterfield, hunted her game and assaulted her servants and tenants. Given that the commission did not refer to Talbot, and that Bedford was to have made his award by the previous February, it would appear that Cokesey had raided her property for a second time.
Cokesey owed his appointment to the earl of Warwick, the hereditary sheriff of Worcestershire. Cokesey’s association with Warwick dated back to at least the mid 1420s and, by about 1431, the earl had granted him a fee of £26 13s. 4d. p.a. The Cokeseys had a long record of serving the Beauchamp family, with whom Sir Hugh’s brother-in-law, John Talbot, also had links. Talbot had entered Warwick’s service after marrying his second wife, the earl’s daughter Margaret Beauchamp, in 1425. Warwick became one of Cokesey’s feoffees, and he arbitrated between Sir Hugh and the Warwickshire esquire Richard Archer of Tanworth in June 1429. The two men had fallen out over an annuity of ten marks that Cokesey’s grandfather Sir Walter Cokesey had granted to Archer’s parents Thomas and Agnes, a daughter of Sir Walter, at the time of their marriage. Payable from the manor of Cokesey, presumably the annuity had fallen into arrears. Warwick ruled that Cokesey should pay £40 to Archer in full satisfaction of all claims, and that in return the latter should surrender the deed by which Sir Walter had granted the annuity.
It is possible that Cokesey returned to France in the 1430s, since there is very little evidence of his activities in England during that decade. By 1439, he was acting as a feoffee of the Gloucestershire manors of Great Rissington and Sapperton on behalf of his brother-in-law, John Greville*. Greville, who had taken Joyce, one of Cokesey’s sisters, for his second wife, was in possession of the manors as the mortgagee of Sir Henry Hussey*, to whom he had given a loan of £320.
By then Cokesey had recently sat in his only known Parliament, as a knight of the shire for his native Worcestershire. It was to his Membership of the Parliament of 1442 that he owed his appointment to his sole ad hoc commission, a body tasked with distributing allowances of the subsidy that he and his fellow MPs had granted to the Crown. While an MP, he stood surety on behalf of Thomas Courtenay, earl of Devon, and others, when the Crown granted the wardship of the son and heir of Sir William Bodrugan* in March 1442. How he came to act for the earl and his associates is a matter for speculation; possibly he and Courtenay had campaigned together in France. Just before the Parliament ended, the Crown made plans to send a new army across the Channel, but it unclear whether Cokesey participated in the subsequent expedition, which set sail in June 1442 under the command of John Talbot, now earl of Shrewsbury. He certainly returned to France with Talbot in the autumn of 1444, as a member of the party sent to escort Henry VI’s bride, Margaret of Anjou, to England. A pair of grooms accompanied him, and he and his servants received wages of £31 17s.
Following his return to England with the queen in the spring of 1445, Cokesey had only months to live, for he died on 15 Dec. that year. Neither of his marriages had produced any surviving children, meaning that his heir was his 40-year old sister Joyce. By then she was the wife of the Gloucestershire esquire Leonard Stapleton, having outlived her previous two husbands, John Greville and Walter Beauchamp. Owing to the provision that her brother had made for his second wife, Joyce did not come into her inheritance until after her sister-in-law Alice died in 1460. Following Cokesey’s death, Alice had married Sir Andrew Ogard*, whom she had also survived.